diff --git a/acceptance/bundle/apps/app_yaml/out.app.yml.txt b/acceptance/bundle/apps/app_yaml/out.app.yml.txt
index 29cb7da70f..e79c7a4f57 100644
--- a/acceptance/bundle/apps/app_yaml/out.app.yml.txt
+++ b/acceptance/bundle/apps/app_yaml/out.app.yml.txt
@@ -1,8 +1,12 @@
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/app/app.yml",
-  "q": {
-    "overwrite": "true"
-  },
-  "raw_body": "command:\n  - python\n  - app.py\n"
+  "path": "/api/2.0/workspace/import",
+  "body": {
+    "multipart_form": {
+      "content": "command:\n  - python\n  - app.py\n",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/app/app.yml"
+    }
+  }
 }
diff --git a/acceptance/bundle/apps/app_yaml/output.txt b/acceptance/bundle/apps/app_yaml/output.txt
index addb91d683..7733b0f8ed 100644
--- a/acceptance/bundle/apps/app_yaml/output.txt
+++ b/acceptance/bundle/apps/app_yaml/output.txt
@@ -19,7 +19,7 @@ Deploying resources...
 Updating deployment state...
 Deployment complete!
 
->>> jq select(.path | test("app.yml")) out.requests.txt
+>>> jq select(.body.multipart_form.path | strings | test("app.yml")) out.requests.txt
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/apps/app_yaml/script b/acceptance/bundle/apps/app_yaml/script
index d0dd8d5f80..adec87dc21 100644
--- a/acceptance/bundle/apps/app_yaml/script
+++ b/acceptance/bundle/apps/app_yaml/script
@@ -1,7 +1,7 @@
 trace $CLI bundle validate
 trace $CLI bundle plan
 trace $CLI bundle deploy
-trace jq 'select(.path | test("app.yml"))' out.requests.txt | sed 's/\\r//g'  > out.app.yml.txt
+trace jq 'select(.body.multipart_form.path | strings | test("app.yml"))' out.requests.txt | sed 's/\\r//g'  > out.app.yml.txt
 #trace print_requests.py //apps  # currently fails due to TF inserting description=""
 rm out.requests.txt
 
diff --git a/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt b/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt
index dd81ba7de2..b9d8cfeb72 100644
--- a/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt
+++ b/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt
@@ -50,9 +50,9 @@ Deployment complete!
 ]
 
 === Expecting wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl
+/Workspace/foo/bar/artifacts/.internal/source.whl
 
 === Expecting environment dependencies to be updated
 >>> jq -s .[] | select(.path=="/api/2.2/jobs/create") | .body.environments out.requests.txt
diff --git a/acceptance/bundle/artifacts/artifact_upload_for_workspace/script b/acceptance/bundle/artifacts/artifact_upload_for_workspace/script
index e6b1437627..cd28cc070f 100644
--- a/acceptance/bundle/artifacts/artifact_upload_for_workspace/script
+++ b/acceptance/bundle/artifacts/artifact_upload_for_workspace/script
@@ -8,7 +8,7 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting wheel to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 title "Expecting environment dependencies to be updated"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.environments' out.requests.txt
diff --git a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt
index 6d24880e6c..d309b10cad 100644
--- a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt
+++ b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt
@@ -6,9 +6,9 @@ Deploying resources...
 Deployment complete!
 
 === Expecting wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl
+/Workspace/foo/bar/artifacts/.internal/source.whl
 
 === Expecting delete request to artifact_path/.internal folder
 >>> jq -s .[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal")) out.requests.txt
diff --git a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script
index 883601185c..b5ee485cbd 100644
--- a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script
+++ b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script
@@ -5,7 +5,7 @@ echo "test wheel content" > whl/source.whl
 trace $CLI bundle deploy
 
 title "Expecting wheel to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 title "Expecting delete request to artifact_path/.internal folder"
 trace jq -s '.[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal"))' out.requests.txt
diff --git a/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt b/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt
index fa725a29d8..7e5436900e 100644
--- a/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt
+++ b/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt
@@ -40,15 +40,15 @@ Deployment complete!
 ]
 
 === Expecting 4 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source1.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source2.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source3.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source4.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source1.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source2.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source3.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source4.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source1.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source2.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source3.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source4.whl
+/Workspace/foo/bar/artifacts/.internal/source1.whl
+/Workspace/foo/bar/artifacts/.internal/source2.whl
+/Workspace/foo/bar/artifacts/.internal/source3.whl
+/Workspace/foo/bar/artifacts/.internal/source4.whl
 
 === Expecting environment dependencies to be updated
 >>> jq -s .[] | select(.path=="/api/2.2/jobs/create") | .body.environments out.requests.txt
diff --git a/acceptance/bundle/artifacts/upload_multiple_libraries/script b/acceptance/bundle/artifacts/upload_multiple_libraries/script
index f615147f8c..7625d8947f 100644
--- a/acceptance/bundle/artifacts/upload_multiple_libraries/script
+++ b/acceptance/bundle/artifacts/upload_multiple_libraries/script
@@ -11,7 +11,7 @@ title "Expecting 5 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting 4 wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 title "Expecting environment dependencies to be updated"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.environments' out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_change_version/output.txt b/acceptance/bundle/artifacts/whl_change_version/output.txt
index 4fc7ff6674..4451e8811e 100644
--- a/acceptance/bundle/artifacts/whl_change_version/output.txt
+++ b/acceptance/bundle/artifacts/whl_change_version/output.txt
@@ -29,23 +29,23 @@ dist/my_test_code-0.1.0-py3-none-any.whl
 ]
 
 === Expecting 1 wheel to be uploaded
->>> jq .path out.requests.txt
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/.gitignore"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.1.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__main__.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/out.requests.txt"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/output.txt"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/repls.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/script"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/setup.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/test.toml"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME"
+>>> jq -r .body.multipart_form.path | strings out.requests.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/.gitignore
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.1.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__main__.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/out.requests.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/output.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/repls.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/script
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/setup.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/test.toml
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME
 
 >>> update_file.py my_test_code/__init__.py 0.1.0 0.2.0
 
@@ -66,16 +66,16 @@ dist/my_test_code-0.2.0-py3-none-any.whl
 json[0].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl";
 
 === Expecting 1 wheel to be uploaded
->>> jq .path out.requests.txt
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/out.requests.txt"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/output.txt"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME"
+>>> jq -r .body.multipart_form.path | strings out.requests.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/out.requests.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/output.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME
 
 === Restore config to target old wheel
 >>> update_file.py databricks.yml ./dist/*.whl ./dist/my*0.1.0*.whl
@@ -98,14 +98,14 @@ dist/my_test_code-0.2.0-py3-none-any.whl
 json[0].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl";
 
 === Expecting 1 wheel to be uploaded
->>> jq .path out.requests.txt
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/out.requests.txt"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/output.txt"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME"
+>>> jq -r .body.multipart_form.path | strings out.requests.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/out.requests.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/output.txt
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME
diff --git a/acceptance/bundle/artifacts/whl_change_version/script b/acceptance/bundle/artifacts/whl_change_version/script
index 9f6f480f0d..68f33c9563 100644
--- a/acceptance/bundle/artifacts/whl_change_version/script
+++ b/acceptance/bundle/artifacts/whl_change_version/script
@@ -6,7 +6,7 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path out.requests.txt | grep import | sort
+trace jq -r '.body.multipart_form.path | strings' out.requests.txt | sort
 
 rm out.requests.txt
 
@@ -20,7 +20,7 @@ title "Expecting 1 wheel in libraries section in /jobs/reset"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/reset") | .body.new_settings.tasks' out.requests.txt | gron.py | grep -w libraries
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path out.requests.txt | grep import | sort
+trace jq -r '.body.multipart_form.path | strings' out.requests.txt | sort
 
 rm out.requests.txt
 
@@ -34,6 +34,6 @@ title "Expecting 1 wheel in libraries section in /jobs/reset"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/reset") | .body.new_settings.tasks' out.requests.txt | gron.py | grep -w libraries
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path out.requests.txt | grep import | sort
+trace jq -r '.body.multipart_form.path | strings' out.requests.txt | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_dbfs/output.txt b/acceptance/bundle/artifacts/whl_dbfs/output.txt
index 306de22de1..2d1d4ecbda 100644
--- a/acceptance/bundle/artifacts/whl_dbfs/output.txt
+++ b/acceptance/bundle/artifacts/whl_dbfs/output.txt
@@ -27,6 +27,6 @@ Deployment complete!
 ]
 
 === Expecting no wheels to be uploaded
->>> errcode sh -c jq .path < out.requests.txt | grep import | grep whl
+>>> errcode sh -c jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl
 
 Exit code: 1
diff --git a/acceptance/bundle/artifacts/whl_dbfs/script b/acceptance/bundle/artifacts/whl_dbfs/script
index d7c93d8f38..3f15b85912 100644
--- a/acceptance/bundle/artifacts/whl_dbfs/script
+++ b/acceptance/bundle/artifacts/whl_dbfs/script
@@ -7,6 +7,6 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting no wheels to be uploaded"
-trace errcode sh -c 'jq .path < out.requests.txt | grep import | grep whl'
+trace errcode sh -c "jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl"
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_dynamic/output.txt b/acceptance/bundle/artifacts/whl_dynamic/output.txt
index c7409f3740..c66cee0294 100644
--- a/acceptance/bundle/artifacts/whl_dynamic/output.txt
+++ b/acceptance/bundle/artifacts/whl_dynamic/output.txt
@@ -58,11 +58,11 @@ json[1].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/defa
 json[1].libraries[1].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl";
 
 === Expecting 2 patched wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/prebuilt/other_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/prebuilt/other_test_code-0.0.1-py3-none-any.whl
 
 === Updating the local wheel and deploying again
 Building my_test_code...
@@ -94,7 +94,7 @@ json[1].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/defa
 json[1].libraries[1].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl";
 
 === Expecting 2 pached wheels to be uploaded (Bad: it is currently uploaded twice)
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][2]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][2]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_dynamic/script b/acceptance/bundle/artifacts/whl_dynamic/script
index 068db16caf..1e02902b5e 100644
--- a/acceptance/bundle/artifacts/whl_dynamic/script
+++ b/acceptance/bundle/artifacts/whl_dynamic/script
@@ -19,7 +19,7 @@ title "Expecting 2 patched wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt | gron.py | grep -w libraries
 
 title "Expecting 2 patched wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
 
@@ -35,4 +35,4 @@ title "Expecting 2 patched wheels in libraries section in /jobs/reset"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/reset") | .body.new_settings.tasks' out.requests.txt | gron.py | grep -w libraries
 
 title "Expecting 2 pached wheels to be uploaded (Bad: it is currently uploaded twice)"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
diff --git a/acceptance/bundle/artifacts/whl_explicit/output.txt b/acceptance/bundle/artifacts/whl_explicit/output.txt
index 6c1c06c46e..bbac28dc11 100644
--- a/acceptance/bundle/artifacts/whl_explicit/output.txt
+++ b/acceptance/bundle/artifacts/whl_explicit/output.txt
@@ -29,9 +29,9 @@ my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
 
 === Expecting delete request to artifact_path/.internal folder
 >>> jq -s .[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal")) out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_explicit/script b/acceptance/bundle/artifacts/whl_explicit/script
index 4988edd815..db664434f0 100644
--- a/acceptance/bundle/artifacts/whl_explicit/script
+++ b/acceptance/bundle/artifacts/whl_explicit/script
@@ -6,7 +6,7 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 title "Expecting delete request to artifact_path/.internal folder"
 trace jq -s '.[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal"))' out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_implicit/output.txt b/acceptance/bundle/artifacts/whl_implicit/output.txt
index 698cc20c51..a3dc47e712 100644
--- a/acceptance/bundle/artifacts/whl_implicit/output.txt
+++ b/acceptance/bundle/artifacts/whl_implicit/output.txt
@@ -29,6 +29,6 @@ dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 1 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_implicit/script b/acceptance/bundle/artifacts/whl_implicit/script
index da61fb91f8..948e73d11d 100644
--- a/acceptance/bundle/artifacts/whl_implicit/script
+++ b/acceptance/bundle/artifacts/whl_implicit/script
@@ -6,6 +6,6 @@ title "Expecting 1 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting 1 wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt b/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt
index 71f1bffc1d..dd3d94f7be 100644
--- a/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt
+++ b/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt
@@ -41,6 +41,6 @@ package/my_test_code-0.0.1-py3-none-any.whl
 }
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/package/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/.internal/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/package/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/foo/bar/.internal/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_implicit_custom_path/script b/acceptance/bundle/artifacts/whl_implicit_custom_path/script
index fdc0723f59..13f1ba1b6e 100644
--- a/acceptance/bundle/artifacts/whl_implicit_custom_path/script
+++ b/acceptance/bundle/artifacts/whl_implicit_custom_path/script
@@ -6,6 +6,6 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body' out.requests.txt
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt b/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt
index 7e393eabc4..1c5bbc1251 100644
--- a/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt
+++ b/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt
@@ -19,6 +19,6 @@ dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_implicit_notebook/script b/acceptance/bundle/artifacts/whl_implicit_notebook/script
index 30196556f1..8d68a61e6d 100644
--- a/acceptance/bundle/artifacts/whl_implicit_notebook/script
+++ b/acceptance/bundle/artifacts/whl_implicit_notebook/script
@@ -6,6 +6,6 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks[0].libraries' out.requests.txt
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_multiple/output.txt b/acceptance/bundle/artifacts/whl_multiple/output.txt
index a03025d910..565f8524b9 100644
--- a/acceptance/bundle/artifacts/whl_multiple/output.txt
+++ b/acceptance/bundle/artifacts/whl_multiple/output.txt
@@ -35,8 +35,8 @@ my_test_code/dist/my_test_code_2-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code_2-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code_2-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code_2-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code_2-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_multiple/script b/acceptance/bundle/artifacts/whl_multiple/script
index 380c6c60f8..dfaa1bbb94 100644
--- a/acceptance/bundle/artifacts/whl_multiple/script
+++ b/acceptance/bundle/artifacts/whl_multiple/script
@@ -6,6 +6,6 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm -fr out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_no_cleanup/output.txt b/acceptance/bundle/artifacts/whl_no_cleanup/output.txt
index a78810dbca..b98f17dab6 100644
--- a/acceptance/bundle/artifacts/whl_no_cleanup/output.txt
+++ b/acceptance/bundle/artifacts/whl_no_cleanup/output.txt
@@ -11,9 +11,9 @@ Deployment complete!
 dist/my_test_code-0.0.1-py3-none-any.whl
 
 === Expecting 1 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
 
 >>> [CLI] bundle deploy
 Building python_artifact...
diff --git a/acceptance/bundle/artifacts/whl_no_cleanup/script b/acceptance/bundle/artifacts/whl_no_cleanup/script
index 4536f92946..21e0d84ace 100644
--- a/acceptance/bundle/artifacts/whl_no_cleanup/script
+++ b/acceptance/bundle/artifacts/whl_no_cleanup/script
@@ -3,7 +3,7 @@ trace $CLI bundle deploy
 trace find.py --expect 1 whl
 
 title "Expecting 1 wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 trace $CLI bundle deploy
 title "No calls to delete internal folder expected"
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt b/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt
index 4fe390e635..02bf0311f7 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt
+++ b/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt
@@ -38,8 +38,8 @@ dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/lib/other_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/lib/other_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_multiple/script b/acceptance/bundle/artifacts/whl_prebuilt_multiple/script
index 9df7ea3d98..977c9431ea 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_multiple/script
+++ b/acceptance/bundle/artifacts/whl_prebuilt_multiple/script
@@ -9,6 +9,6 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt b/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt
index 369db2e47a..39495b82b1 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt
@@ -32,6 +32,6 @@ Deployment complete!
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside/script b/acceptance/bundle/artifacts/whl_prebuilt_outside/script
index 939847f6c1..7459288248 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside/script
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside/script
@@ -11,6 +11,6 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requests.txt
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt
index 570b124a5b..2615973a40 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt
@@ -56,6 +56,6 @@ Deployment complete!
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script
index af4e84b8b3..7306df94e9 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script
@@ -14,6 +14,6 @@ trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' out.requ
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.environments' out.requests.txt
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_via_environment_key/output.txt b/acceptance/bundle/artifacts/whl_via_environment_key/output.txt
index 8afa59e7d8..a5468f4dae 100644
--- a/acceptance/bundle/artifacts/whl_via_environment_key/output.txt
+++ b/acceptance/bundle/artifacts/whl_via_environment_key/output.txt
@@ -49,6 +49,6 @@ my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
 }
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> jq -r .body.multipart_form.path | strings
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_via_environment_key/script b/acceptance/bundle/artifacts/whl_via_environment_key/script
index 3a0dd929c0..0a4fbfcff2 100644
--- a/acceptance/bundle/artifacts/whl_via_environment_key/script
+++ b/acceptance/bundle/artifacts/whl_via_environment_key/script
@@ -6,6 +6,6 @@ title "Expecting 1 wheel in environments section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body' out.requests.txt
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < out.requests.txt | grep import | grep whl | sort
+trace jq -r '.body.multipart_form.path | strings' < out.requests.txt | grep whl | sort
 
 rm out.requests.txt
diff --git a/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt b/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt
index af42322dee..04f3b651bf 100644
--- a/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt
+++ b/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt
@@ -1,5 +1,5 @@
 
->>> print_requests.py ^//import-file/ ^//workspace/
+>>> print_requests.py ^//workspace/
 
 >>> [CLI] bundle summary -o json
 
@@ -31,4 +31,4 @@ Deploying resources...
 Updating deployment state...
 Deployment complete!
 
->>> print_requests.py ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
diff --git a/acceptance/bundle/deployment/bind/pipelines/recreate/script b/acceptance/bundle/deployment/bind/pipelines/recreate/script
index aba4cfb97a..a6dcfbf583 100644
--- a/acceptance/bundle/deployment/bind/pipelines/recreate/script
+++ b/acceptance/bundle/deployment/bind/pipelines/recreate/script
@@ -6,11 +6,11 @@ add_repl.py $NEW_PIPELINE_ID NEW_PIPELINE_ID
 
 rm -f out.requests.txt
 trace musterr $CLI bundle deployment bind foo $NEW_PIPELINE_ID &> out.bind-fail.$DATABRICKS_BUNDLE_ENGINE.txt
-print_requests.py '^//import-file/' '^//workspace/'
+print_requests.py '^//workspace/'
 
 rm -f out.requests.txt
 trace $CLI bundle deployment bind foo $NEW_PIPELINE_ID --auto-approve &> out.bind-success.$DATABRICKS_BUNDLE_ENGINE.txt
-trace print_requests.py '^//import-file/' '^//workspace/'
+trace print_requests.py '^//workspace/'
 
 trace $CLI bundle summary -o json | jq .resources > out.summary.json
 trace $CLI bundle plan
@@ -19,4 +19,4 @@ trace musterr $CLI bundle deploy
 
 rm -f out.requests.txt
 trace $CLI bundle deploy --auto-approve
-trace print_requests.py '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
+trace print_requests.py '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
diff --git a/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.direct.json b/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.direct.json
index 78f256ba44..0ff6df9c9c 100644
--- a/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.direct.json
+++ b/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.direct.json
@@ -1,17 +1,3 @@
-{
-  "method": "POST",
-  "path": "/api/2.0/workspace/mkdirs",
-  "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-pipeline-recreate/default/artifacts/.internal"
-  }
-}
-{
-  "method": "POST",
-  "path": "/api/2.0/workspace/mkdirs",
-  "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-pipeline-recreate/default/files"
-  }
-}
 {
   "method": "PUT",
   "path": "/api/2.0/pipelines/[NEW_PIPELINE_ID]",
diff --git a/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.terraform.json b/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.terraform.json
index 3c8d1946b8..ab034f0d55 100644
--- a/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.terraform.json
+++ b/acceptance/bundle/deployment/bind/pipelines/update/out.deploy.requests.terraform.json
@@ -1,17 +1,3 @@
-{
-  "method": "POST",
-  "path": "/api/2.0/workspace/mkdirs",
-  "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-pipeline-recreate/default/artifacts/.internal"
-  }
-}
-{
-  "method": "POST",
-  "path": "/api/2.0/workspace/mkdirs",
-  "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-pipeline-recreate/default/files"
-  }
-}
 {
   "method": "PUT",
   "path": "/api/2.0/pipelines/[NEW_PIPELINE_ID]",
diff --git a/acceptance/bundle/deployment/bind/pipelines/update/output.txt b/acceptance/bundle/deployment/bind/pipelines/update/output.txt
index f88ed70d69..da118c9981 100644
--- a/acceptance/bundle/deployment/bind/pipelines/update/output.txt
+++ b/acceptance/bundle/deployment/bind/pipelines/update/output.txt
@@ -12,4 +12,4 @@ Deploying resources...
 Updating deployment state...
 Deployment complete!
 
->>> print_requests.py ^//import-file/ ^//workspace/delete ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
diff --git a/acceptance/bundle/deployment/bind/pipelines/update/script b/acceptance/bundle/deployment/bind/pipelines/update/script
index 5d2e487f10..8b1441a746 100644
--- a/acceptance/bundle/deployment/bind/pipelines/update/script
+++ b/acceptance/bundle/deployment/bind/pipelines/update/script
@@ -3,15 +3,15 @@ add_repl.py $NEW_PIPELINE_ID NEW_PIPELINE_ID
 
 rm -f out.requests.txt
 trace musterr $CLI bundle deployment bind foo $NEW_PIPELINE_ID &> out.bind-fail.$DATABRICKS_BUNDLE_ENGINE.txt
-print_requests.py '^//import-file/' '^//workspace/delete'
+print_requests.py '^//workspace/'
 
 rm -f out.requests.txt
 trace $CLI bundle deployment bind foo $NEW_PIPELINE_ID --auto-approve &> out.bind-success.$DATABRICKS_BUNDLE_ENGINE.txt
-print_requests.py '^//import-file/' '^//workspace/delete'
+print_requests.py '^//workspace/'
 
 trace $CLI bundle summary -o json > out.summary.json
 trace $CLI bundle plan
 
 rm -f out.requests.txt
 trace $CLI bundle deploy --auto-approve
-trace print_requests.py '^//import-file/' '^//workspace/delete' '^//telemetry-ext' > out.deploy.requests.$DATABRICKS_BUNDLE_ENGINE.json
+trace print_requests.py '^//workspace/' '^//telemetry-ext' > out.deploy.requests.$DATABRICKS_BUNDLE_ENGINE.json
diff --git a/acceptance/bundle/libraries/outside_of_bundle_root/output.txt b/acceptance/bundle/libraries/outside_of_bundle_root/output.txt
index e7d6530536..85c2d65d20 100644
--- a/acceptance/bundle/libraries/outside_of_bundle_root/output.txt
+++ b/acceptance/bundle/libraries/outside_of_bundle_root/output.txt
@@ -53,8 +53,12 @@ Deployment complete!
 >>> cat out.requests.txt
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl",
-  "q": {
-    "overwrite": "true"
+  "path": "/api/2.0/workspace/import",
+  "body": {
+    "multipart_form": {
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl"
+    }
   }
 }
diff --git a/acceptance/bundle/libraries/outside_of_bundle_root/script b/acceptance/bundle/libraries/outside_of_bundle_root/script
index ff72be1b69..74f4f15cf8 100644
--- a/acceptance/bundle/libraries/outside_of_bundle_root/script
+++ b/acceptance/bundle/libraries/outside_of_bundle_root/script
@@ -11,6 +11,6 @@ title "Check that the job libraries are uploaded and the path is correct in the
 trace cat out.requests.txt | jq 'select(.path == "/api/2.2/jobs/create")' | jq '.body.tasks[0].libraries'
 trace cat out.requests.txt | jq 'select(.path == "/api/2.2/jobs/create")' | jq '.body.environments[0].spec.dependencies'
 trace cat out.requests.txt | jq 'select(.path == "/api/2.0/pipelines" and .method == "POST")' | jq '.body.environment.dependencies'
-trace cat out.requests.txt | jq 'select(.path | test("/api/2.0/workspace-files/import-file/Workspace/Users/.*/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl"))'
+trace cat out.requests.txt | jq 'select(.path == "/api/2.0/workspace/import" and (.body.multipart_form.path // "" | test("/Workspace/Users/.*/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl")))' | jq 'del(.body.multipart_form.content)'
 
 rm out.requests.txt
diff --git a/acceptance/bundle/resource_deps/remote_app_url/output.txt b/acceptance/bundle/resource_deps/remote_app_url/output.txt
index 81b300ab11..279b795afb 100644
--- a/acceptance/bundle/resource_deps/remote_app_url/output.txt
+++ b/acceptance/bundle/resource_deps/remote_app_url/output.txt
@@ -14,7 +14,7 @@ create pipelines.mypipeline
 
 Plan: 2 to add, 0 to change, 0 to delete, 0 unchanged
 
->>> print_requests.py ^//import-file/
+>>> print_requests.py ^//workspace/import
 {
   "method": "POST",
   "path": "/api/2.0/workspace/mkdirs",
@@ -29,7 +29,7 @@ Deploying resources...
 Updating deployment state...
 Deployment complete!
 
->>> print_requests.py ^//import-file/
+>>> print_requests.py ^//workspace/import
 {
   "method": "POST",
   "path": "/api/2.0/workspace/delete",
@@ -91,7 +91,7 @@ All files and directories at the following location will be deleted: /Workspace/
 Deleting files...
 Destroy complete!
 
->>> print_requests.py --sort ^//import-file/
+>>> print_requests.py --sort ^//workspace/import
 {
   "method": "DELETE",
   "path": "/api/2.0/apps/myapp"
diff --git a/acceptance/bundle/resource_deps/remote_app_url/script b/acceptance/bundle/resource_deps/remote_app_url/script
index d38692366b..51ce6274ed 100644
--- a/acceptance/bundle/resource_deps/remote_app_url/script
+++ b/acceptance/bundle/resource_deps/remote_app_url/script
@@ -1,9 +1,9 @@
 trace $CLI bundle validate
 trace $CLI bundle plan
-trace print_requests.py '^//import-file/'
+trace print_requests.py '^//workspace/import'
 
 trace $CLI bundle deploy
-trace print_requests.py '^//import-file/'
+trace print_requests.py '^//workspace/import'
 
 trace $CLI bundle destroy --auto-approve
-trace print_requests.py --sort '^//import-file/'
+trace print_requests.py --sort '^//workspace/import'
diff --git a/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt b/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt
index 08f6c53ae1..b569000be3 100644
--- a/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt
@@ -23,7 +23,7 @@ Deployment complete!
 >>> [CLI] bundle plan
 Plan: 0 to add, 0 to change, 0 to delete, 1 unchanged
 
->>> print_requests.py ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/resources/quality_monitors/change_assets_dir/script b/acceptance/bundle/resources/quality_monitors/change_assets_dir/script
index 6caf49a7f4..2bdc84ee12 100644
--- a/acceptance/bundle/resources/quality_monitors/change_assets_dir/script
+++ b/acceptance/bundle/resources/quality_monitors/change_assets_dir/script
@@ -26,5 +26,5 @@ trace errcode $CLI bundle plan -o json &> out.plan.$DATABRICKS_BUNDLE_ENGINE.jso
 
 rm out.requests.txt
 trace errcode $CLI bundle deploy &> out.deploy.$DATABRICKS_BUNDLE_ENGINE.txt
-trace print_requests.py '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.$DATABRICKS_BUNDLE_ENGINE.json
+trace print_requests.py '^//workspace/' '^//telemetry-ext' > out.deploy.requests.$DATABRICKS_BUNDLE_ENGINE.json
 trace errcode $CLI bundle plan &> out.plan_after_deploy.$DATABRICKS_BUNDLE_ENGINE.txt
diff --git a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt
index d67ee41975..0f021b4f87 100644
--- a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt
@@ -36,7 +36,7 @@ Deploying resources...
 Updating deployment state...
 Deployment complete!
 
->>> print_requests.py ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle plan
 Plan: 0 to add, 0 to change, 0 to delete, 1 unchanged
diff --git a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script
index 72c57e0840..e7e800e526 100644
--- a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script
+++ b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script
@@ -27,6 +27,6 @@ trace $CLI bundle plan -o json > out.plan.$DATABRICKS_BUNDLE_ENGINE.json
 rm out.requests.txt
 trace $CLI bundle deploy
 # dashboard_id is output only field that terraform adds
-trace print_requests.py '^//import-file/' '^//workspace/' '^//telemetry-ext' | grep -v '"dashboard_id":' > out.deploy.requests.json
+trace print_requests.py '^//workspace/' '^//telemetry-ext' | grep -v '"dashboard_id":' > out.deploy.requests.json
 
 trace $CLI bundle plan | contains.py "1 unchanged"
diff --git a/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt b/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt
index 879222aa8a..48520444bb 100644
--- a/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt
@@ -23,7 +23,7 @@ Deployment complete!
 >>> [CLI] bundle plan
 Plan: 0 to add, 0 to change, 0 to delete, 1 unchanged
 
->>> print_requests.py ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/resources/quality_monitors/change_table_name/script b/acceptance/bundle/resources/quality_monitors/change_table_name/script
index 891aece1c1..0bec176f6a 100644
--- a/acceptance/bundle/resources/quality_monitors/change_table_name/script
+++ b/acceptance/bundle/resources/quality_monitors/change_table_name/script
@@ -26,7 +26,7 @@ trace errcode $CLI bundle plan -o json &> out.plan.$DATABRICKS_BUNDLE_ENGINE.jso
 
 rm out.requests.txt
 trace errcode $CLI bundle deploy &> out.deploy.$DATABRICKS_BUNDLE_ENGINE.txt
-trace print_requests.py '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.$DATABRICKS_BUNDLE_ENGINE.json
+trace print_requests.py '^//workspace/' '^//telemetry-ext' > out.deploy.requests.$DATABRICKS_BUNDLE_ENGINE.json
 trace errcode $CLI bundle plan &> out.plan_after_deploy.$DATABRICKS_BUNDLE_ENGINE.txt
 
 trace errcode $CLI quality-monitors get ${TABLE_NAME}_2 2> /dev/null > out.get.$DATABRICKS_BUNDLE_ENGINE.json
diff --git a/acceptance/bundle/resources/quality_monitors/create/output.txt b/acceptance/bundle/resources/quality_monitors/create/output.txt
index 8037d5ec9c..7afde18578 100644
--- a/acceptance/bundle/resources/quality_monitors/create/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/create/output.txt
@@ -16,7 +16,7 @@ Table main.qm_test_[UNIQUE_NAME].test_table is now visible (catalog_name=main)
 
 >>> [CLI] bundle plan -o json
 
->>> print_requests.py ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle plan -o json
 
diff --git a/acceptance/bundle/resources/quality_monitors/create/script b/acceptance/bundle/resources/quality_monitors/create/script
index 78c7853b26..d14dee8fbe 100644
--- a/acceptance/bundle/resources/quality_monitors/create/script
+++ b/acceptance/bundle/resources/quality_monitors/create/script
@@ -21,7 +21,7 @@ trace $CLI bundle plan -o json > out.plan_create.$DATABRICKS_BUNDLE_ENGINE.json
 
 rm out.requests.txt
 trace $CLI bundle deploy &> out.deploy.$DATABRICKS_BUNDLE_ENGINE.txt
-trace print_requests.py '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
+trace print_requests.py '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
 
 # store state to ensure we have table_name there
 print_state.py | grep name > out.state.$DATABRICKS_BUNDLE_ENGINE.txt
diff --git a/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt b/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt
index 2d469e4abc..b67ab28777 100644
--- a/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt
+++ b/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt
@@ -1,5 +1,5 @@
 
->>> print_requests.py ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
 {
   "method": "POST",
   "path": "/api/2.0/secrets/scopes/delete",
diff --git a/acceptance/bundle/resources/secret_scopes/delete_scope/script b/acceptance/bundle/resources/secret_scopes/delete_scope/script
index b12e98775a..02a7ca6d1e 100755
--- a/acceptance/bundle/resources/secret_scopes/delete_scope/script
+++ b/acceptance/bundle/resources/secret_scopes/delete_scope/script
@@ -15,4 +15,4 @@ trace $CLI bundle plan &> out.plan.$DATABRICKS_BUNDLE_ENGINE.txt
 rm out.requests.txt
 
 trace $CLI bundle deploy
-trace print_requests.py '^//import-file/' '^//workspace/' '^//telemetry-ext' &> out.deploy.requests.txt
+trace print_requests.py '^//workspace/' '^//telemetry-ext' &> out.deploy.requests.txt
diff --git a/acceptance/bundle/sync-upload-edge-cases/databricks.yml b/acceptance/bundle/sync-upload-edge-cases/databricks.yml
new file mode 100644
index 0000000000..2261ff177c
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/databricks.yml
@@ -0,0 +1,2 @@
+bundle:
+  name: upload-edge-cases
diff --git a/acceptance/bundle/sync-upload-edge-cases/out.test.toml b/acceptance/bundle/sync-upload-edge-cases/out.test.toml
new file mode 100644
index 0000000000..e90b6d5d1b
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/out.test.toml
@@ -0,0 +1,3 @@
+Local = true
+Cloud = false
+EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["direct"]
diff --git a/acceptance/bundle/sync-upload-edge-cases/output.txt b/acceptance/bundle/sync-upload-edge-cases/output.txt
new file mode 100644
index 0000000000..14a80b3044
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/output.txt
@@ -0,0 +1,72 @@
+
+>>> [CLI] bundle sync --output text
+Action: PUT: .gitignore, dashboard.lvdash.json, databricks.yml, empty.txt, héllo.txt, large.bin, notebook.py, with spaces.txt
+Initial Sync Complete
+Uploaded .gitignore
+Uploaded dashboard.lvdash.json
+Uploaded databricks.yml
+Uploaded empty.txt
+Uploaded héllo.txt
+Uploaded large.bin
+Uploaded notebook.py
+Uploaded with spaces.txt
+
+=== uploaded paths from each multipart POST /workspace/import (sorted)
+>>> jq -rs 
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(.body.multipart_form.path) |
+  sort | .[]
+ out.requests.txt
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/.gitignore
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/dashboard.lvdash.json
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/databricks.yml
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/empty.txt
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/héllo.txt
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/large.bin
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/notebook.py
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/with spaces.txt
+
+=== every upload set format=AUTO
+>>> jq -rs 
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(.body.multipart_form.format) | unique
+ out.requests.txt
+[
+  "AUTO"
+]
+
+=== recorded content for the small text inputs
+>>> jq -rs 
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(select(.body.multipart_form.path | test("/(notebook\\.py|héllo\\.txt|with spaces\\.txt|empty\\.txt|dashboard\\.lvdash\\.json)$"))) |
+  map({path: (.body.multipart_form.path | sub(".*/"; "")), content: .body.multipart_form.content}) |
+  sort_by(.path) | .[]
+ out.requests.txt
+{
+  "path": "dashboard.lvdash.json",
+  "content": "{\"datasets\":[],\"pages\":[]}\n"
+}
+{
+  "path": "empty.txt",
+  "content": ""
+}
+{
+  "path": "héllo.txt",
+  "content": "hello, naïve world\n"
+}
+{
+  "path": "notebook.py",
+  "content": "# Databricks notebook source\nprint(\"hello\")\n"
+}
+{
+  "path": "with spaces.txt",
+  "content": "hello, world\n"
+}
+
+=== 12 MiB binary upload is summarized, not stored byte-for-byte
+>>> jq -rs 
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(select(.body.multipart_form.path | endswith("/large.bin"))) |
+  .[].body.multipart_form.content
+ out.requests.txt
+[binary content [NUMID] bytes]
diff --git a/acceptance/bundle/sync-upload-edge-cases/script b/acceptance/bundle/sync-upload-edge-cases/script
new file mode 100644
index 0000000000..cc5233f045
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/script
@@ -0,0 +1,75 @@
+# Confidence checks that /workspace/import is a drop-in for the legacy import-file:
+# verify the CLI's multipart upload pipeline handles the cases that differ between the
+# two endpoints — large content (>10 MiB), empty content, varied extensions/object types,
+# and non-ASCII / spaced filenames in the multipart `path` field.
+
+# Exclude framework-generated and script-internal files from the sync. We only want the
+# inputs we explicitly generate below to show up in the recorded uploads.
+cat > .gitignore <<'EOF'
+script
+output.txt
+out.requests.txt
+repls.json
+test.toml
+EOF
+
+# 12 MiB binary file. The legacy /workspace/import JSON-body cap is 10 MiB; multipart has
+# no such cap. Generated dynamically to keep the repo small.
+python3 -c "open('large.bin', 'wb').write(b'\\0' * (12 * 1024 * 1024))"
+
+# Empty file (multipart encodes an empty `content` part — distinct from JSON's empty string).
+touch empty.txt
+
+# Python notebook: auto-detected as NOTEBOOK by /workspace/import; testserver mirrors
+# this and stores the object at the path with .py stripped.
+cat > notebook.py <<'EOF'
+# Databricks notebook source
+print("hello")
+EOF
+
+# Lakeview dashboard descriptor: the real /workspace/import assigns object_type=DASHBOARD
+# and preserves the .lvdash.json extension. The testserver doesn't emulate that and stores
+# it as a generic FILE — but the upload-side request shape (which is what this test asserts)
+# is identical.
+echo '{"datasets":[],"pages":[]}' > dashboard.lvdash.json
+
+# Non-ASCII filename. Multipart encodes filenames with RFC 5987 / quoted-string rules,
+# distinct from URL-encoding in the legacy import-file endpoint.
+echo "hello, naïve world" > "héllo.txt"
+
+# Filename with a space.
+echo "hello, world" > "with spaces.txt"
+
+trace $CLI bundle sync --output text 2>&1 | sort
+
+title "uploaded paths from each multipart POST /workspace/import (sorted)"
+trace jq -rs '
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(.body.multipart_form.path) |
+  sort | .[]
+' out.requests.txt
+
+title "every upload set format=AUTO"
+trace jq -rs '
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(.body.multipart_form.format) | unique
+' out.requests.txt
+
+title "recorded content for the small text inputs"
+trace jq -rs '
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(select(.body.multipart_form.path | test("/(notebook\\.py|héllo\\.txt|with spaces\\.txt|empty\\.txt|dashboard\\.lvdash\\.json)$"))) |
+  map({path: (.body.multipart_form.path | sub(".*/"; "")), content: .body.multipart_form.content}) |
+  sort_by(.path) | .[]
+' out.requests.txt
+
+title "12 MiB binary upload is summarized, not stored byte-for-byte"
+trace jq -rs '
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(select(.body.multipart_form.path | endswith("/large.bin"))) |
+  .[].body.multipart_form.content
+' out.requests.txt
+
+# Drop the recorded requests; their workspace-prefixed paths are noisy and the
+# assertions above already pin the relevant fields.
+rm out.requests.txt .gitignore
diff --git a/acceptance/bundle/sync-upload-edge-cases/test.toml b/acceptance/bundle/sync-upload-edge-cases/test.toml
new file mode 100644
index 0000000000..877dd9b2a9
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/test.toml
@@ -0,0 +1,14 @@
+RecordRequests = true
+
+# All sync uploads go through the same /workspace/import multipart code path; running
+# both engine variants is unnecessary here.
+EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["direct"]
+
+Ignore = [
+  "large.bin",
+  "empty.txt",
+  "notebook.py",
+  "dashboard.lvdash.json",
+  "héllo.txt",
+  "with spaces.txt",
+]
diff --git a/acceptance/bundle/templates/default-python/classic/script b/acceptance/bundle/templates/default-python/classic/script
index 6b79c6f225..1cf42e037e 100644
--- a/acceptance/bundle/templates/default-python/classic/script
+++ b/acceptance/bundle/templates/default-python/classic/script
@@ -13,12 +13,12 @@ $CLI bundle plan -o json -t prod > ../../out.plan_prod.$DATABRICKS_BUNDLE_ENGINE
 rm ../../out.requests.txt
 # With --plan variant we don't build artifacts, so we can filter out relevant log lines
 $CLI bundle deploy -t dev $(readplanarg ../../out.plan_dev.direct.json) 2>&1 | grep -vE '^Building python_artifact|^Uploading .databricks'
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.dev.$DATABRICKS_BUNDLE_ENGINE.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.dev.$DATABRICKS_BUNDLE_ENGINE.txt
 trace $CLI bundle plan -t dev  # check if if there is drift
 trace $CLI bundle plan -t dev -o json > ../../out.plan_after_deploy_dev.$DATABRICKS_BUNDLE_ENGINE.json
 
 $CLI bundle deploy -t prod $(readplanarg ../../out.plan_prod.direct.json) 2>&1 | grep -vE '^Building python_artifact|^Uploading dist'
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.prod.$DATABRICKS_BUNDLE_ENGINE.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.prod.$DATABRICKS_BUNDLE_ENGINE.txt
 trace $CLI bundle plan -t prod  # check if there is drift
 trace $CLI bundle plan -t prod -o json > ../../out.plan_after_deploy_prod.$DATABRICKS_BUNDLE_ENGINE.json
 
diff --git a/acceptance/bundle/templates/default-python/serverless/script b/acceptance/bundle/templates/default-python/serverless/script
index 86272b4a26..12d51337bd 100644
--- a/acceptance/bundle/templates/default-python/serverless/script
+++ b/acceptance/bundle/templates/default-python/serverless/script
@@ -12,12 +12,12 @@ $CLI bundle plan -o json -t prod > ../../out.plan_prod.$DATABRICKS_BUNDLE_ENGINE
 
 rm ../../out.requests.txt
 trace $CLI bundle deploy -t dev
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.dev.$DATABRICKS_BUNDLE_ENGINE.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.dev.$DATABRICKS_BUNDLE_ENGINE.txt
 trace $CLI bundle plan -t dev  # check if if there is drift
 trace $CLI bundle plan -t dev -o json > ../../out.plan_after_deploy_dev.$DATABRICKS_BUNDLE_ENGINE.json
 
 trace $CLI bundle deploy -t prod
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.prod.$DATABRICKS_BUNDLE_ENGINE.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.prod.$DATABRICKS_BUNDLE_ENGINE.txt
 trace $CLI bundle plan -t prod  # check if there is drift
 trace $CLI bundle plan -t prod -o json > ../../out.plan_after_deploy_prod.$DATABRICKS_BUNDLE_ENGINE.json
 
diff --git a/acceptance/bundle/upload/internal_server_error/output.txt b/acceptance/bundle/upload/internal_server_error/output.txt
index 5cde6aad65..24d8b2cc4a 100644
--- a/acceptance/bundle/upload/internal_server_error/output.txt
+++ b/acceptance/bundle/upload/internal_server_error/output.txt
@@ -1,7 +1,7 @@
-Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files...
+Error: Failed to acquire deployment lock: Internal Server Error
 Error: Internal Server Error (500)
 
-Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace-files/import-file/Workspace%2FUsers%2F[USERNAME]%2F.bundle%2Ftest-bundle%2Fdefault%2Ffiles%2Ffile_to_upload.txt?overwrite=true
+Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace/import
 HTTP Status: 500 Internal Server Error
 API error_code: 
 API message: Internal Server Error
diff --git a/acceptance/bundle/upload/internal_server_error/test.toml b/acceptance/bundle/upload/internal_server_error/test.toml
index 8ff8501b6d..b1d2b7dc49 100644
--- a/acceptance/bundle/upload/internal_server_error/test.toml
+++ b/acceptance/bundle/upload/internal_server_error/test.toml
@@ -1,3 +1,3 @@
 [[Server]]
-Pattern = "POST /api/2.0/workspace-files/import-file/Workspace/Users/tester@databricks.com/.bundle/test-bundle/default/files/file_to_upload.txt"
+Pattern = "POST /api/2.0/workspace/import"
 Response.StatusCode = 500
diff --git a/acceptance/bundle/upload/timeout/output.txt b/acceptance/bundle/upload/timeout/output.txt
index c314a24770..3b6eb72f28 100644
--- a/acceptance/bundle/upload/timeout/output.txt
+++ b/acceptance/bundle/upload/timeout/output.txt
@@ -1,3 +1,3 @@
-Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files...
-Error: Post "[DATABRICKS_URL]/api/2.0/workspace-files/import-file/Workspace%2FUsers%2F[USERNAME]%2F.bundle%2Ftest-bundle%2Fdefault%2Ffiles%2Ffile_to_upload.txt?overwrite=true": request timed out after 5s of inactivity
+Error: Failed to acquire deployment lock: Post "[DATABRICKS_URL]/api/2.0/workspace/import": request timed out after 5s of inactivity
+Error: Post "[DATABRICKS_URL]/api/2.0/workspace/import": request timed out after 5s of inactivity
 
diff --git a/acceptance/bundle/upload/timeout/test.toml b/acceptance/bundle/upload/timeout/test.toml
index de2d8ce015..ed84a5d1db 100644
--- a/acceptance/bundle/upload/timeout/test.toml
+++ b/acceptance/bundle/upload/timeout/test.toml
@@ -4,5 +4,5 @@ DATABRICKS_BUNDLE_HTTP_TIMEOUT_SECONDS = "5"
 [[Server]]
 # CLI aborts after a single attempt when the HTTP timeout fires.
 Delay = "30s"
-Pattern = "POST /api/2.0/workspace-files/import-file/Workspace/Users/tester@databricks.com/.bundle/test-bundle/default/files/file_to_upload.txt"
+Pattern = "POST /api/2.0/workspace/import"
 Response.StatusCode = 200
diff --git a/acceptance/bundle/user_agent/output.txt b/acceptance/bundle/user_agent/output.txt
index bf12862427..877fbff9c0 100644
--- a/acceptance/bundle/user_agent/output.txt
+++ b/acceptance/bundle/user_agent/output.txt
@@ -8,13 +8,13 @@ OK  	deploy.direct	/api/2.0/workspace/get-status	engine/direct
 OK  	deploy.direct	/api/2.0/workspace/get-status	engine/direct
 OK  	deploy.direct	/api/2.0/workspace/get-status	engine/direct
 OK  	deploy.direct	/api/2.0/workspace/get-status	engine/direct
-OK  	deploy.direct	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py	engine/direct
-OK  	deploy.direct	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock	engine/direct
-OK  	deploy.direct	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json	engine/direct
-OK  	deploy.direct	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json	engine/direct
-OK  	deploy.direct	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json	engine/direct
 OK  	deploy.direct	/api/2.0/workspace/delete	engine/direct
 OK  	deploy.direct	/api/2.0/workspace/delete	engine/direct
+OK  	deploy.direct	/api/2.0/workspace/import	engine/direct
+OK  	deploy.direct	/api/2.0/workspace/import	engine/direct
+OK  	deploy.direct	/api/2.0/workspace/import	engine/direct
+OK  	deploy.direct	/api/2.0/workspace/import	engine/direct
+OK  	deploy.direct	/api/2.0/workspace/import	engine/direct
 OK  	deploy.direct	/api/2.0/workspace/mkdirs	engine/direct
 OK  	deploy.direct	/api/2.1/unity-catalog/schemas	engine/direct
 MISS	deploy.direct	/.well-known/databricks-config	'cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS]'
@@ -28,13 +28,13 @@ OK  	deploy.terraform	/api/2.0/workspace/get-status	engine/terraform
 OK  	deploy.terraform	/api/2.0/workspace/get-status	engine/terraform
 OK  	deploy.terraform	/api/2.0/workspace/get-status	engine/terraform
 OK  	deploy.terraform	/api/2.0/workspace/get-status	engine/terraform
-OK  	deploy.terraform	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py	engine/terraform
-OK  	deploy.terraform	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock	engine/terraform
-OK  	deploy.terraform	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json	engine/terraform
-OK  	deploy.terraform	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json	engine/terraform
-OK  	deploy.terraform	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/terraform.tfstate	engine/terraform
 OK  	deploy.terraform	/api/2.0/workspace/delete	engine/terraform
 OK  	deploy.terraform	/api/2.0/workspace/delete	engine/terraform
+OK  	deploy.terraform	/api/2.0/workspace/import	engine/terraform
+OK  	deploy.terraform	/api/2.0/workspace/import	engine/terraform
+OK  	deploy.terraform	/api/2.0/workspace/import	engine/terraform
+OK  	deploy.terraform	/api/2.0/workspace/import	engine/terraform
+OK  	deploy.terraform	/api/2.0/workspace/import	engine/terraform
 OK  	deploy.terraform	/api/2.0/workspace/mkdirs	engine/terraform
 MISS	deploy.terraform	/.well-known/databricks-config	'cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS]'
 MISS	deploy.terraform	/api/2.1/unity-catalog/schemas/mycatalog.myschema	'databricks-tf-provider/1.113.0 databricks-sdk-go/[SDK_VERSION] go/1.24.0 os/[OS] cli/[DEV_VERSION] terraform/1.5.5 sdk/sdkv2 resource/schema auth/pat'
@@ -53,8 +53,8 @@ OK  	destroy.direct	/api/2.0/workspace/get-status	engine/direct
 OK  	destroy.direct	/api/2.0/workspace/get-status	engine/direct
 OK  	destroy.direct	/api/2.0/workspace/get-status	engine/direct
 OK  	destroy.direct	/api/2.1/unity-catalog/schemas/mycatalog.myschema	engine/direct
-OK  	destroy.direct	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock	engine/direct
 OK  	destroy.direct	/api/2.0/workspace/delete	engine/direct
+OK  	destroy.direct	/api/2.0/workspace/import	engine/direct
 MISS	destroy.direct	/.well-known/databricks-config	'cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS]'
 MISS	destroy.terraform	/api/2.0/preview/scim/v2/Me	'cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS] cmd/bundle_destroy cmd-exec-id/[UUID] interactive/none auth/pat'
 MISS	destroy.terraform	/api/2.0/workspace-files/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/terraform.tfstate	'cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS] cmd/bundle_destroy cmd-exec-id/[UUID] interactive/none auth/pat'
@@ -64,8 +64,8 @@ OK  	destroy.terraform	/api/2.0/workspace/export	engine/terraform
 OK  	destroy.terraform	/api/2.0/workspace/get-status	engine/terraform
 OK  	destroy.terraform	/api/2.0/workspace/get-status	engine/terraform
 OK  	destroy.terraform	/api/2.0/workspace/get-status	engine/terraform
-OK  	destroy.terraform	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock	engine/terraform
 OK  	destroy.terraform	/api/2.0/workspace/delete	engine/terraform
+OK  	destroy.terraform	/api/2.0/workspace/import	engine/terraform
 MISS	destroy.terraform	/.well-known/databricks-config	'cli/[DEV_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS]'
 MISS	destroy.terraform	/api/2.1/unity-catalog/schemas/mycatalog.myschema	'databricks-tf-provider/1.113.0 databricks-sdk-go/[SDK_VERSION] go/1.24.0 os/[OS] cli/[DEV_VERSION] terraform/1.5.5 sdk/sdkv2 resource/schema auth/pat'
 MISS	destroy.terraform	/api/2.1/unity-catalog/current-metastore-assignment	'databricks-tf-provider/1.113.0 databricks-sdk-go/[SDK_VERSION] go/1.24.0 os/[OS] cli/[DEV_VERSION] terraform/1.5.5 sdk/sdkv2 resource/schema auth/pat'
diff --git a/acceptance/bundle/user_agent/simple/out.requests.deploy.direct.json b/acceptance/bundle/user_agent/simple/out.requests.deploy.direct.json
index cc39aad6e9..af26270725 100644
--- a/acceptance/bundle/user_agent/simple/out.requests.deploy.direct.json
+++ b/acceptance/bundle/user_agent/simple/out.requests.deploy.direct.json
@@ -130,9 +130,10 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py",
-  "q": {
-    "overwrite": "true"
+  "path": "/api/2.0/workspace/delete",
+  "body": {
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal",
+    "recursive": true
   }
 }
 {
@@ -142,15 +143,9 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock",
-  "q": {
-    "overwrite": "false"
-  },
+  "path": "/api/2.0/workspace/delete",
   "body": {
-    "ID": "[UUID]",
-    "AcquisitionTime": "[TIMESTAMP]",
-    "IsForced": false,
-    "User": "[USERNAME]"
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
   }
 }
 {
@@ -160,22 +155,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "version": 1,
-    "seq": 1,
-    "cli_version": "[DEV_VERSION]",
-    "timestamp": "[TIMESTAMP]",
-    "files": [
-      {
-        "local_path": "empty.py",
-        "is_notebook": false
-      }
-    ],
-    "id": "[UUID]"
+    "multipart_form": {
+      "content": "",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py"
+    }
   }
 }
 {
@@ -185,29 +172,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "version": 1,
-    "config": {
-      "bundle": {
-        "name": "test-bundle",
-        "target": "default",
-        "git": {
-          "bundle_root_path": "."
-        }
-      },
-      "workspace": {
-        "file_path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files"
-      },
-      "resources": {},
-      "presets": {
-        "source_linked_deployment": false
-      }
-    },
-    "extra": {}
+    "multipart_form": {
+      "content": "{\"ID\":\"[UUID]\",\"AcquisitionTime\":\"[TIMESTAMP]\",\"IsForced\":false,\"User\":\"[USERNAME]\"}",
+      "format": "AUTO",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    }
   }
 }
 {
@@ -217,23 +188,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "state_version": 2,
-    "cli_version": "[DEV_VERSION]",
-    "lineage": "[UUID]",
-    "serial": 1,
-    "state": {
-      "resources.schemas.foo": {
-        "__id__": "mycatalog.myschema",
-        "state": {
-          "catalog_name": "mycatalog",
-          "name": "myschema"
-        }
-      }
+    "multipart_form": {
+      "content": "{\"version\":1,\"seq\":1,\"cli_version\":\"[DEV_VERSION]\",\"timestamp\":\"[TIMESTAMP]\",\"files\":[{\"local_path\":\"empty.py\",\"is_notebook\":false}],\"id\":\"[UUID]\"}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
     }
   }
 }
@@ -244,10 +205,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal",
-    "recursive": true
+    "multipart_form": {
+      "content": "{\n  \"version\": 1,\n  \"config\": {\n    \"bundle\": {\n      \"name\": \"test-bundle\",\n      \"target\": \"default\",\n      \"git\": {\n        \"bundle_root_path\": \".\"\n      }\n    },\n    \"workspace\": {\n      \"file_path\": \"/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files\"\n    },\n    \"resources\": {},\n    \"presets\": {\n      \"source_linked_deployment\": false\n    }\n  },\n  \"extra\": {}\n}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
+    }
   }
 }
 {
@@ -257,9 +222,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    "multipart_form": {
+      "content": "{\n \"state_version\": 2,\n \"cli_version\": \"[DEV_VERSION]\",\n \"lineage\": \"[UUID]\",\n \"serial\": 1,\n \"state\": {\n  \"resources.schemas.foo\": {\n   \"__id__\": \"mycatalog.myschema\",\n   \"state\": {\n    \"catalog_name\": \"mycatalog\",\n    \"name\": \"myschema\"\n   }\n  }\n }\n}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json"
+    }
   }
 }
 {
diff --git a/acceptance/bundle/user_agent/simple/out.requests.deploy.terraform.json b/acceptance/bundle/user_agent/simple/out.requests.deploy.terraform.json
index 435b188af3..406e02851c 100644
--- a/acceptance/bundle/user_agent/simple/out.requests.deploy.terraform.json
+++ b/acceptance/bundle/user_agent/simple/out.requests.deploy.terraform.json
@@ -130,9 +130,10 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py",
-  "q": {
-    "overwrite": "true"
+  "path": "/api/2.0/workspace/delete",
+  "body": {
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal",
+    "recursive": true
   }
 }
 {
@@ -142,15 +143,9 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock",
-  "q": {
-    "overwrite": "false"
-  },
+  "path": "/api/2.0/workspace/delete",
   "body": {
-    "ID": "[UUID]",
-    "AcquisitionTime": "[TIMESTAMP]",
-    "IsForced": false,
-    "User": "[USERNAME]"
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
   }
 }
 {
@@ -160,22 +155,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "version": 1,
-    "seq": 1,
-    "cli_version": "[DEV_VERSION]",
-    "timestamp": "[TIMESTAMP]",
-    "files": [
-      {
-        "local_path": "empty.py",
-        "is_notebook": false
-      }
-    ],
-    "id": "[UUID]"
+    "multipart_form": {
+      "content": "",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py"
+    }
   }
 }
 {
@@ -185,29 +172,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "version": 1,
-    "config": {
-      "bundle": {
-        "name": "test-bundle",
-        "target": "default",
-        "git": {
-          "bundle_root_path": "."
-        }
-      },
-      "workspace": {
-        "file_path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files"
-      },
-      "resources": {},
-      "presets": {
-        "source_linked_deployment": false
-      }
-    },
-    "extra": {}
+    "multipart_form": {
+      "content": "{\"ID\":\"[UUID]\",\"AcquisitionTime\":\"[TIMESTAMP]\",\"IsForced\":false,\"User\":\"[USERNAME]\"}",
+      "format": "AUTO",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    }
   }
 }
 {
@@ -217,46 +188,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/terraform.tfstate",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "version": 4,
-    "terraform_version": "1.5.5",
-    "serial": 1,
-    "lineage": "[UUID]",
-    "outputs": {},
-    "resources": [
-      {
-        "mode": "managed",
-        "type": "databricks_schema",
-        "name": "foo",
-        "provider": "provider[\"registry.terraform.io/databricks/databricks\"]",
-        "instances": [
-          {
-            "schema_version": 0,
-            "attributes": {
-              "catalog_name": "mycatalog",
-              "comment": null,
-              "enable_predictive_optimization": "INHERIT",
-              "force_destroy": true,
-              "id": "mycatalog.myschema",
-              "metastore_id": "[UUID]",
-              "name": "myschema",
-              "owner": "[USERNAME]",
-              "properties": null,
-              "provider_config": [],
-              "schema_id": "[UUID]",
-              "storage_root": null
-            },
-            "sensitive_attributes": [],
-            "private": "bnVsbA=="
-          }
-        ]
-      }
-    ],
-    "check_results": null
+    "multipart_form": {
+      "content": "{\"version\":1,\"seq\":1,\"cli_version\":\"[DEV_VERSION]\",\"timestamp\":\"[TIMESTAMP]\",\"files\":[{\"local_path\":\"empty.py\",\"is_notebook\":false}],\"id\":\"[UUID]\"}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
+    }
   }
 }
 {
@@ -266,10 +205,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal",
-    "recursive": true
+    "multipart_form": {
+      "content": "{\n  \"version\": 1,\n  \"config\": {\n    \"bundle\": {\n      \"name\": \"test-bundle\",\n      \"target\": \"default\",\n      \"git\": {\n        \"bundle_root_path\": \".\"\n      }\n    },\n    \"workspace\": {\n      \"file_path\": \"/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files\"\n    },\n    \"resources\": {},\n    \"presets\": {\n      \"source_linked_deployment\": false\n    }\n  },\n  \"extra\": {}\n}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
+    }
   }
 }
 {
@@ -279,9 +222,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    "multipart_form": {
+      "content": "{\n  \"version\": 4,\n  \"terraform_version\": \"1.5.5\",\n  \"serial\": 1,\n  \"lineage\": \"[UUID]\",\n  \"outputs\": {},\n  \"resources\": [\n    {\n      \"mode\": \"managed\",\n      \"type\": \"databricks_schema\",\n      \"name\": \"foo\",\n      \"provider\": \"provider[\\\"registry.terraform.io/databricks/databricks\\\"]\",\n      \"instances\": [\n        {\n          \"schema_version\": 0,\n          \"attributes\": {\n            \"catalog_name\": \"mycatalog\",\n            \"comment\": null,\n            \"enable_predictive_optimization\": \"INHERIT\",\n            \"force_destroy\": true,\n            \"id\": \"mycatalog.myschema\",\n            \"metastore_id\": \"[UUID]\",\n            \"name\": \"myschema\",\n            \"owner\": \"[USERNAME]\",\n            \"properties\": null,\n            \"provider_config\": [],\n            \"schema_id\": \"[UUID]\",\n            \"storage_root\": null\n          },\n          \"sensitive_attributes\": [],\n          \"private\": \"bnVsbA==\"\n        }\n      ]\n    }\n  ],\n  \"check_results\": null\n}\n",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/terraform.tfstate"
+    }
   }
 }
 {
diff --git a/acceptance/bundle/user_agent/simple/out.requests.destroy.direct.json b/acceptance/bundle/user_agent/simple/out.requests.destroy.direct.json
index 24f3c5bf13..c04d397f90 100644
--- a/acceptance/bundle/user_agent/simple/out.requests.destroy.direct.json
+++ b/acceptance/bundle/user_agent/simple/out.requests.destroy.direct.json
@@ -121,15 +121,10 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock",
-  "q": {
-    "overwrite": "false"
-  },
+  "path": "/api/2.0/workspace/delete",
   "body": {
-    "ID": "[UUID]",
-    "AcquisitionTime": "[TIMESTAMP]",
-    "IsForced": false,
-    "User": "[USERNAME]"
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default",
+    "recursive": true
   }
 }
 {
@@ -139,10 +134,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default",
-    "recursive": true
+    "multipart_form": {
+      "content": "{\"ID\":\"[UUID]\",\"AcquisitionTime\":\"[TIMESTAMP]\",\"IsForced\":false,\"User\":\"[USERNAME]\"}",
+      "format": "AUTO",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    }
   }
 }
 {
diff --git a/acceptance/bundle/user_agent/simple/out.requests.destroy.terraform.json b/acceptance/bundle/user_agent/simple/out.requests.destroy.terraform.json
index f8ab210ec7..8c86fbe4ac 100644
--- a/acceptance/bundle/user_agent/simple/out.requests.destroy.terraform.json
+++ b/acceptance/bundle/user_agent/simple/out.requests.destroy.terraform.json
@@ -100,15 +100,10 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock",
-  "q": {
-    "overwrite": "false"
-  },
+  "path": "/api/2.0/workspace/delete",
   "body": {
-    "ID": "[UUID]",
-    "AcquisitionTime": "[TIMESTAMP]",
-    "IsForced": false,
-    "User": "[USERNAME]"
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default",
+    "recursive": true
   }
 }
 {
@@ -118,10 +113,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default",
-    "recursive": true
+    "multipart_form": {
+      "content": "{\"ID\":\"[UUID]\",\"AcquisitionTime\":\"[TIMESTAMP]\",\"IsForced\":false,\"User\":\"[USERNAME]\"}",
+      "format": "AUTO",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    }
   }
 }
 {
diff --git a/acceptance/bundle/validate/sync_patterns/out.sync.txt b/acceptance/bundle/validate/sync_patterns/out.sync.txt
index ac5aba9ab2..fd939c9721 100644
--- a/acceptance/bundle/validate/sync_patterns/out.sync.txt
+++ b/acceptance/bundle/validate/sync_patterns/out.sync.txt
@@ -1,7 +1,12 @@
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/conf/dir/test.yml",
-  "q": {
-    "overwrite": "true"
+  "path": "/api/2.0/workspace/import",
+  "body": {
+    "multipart_form": {
+      "content": "",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/conf/dir/test.yml"
+    }
   }
 }
diff --git a/acceptance/bundle/validate/sync_patterns/script b/acceptance/bundle/validate/sync_patterns/script
index d2aae85444..ce8e5cbb1b 100644
--- a/acceptance/bundle/validate/sync_patterns/script
+++ b/acceptance/bundle/validate/sync_patterns/script
@@ -1,5 +1,5 @@
 trace $CLI bundle validate
 trace $CLI bundle validate -o json | jq '.sync'
 trace $CLI bundle deploy
-jq 'select(.path | test("dir/test.yml"))' out.requests.txt  > out.sync.txt
+jq 'select(.body.multipart_form.path | strings | test("dir/test.yml"))' out.requests.txt  > out.sync.txt
 rm out.requests.txt
diff --git a/acceptance/internal/prepare_server.go b/acceptance/internal/prepare_server.go
index 702b4e145e..f81b07f7f4 100644
--- a/acceptance/internal/prepare_server.go
+++ b/acceptance/internal/prepare_server.go
@@ -1,8 +1,12 @@
 package internal
 
 import (
+	"bytes"
 	"encoding/json"
 	"fmt"
+	"io"
+	"mime"
+	"mime/multipart"
 	"net/http"
 	"os"
 	"path/filepath"
@@ -323,6 +327,11 @@ func getLoggedRequest(req *testserver.Request, includedHeaders []string) LoggedR
 
 	if json.Valid(req.Body) {
 		result.Body = json.RawMessage(req.Body)
+	} else if normalized, ok := normalizeMultipartBody(req); ok {
+		// Multipart bodies contain a randomly generated boundary string and binary
+		// content; record a normalized form (sorted form-field names with sizes for
+		// file parts) so recorded requests stay deterministic and reviewable.
+		result.Body = normalized
 	} else {
 		result.RawBody = string(req.Body)
 	}
@@ -330,6 +339,55 @@ func getLoggedRequest(req *testserver.Request, includedHeaders []string) LoggedR
 	return result
 }
 
+// normalizeMultipartBody returns a deterministic representation of a multipart
+// form body if the request's Content-Type is multipart/*. The second return
+// value is false if the body is not multipart or cannot be parsed.
+//
+// Text parts are recorded as their literal content so reviewers can read what
+// was uploaded; existing global UNIX_TIME / UUID / USERNAME replacements
+// normalize the timestamp / id / email fields embedded in deploy.lock and
+// similar payloads. Non-UTF-8 (binary) parts and parts whose serialized
+// content would bloat the recording past multipartContentLimit are
+// summarized as "[binary content N bytes]".
+func normalizeMultipartBody(req *testserver.Request) (any, bool) {
+	contentType := req.Headers.Get("Content-Type")
+	mediaType, params, err := mime.ParseMediaType(contentType)
+	if err != nil || !strings.HasPrefix(mediaType, "multipart/") {
+		return nil, false
+	}
+	boundary := params["boundary"]
+	if boundary == "" {
+		return nil, false
+	}
+	mr := multipart.NewReader(bytes.NewReader(req.Body), boundary)
+	parts := map[string]any{}
+	for {
+		part, err := mr.NextPart()
+		if err == io.EOF {
+			break
+		}
+		if err != nil {
+			return nil, false
+		}
+		data, err := io.ReadAll(part)
+		if err != nil {
+			return nil, false
+		}
+		name := part.FormName()
+		if !utf8.Valid(data) || len(data) > multipartContentLimit {
+			parts[name] = fmt.Sprintf("[binary content %d bytes]", len(data))
+			continue
+		}
+		parts[name] = string(data)
+	}
+	return map[string]any{"multipart_form": parts}, true
+}
+
+// Multipart parts larger than this limit are summarized as a size placeholder
+// to keep recorded fixtures small. Reviewers care about *what* was uploaded
+// (path, format, overwrite flag), not the bytes themselves, for large blobs.
+const multipartContentLimit = 4096
+
 func filterHeaders(h http.Header, includedHeaders []string) http.Header {
 	headers := make(http.Header)
 	for k, v := range h {
diff --git a/libs/filer/workspace_files_client.go b/libs/filer/workspace_files_client.go
index 54103f8158..d7ca720daf 100644
--- a/libs/filer/workspace_files_client.go
+++ b/libs/filer/workspace_files_client.go
@@ -9,7 +9,6 @@ import (
 	"io"
 	"io/fs"
 	"net/http"
-	"net/url"
 	"path"
 	"slices"
 	"strings"
@@ -157,35 +156,34 @@ func (w *WorkspaceFilesClient) Write(ctx context.Context, name string, reader io
 		return err
 	}
 
-	// Remove leading "/" so we can use it in the URL.
-	overwrite := slices.Contains(mode, OverwriteIfExists)
-	urlPath := fmt.Sprintf(
-		"/api/2.0/workspace-files/import-file/%s?overwrite=%t",
-		url.PathEscape(strings.TrimLeft(absPath, "/")),
-		overwrite,
-	)
-
 	// Buffer the file contents because we may need to retry below and we cannot read twice.
 	body, err := io.ReadAll(reader)
 	if err != nil {
 		return err
 	}
 
-	err = w.apiClient.Do(ctx, http.MethodPost, urlPath, w.orgIDHeaders(), nil, body, nil)
+	// Use Workspace.Upload (multipart /api/2.0/workspace/import) instead of the
+	// JSON-body variant of the same endpoint, which caps payloads at 10 MiB for
+	// AUTO format (databricks.webapp.autoExportFormatLimitBytes). The multipart
+	// variant accepts up to 200 MiB (databricks.workspaceFilesystem.maxImportSizeBytes),
+	// matching the legacy /workspace-files/import-file endpoint we are migrating
+	// away from.
+	overwrite := slices.Contains(mode, OverwriteIfExists)
+	uploadOpts := []func(*workspace.Import){
+		workspace.UploadFormat(workspace.ImportFormatAuto),
+	}
+	if overwrite {
+		uploadOpts = append(uploadOpts, workspace.UploadOverwrite())
+	}
+	err = w.workspaceClient.Workspace.Upload(ctx, absPath, bytes.NewReader(body), uploadOpts...)
 
 	// Return early on success.
 	if err == nil {
 		return nil
 	}
 
-	// Special handling of this error only if it is an API error.
-	var aerr *apierr.APIError
-	if !errors.As(err, &aerr) {
-		return err
-	}
-
-	// This API returns a 404 if the parent directory does not exist.
-	if aerr.StatusCode == http.StatusNotFound {
+	// Parent directory does not exist.
+	if errors.Is(err, apierr.ErrNotFound) {
 		if !slices.Contains(mode, CreateParentDirectories) {
 			return noSuchDirectoryError{path.Dir(absPath)}
 		}
@@ -193,7 +191,7 @@ func (w *WorkspaceFilesClient) Write(ctx context.Context, name string, reader io
 		// Create parent directory.
 		err = w.workspaceClient.Workspace.MkdirsByPath(ctx, path.Dir(absPath)) //nolint:staticcheck // Deprecated in SDK v0.127.0. Migration to WorkspaceHierarchyService tracked separately.
 		if err != nil {
-			if errors.As(err, &aerr) && aerr.StatusCode == http.StatusForbidden {
+			if errors.Is(err, apierr.ErrPermissionDenied) {
 				return permissionError{absPath}
 			}
 			return fmt.Errorf("unable to mkdir to write file %s: %w", absPath, err)
@@ -203,23 +201,27 @@ func (w *WorkspaceFilesClient) Write(ctx context.Context, name string, reader io
 		return w.Write(ctx, name, bytes.NewReader(body), sliceWithout(mode, CreateParentDirectories)...)
 	}
 
-	// This API returns 409 if the file already exists, when the object type is file
-	if aerr.StatusCode == http.StatusConflict {
+	// File already exists at the path. The /workspace/import endpoint reports this
+	// with two different error_codes depending on whether the conflict was detected
+	// sequentially (400 RESOURCE_ALREADY_EXISTS) or under concurrent contention
+	// (409 ALREADY_EXISTS, observed in TestLock). Both are already-exists from the
+	// caller's perspective.
+	//
+	// Existing-object-with-mismatched-node-type (e.g. uploading a regular .py when a
+	// NOTEBOOK is at the path) surfaces as 400 INVALID_PARAMETER_VALUE with a
+	// "Requested node type" message — also already-exists from the caller's perspective.
+	if errors.Is(err, apierr.ErrResourceAlreadyExists) || errors.Is(err, apierr.ErrAlreadyExists) {
 		return fileAlreadyExistsError{absPath}
 	}
-
-	// This API returns 400 if the file already exists when the object type is notebook.
-	// Both the historical "Path (<path>) already exists." format and the newer
-	// "RESOURCE_ALREADY_EXISTS: <path> already exists. ..." format end with the same
-	// "already exists." marker; the JSON error_code is empty in both. The new format
-	// might not have been rolled out to all workspaces yet, so we anchor on the shared
-	// marker and return absPath rather than parsing the message.
-	if aerr.StatusCode == http.StatusBadRequest && strings.Contains(aerr.Message, "already exists.") {
-		return fileAlreadyExistsError{absPath}
+	if errors.Is(err, apierr.ErrInvalidParameterValue) {
+		var aerr *apierr.APIError
+		if errors.As(err, &aerr) && strings.Contains(aerr.Message, "Requested node type") {
+			return fileAlreadyExistsError{absPath}
+		}
 	}
 
-	// This API returns StatusForbidden when you have read access but don't have write access to a file
-	if aerr.StatusCode == http.StatusForbidden {
+	// Caller has read access but no write access.
+	if errors.Is(err, apierr.ErrPermissionDenied) {
 		return permissionError{absPath}
 	}
 
@@ -273,19 +275,14 @@ func (w *WorkspaceFilesClient) Delete(ctx context.Context, name string, mode ...
 		return nil
 	}
 
-	// Special handling of this error only if it is an API error.
-	var aerr *apierr.APIError
-	if !errors.As(err, &aerr) {
-		return err
+	if errors.Is(err, apierr.ErrNotFound) {
+		return fileDoesNotExistError{absPath}
 	}
 
-	switch aerr.StatusCode {
-	case http.StatusBadRequest:
-		if aerr.ErrorCode == "DIRECTORY_NOT_EMPTY" {
-			return directoryNotEmptyError{absPath}
-		}
-	case http.StatusNotFound:
-		return fileDoesNotExistError{absPath}
+	// No SDK sentinel for DIRECTORY_NOT_EMPTY; match the error_code directly.
+	var aerr *apierr.APIError
+	if errors.As(err, &aerr) && aerr.ErrorCode == "DIRECTORY_NOT_EMPTY" {
+		return directoryNotEmptyError{absPath}
 	}
 
 	return err
@@ -306,15 +303,9 @@ func (w *WorkspaceFilesClient) ReadDir(ctx context.Context, name string) ([]fs.D
 	}
 
 	if err != nil {
-		// If we got an API error we deal with it below.
-		var aerr *apierr.APIError
-		if !errors.As(err, &aerr) {
-			return nil, err
-		}
-
 		// NOTE: This API returns a 404 if the specified path does not exist,
 		// but can also do so if we don't have read access.
-		if aerr.StatusCode == http.StatusNotFound {
+		if errors.Is(err, apierr.ErrNotFound) {
 			return nil, noSuchDirectoryError{path.Dir(absPath)}
 		}
 		return nil, err
@@ -358,14 +349,8 @@ func (w *WorkspaceFilesClient) Stat(ctx context.Context, name string) (fs.FileIn
 		&stat,
 	)
 	if err != nil {
-		// If we got an API error we deal with it below.
-		var aerr *apierr.APIError
-		if !errors.As(err, &aerr) {
-			return nil, err
-		}
-
 		// This API returns a 404 if the specified path does not exist.
-		if aerr.StatusCode == http.StatusNotFound {
+		if errors.Is(err, apierr.ErrNotFound) {
 			return nil, fileDoesNotExistError{absPath}
 		}
 	}
diff --git a/libs/filer/workspace_files_client_test.go b/libs/filer/workspace_files_client_test.go
index 2603d31d6d..e37389f8ca 100644
--- a/libs/filer/workspace_files_client_test.go
+++ b/libs/filer/workspace_files_client_test.go
@@ -1,15 +1,23 @@
 package filer
 
 import (
+	"bytes"
+	"context"
 	"encoding/json"
+	"io"
 	"io/fs"
+	"net/http"
+	"strings"
 	"testing"
 	"time"
 
 	"github.com/databricks/databricks-sdk-go"
+	"github.com/databricks/databricks-sdk-go/apierr"
 	"github.com/databricks/databricks-sdk-go/config"
+	"github.com/databricks/databricks-sdk-go/experimental/mocks"
 	"github.com/databricks/databricks-sdk-go/service/workspace"
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/mock"
 	"github.com/stretchr/testify/require"
 )
 
@@ -95,6 +103,173 @@ func TestWorkspaceFilesClientOrgIDHeaders(t *testing.T) {
 	})
 }
 
+func TestWorkspaceFilesClientWriteSuccess(t *testing.T) {
+	tests := []struct {
+		name           string
+		modes          []WriteMode
+		expectOverride bool
+	}{
+		{
+			name:           "no overwrite",
+			modes:          nil,
+			expectOverride: false,
+		},
+		{
+			name:           "overwrite",
+			modes:          []WriteMode{OverwriteIfExists},
+			expectOverride: true,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			mw := mocks.NewMockWorkspaceClient(t)
+			workspaceApi := mw.GetMockWorkspaceAPI()
+
+			workspaceApi.EXPECT().Upload(
+				mock.Anything,
+				"/dir/file.txt",
+				mock.Anything,
+				mock.Anything,
+				mock.Anything,
+			).RunAndReturn(func(_ context.Context, _ string, r io.Reader, opts ...func(*workspace.Import)) error {
+				body, err := io.ReadAll(r)
+				require.NoError(t, err)
+				assert.Equal(t, "hello", string(body))
+
+				i := &workspace.Import{}
+				for _, opt := range opts {
+					opt(i)
+				}
+				assert.Equal(t, workspace.ImportFormatAuto, i.Format)
+				assert.Equal(t, tc.expectOverride, i.Overwrite)
+				return nil
+			}).Once()
+
+			c := WorkspaceFilesClient{
+				workspaceClient: mw.WorkspaceClient,
+				root:            NewWorkspaceRootPath("/dir"),
+			}
+			err := c.Write(t.Context(), "file.txt", strings.NewReader("hello"), tc.modes...)
+			require.NoError(t, err)
+		})
+	}
+}
+
+func TestWorkspaceFilesClientWriteErrorMapping(t *testing.T) {
+	tests := []struct {
+		name            string
+		mode            []WriteMode
+		apiErr          *apierr.APIError
+		expectErrTarget any
+	}{
+		{
+			name:            "404 without create-parent maps to noSuchDirectoryError",
+			apiErr:          &apierr.APIError{StatusCode: http.StatusNotFound, Message: "not found"},
+			expectErrTarget: noSuchDirectoryError{},
+		},
+		{
+			name: "400 RESOURCE_ALREADY_EXISTS maps to fileAlreadyExistsError",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusBadRequest,
+				ErrorCode:  "RESOURCE_ALREADY_EXISTS",
+				Message:    "/dir/file.txt already exists. Please pass overwrite=true to overwrite it.",
+			},
+			expectErrTarget: fileAlreadyExistsError{},
+		},
+		{
+			name: "409 ALREADY_EXISTS (concurrent contention) maps to fileAlreadyExistsError",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusConflict,
+				ErrorCode:  "ALREADY_EXISTS",
+				Message:    "Node with name /dir/file.txt already exists. Please pass overwrite=true to update it.",
+			},
+			expectErrTarget: fileAlreadyExistsError{},
+		},
+		{
+			name: "400 INVALID_PARAMETER_VALUE node type mismatch maps to fileAlreadyExistsError",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusBadRequest,
+				ErrorCode:  "INVALID_PARAMETER_VALUE",
+				Message:    "Requested node type [FILE] is different from the existing node type [NOTEBOOK]",
+			},
+			expectErrTarget: fileAlreadyExistsError{},
+		},
+		{
+			name: "400 INVALID_PARAMETER_VALUE other message passes through",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusBadRequest,
+				ErrorCode:  "INVALID_PARAMETER_VALUE",
+				Message:    "some other validation failure",
+			},
+			expectErrTarget: nil,
+		},
+		{
+			name:            "403 maps to permissionError",
+			apiErr:          &apierr.APIError{StatusCode: http.StatusForbidden, Message: "denied"},
+			expectErrTarget: permissionError{},
+		},
+		{
+			name:            "500 passes through",
+			apiErr:          &apierr.APIError{StatusCode: http.StatusInternalServerError, Message: "boom"},
+			expectErrTarget: nil,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			mw := mocks.NewMockWorkspaceClient(t)
+			workspaceApi := mw.GetMockWorkspaceAPI()
+			workspaceApi.EXPECT().Upload(
+				mock.Anything, "/dir/file.txt", mock.Anything, mock.Anything, mock.Anything,
+			).Return(tc.apiErr).Once()
+
+			c := WorkspaceFilesClient{
+				workspaceClient: mw.WorkspaceClient,
+				root:            NewWorkspaceRootPath("/dir"),
+			}
+			err := c.Write(t.Context(), "file.txt", bytes.NewReader([]byte("data")), tc.mode...)
+			require.Error(t, err)
+			switch target := tc.expectErrTarget.(type) {
+			case noSuchDirectoryError:
+				assert.ErrorAs(t, err, &target)
+			case fileAlreadyExistsError:
+				assert.ErrorAs(t, err, &target)
+			case permissionError:
+				assert.ErrorAs(t, err, &target)
+			case nil:
+				// passthrough — same APIError pointer
+				var aerr *apierr.APIError
+				require.ErrorAs(t, err, &aerr)
+				assert.Equal(t, tc.apiErr.StatusCode, aerr.StatusCode)
+			}
+		})
+	}
+}
+
+func TestWorkspaceFilesClientWriteCreatesParentDirectories(t *testing.T) {
+	mw := mocks.NewMockWorkspaceClient(t)
+	workspaceApi := mw.GetMockWorkspaceAPI()
+
+	// First Upload returns 404, second returns success after MkdirsByPath.
+	workspaceApi.EXPECT().Upload(
+		mock.Anything, "/dir/sub/file.txt", mock.Anything, mock.Anything, mock.Anything,
+	).Return(&apierr.APIError{StatusCode: http.StatusNotFound, Message: "not found"}).Once()
+
+	workspaceApi.EXPECT().MkdirsByPath(mock.Anything, "/dir/sub").Return(nil).Once()
+
+	workspaceApi.EXPECT().Upload(
+		mock.Anything, "/dir/sub/file.txt", mock.Anything, mock.Anything, mock.Anything,
+	).Return(nil).Once()
+
+	c := WorkspaceFilesClient{
+		workspaceClient: mw.WorkspaceClient,
+		root:            NewWorkspaceRootPath("/dir"),
+	}
+	err := c.Write(t.Context(), "sub/file.txt", strings.NewReader("data"), CreateParentDirectories)
+	require.NoError(t, err)
+}
+
 func TestWorkspaceFilesClient_wsfsUnmarshal(t *testing.T) {
 	payload := `
 		{
diff --git a/libs/testserver/handlers.go b/libs/testserver/handlers.go
index 8bd5339184..8f3983fb07 100644
--- a/libs/testserver/handlers.go
+++ b/libs/testserver/handlers.go
@@ -1,9 +1,13 @@
 package testserver
 
 import (
+	"bytes"
 	"encoding/base64"
 	"encoding/json"
 	"fmt"
+	"io"
+	"mime"
+	"mime/multipart"
 	"net/http"
 	"path"
 	"strings"
@@ -116,6 +120,72 @@ func AddDefaultHandlers(server *Server) {
 	})
 
 	server.Handle("POST", "/api/2.0/workspace/import", func(req Request) any {
+		// /workspace/import accepts both a JSON body (matching workspace.Import) and a
+		// multipart form body. The multipart variant is what databricks-sdk-go's
+		// Workspace.Upload uses; the JSON variant is kept for back-compat with anything
+		// that still hits Workspace.Import directly.
+		contentType := req.Headers.Get("Content-Type")
+		mediaType, params, _ := mime.ParseMediaType(contentType)
+		if strings.HasPrefix(mediaType, "multipart/") {
+			mr := multipart.NewReader(bytes.NewReader(req.Body), params["boundary"])
+			var (
+				filePath  string
+				content   []byte
+				format    string
+				overwrite bool
+			)
+			for {
+				part, err := mr.NextPart()
+				if err == io.EOF {
+					break
+				}
+				if err != nil {
+					return Response{
+						Body:       fmt.Sprintf("internal error: %s", err),
+						StatusCode: http.StatusInternalServerError,
+					}
+				}
+				data, err := io.ReadAll(part)
+				if err != nil {
+					return Response{
+						Body:       fmt.Sprintf("internal error: %s", err),
+						StatusCode: http.StatusInternalServerError,
+					}
+				}
+				switch part.FormName() {
+				case "path":
+					filePath = string(data)
+				case "content":
+					content = data
+				case "format":
+					format = string(data)
+				case "overwrite":
+					overwrite = string(data) == "true"
+				}
+			}
+
+			if format != "" && format != string(workspace.ImportFormatAuto) {
+				return Response{
+					Body:       "internal error: The test server only supports auto format.",
+					StatusCode: http.StatusInternalServerError,
+				}
+			}
+
+			// Translate any 409 from the shared fake into the 400 + errorCode
+			// RESOURCE_ALREADY_EXISTS shape returned by the real /workspace/import endpoint.
+			resp := req.Workspace.WorkspaceFilesImportFile(filePath, content, overwrite)
+			if resp.StatusCode == http.StatusConflict {
+				return Response{
+					StatusCode: http.StatusBadRequest,
+					Body: map[string]string{
+						"error_code": "RESOURCE_ALREADY_EXISTS",
+						"message":    fmt.Sprintf("Path (%s) already exists.", filePath),
+					},
+				}
+			}
+			return resp
+		}
+
 		var request workspace.Import
 		err := json.Unmarshal(req.Body, &request)
 		if err != nil {