diff --git a/deploy/cleanup_vcpkg_archive_cache.py b/deploy/cleanup_vcpkg_archive_cache.py
index c5f31d01f3..8d73afed47 100644
--- a/deploy/cleanup_vcpkg_archive_cache.py
+++ b/deploy/cleanup_vcpkg_archive_cache.py
@@ -82,18 +82,26 @@ def read_vcpkg_abi_info(archive, package, packages):
         print('Failed to read the file', file_name, 'from', archive, ':', ex)
         return ''
 
-def mark_outdated_packages(packages):
+def mark_outdated_packages(packages, modification_dates):
     outdated = []
     for architecture in packages:
         for package in packages[architecture]:
-            if (len(packages[architecture][package]) == 1):
-                continue
+            archives_with_same_version = {}
             max_version = sorted(packages[architecture][package].keys(), reverse=True)[0]
             for version in packages[architecture][package]:
                 if (version != max_version):
                     for archive in packages[architecture][package][version]:
                         outdated.append(archive)
-
+                else:
+                    if (len(packages[architecture][package][version]) == 1):
+                        continue
+                    for archive in packages[architecture][package][version]:
+                        if (modification_dates[archive] not in archives_with_same_version and archive in modification_dates):
+                            archives_with_same_version[modification_dates[archive]] = archive
+                    max_date = sorted(archives_with_same_version.keys(), reverse=True)[0]
+                    for archive in packages[architecture][package][version]:
+                        if (archive != archives_with_same_version[max_date]):
+                            outdated.append(archive)
     return outdated
 
 def get_hash_list(packages):
@@ -175,10 +183,10 @@ bucket_name = sys.argv[2]
 access_key = sys.argv[3]
 secret_key = sys.argv[4]
 
-s3.download_all(dir_name, bucket_name)
+modification_dates = s3.download_all(dir_name, bucket_name)
 packages = get_packages(get_files(dir_name))
 print_packages(packages)
-outdated = mark_outdated_packages(packages)
+outdated = mark_outdated_packages(packages, modification_dates)
 
 mark_duplicate_packages(packages, outdated)
 print('Outdated packages:')
diff --git a/deploy/s3.py b/deploy/s3.py
index 9c649a5b3b..f766e21a8e 100644
--- a/deploy/s3.py
+++ b/deploy/s3.py
@@ -66,6 +66,8 @@ def cleanup(dir):
         try:
             if os.path.isfile(file_path):
                 os.unlink(file_path)
+            elif os.path.isdir(file_path):
+                cleanup(file_path)
         except Exception as e:
             print('Failed to delete %s. Reason: %s' % (file_path, e))
 
@@ -85,6 +87,7 @@ def download(os_name, dir, bucket):
                 s3_download(local_file, key, bucket)
 
 def download_all(dir, bucket):
+    files = {}
     cleanup(dir)
     os.makedirs(dir, exist_ok=True)
     objects = s3_list(bucket)
@@ -92,7 +95,9 @@ def download_all(dir, bucket):
         for object in objects:
             key = object['Key']
             local_file = os.path.join(dir, key)
+            files[local_file] = object['LastModified']
             s3_download(local_file, key, bucket)
+    return files
 
 def s3_remove(s3_file, bucket, access_key, secret_key):
     print('Removing', s3_file)