diff --git a/CHANGELOG.md b/CHANGELOG.md
index 76abc6fc9..78ef5c35e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -31,6 +31,7 @@
 - Structured logs: respect printf argument widths when extracting log parameters to avoid stack-data disclosure and corrupted attributes on 32-bit platforms. ([#1752](https://github.com/getsentry/sentry-native/pull/1752))
 - Fix a potential out-of-bounds read when parsing non-NUL-terminated `sentry-trace` headers. ([#1749](https://github.com/getsentry/sentry-native/pull/1749))
 - Fix division by zero when breadcrumbs are disabled. ([#1767](https://github.com/getsentry/sentry-native/pull/1767))
+- Handle memory allocation failures during JSON serialization to prevent truncated output. ([#1772](https://github.com/getsentry/sentry-native/pull/1772))
 
 ## 0.14.2
 
diff --git a/src/sentry_json.c b/src/sentry_json.c
index 2f691be4c..8d2d94748 100644
--- a/src/sentry_json.c
+++ b/src/sentry_json.c
@@ -25,9 +25,9 @@
 
 typedef struct {
     void (*free)(sentry_jsonwriter_t *writer);
-    void (*write_str)(sentry_jsonwriter_t *writer, const char *str);
-    void (*write_buf)(sentry_jsonwriter_t *writer, const char *buf, size_t len);
-    void (*write_char)(sentry_jsonwriter_t *writer, char c);
+    bool (*write_str)(sentry_jsonwriter_t *writer, const char *str);
+    bool (*write_buf)(sentry_jsonwriter_t *writer, const char *buf, size_t len);
+    bool (*write_char)(sentry_jsonwriter_t *writer, char c);
     char *(*into_string)(sentry_jsonwriter_t *jw, size_t *len_out);
 } sentry_jsonwriter_ops_t;
 
@@ -40,6 +40,7 @@ struct sentry_jsonwriter_s {
     uint32_t depth;
     bool last_was_key;
     bool owns_sb;
+    bool failed;
     sentry_jsonwriter_ops_t *ops;
 };
 
@@ -65,40 +66,42 @@ jsonwriter_free_file(sentry_jsonwriter_t *jw)
     sentry_free(jw);
 }
 
-static void
+static bool
 write_char_sb(sentry_jsonwriter_t *jw, char c)
 {
-    sentry__stringbuilder_append_char(jw->output.sb, c);
+    return sentry__stringbuilder_append_char(jw->output.sb, c) == 0;
 }
 
-static void
+static bool
 write_str_sb(sentry_jsonwriter_t *jw, const char *str)
 {
-    sentry__stringbuilder_append(jw->output.sb, str);
+    return sentry__stringbuilder_append(jw->output.sb, str) == 0;
 }
 
-static void
+static bool
 write_buf_sb(sentry_jsonwriter_t *jw, const char *buf, size_t len)
 {
-    sentry__stringbuilder_append_buf(jw->output.sb, buf, len);
+    return sentry__stringbuilder_append_buf(jw->output.sb, buf, len) == 0;
 }
 
-static void
+static bool
 write_char_file(sentry_jsonwriter_t *jw, char c)
 {
-    sentry__filewriter_write(jw->output.fw, &c, sizeof(char));
+    return sentry__filewriter_write(jw->output.fw, &c, sizeof(char)) == 0;
 }
 
-static void
+static bool
 write_str_file(sentry_jsonwriter_t *jw, const char *str)
 {
-    sentry__filewriter_write(jw->output.fw, str, sizeof(char) * strlen(str));
+    return sentry__filewriter_write(
+               jw->output.fw, str, sizeof(char) * strlen(str))
+        == 0;
 }
 
-static void
+static bool
 write_buf_file(sentry_jsonwriter_t *jw, const char *buf, size_t len)
 {
-    sentry__filewriter_write(jw->output.fw, buf, len);
+    return sentry__filewriter_write(jw->output.fw, buf, len) == 0;
 }
 
 static char *
@@ -107,9 +110,11 @@ into_string_sb(sentry_jsonwriter_t *jw, size_t *len_out)
     char *rv = NULL;
     sentry_stringbuilder_t *sb = jw->output.sb;
     if (len_out) {
-        *len_out = sb->len;
+        *len_out = jw->failed ? 0 : sb->len;
+    }
+    if (!jw->failed) {
+        rv = sentry__stringbuilder_into_string(sb);
     }
-    rv = sentry__stringbuilder_into_string(sb);
     sentry__jsonwriter_free(jw);
     return rv;
 }
@@ -156,6 +161,7 @@ sentry__jsonwriter_new_sb(sentry_stringbuilder_t *sb)
     rv->depth = 0;
     rv->last_was_key = 0;
     rv->owns_sb = owns_sb;
+    rv->failed = false;
     rv->ops = &sb_ops;
     return rv;
 }
@@ -182,6 +188,7 @@ sentry__jsonwriter_new_fw(sentry_filewriter_t *fw)
     rv->depth = 0;
     rv->last_was_key = 0;
     rv->owns_sb = owns_sb;
+    rv->failed = false;
     rv->ops = &file_ops;
     return rv;
 }
@@ -198,6 +205,7 @@ sentry__jsonwriter_reset(sentry_jsonwriter_t *jw)
     jw->want_comma = 0;
     jw->depth = 0;
     jw->last_was_key = 0;
+    jw->failed = false;
 }
 
 char *
@@ -228,13 +236,25 @@ set_comma(sentry_jsonwriter_t *jw, bool val)
 static void
 write_char(sentry_jsonwriter_t *jw, char c)
 {
-    jw->ops->write_char(jw, c);
+    if (!jw->ops->write_char(jw, c)) {
+        jw->failed = true;
+    }
 }
 
 static void
 write_str(sentry_jsonwriter_t *jw, const char *str)
 {
-    jw->ops->write_str(jw, str);
+    if (!jw->ops->write_str(jw, str)) {
+        jw->failed = true;
+    }
+}
+
+static void
+write_buf(sentry_jsonwriter_t *jw, const char *buf, size_t len)
+{
+    if (!jw->ops->write_buf(jw, buf, len)) {
+        jw->failed = true;
+    }
 }
 
 // The Lookup table and algorithm below are adapted from:
@@ -270,14 +290,18 @@ write_json_str(sentry_jsonwriter_t *jw, const char *str)
     write_char(jw, '"');
 
     const unsigned char *start = ptr;
-    for (; *ptr; ptr++) {
+    for (; *ptr && !jw->failed; ptr++) {
         if (!needs_escaping[*ptr]) {
             continue;
         }
 
         size_t len = (size_t)(ptr - start);
         if (len) {
-            jw->ops->write_buf(jw, (const char *)start, len);
+            write_buf(jw, (const char *)start, len);
+        }
+
+        if (jw->failed) {
+            return;
         }
 
         switch (*ptr) {
@@ -315,12 +339,16 @@ write_json_str(sentry_jsonwriter_t *jw, const char *str)
             }
         }
 
+        if (jw->failed) {
+            return;
+        }
+
         start = ptr + 1;
     }
 
     size_t len = (size_t)(ptr - start);
     if (len) {
-        jw->ops->write_buf(jw, (const char *)start, len);
+        write_buf(jw, (const char *)start, len);
     }
 
     write_char(jw, '"');
@@ -329,7 +357,7 @@ write_json_str(sentry_jsonwriter_t *jw, const char *str)
 static bool
 can_write_item(sentry_jsonwriter_t *jw)
 {
-    if (at_max_depth(jw)) {
+    if (at_max_depth(jw) || jw->failed) {
         return false;
     }
     if (jw->last_was_key) {
@@ -341,7 +369,7 @@ can_write_item(sentry_jsonwriter_t *jw)
     } else {
         set_comma(jw, true);
     }
-    return true;
+    return !jw->failed;
 }
 
 void