From 12757197c2c736fa77461e725636c9df84dd3bcc Mon Sep 17 00:00:00 2001
From: Bolor <bjagdagdorj@microsoft.com>
Date: Thu, 26 Mar 2026 13:48:45 -0700
Subject: [PATCH 1/3] fix for file names for media on disk

---
 pyrit/backend/services/attack_service.py | 9 +++++++--
 1 file changed, 7 insertions(+), 2 deletions(-)

diff --git a/pyrit/backend/services/attack_service.py b/pyrit/backend/services/attack_service.py
index 16a8fb7047..28a7d60a2f 100644
--- a/pyrit/backend/services/attack_service.py
+++ b/pyrit/backend/services/attack_service.py
@@ -858,8 +858,13 @@ async def _persist_base64_pieces_async(request: AddMessageRequest) -> None:
                         piece.converted_value = file_path
                 continue
 
-            # Already an existing file on disk — keep as-is
-            if Path(piece.original_value).is_file():
+            # Already an existing file on disk — keep as-is.
+            # Guard against base64 strings that would exceed OS path length limits.
+            try:
+                is_existing_file = len(piece.original_value) < 4096 and Path(piece.original_value).is_file()
+            except OSError:
+                is_existing_file = False
+            if is_existing_file:
                 if piece.converted_value is None:
                     piece.converted_value = piece.original_value
                 continue

From 2234c7291870ddbf30d230f0166c07349db4ddb4 Mon Sep 17 00:00:00 2001
From: jbolor21 <86250273+jbolor21@users.noreply.github.com>
Date: Wed, 8 Apr 2026 13:31:16 -0700
Subject: [PATCH 2/3] add unit test

---
 tests/unit/backend/test_attack_service.py | 29 +++++++++++++++++++++++
 1 file changed, 29 insertions(+)

diff --git a/tests/unit/backend/test_attack_service.py b/tests/unit/backend/test_attack_service.py
index f3e2e91a0c..11da01effe 100644
--- a/tests/unit/backend/test_attack_service.py
+++ b/tests/unit/backend/test_attack_service.py
@@ -1596,6 +1596,35 @@ async def test_non_path_data_types_are_skipped(self, attack_service) -> None:
 
         assert request.pieces[0].original_value == "thinking step"
 
+    @pytest.mark.asyncio
+    async def test_long_base64_audio_does_not_crash(self, attack_service) -> None:
+        """Base64 audio data longer than OS path limits should be saved, not crash with OSError."""
+        # Simulate a base64-encoded WAV file (>4096 chars, exceeds Linux filename limit of 255)
+        long_b64 = "UklGRiQ" + "A" * 5000  # fake WAV header + padding
+        request = AddMessageRequest(
+            role="user",
+            pieces=[
+                MessagePieceRequest(
+                    data_type="audio_path",
+                    original_value=long_b64,
+                    mime_type="audio/wav",
+                )
+            ],
+            send=False,
+            target_conversation_id="test-id",
+        )
+
+        with patch("pyrit.backend.services.attack_service.data_serializer_factory") as mock_factory:
+            mock_serializer = AsyncMock()
+            mock_serializer.value = "/tmp/saved_audio.wav"
+            mock_factory.return_value = mock_serializer
+
+            await AttackService._persist_base64_pieces_async(request)
+
+            mock_factory.assert_called_once()
+            mock_serializer.save_b64_image.assert_called_once_with(data=long_b64)
+            assert request.pieces[0].original_value == "/tmp/saved_audio.wav"
+
 
 # ============================================================================
 # Related Conversations Tests

From 2fda94d3952437340b4e307d5e6a94765fb5fc7f Mon Sep 17 00:00:00 2001
From: jbolor21 <86250273+jbolor21@users.noreply.github.com>
Date: Thu, 9 Apr 2026 02:27:48 -0700
Subject: [PATCH 3/3] minor feedback

---
 pyrit/backend/services/attack_service.py | 14 ++++++--------
 1 file changed, 6 insertions(+), 8 deletions(-)

diff --git a/pyrit/backend/services/attack_service.py b/pyrit/backend/services/attack_service.py
index 03b6d8a312..9437632392 100644
--- a/pyrit/backend/services/attack_service.py
+++ b/pyrit/backend/services/attack_service.py
@@ -871,15 +871,13 @@ async def _persist_base64_pieces_async(request: AddMessageRequest) -> None:
                 continue
 
             # Already an existing file on disk — keep as-is.
-            # Guard against base64 strings that would exceed OS path length limits.
             try:
-                is_existing_file = len(piece.original_value) < 4096 and Path(piece.original_value).is_file()
-            except OSError:
-                is_existing_file = False
-            if is_existing_file:
-                if piece.converted_value is None:
-                    piece.converted_value = piece.original_value
-                continue
+                if Path(piece.original_value).is_file():
+                    if piece.converted_value is None:
+                        piece.converted_value = piece.original_value
+                    continue
+            except (OSError, ValueError):
+                pass
 
             # Derive file extension from the MIME type sent by the frontend
             ext = None