diff --git a/.changeset/tender-points-sleep.md b/.changeset/tender-points-sleep.md
new file mode 100644
index 00000000000..3206a87c20e
--- /dev/null
+++ b/.changeset/tender-points-sleep.md
@@ -0,0 +1,5 @@
+---
+"effect": patch
+---
+
+Generate unique persisted paths for multipart files with duplicate filenames.
diff --git a/packages/effect/src/unstable/http/Multipart.ts b/packages/effect/src/unstable/http/Multipart.ts
index b5e7e42a589..08a32651428 100644
--- a/packages/effect/src/unstable/http/Multipart.ts
+++ b/packages/effect/src/unstable/http/Multipart.ts
@@ -678,6 +678,8 @@ export const toPersisted = (
     const path_ = yield* Path.Path
     const dir = yield* fs.makeTempDirectoryScoped()
     const persisted: Record<string, Array<PersistedFile> | Array<string> | string> = Object.create(null)
+    const usedPaths = new Set<string>()
+    let fileIndex = 0
     yield* Stream.runForEach(stream, (part) => {
       if (part._tag === "Field") {
         if (!(part.key in persisted)) {
@@ -692,7 +694,12 @@ export const toPersisted = (
         return Effect.void
       }
       const file = part
-      const path = path_.join(dir, path_.basename(file.name).slice(-128))
+      const fileName = path_.basename(file.name).slice(-128)
+      let path = path_.join(dir, fileName)
+      while (usedPaths.has(path)) {
+        path = path_.join(dir, `${fileIndex++}-${fileName}`)
+      }
+      usedPaths.add(path)
       const filePart = new PersistedFileImpl(
         file.key,
         file.name,
diff --git a/packages/effect/test/unstable/http/Multipart.test.ts b/packages/effect/test/unstable/http/Multipart.test.ts
index 1dafd5a5631..701914eea12 100644
--- a/packages/effect/test/unstable/http/Multipart.test.ts
+++ b/packages/effect/test/unstable/http/Multipart.test.ts
@@ -1,8 +1,8 @@
 import { describe, it } from "@effect/vitest"
-import { Effect, ErrorReporter, identity, Schema, Stream, Unify } from "effect"
-import { Multipart } from "effect/unstable/http"
+import { Effect, ErrorReporter, FileSystem, identity, Path, Schema, Stream, Unify } from "effect"
+import { HttpClientRequest, HttpServerRequest, Multipart } from "effect/unstable/http"
 import * as HttpServerRespondable from "effect/unstable/http/HttpServerRespondable"
-import { deepStrictEqual, strictEqual } from "node:assert"
+import { deepStrictEqual, notStrictEqual, strictEqual } from "node:assert"
 
 describe("Multipart", () => {
   it.effect("parses fields and streams file content", () =>
@@ -60,6 +60,34 @@ describe("Multipart", () => {
       strictEqual(error.reason._tag, "TooManyParts")
     }))
 
+  it.effect("returns distinct persisted file paths for files with the same client filename", () =>
+    Effect.scoped(Effect.gen(function*() {
+      const formData = new FormData()
+      formData.append("first", new File(["one"], "same.txt"))
+      formData.append("second", new File(["two"], "same.txt"))
+      const request = HttpServerRequest.fromClientRequest(
+        HttpClientRequest.bodyFormData(HttpClientRequest.post("https://example.com"), formData)
+      )
+      const writes: Array<string> = []
+      const persisted = yield* Multipart.toPersisted(
+        request.multipartStream,
+        (path) => Effect.sync(() => writes.push(path))
+      ).pipe(
+        Effect.provideService(
+          FileSystem.FileSystem,
+          FileSystem.makeNoop({
+            makeTempDirectoryScoped: () => Effect.succeed("/tmp/audit")
+          })
+        ),
+        Effect.provide(Path.layer)
+      )
+      const first = (persisted.first as Array<Multipart.PersistedFile>)[0]
+      const second = (persisted.second as Array<Multipart.PersistedFile>)[0]
+      strictEqual(first.path, "/tmp/audit/same.txt")
+      notStrictEqual(first.path, second.path)
+      deepStrictEqual(writes, [first.path, second.path])
+    })))
+
   it.effect("responds based on the reason and is ignored by the ErrorReporter", () =>
     Effect.gen(function*() {
       const cases = [