diff --git a/netbox/extras/events.py b/netbox/extras/events.py
index e2912758a..6f4854ff3 100644
--- a/netbox/extras/events.py
+++ b/netbox/extras/events.py
@@ -119,7 +119,9 @@ def process_event_rules(event_rules, object_type, event_type, data, username=Non
             if snapshots:
                 params["snapshots"] = snapshots
             if request:
-                params["request"] = copy_safe_request(request)
+                # Exclude FILES - webhooks don't need uploaded files,
+                # which can cause pickle errors with Pillow.
+                params["request"] = copy_safe_request(request, include_files=False)
 
             # Enqueue the task
             rq_queue.enqueue(
diff --git a/netbox/utilities/request.py b/netbox/utilities/request.py
index eadbe0f5c..92b879139 100644
--- a/netbox/utilities/request.py
+++ b/netbox/utilities/request.py
@@ -35,27 +35,34 @@ class NetBoxFakeRequest:
 # Utility functions
 #
 
-def copy_safe_request(request):
+def copy_safe_request(request, include_files=True):
     """
     Copy selected attributes from a request object into a new fake request object. This is needed in places where
     thread safe pickling of the useful request data is needed.
+
+    Args:
+        request: The original request object
+        include_files: Whether to include request.FILES.
     """
     meta = {
         k: request.META[k]
         for k in HTTP_REQUEST_META_SAFE_COPY
         if k in request.META and isinstance(request.META[k], str)
     }
-    return NetBoxFakeRequest({
+    data = {
         'META': meta,
         'COOKIES': request.COOKIES,
         'POST': request.POST,
         'GET': request.GET,
-        'FILES': request.FILES,
         'user': request.user,
         'method': request.method,
         'path': request.path,
         'id': getattr(request, 'id', None),  # UUID assigned by middleware
-    })
+    }
+    if include_files:
+        data['FILES'] = request.FILES
+
+    return NetBoxFakeRequest(data)
 
 
 def get_client_ip(request, additional_headers=()):