diff --git a/salt/states/file.py b/salt/states/file.py
index e45b1a14e955..b27907f8b468 100644
--- a/salt/states/file.py
+++ b/salt/states/file.py
@@ -6062,7 +6062,7 @@ def comment(name, regex, char="#", backup=".bak", ignore_missing=False):
     # remove (?i)-like flags, ^ and $
     unanchor_regex = re.sub(r"^(\(\?[iLmsux]\))?\^?(.*?)\$?$", r"\2", regex)
 
-    uncomment_regex = "[^{}]?".format(char) + unanchor_regex
+    uncomment_regex = "^(?!.*{}).*".format(char) + unanchor_regex
     comment_regex = char + unanchor_regex
 
     # Make sure the pattern appears in the file before continuing