diff --git a/sky/tools/sky_utils.py b/sky/tools/sky_utils.py
index 72ca3647d0658..c79fb115f976c 100644
--- a/sky/tools/sky_utils.py
+++ b/sky/tools/sky_utils.py
@@ -33,18 +33,25 @@ def assert_valid_codesign_config(
   either entitlements or without_entitlements."""
   if _contains_duplicates(entitlements):
     log_error('ERROR: duplicate value(s) found in entitlements.txt')
+    log_error_items(sorted(entitlements))
     sys.exit(os.EX_DATAERR)
 
   if _contains_duplicates(without_entitlements):
     log_error('ERROR: duplicate value(s) found in without_entitlements.txt')
+    log_error_items(sorted(without_entitlements))
     sys.exit(os.EX_DATAERR)
 
   if _contains_duplicates(unsigned_binaries):
     log_error('ERROR: duplicate value(s) found in unsigned_binaries.txt')
+    log_error_items(sorted(unsigned_binaries))
     sys.exit(os.EX_DATAERR)
 
   if _contains_duplicates(entitlements + without_entitlements + unsigned_binaries):
-    log_error('ERROR: value(s) found in both entitlements and without_entitlements.txt')
+    log_error(
+        'ERROR: duplicate value(s) found between '
+        'entitlements.txt, without_entitlements.txt, unsigned_binaries.txt'
+    )
+    log_error_items(sorted(entitlements + without_entitlements + unsigned_binaries))
     sys.exit(os.EX_DATAERR)
 
   binaries = set()
@@ -254,6 +261,12 @@ def log_error(message):
   print(message, file=sys.stderr)
 
 
+def log_error_items(items):
+  """Writes each item indented to stderr, followed by a newline."""
+  for item in items:
+    log_error('  ' + item)
+
+
 def strip_binary(binary_path, unstripped_copy_path):
   """Makes a copy of an unstripped binary, then strips symbols from the binary."""
   assert_file(binary_path, 'binary to strip')