diff --git a/zerver/lib/export.py b/zerver/lib/export.py
index d50e762aca..bdc674fbab 100644
--- a/zerver/lib/export.py
+++ b/zerver/lib/export.py
@@ -1461,7 +1461,15 @@ def import_uploads_local(import_dir: Path, processing_avatars: bool=False,
         for record in records:
             if record['s3_path'].endswith('.original'):
                 user_profile = get_user_profile_by_id(record['user_profile_id'])
-                # If medium sized avatar does not exist, this creates it using the original image
+                avatar_path = user_avatar_path_from_ids(user_profile.id, record['realm_id'])
+                medium_file_path = os.path.join(settings.LOCAL_UPLOADS_DIR, "avatars",
+                                                avatar_path) + '-medium.png'
+                if os.path.exists(medium_file_path):
+                    # We remove the image here primarily to deal with
+                    # issues when running the import script multiple
+                    # times in development (where one might reuse the
+                    # same realm ID from a previous iteration).
+                    os.remove(medium_file_path)
                 upload_backend.ensure_medium_avatar_image(user_profile=user_profile)
 
 def import_uploads_s3(bucket_name: str, import_dir: Path, processing_avatars: bool=False,