diff --git a/src/guiguts/misc_tools.py b/src/guiguts/misc_tools.py
index abe0ebda..2b4d7306 100644
--- a/src/guiguts/misc_tools.py
+++ b/src/guiguts/misc_tools.py
@@ -1910,6 +1910,7 @@ def populate(self) -> None:
         search_start = maintext().start()
         search_end = maintext().index(tk.END)
         last_open_double_idx = ""
+        punctuation = ".,;:!?"
         while match := maintext().find_match(
             rf"^$|[{DQUOTES}{SQUOTES}\"']",
             IndexRange(search_start, search_end),
@@ -1950,6 +1951,8 @@ def add_quote_entry(prefix: str) -> None:
                     add_quote_entry("DOUBLE OPEN QUOTE FOLLOWED BY SPACE: ")
                 elif context[0].isalnum():
                     add_quote_entry("DOUBLE OPEN QUOTE PRECEDED BY WORD CHARACTER: ")
+                elif context[0] in punctuation:
+                    add_quote_entry("DOUBLE OPEN QUOTE PRECEDED BY PUNCTUATION: ")
                 dqtype = 1
                 last_open_double_idx = match.rowcol.index()
             elif match_text == DQUOTES[1]:  # Close double
@@ -1985,6 +1988,8 @@ def add_quote_entry(prefix: str) -> None:
                     add_quote_entry("SINGLE OPEN QUOTE FOLLOWED BY SPACE: ")
                 elif context[0].isalnum():
                     add_quote_entry("SINGLE OPEN QUOTE PRECEDED BY WORD CHARACTER: ")
+                elif context[0] in punctuation:
+                    add_quote_entry("SINGLE OPEN QUOTE PRECEDED BY PUNCTUATION: ")
             elif match_text == SQUOTES[1]:  # Close single
                 pass  # Close singles/apostrophes can go almost anywhere
             elif match_text == '"':  # Straight double