diff --git a/poetry.lock b/poetry.lock
index 7c02aeb0a9..0b4deb6a9b 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 1.8.5 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.8.3 and should not be changed by hand.
 
 [[package]]
 name = "annotated-types"
@@ -1508,6 +1508,17 @@ files = [
 [package.extras]
 cli = ["click (>=5.0)"]
 
+[[package]]
+name = "python-magic"
+version = "0.4.27"
+description = "File type identification using libmagic"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+files = [
+    {file = "python-magic-0.4.27.tar.gz", hash = "sha256:c1ba14b08e4a5f5c31a302b7721239695b2f0f058d125bd5ce1ee36b9d9d3c3b"},
+    {file = "python_magic-0.4.27-py2.py3-none-any.whl", hash = "sha256:c212960ad306f700aa0d01e5d7a325d20548ff97eb9920dcd29513174f0294d3"},
+]
+
 [[package]]
 name = "pytz"
 version = "2025.2"
@@ -1939,4 +1950,4 @@ files = [
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.9"
-content-hash = "1b8454cccabd078901e3f0c18b5346e23207195c7b9082617d57e862703002fe"
+content-hash = "4956474fab0c68f081b170c162156d89f85218918c802781fcc6c2130cf4db17"
diff --git a/pyproject.toml b/pyproject.toml
index a5a4820e4a..993b63cf44 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -47,6 +47,7 @@ pydantic-core = ">=2.18.2"
 pydash = ">=7.0.0,<8.0.0"
 python-dateutil = ">=2.8.0,<3.0.0"
 python-dotenv = ">=1.0.0,<2.0.0"
+python-magic = "==0.4.27"
 pytz = ">=2022.0,<2026.0"
 pyyaml = ">=6.0.0,<7.0.0"
 requests = ">=2.31.0,<3.0.0"
diff --git a/src/vellum/utils/files/extensions.py b/src/vellum/utils/files/extensions.py
index de81acc55f..e152355e9b 100644
--- a/src/vellum/utils/files/extensions.py
+++ b/src/vellum/utils/files/extensions.py
@@ -1,13 +1,23 @@
 """File extension inference utilities."""
 
+import logging
 import mimetypes
 import os
-from typing import Optional
+from typing import IO, Optional, Union
+
+try:
+    import magic
+except ImportError:
+    magic = None  # type: ignore
 
 from vellum.utils.files.constants import EXTENSION_OVERRIDES, MIME_TYPE_TO_EXTENSION
 
+logger = logging.getLogger(__name__)
+
 
-def ensure_filename_with_extension(filename: Optional[str], mime_type: str) -> str:
+def ensure_filename_with_extension(
+    filename: Optional[str], mime_type: str, contents: Optional[Union[bytes, IO[bytes]]] = None
+) -> str:
     """
     Ensure the filename has an appropriate extension, infering one based on the provided MIME type if necessary.
 
@@ -15,6 +25,8 @@ def ensure_filename_with_extension(filename: Optional[str], mime_type: str) -> s
         filename: Optional filename provided by the user
         mime_type: The MIME type of the file (e.g., "application/pdf", "image/png"). This'll be used to infer the
             extension if the filename lacks one.
+        contents: Optional file contents (bytes or file-like object) to use for MIME type detection via python-magic
+            when the provided MIME type is generic or missing.
 
     Returns:
         A filename with an appropriate extension
@@ -46,6 +58,23 @@ def ensure_filename_with_extension(filename: Optional[str], mime_type: str) -> s
     if filename and has_extension:
         return filename
 
+    if mime_type == "application/octet-stream" and contents and magic:
+        try:
+            if isinstance(contents, bytes):
+                sample = contents[:2048]
+            else:
+                original_position = contents.tell() if hasattr(contents, "tell") else None
+                sample = contents.read(2048)
+                if hasattr(contents, "seek") and original_position is not None:
+                    contents.seek(original_position)
+
+            detected_mime_type = magic.from_buffer(sample, mime=True)
+            if detected_mime_type:
+                # Strip any charset parameters from detected MIME type
+                mime_type = detected_mime_type.split(";")[0].strip()
+        except Exception:
+            logger.exception("Failed to guess content type using python-magic")
+
     # Otherwise, infer extension from MIME type
     extension = mimetypes.guess_extension(mime_type)
 
diff --git a/src/vellum/utils/files/tests/test_extensions.py b/src/vellum/utils/files/tests/test_extensions.py
index a4b1844f8d..80c761ebb4 100644
--- a/src/vellum/utils/files/tests/test_extensions.py
+++ b/src/vellum/utils/files/tests/test_extensions.py
@@ -1,6 +1,8 @@
 """Tests for file extension inference utilities."""
 
 import pytest
+from io import BytesIO
+from unittest.mock import patch
 
 from vellum.utils.files.extensions import ensure_filename_with_extension
 
@@ -52,3 +54,95 @@ def test_ensure_filename_with_extension(filename, mime_type, expected):
     """Test filename extension inference for various filename and MIME type combinations."""
     result = ensure_filename_with_extension(filename, mime_type)
     assert result == expected
+
+
+@patch("vellum.utils.files.extensions.magic")
+def test_ensure_filename_with_extension__with_pdf_bytes_and_octet_stream_mime(mock_magic):
+    """
+    Test that python-magic detects PDF from bytes when MIME type is application/octet-stream.
+    """
+    mock_magic.from_buffer.return_value = "application/pdf"
+
+    pdf_bytes = b"%PDF-1.4\n%\xe2\xe3\xcf\xd3\n"
+
+    result = ensure_filename_with_extension(None, "application/octet-stream", pdf_bytes)
+
+    # THEN the filename should have a .pdf extension
+    assert result == "file.pdf"
+
+
+@patch("vellum.utils.files.extensions.magic")
+def test_ensure_filename_with_extension__with_text_bytes_and_octet_stream_mime(mock_magic):
+    """
+    Test that python-magic detects text/plain from bytes when MIME type is application/octet-stream.
+    """
+    mock_magic.from_buffer.return_value = "text/plain"
+
+    text_bytes = b"Hello, this is a plain text file.\n"
+
+    result = ensure_filename_with_extension(None, "application/octet-stream", text_bytes)
+
+    # THEN the filename should have a .txt extension
+    assert result == "file.txt"
+
+
+@patch("vellum.utils.files.extensions.magic")
+def test_ensure_filename_with_extension__with_bytesio_and_octet_stream_mime(mock_magic):
+    """
+    Test that python-magic works with BytesIO objects and seeks back to original position.
+    """
+    mock_magic.from_buffer.return_value = "application/pdf"
+
+    pdf_bytes = b"%PDF-1.4\n%\xe2\xe3\xcf\xd3\n"
+    bytes_io = BytesIO(pdf_bytes)
+
+    assert bytes_io.tell() == 0
+
+    result = ensure_filename_with_extension("document", "application/octet-stream", bytes_io)
+
+    # THEN the filename should have a .pdf extension
+    assert result == "document.pdf"
+
+    assert bytes_io.tell() == 0
+
+
+def test_ensure_filename_with_extension__with_existing_extension_ignores_contents():
+    """
+    Test that existing filename extensions are preserved even when contents suggest a different type.
+    """
+    # GIVEN a filename with .txt extension
+    filename = "document.txt"
+
+    pdf_bytes = b"%PDF-1.4\n%\xe2\xe3\xcf\xd3\n"
+
+    result = ensure_filename_with_extension(filename, "application/octet-stream", pdf_bytes)
+
+    assert result == "document.txt"
+
+
+def test_ensure_filename_with_extension__with_non_octet_stream_mime_ignores_contents():
+    """
+    Test that python-magic is only used when MIME type is application/octet-stream.
+    """
+    mime_type = "image/jpeg"
+
+    pdf_bytes = b"%PDF-1.4\n%\xe2\xe3\xcf\xd3\n"
+
+    result = ensure_filename_with_extension(None, mime_type, pdf_bytes)
+
+    assert result == "file.jpg"
+
+
+@patch("vellum.utils.files.extensions.magic")
+def test_ensure_filename_with_extension__with_charset_in_detected_mime(mock_magic):
+    """
+    Test that charset parameters are stripped from python-magic detected MIME types.
+    """
+    mock_magic.from_buffer.return_value = "text/html; charset=utf-8"
+
+    html_bytes = b"<!DOCTYPE html><html><body>Hello</body></html>"
+
+    result = ensure_filename_with_extension(None, "application/octet-stream", html_bytes)
+
+    # THEN the filename should have an .html extension (charset should be stripped)
+    assert result == "file.html"
diff --git a/src/vellum/utils/files/upload.py b/src/vellum/utils/files/upload.py
index 78513f51bd..52e12dbffe 100644
--- a/src/vellum/utils/files/upload.py
+++ b/src/vellum/utils/files/upload.py
@@ -92,7 +92,7 @@ def upload_vellum_file(
         decoded = base64.b64decode(base64_content)
 
         # Ensure filename has appropriate extension
-        resolved_filename = ensure_filename_with_extension(filename, mime_type)
+        resolved_filename = ensure_filename_with_extension(filename, mime_type, decoded)
         file_content: File = (resolved_filename, BytesIO(decoded), mime_type)
 
         try:
@@ -130,7 +130,7 @@ def upload_vellum_file(
     content_type = response.headers.get("content-type", "application/octet-stream")
 
     # Ensure filename has appropriate extension
-    resolved_filename = ensure_filename_with_extension(filename, content_type)
+    resolved_filename = ensure_filename_with_extension(filename, content_type, content)
     file_content = (resolved_filename, BytesIO(content), content_type)
 
     try: