diff --git a/CHANGELOG.md b/CHANGELOG.md
index db53af9..70bd1a6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -349,6 +349,11 @@ No behavior change.
   approves each probe). Reduces dual-use false-positive pauses. The README hero line now leads with a
   defensive, ownership-asserting phrasing and the PyPI install. **No behavior change** — wording/order
   only; the live-fire confirmation checkpoint is intentionally preserved.
+## [Unreleased]
+
+### Fixed
+- **UploadSecurityExtractor False Positives**: Refined `KEY_FROM_NAME` regex in `upload_security.py` to prevent false positive `upload-key-from-filename` findings on safe metadata assignments, original name logging, and comments containing the original file name. Added regression tests to `FalsePositiveRegressionTests`.
+
 
 ## [0.6.2] — 2026-06-12
 
diff --git a/src/websec_validator/extractors/upload_security.py b/src/websec_validator/extractors/upload_security.py
index dc0c2ba..e3e8b69 100644
--- a/src/websec_validator/extractors/upload_security.py
+++ b/src/websec_validator/extractors/upload_security.py
@@ -25,9 +25,9 @@
 ALLOW_LIST = re.compile(r"isAllowedMediaType|allowedMimeTypes|allow[_-]?list|whitelist|ALLOWED_(?:MIME|TYPES|EXT)"
                         r"|ACCEPTED_(?:MIME|TYPES?|EXT)|accepted(?:Mime|File|Content)?(?:Types?|Extensions?)"
                         r"|\bfile-type\b|fileTypeFrom|magic[_-]?byte|detectContentType|\.fromBuffer\b|sniff", re.I)
-KEY_FROM_NAME = re.compile(r"(?:Key|key|path|filename|filepath|destination|filename\s*\()\s*[:=(][^;\n]{0,90}"
-                           r"\b(?:originalname|originalName|file\.name)\b"
-                           r"|`[^`]*\$\{[^}]*\boriginalname\b[^}]*\}[^`]*`", re.I)
+KEY_FROM_NAME = re.compile(r"(?:Key|key|path|filename|filepath|destination)\s*[:=]\s*(?:(?!(?:\w+|['\"]\w+['\"])\s*:|\/\/|\/\*)[^;\n])*?\b(?:originalname|originalName|file\.name)\b"
+                           r"|\b(?:path|filename|destination)\s*\(\s*(?:(?!(?:\w+|['\"]\w+['\"])\s*:|\/\/|\/\*)[^;\n])*?\b(?:originalname|originalName|file\.name)\b"
+                           r"|(?:Key|key|path|filename|filepath|destination)\s*[:=]\s*`[^`]*\$\{[^}]*\b(?:originalname|originalName|file\.name)\b", re.I)
 TRUST_CLIENT_MIME = re.compile(r"(?:req\.files?\.[\w$.]*\.|\bfile\.)mimetype\b|headers\[['\"]content-type['\"]\]", re.I)
 ACCEPT_SVG = re.compile(r"image/svg\+xml|['\"]svg['\"]", re.I)
 # file-serving: streaming a STORED/PROXIED object back to the client. Tightened to genuine
diff --git a/tests/test_pentest_regressions.py b/tests/test_pentest_regressions.py
index 734194f..9775a4a 100644
--- a/tests/test_pentest_regressions.py
+++ b/tests/test_pentest_regressions.py
@@ -525,6 +525,29 @@ def test_classes_reach_ledger_with_citations(self):
 class FalsePositiveRegressionTests(unittest.TestCase):
     """Lock in the accuracy fixes found by dogfooding on real repos (68 → 11 new-group findings)."""
 
+    def test_upload_key_from_filename_fps(self):
+        from websec_validator.extractors.upload_security import UploadSecurityExtractor
+        # False positives:
+        # 1. safe assignment to Metadata (not Key)
+        # 2. logging originalname
+        # 3. safe Key assignment with a comment containing originalname
+        # 4. originalname used in a totally separate path variable
+        snippets = {
+            "src/fp_metadata.js": "const upload = multer(); const params = { Key: uuid(), Metadata: { 'original-name': file.originalname } };",
+            "src/fp_log.js": "const upload = multer(); console.log(`Received file: ${req.file.originalname}`);",
+            "src/fp_comment.js": "const upload = multer(); const params = { Key: uuid(), // not file.originalname\n };",
+            "src/fp_other.js": "const upload = multer(); const dest = path.join('uploads', uuid()); const meta = path.join('meta', file.originalname);",
+            "src/fp_string.js": "const upload = multer(); const safeKey = crypto.randomUUID(); const msg = `Uploaded ${req.file.originalname} as ${safeKey}`;",
+            "src/fp_unrelated.js": "const upload = multer(); res.json({ success: true, originalname: req.file.originalname, savedAs: uuid() });",
+            "src/fp_array.js": "const upload = multer(); const uploads = []; uploads.push(file.originalname);"
+        }
+        for name, content in snippets.items():
+            out = UploadSecurityExtractor().extract(repo({name: content}), {})
+            self.assertFalse(
+                any(f["kind"] == "upload-key-from-filename" for f in out.get("findings", [])),
+                f"False positive triggered for {name}"
+            )
+
     def test_aws_sam_and_cdk_out_dirs_skipped(self):
         # regression: vendored SDK code under an AWS SAM build dir must not be scanned
         ctx = repo({"aws/.aws-sam/deps/abc/models.py": "account_number='x'\n",