diff --git a/TodoParser.py b/TodoParser.py
index 42173d0..6995aed 100644
--- a/TodoParser.py
+++ b/TodoParser.py
@@ -547,7 +547,7 @@ class TodoParser(object):
             comment = comment.strip()
             pre_marker_length = original_comment.find(comment)
         else:
-            comment_segments = re.search(fr'^(.*?)({marker["pattern"]})(\s*)(.*)', comment)
+            comment_segments = re.search(fr'^(.*?)({marker["pattern"]})(\s*)(.*?)\s*$', comment)
             if comment_segments:
                 pre_marker_text, _, post_marker_whitespace, comment = comment_segments.groups()
                 pre_marker_length = len(pre_marker_text)
diff --git a/main.py b/main.py
index 845d82b..d687cb4 100644
--- a/main.py
+++ b/main.py
@@ -76,7 +76,7 @@ def process_diff(diff, client=Client(), insert_issue_urls=False, parser=TodoPars
                     if line_number < len(file_lines):
                         # Duplicate the line to retain the comment syntax.
                         old_line = file_lines[line_number]
-                        remove = fr'(?i:{re.escape(raw_issue.identifier)}).*{re.escape(raw_issue.title)}'
+                        remove = fr'(?i:{re.escape(raw_issue.identifier)}).*{re.escape(raw_issue.title)}.*?(\r|\r\n|\n)?$'
                         insert = f'Issue URL: {client.get_issue_url(new_issue_number)}'
                         new_line = re.sub('^.*'+remove, raw_issue.prefix + insert, old_line)
                         # make sure the above operation worked as intended