FIX Infer Azure Blob MIME types from file extensions

pyrit/memory/storage/serializers.py

@@ -209,6 +209,7 @@ async def save_formatted_audio_async(
         Raises:
             RuntimeError: If storage IO is not initialized.
         """
+        self.file_extension = "wav"
         file_path = await self.get_data_filename_async(file_name=output_filename)
 
         # save audio file locally first if in AzureStorageBlob so we can use wave.open to set audio parameters
@@ -346,6 +347,9 @@ async def get_data_filename_async(self, file_name: str | None = None) -> Path |
 
             results_path = str(DB_DATA_PATH)
         file_name = file_name if file_name else str(ticks)
+        file_suffix = Path(file_name).suffix
+        if file_suffix:
+            file_name = file_name[: -len(file_suffix)]
 
         if self._is_azure_storage_url(results_path):
             full_data_directory_path = results_path + self.data_sub_directory

pyrit/memory/storage/storage.py

@@ -7,7 +7,7 @@
 from abc import ABC, abstractmethod
 from enum import Enum
 from pathlib import Path
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, ClassVar
 from urllib.parse import urlparse
 
 import aiofiles
@@ -157,6 +157,41 @@ class AzureBlobStorageIO(StorageIO):
     Implementation of StorageIO for Azure Blob Storage.
     """
 
+    _EXTENSION_TO_CONTENT_TYPE: ClassVar[dict[str, str]] = {
+        ".txt": "text/plain",
+        ".html": "text/html",
+        ".htm": "text/html",
+        ".csv": "text/csv",
+        ".md": "text/markdown",
+        ".json": "application/json",
+        ".xml": "application/xml",
+        ".png": "image/png",
+        ".jpg": "image/jpeg",
+        ".jpeg": "image/jpeg",
+        ".gif": "image/gif",
+        ".webp": "image/webp",
+        ".svg": "image/svg+xml",
+        ".bmp": "image/bmp",
+        ".wav": "audio/wav",
+        ".mp3": "audio/mpeg",
+        ".ogg": "audio/ogg",
+        ".flac": "audio/flac",
+        ".m4a": "audio/mp4",
+        ".mp4": "video/mp4",
+        ".webm": "video/webm",
+        ".ogv": "video/ogg",
+        ".avi": "video/x-msvideo",
+        ".pdf": "application/pdf",
+        ".doc": "application/msword",
+        ".docx": "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+        ".xls": "application/vnd.ms-excel",
+        ".xlsx": "application/vnd.openxmlformats-officedocument.spreadsheetml.sheet",
+        ".ppt": "application/vnd.ms-powerpoint",
+        ".pptx": "application/vnd.openxmlformats-officedocument.presentationml.presentation",
+        ".rtf": "application/rtf",
+        ".zip": "application/zip",
+    }
+
     def __init__(
         self,
         *,
@@ -382,8 +417,9 @@ async def write_file_async(self, path: Path | str, data: bytes) -> None:
         if not self._client_async:
             self._client_async = await self._create_container_client_async()
         blob_name = self._resolve_blob_name(path)
+        content_type = self._EXTENSION_TO_CONTENT_TYPE.get(Path(blob_name).suffix.lower(), self._blob_content_type)
         try:
-            await self._upload_blob_async(file_name=blob_name, data=data, content_type=self._blob_content_type)
+            await self._upload_blob_async(file_name=blob_name, data=data, content_type=content_type)
         except Exception as exc:
             logger.exception(f"Failed to write file at {blob_name}: {exc}")
             raise

tests/unit/memory/storage/test_serializers.py

@@ -5,6 +5,7 @@
 import os
 import re
 import tempfile
+from pathlib import Path
 from typing import get_args
 from unittest.mock import AsyncMock, MagicMock, PropertyMock, patch
 
@@ -13,10 +14,12 @@
 
 from pyrit.memory.storage import (
     AllowedCategories,
+    AzureBlobStorageIO,
     BinaryPathDataTypeSerializer,
     DataTypeSerializer,
     ErrorDataTypeSerializer,
     ImagePathDataTypeSerializer,
+    StorageIO,
     TextDataTypeSerializer,
     data_serializer_factory,
     set_message_piece_sha256_async,
@@ -25,6 +28,35 @@
 from pyrit.models import MessagePiece, SeedPrompt
 
 
+class LegacyStorageIO(StorageIO):
+    """
+    Test double representing an existing third-party ``StorageIO`` implementation.
+
+    Its ``write_file_async(path, data)`` method intentionally retains the original
+    two-argument contract. Tests using this class ensure serializers do not pass a
+    new content-type keyword argument that would break pre-existing custom storage
+    backends when Azure Blob Storage adds MIME metadata internally.
+    """
+
+    def __init__(self) -> None:
+        self.writes: list[tuple[Path | str, bytes]] = []
+
+    async def read_file_async(self, path: Path | str) -> bytes:
+        return b""
+
+    async def write_file_async(self, path: Path | str, data: bytes) -> None:
+        self.writes.append((path, data))
+
+    async def path_exists_async(self, path: Path | str) -> bool:
+        return False
+
+    async def is_file_async(self, path: Path | str) -> bool:
+        return False
+
+    async def create_directory_if_not_exists_async(self, path: Path | str) -> None:
+        return None
+
+
 def test_allowed_categories():
     entries = get_args(AllowedCategories)
     assert len(entries) == 2
@@ -285,6 +317,29 @@ async def test_get_data_filename(sqlite_instance):
     assert not os.path.exists(filename)  # File should not exist yet
 
 
+async def test_get_data_filename_does_not_duplicate_extension(sqlite_instance):
+    serializer = data_serializer_factory(category="prompt-memory-entries", data_type="image_path")
+
+    filename = await serializer.get_data_filename_async(file_name="photo.png")
+
+    assert Path(filename).name == "photo.png"
+
+
+async def test_save_data_supports_legacy_storage_io_write_signature():
+    storage = LegacyStorageIO()
+    mock_memory = MagicMock()
+    mock_memory.results_path = "https://account.blob.core.windows.net/container/results"
+    mock_memory.results_storage_io = storage
+    serializer = data_serializer_factory(category="prompt-memory-entries", data_type="image_path")
+
+    with patch.object(type(serializer), "_memory", new_callable=PropertyMock, return_value=mock_memory):
+        await serializer.save_data_async(b"\x89PNG", output_filename="photo.png")
+
+    assert storage.writes == [
+        ("https://account.blob.core.windows.net/container/results/prompt-memory-entries/images/photo.png", b"\x89PNG")
+    ]
+
+
 def test_binary_path_normalizer_factory(sqlite_instance):
     """Test factory creates BinaryPathDataTypeSerializer correctly."""
     serializer = data_serializer_factory(category="prompt-memory-entries", data_type="binary_path")
@@ -433,6 +488,36 @@ async def test_save_formatted_audio_writes_local_wav_via_to_thread(sqlite_instan
         assert wav_file.readframes(wav_file.getnframes()) == pcm
 
 
+async def test_save_formatted_audio_uses_wav_filename_content_and_metadata(tmp_path):
+    import io
+    import wave
+
+    storage = AzureBlobStorageIO(container_url="https://account.blob.core.windows.net/container")
+    mock_container_client = AsyncMock()
+    storage._client_async = mock_container_client
+    mock_memory = MagicMock()
+    mock_memory.results_path = "https://account.blob.core.windows.net/container/results"
+    mock_memory.results_storage_io = storage
+    serializer = data_serializer_factory(category="prompt-memory-entries", data_type="audio_path")
+    pcm = b"\x01\x00\x02\x00\x03\x00\x04\x00"
+
+    with (
+        patch.object(type(serializer), "_memory", new_callable=PropertyMock, return_value=mock_memory),
+        patch("pyrit.memory.storage.serializers.DB_DATA_PATH", tmp_path),
+    ):
+        await serializer.save_formatted_audio_async(data=pcm, output_filename="recording.mp3")
+
+    upload_kwargs = mock_container_client.upload_blob.await_args.kwargs
+    assert upload_kwargs["name"] == "results/prompt-memory-entries/audio/recording.wav"
+    assert upload_kwargs["content_settings"].content_type == "audio/wav"
+    assert serializer.value.endswith("/audio/recording.wav")
+    with wave.open(io.BytesIO(upload_kwargs["data"]), "rb") as wav_file:
+        assert wav_file.getnchannels() == 1
+        assert wav_file.getsampwidth() == 2
+        assert wav_file.getframerate() == 16000
+        assert wav_file.readframes(wav_file.getnframes()) == pcm
+
+
 def test_write_wav_sync_produces_readable_wav(tmp_path):
     """_write_wav_sync should produce a WAV file readable by wave.open with the same metadata and frames."""
     import wave

tests/unit/memory/storage/test_storage.py

@@ -162,6 +162,43 @@ async def test_azure_blob_storage_io_write_file_with_relative_path():
         )
 
 
+@pytest.mark.parametrize(
+    ("path", "expected_content_type"),
+    [
+        ("notes.HTML", "text/html"),
+        ("photo.JPEG", "image/jpeg"),
+        ("recording.wav", "audio/wav"),
+        ("movie.mp4", "video/mp4"),
+        ("report.pdf", "application/pdf"),
+    ],
+)
+async def test_azure_blob_storage_io_write_file_sets_content_type_from_extension(path, expected_content_type):
+    storage = AzureBlobStorageIO(container_url="https://account.blob.core.windows.net/container")
+    mock_container_client = AsyncMock()
+    storage._client_async = mock_container_client
+
+    await storage.write_file_async(path, b"data")
+
+    upload_kwargs = mock_container_client.upload_blob.await_args.kwargs
+    assert upload_kwargs["name"] == path
+    assert upload_kwargs["content_settings"].content_type == expected_content_type
+
+
+@pytest.mark.parametrize("path", ["data.unknown", "README"])
+async def test_azure_blob_storage_io_write_file_uses_configured_fallback_content_type(path):
+    storage = AzureBlobStorageIO(
+        container_url="https://account.blob.core.windows.net/container",
+        blob_content_type=SupportedContentType.PLAIN_TEXT,
+    )
+    mock_container_client = AsyncMock()
+    storage._client_async = mock_container_client
+
+    await storage.write_file_async(path, b"data")
+
+    upload_kwargs = mock_container_client.upload_blob.await_args.kwargs
+    assert upload_kwargs["content_settings"].content_type == SupportedContentType.PLAIN_TEXT.value
+
+
 async def test_azure_blob_storage_io_create_container_client_uses_explicit_sas_token():
     container_url = "https://youraccount.blob.core.windows.net/yourcontainer"
     sas_token = "explicit-sas-token"