diff --git a/ctfcli/core/challenge.py b/ctfcli/core/challenge.py
index 517f550..5e25132 100644
--- a/ctfcli/core/challenge.py
+++ b/ctfcli/core/challenge.py
@@ -736,7 +736,7 @@ def sync(self, ignore: Tuple[str] = ()) -> None:
                         ) as lf:
                             local_file_sha1sum = hash_file(lf)
 
-                        if local_file_sha1sum == remote_file_sha1sum:
+                        if not "checksum" in ignore and local_file_sha1sum == remote_file_sha1sum:
                             continue
 
                     # if sha1sums are not present, or the hashes are different, re-upload the file