diff --git a/py/routes/handlers/preview_handlers.py b/py/routes/handlers/preview_handlers.py
index 7916e716..4b88cb4e 100644
--- a/py/routes/handlers/preview_handlers.py
+++ b/py/routes/handlers/preview_handlers.py
@@ -3,6 +3,7 @@
 from __future__ import annotations
 
 import logging
+import mimetypes
 import urllib.parse
 from pathlib import Path
 
@@ -12,6 +13,12 @@ from ...config import config as global_config
 
 logger = logging.getLogger(__name__)
 
+_CHUNK_SIZE = 256 * 1024  # 256 KB
+
+# Video file extensions that bypass native sendfile on Windows
+# to avoid IOCP/ProactorEventLoop crashes during client disconnect.
+_VIDEO_EXTENSIONS = frozenset({".mp4", ".webm", ".mov", ".avi", ".mkv"})
+
 
 class PreviewHandler:
     """Serve preview assets for the active library at request time."""
@@ -48,8 +55,51 @@ class PreviewHandler:
             logger.debug("Preview file not found at %s", str(resolved))
             raise web.HTTPNotFound(text="Preview file not found")
 
+        # Video files: stream manually to avoid Windows native sendfile crash.
+        # aiohttp's FileResponse uses _sendfile_native on Windows (IOCP-based),
+        # which breaks when the client disconnects mid-transfer — this happens
+        # constantly when users scroll through a gallery of animated previews.
+        suffix = resolved.suffix.lower()
+        if suffix in _VIDEO_EXTENSIONS:
+            return await self._stream_file(request, resolved)
+
         # aiohttp's FileResponse handles range requests and content headers for us.
-        return web.FileResponse(path=resolved, chunk_size=256 * 1024)
+        return web.FileResponse(path=resolved, chunk_size=_CHUNK_SIZE)
+
+    async def _stream_file(
+        self, request: web.Request, path: Path
+    ) -> web.StreamResponse:
+        """Stream a file chunk-by-chunk, bypassing native sendfile.
+
+        This avoids the Windows IOCP ``_sendfile_native`` crash that occurs
+        when the client disconnects during a large file transfer.
+        """
+        content_type, _ = mimetypes.guess_type(str(path))
+        if content_type is None:
+            content_type = "application/octet-stream"
+
+        file_size = path.stat().st_size
+        resp = web.StreamResponse()
+        resp.content_type = content_type
+        resp.content_length = file_size
+
+        await resp.prepare(request)
+
+        try:
+            with open(path, "rb") as f:
+                while True:
+                    chunk = f.read(_CHUNK_SIZE)
+                    if not chunk:
+                        break
+                    await resp.write(chunk)
+        except (ConnectionResetError, ConnectionAbortedError):
+            # Client disconnected during streaming — expected when scrolling
+            # rapidly through a library with animated previews.
+            pass
+        except OSError as exc:
+            logger.debug("I/O error streaming preview %s: %s", path, exc)
+
+        return resp
 
 
 __all__ = ["PreviewHandler"]