diff --git a/tools/upload-release b/tools/upload-release
index 30fd910250..37f54590c1 100755
--- a/tools/upload-release
+++ b/tools/upload-release
@@ -2,9 +2,10 @@
 import argparse
 import hashlib
 import os
+import re
 import sys
 import tempfile
-from typing import IO, Dict
+from typing import IO, Dict, List, cast
 
 sys.path.insert(0, os.path.join(os.path.dirname(__file__), ".."))
 from scripts.lib.setup_path import setup_path
@@ -71,7 +72,7 @@ for obj_summary in bucket.objects.filter(Prefix="server/zulip-server-"):
 
     file_hashes[filename] = metadata["sha256sum"]
 
-ordered_filenames = natsorted(file_hashes.keys(), reverse=True)
+ordered_filenames = cast(List[str], natsorted(file_hashes.keys(), reverse=True))
 assert ordered_filenames[0] == "zulip-server-latest.tar.gz"
 
 print(f"Uploading {new_basename}..")
@@ -86,14 +87,19 @@ bucket.upload_file(
     ExtraArgs=extra,
 )
 
-if ordered_filenames[1] == new_basename:
-    print("Copying to zulip-server-latest.tar.gz..")
+if (
+    next(name for name in ordered_filenames if re.match(r"^zulip-server-(\d+\.\d+)\.tar.gz$", name))
+    == new_basename
+):
+    print("This looks like the most recent full release; copying to zulip-server-latest.tar.gz..")
     bucket.copy(
         CopySource={"Bucket": bucket.name, "Key": f"server/{new_basename}"},
         Key="server/zulip-server-latest.tar.gz",
         ExtraArgs=extra,
     )
     file_hashes["zulip-server-latest.tar.gz"] = file_hashes[new_basename]
+else:
+    print("Not copying to zulip-server-latest.tar.gz!")
 
 print("Updating SHA256SUMS.txt..")
 contents = ""