diff --git a/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py b/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py
index 431a8212507..c61b6a59301 100644
--- a/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py
+++ b/enterprise/litellm_enterprise/enterprise_callbacks/secret_detection.py
@@ -495,7 +495,17 @@ def _parseable_lines(text: str) -> Generator[str, None, None]:
         if not stripped:
             yield line
         elif stripped[0] in "#;":
-            open_option = False
+            # configparser reads a comment inside a value without closing it, so leaving
+            # open_option alone keeps the indented lines under the comment reachable.
+            yield line
+        elif assignment is not None:
+            open_option = True
+            # Dedenting reaches the assignments inside a pasted config, and the line number
+            # keeps every key distinct so a config repeating api_key per model keeps them all.
+            yield f"{assignment.group()[:-1].strip()}_{number}{stripped[assignment.end() - 1:]}"
+        elif line[0].isspace() and open_option:
+            # An indented line inside an open value is part of that value to configparser,
+            # brackets included, so this has to be tested before the section header below.
             yield line
         elif stripped[0] == "[":
             open_option = False
@@ -503,13 +513,6 @@ def _parseable_lines(text: str) -> Generator[str, None, None]:
             # it aborts the whole parse, taking every assignment below down with it.
             if "]" in stripped[2:]:
                 yield line
-        elif assignment is not None:
-            open_option = True
-            # Dedenting reaches the assignments inside a pasted config, and the line number
-            # keeps every key distinct so a config repeating api_key per model keeps them all.
-            yield f"{assignment.group()[:-1].strip()}_{number}{stripped[assignment.end() - 1:]}"
-        elif line[0].isspace() and open_option:
-            yield line
         else:
             open_option = False
 
diff --git a/tests/test_litellm/enterprise/enterprise_callbacks/test_secret_detection.py b/tests/test_litellm/enterprise/enterprise_callbacks/test_secret_detection.py
index 85dc1ead6c8..4def77173ed 100644
--- a/tests/test_litellm/enterprise/enterprise_callbacks/test_secret_detection.py
+++ b/tests/test_litellm/enterprise/enterprise_callbacks/test_secret_detection.py
@@ -332,6 +332,10 @@ def test_scan_message_keeps_every_value_when_a_config_repeats_a_key():
         ("api_key: >\n  aB3dE6gH9jK2mN5p", "aB3dE6gH9jK2mN5p"),
         ("api_key: |-\n  aB3dE6gH9jK2mN5p", "aB3dE6gH9jK2mN5p"),
         ("secret= \\\n    aB3dE6gH9jK2mN5p", "aB3dE6gH9jK2mN5p"),
+        ("password =\n# rotate me\n    Zx4Kp9Lm2Qr7Ns3Vt", "Zx4Kp9Lm2Qr7Ns3Vt"),
+        ("api_key =\n; rotate me\n    aB3dE6gH9jK2mN5p", "aB3dE6gH9jK2mN5p"),
+        ("  # pasted from the vault\napi_key=aB3dE6gH9jK2mN5p", "aB3dE6gH9jK2mN5p"),
+        ("  [db]\napi_key=aB3dE6gH9jK2mN5p", "aB3dE6gH9jK2mN5p"),
     ],
     ids=[
         "flat-assignment",
@@ -344,6 +348,10 @@ def test_scan_message_keeps_every_value_when_a_config_repeats_a_key():
         "yaml-folded-block",
         "yaml-literal-block",
         "backslash-continuation",
+        "comment-inside-a-value",
+        "semicolon-comment-inside-a-value",
+        "indented-comment-above",
+        "indented-section-header-above",
     ],
 )
 def test_scan_message_still_sees_assignments_sharing_a_message_with_a_vendor_key(