diff --git a/github_release.py b/github_release.py
index e59a0cbf..10657e48 100755
--- a/github_release.py
+++ b/github_release.py
@@ -166,7 +166,16 @@ def parse_args():
 
 def upload_asset(release, filepath, filename, release_version, kv_account_id, namespace_id, kv_api_token):
     logging.info("Uploading asset: %s", filename)
-    release.upload_asset(filepath, name=filename)
+    assets = release.get_assets()
+    uploaded = False
+    for asset in assets:
+        if asset.name == filename:
+            logging.info("asset already uploaded, skipping upload")
+            uploaded = True
+            break
+    
+    if not uploaded:
+        release.upload_asset(filepath, name=filename)
 
     # check and extract if the file is a tar and gzipped file (as is the case with the macos builds)
     binary_path = filepath
@@ -182,6 +191,7 @@ def upload_asset(release, filepath, filename, release_version, kv_account_id, na
         binary_path = os.path.join(os.getcwd(), 'cfd', 'cloudflared')
 
     # send the sha256 (the checksum) to workers kv
+    logging.info("Uploading sha256 checksum for: %s", filename)
     pkg_hash = get_sha256(binary_path)
     send_hash(pkg_hash, filename, release_version, kv_account_id, namespace_id, kv_api_token)