diff --git a/Lib/_pyrepl/readline.py b/Lib/_pyrepl/readline.py
index 3d94f91753587e..18ac70d2f91587 100644
--- a/Lib/_pyrepl/readline.py
+++ b/Lib/_pyrepl/readline.py
@@ -249,7 +249,7 @@ def _should_auto_indent(buffer: list[str], pos: int) -> bool:
     while pos > 0:
         pos -= 1
         if last_char is None:
-            if buffer[pos] not in " \t\n":  # ignore whitespaces
+            if buffer[pos] not in " \t\n#":  # ignore whitespaces
                 last_char = buffer[pos]
         else:
             # even if we found a non-whitespace character before
@@ -258,7 +258,16 @@ def _should_auto_indent(buffer: list[str], pos: int) -> bool:
             if buffer[pos] == "\n":
                 break
             if buffer[pos] == "#":
-                last_char = None
+                while pos:
+                    pos -= 1
+                    char = buffer[pos]
+                    if char == "\n":
+                        return False
+                    elif char not in " \t#":
+                        last_char = char
+                        break
+                else:
+                    return False
     return last_char == ":"