diff --git a/src/routers/messages.py b/src/routers/messages.py
index 02838c48..82f8a1d9 100644
--- a/src/routers/messages.py
+++ b/src/routers/messages.py
@@ -151,15 +151,15 @@ async def create_messages_with_file(
 
     # Validate file size
     max_file_size = settings.MAX_FILE_SIZE
-    if (
-        file.size
-        and file.size > settings.MAX_FILE_SIZE
-        and is_audio_transcription_enabled()
-        and is_audio_upload(file)
-        and file.size <= settings.AUDIO.MAX_FILE_SIZE_BYTES
-        and await is_validated_audio_upload(file)
-    ):
-        max_file_size = settings.AUDIO.MAX_FILE_SIZE_BYTES
+    if file.size and file.size > settings.MAX_FILE_SIZE:
+        is_valid_audio_upload = (
+            is_audio_transcription_enabled()
+            and is_audio_upload(file)
+            and file.size <= settings.AUDIO.MAX_FILE_SIZE_BYTES
+            and await is_validated_audio_upload(file)
+        )
+        if is_valid_audio_upload:
+            max_file_size = settings.AUDIO.MAX_FILE_SIZE_BYTES
 
     if file.size and file.size > max_file_size:
         raise FileTooLargeError(
diff --git a/src/utils/files.py b/src/utils/files.py
index b57a691c..2f66761f 100644
--- a/src/utils/files.py
+++ b/src/utils/files.py
@@ -1,6 +1,7 @@
 # ruff: noqa: I001
 import asyncio
 import datetime
+from dataclasses import dataclass, field
 import logging
 import subprocess
 import tempfile
@@ -40,23 +41,14 @@ GENERIC_CONTENT_TYPES = {
 }
 
 
-class ExtractedFileText(str):
-    metadata: dict[str, Any]
-
-    def __new__(
-        cls, text: str, metadata: dict[str, Any] | None = None
-    ) -> "ExtractedFileText":
-        obj = str.__new__(cls, text)
-        obj.metadata = metadata or {}
-        return obj
-
-    @property
-    def text(self) -> str:
-        return str(self)
+@dataclass
+class FileExtractionResult:
+    text: str
+    metadata: dict[str, Any] = field(default_factory=dict)
 
 
 class FileProcessor(Protocol):
-    async def extract_text(self, content: bytes) -> ExtractedFileText: ...
+    async def extract_text(self, content: bytes) -> str: ...
     def supports_file_type(self, content_type: str) -> bool: ...
 
 
@@ -64,7 +56,7 @@ class PDFProcessor:
     def supports_file_type(self, content_type: str) -> bool:
         return content_type == "application/pdf"
 
-    async def extract_text(self, content: bytes) -> ExtractedFileText:
+    async def extract_text(self, content: bytes) -> str:
         import pdfplumber
 
         with pdfplumber.open(BytesIO(content)) as pdf_reader:
@@ -73,18 +65,18 @@ class PDFProcessor:
                 text = page.extract_text()
                 if text and text.strip():
                     text_parts.append(f"[Page {page_num + 1}]\n{text}")
-            return ExtractedFileText(text="\n\n".join(text_parts))
+            return "\n\n".join(text_parts)
 
 
 class TextProcessor:
     def supports_file_type(self, content_type: str) -> bool:
         return content_type.startswith("text/")
 
-    async def extract_text(self, content: bytes) -> ExtractedFileText:
+    async def extract_text(self, content: bytes) -> str:
         # Try different encodings
         for encoding in ["utf-8", "utf-16", "latin-1"]:
             try:
-                return ExtractedFileText(text=content.decode(encoding))
+                return content.decode(encoding)
             except UnicodeDecodeError:
                 continue
         raise ValueError("Could not decode text file")
@@ -94,7 +86,7 @@ class JSONProcessor:
     def supports_file_type(self, content_type: str) -> bool:
         return content_type == "application/json"
 
-    async def extract_text(self, content: bytes) -> ExtractedFileText:
+    async def extract_text(self, content: bytes) -> str:
         import json
 
         try:
@@ -103,7 +95,7 @@ class JSONProcessor:
             raise ValidationException("JSON uploads must be UTF-8 encoded") from exc
 
         if not decoded_content.strip():
-            return ExtractedFileText(text="")
+            return ""
 
         try:
             data = json.loads(decoded_content)
@@ -111,7 +103,7 @@ class JSONProcessor:
             raise ValidationException("Uploaded JSON is invalid") from exc
 
         # Convert JSON to readable text format
-        return ExtractedFileText(text=json.dumps(data, ensure_ascii=False))
+        return json.dumps(data, ensure_ascii=False)
 
 
 class AudioProcessor:
@@ -142,7 +134,7 @@ class AudioProcessor:
         *,
         filename: str | None,
         content_type: str,
-    ) -> ExtractedFileText:
+    ) -> FileExtractionResult:
         if not filename:
             raise ValidationException("Audio upload requires a filename")
         if not content:
@@ -161,7 +153,7 @@ class AudioProcessor:
             filename=normalized_filename,
             content_type=normalized_content_type,
         )
-        return ExtractedFileText(
+        return FileExtractionResult(
             text=text,
             metadata={
                 "processing_type": "audio_transcription",
@@ -279,7 +271,7 @@ class FileProcessingService:
             # Add more processors as needed
         ]
 
-    async def extract_text_from_upload(self, file: UploadFile) -> ExtractedFileText:
+    async def extract_text_from_upload(self, file: UploadFile) -> FileExtractionResult:
         """Extract text from uploaded file without saving to disk."""
         content = await file.read()
         await file.seek(0)
@@ -305,7 +297,7 @@ class FileProcessingService:
                 f"Unsupported file type: {file.content_type}. Supported types: {[p.__class__.__name__ for p in self.processors]}"
             )
 
-        return await processor.extract_text(content)
+        return FileExtractionResult(text=await processor.extract_text(content))
 
     def _get_processor(self, content_type: str) -> FileProcessor | None:
         for processor in self.processors:
@@ -409,7 +401,8 @@ async def process_file_uploads_for_messages(
     file_processor = FileProcessingService()
     all_message_data: list[dict[str, Any]] = []
 
-    extracted_text = await file_processor.extract_text_from_upload(file)
+    extracted = await file_processor.extract_text_from_upload(file)
+    extracted_text = extracted.text
 
     # Split into chunks and create messages
     chunks = split_text_into_chunks(extracted_text, max_chars=max_chars)
@@ -441,7 +434,7 @@ async def process_file_uploads_for_messages(
                 min((i + 1) * max_chars, len(extracted_text)),
             ],
         }
-        file_metadata.update(extracted_text.metadata)
+        file_metadata.update(extracted.metadata)
 
         all_message_data.append(
             {
diff --git a/tests/routes/test_files.py b/tests/routes/test_files.py
index 01d7f933..fb44e222 100644
--- a/tests/routes/test_files.py
+++ b/tests/routes/test_files.py
@@ -18,7 +18,7 @@ from src import models, schemas
 from src.config import settings
 from src.models import Peer, Workspace
 from src.routers.messages import create_messages_with_file
-from src.utils.files import ExtractedFileText
+from src.utils.files import FileExtractionResult
 
 
 async def _create_test_session(
@@ -637,7 +637,7 @@ async def test_create_messages_with_mp3_file(
     files = {"file": ("call.mp3", file_data, "audio/mpeg")}
     form_data = {"peer_id": test_peer.name}
 
-    extracted = ExtractedFileText(
+    extracted = FileExtractionResult(
         text="First sentence.\nSecond sentence.",
         metadata={
             "processing_type": "audio_transcription",
@@ -686,7 +686,7 @@ async def test_audio_upload_over_generic_limit_uses_audio_size_limit_when_valida
     original_audio_max = settings.AUDIO.MAX_FILE_SIZE_BYTES
     settings.MAX_FILE_SIZE = 5
     settings.AUDIO.MAX_FILE_SIZE_BYTES = 10
-    extracted = ExtractedFileText(
+    extracted = FileExtractionResult(
         text="Transcribed audio",
         metadata={
             "processing_type": "audio_transcription",
@@ -736,7 +736,7 @@ async def test_extension_only_audio_upload_over_generic_limit_uses_audio_size_li
     original_audio_max = settings.AUDIO.MAX_FILE_SIZE_BYTES
     settings.MAX_FILE_SIZE = 5
     settings.AUDIO.MAX_FILE_SIZE_BYTES = 10
-    extracted = ExtractedFileText(
+    extracted = FileExtractionResult(
         text="Transcribed extension-only audio",
         metadata={
             "processing_type": "audio_transcription",
@@ -906,7 +906,7 @@ async def test_create_messages_with_wav_file_accepts_audio_wave_mime(
     files = {"file": ("call.wav", file_data, "audio/wave")}
     form_data = {"peer_id": test_peer.name}
 
-    extracted = ExtractedFileText(
+    extracted = FileExtractionResult(
         text="WAV transcript",
         metadata={
             "processing_type": "audio_transcription",
@@ -991,7 +991,7 @@ async def test_large_audio_upload_applies_audio_metadata_to_all_message_chunks(
     form_data = {"peer_id": test_peer.name}
 
     long_text = "Segment line. " * 4000
-    extracted = ExtractedFileText(
+    extracted = FileExtractionResult(
         text=long_text,
         metadata={
             "processing_type": "audio_transcription",