From 23801f81d95bd55cd1a7f7ff190bbb6d1a94884e Mon Sep 17 00:00:00 2001
From: ANIS <119749586+assinscreedFC@users.noreply.github.com>
Date: Fri, 5 Jun 2026 19:24:24 +0200
Subject: [PATCH] Fix #405: no spurious space between emphasis and following
 punctuation

After a closing emphasis marker html2text inserted a separating space
before anything except whitespace, brackets and `.!?`. That wrongly added
a space before other punctuation, e.g. `<em>hello</em>,` produced
`_hello_ ,` instead of `_hello_,`.

The separating space is only needed before a word character, which would
otherwise attach to the closing marker and stop Markdown from recognising
the emphasis. The condition is now `re.match(r"\w", data[0])`.

Adds a regression fixture (test/emphasis_punctuation.*) and a ChangeLog
entry.

Co-authored-by: Claude <noreply@anthropic.com>
---
 AUTHORS.rst                    | 1 +
 ChangeLog.rst                  | 6 ++++++
 html2text/__init__.py          | 8 ++++++--
 test/emphasis_punctuation.html | 4 ++++
 test/emphasis_punctuation.md   | 8 ++++++++
 5 files changed, 25 insertions(+), 2 deletions(-)
 create mode 100644 test/emphasis_punctuation.html
 create mode 100644 test/emphasis_punctuation.md

diff --git a/AUTHORS.rst b/AUTHORS.rst
index 5b3ac10..cb1e625 100644
--- a/AUTHORS.rst
+++ b/AUTHORS.rst
@@ -40,6 +40,7 @@ The AUTHORS/Contributors are (and/or have been):
 * Edward Ross <gh: EdwardJRoss>
 * Gregory Anders <gh: gpanders>
 * Alex Vandiver <gh: alexmv>
+* Anis <gh: assinscreedFC>
 
 Maintainer:
 
diff --git a/ChangeLog.rst b/ChangeLog.rst
index 2d96e3b..2961aba 100644
--- a/ChangeLog.rst
+++ b/ChangeLog.rst
@@ -1,3 +1,9 @@
+Unreleased
+==========
+----
+
+* Fix #405: Don't insert a spurious space between a closing emphasis marker and following punctuation.
+
 2025.4.15
 =========
 ----
diff --git a/html2text/__init__.py b/html2text/__init__.py
index 621fa74..cf10dec 100644
--- a/html2text/__init__.py
+++ b/html2text/__init__.py
@@ -881,11 +881,15 @@ def handle_data(self, data: str, entity_char: bool = False) -> None:
             self.preceding_stressed = True
         elif self.preceding_stressed:
             if (
-                re.match(r"[^][(){}\s.!?]", data[0])
+                re.match(r"\w", data[0])
                 and not hn(self.current_tag)
                 and self.current_tag not in ["a", "code", "pre"]
             ):
-                # should match a letter or common punctuation
+                # A following word character (letter, digit or underscore)
+                # attaches to the closing emphasis marker and stops Markdown
+                # from recognising it, so the separating space is needed only
+                # before word characters -- not before punctuation, which
+                # previously received a spurious space.
                 data = " " + data
             self.preceding_stressed = False
 
diff --git a/test/emphasis_punctuation.html b/test/emphasis_punctuation.html
new file mode 100644
index 0000000..91f3a3e
--- /dev/null
+++ b/test/emphasis_punctuation.html
@@ -0,0 +1,4 @@
+<p>An <em>emphasized</em>, then <em>another</em>: also <em>more</em>; right?</p>
+<p>A <strong>strong</strong>, and a quote <em>here</em>"end".</p>
+<p><em>word</em>boundary keeps its space, as does a digit <em>v</em>2.</p>
+<p>No space before an apostrophe: <em>cat</em>'s tail.</p>
diff --git a/test/emphasis_punctuation.md b/test/emphasis_punctuation.md
new file mode 100644
index 0000000..63d17d6
--- /dev/null
+++ b/test/emphasis_punctuation.md
@@ -0,0 +1,8 @@
+An _emphasized_, then _another_: also _more_; right?
+
+A **strong**, and a quote _here_"end".
+
+_word_ boundary keeps its space, as does a digit _v_ 2.
+
+No space before an apostrophe: _cat_'s tail.
+