diff --git a/.Jules/sentinel.md b/.Jules/sentinel.md
new file mode 100644
index 00000000..da3742a6
--- /dev/null
+++ b/.Jules/sentinel.md
@@ -0,0 +1,4 @@
+## 2024-03-24 - [Information Leakage in Python Exception Handling]
+**Vulnerability:** Raw exception strings containing internal file paths and system details were being serialized into JSON responses (e.g., `f"Failed to read job file: {e}"`).
+**Learning:** Catch-all exception blocks (like `except Exception as e:`) can inadvertently expose sensitive system state to end users if the string representation of the exception is returned directly.
+**Prevention:** Replace raw exception interpolations with generic, safe error messages intended for external consumption, logging the full stack trace internally if needed.
diff --git a/services/analysis-engine/src/bandscope_analysis/api.py b/services/analysis-engine/src/bandscope_analysis/api.py
index a193bce2..9e99521a 100644
--- a/services/analysis-engine/src/bandscope_analysis/api.py
+++ b/services/analysis-engine/src/bandscope_analysis/api.py
@@ -840,8 +840,8 @@ def _stem_separation_worker(
         result_queue.put(("value_error", str(error)))
     except RuntimeError as error:
         result_queue.put(("runtime_error", str(error)))
-    except Exception as error:
-        result_queue.put(("runtime_error", str(error)))
+    except Exception:
+        result_queue.put(("runtime_error", "An unexpected error occurred during stem separation."))
 
 
 def _multiprocessing_context() -> mp.context.BaseContext:
diff --git a/services/analysis-engine/src/bandscope_analysis/cli.py b/services/analysis-engine/src/bandscope_analysis/cli.py
index c73f311d..390fe78f 100644
--- a/services/analysis-engine/src/bandscope_analysis/cli.py
+++ b/services/analysis-engine/src/bandscope_analysis/cli.py
@@ -46,8 +46,12 @@ def main() -> int:
                 try:
                     with open(input_data, "r", encoding="utf-8") as f:
                         input_data = f.read()
-                except Exception as e:
-                    json.dump(failed_cli_response(f"Failed to read job file: {e}"), sys.stdout)
+                except Exception:
+                    msg = (
+                        "Failed to read job file. "
+                        "Please ensure the file path is correct and accessible."
+                    )
+                    json.dump(failed_cli_response(msg), sys.stdout)
                     return 1
 
     if not input_data:
diff --git a/services/analysis-engine/tests/test_api.py b/services/analysis-engine/tests/test_api.py
index ea55cba2..bfd6de56 100644
--- a/services/analysis-engine/tests/test_api.py
+++ b/services/analysis-engine/tests/test_api.py
@@ -848,18 +848,22 @@ def put(self, item: tuple[str, object]) -> None:
             self.items.append(item)
 
     cases = [
-        (FileNotFoundError("missing"), "file_not_found"),
-        (ValueError("bad media"), "value_error"),
-        (RuntimeError("oom"), "runtime_error"),
-        (Exception("unexpected"), "runtime_error"),
+        (FileNotFoundError("missing"), "file_not_found", "missing"),
+        (ValueError("bad media"), "value_error", "bad media"),
+        (RuntimeError("oom"), "runtime_error", "oom"),
+        (
+            Exception("unexpected"),
+            "runtime_error",
+            "An unexpected error occurred during stem separation.",
+        ),
     ]
 
-    for error, expected_kind in cases:
+    for error, expected_kind, expected_msg in cases:
         fake_queue = FakeQueue()
         with patch("bandscope_analysis.api.AudioStemSeparator") as separator_class:
             separator_class.return_value.separate.side_effect = error
             _stem_separation_worker("/tmp/audio.wav", fake_queue)
-        assert fake_queue.items == [(expected_kind, str(error))]
+        assert fake_queue.items == [(expected_kind, expected_msg)]
 
     fake_queue = FakeQueue()
     with patch("bandscope_analysis.api.AudioStemSeparator") as separator_class: