diff --git a/CHANGELOG.md b/CHANGELOG.md
index cb681d9..df85f2b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,6 +9,8 @@ All notable changes to this project will be documented in this file.
 - Add `force_refs_lower` to enable `:ref:` links with mixed-case program names and arguments.
 - Fix Sphinx smart quotes rewriting `--` to an en dash in `--option` names within descriptions, epilogs, and help text.
 - Register flags and positional arguments as Sphinx program options so the `:option:` role links to them.
+- Leave apostrophes inside words (`don't`, `it's`) alone in help text instead of turning them into broken inline
+  literals.
 
 ## 1.13.1
 
diff --git a/roots/test-help-apostrophe/conf.py b/roots/test-help-apostrophe/conf.py
new file mode 100644
index 0000000..9f2a54a
--- /dev/null
+++ b/roots/test-help-apostrophe/conf.py
@@ -0,0 +1,8 @@
+from __future__ import annotations
+
+import sys
+from pathlib import Path
+
+sys.path.insert(0, str(Path(__file__).parent))
+extensions = ["sphinx_argparse_cli"]
+nitpicky = True
diff --git a/roots/test-help-apostrophe/index.rst b/roots/test-help-apostrophe/index.rst
new file mode 100644
index 0000000..708ad9c
--- /dev/null
+++ b/roots/test-help-apostrophe/index.rst
@@ -0,0 +1,3 @@
+.. sphinx_argparse_cli::
+  :module: parser
+  :func: make
diff --git a/roots/test-help-apostrophe/parser.py b/roots/test-help-apostrophe/parser.py
new file mode 100644
index 0000000..50068d2
--- /dev/null
+++ b/roots/test-help-apostrophe/parser.py
@@ -0,0 +1,10 @@
+from __future__ import annotations
+
+from argparse import ArgumentParser
+
+
+def make() -> ArgumentParser:
+    parser = ArgumentParser(prog="prog", add_help=False)
+    parser.add_argument("--a", help="don't use it's value")
+    parser.add_argument("--b", help="it's a 'thing' to see")
+    return parser
diff --git a/src/sphinx_argparse_cli/_logic.py b/src/sphinx_argparse_cli/_logic.py
index 21f3bef..c655bb7 100644
--- a/src/sphinx_argparse_cli/_logic.py
+++ b/src/sphinx_argparse_cli/_logic.py
@@ -411,8 +411,9 @@ def make_id(key: str) -> str:
 
 
 _HELP_SUBSTITUTIONS: Final[list[tuple[re.Pattern[str], str]]] = [
-    (re.compile(r"[']+(.+?)[']+"), "``'\\1'``"),
-    (re.compile(r'["]+(.+?)["]+'), '``"\\1"``'),
+    # a quote glued to a word character is an apostrophe (don't, it's), not the edge of a quoted span
+    (re.compile(r"(?<!\w)'([^']+?)'(?!\w)"), "``'\\1'``"),
+    (re.compile(r'(?<!\w)"([^"]+?)"(?!\w)'), '``"\\1"``'),
     (re.compile(r"[{](.+?)[}]"), "``{\\1}``"),
 ]
 
diff --git a/tests/test_logic.py b/tests/test_logic.py
index a64c1ab..8bd6d6b 100644
--- a/tests/test_logic.py
+++ b/tests/test_logic.py
@@ -175,6 +175,27 @@ def test_set_usage_first(build_outcome: str) -> None:
     assert "complex first [-h]" in build_outcome.split("a-first-desc", maxsplit=1)[0]
 
 
+@pytest.mark.sphinx(buildername="text", testroot="help-apostrophe")
+def test_help_apostrophe(build_outcome: str, warning: StringIO) -> None:
+    assert (
+        build_outcome
+        == """prog - CLI interface
+********************
+
+   prog [--a A] [--b B]
+
+
+prog options
+============
+
+* **"--a"** "A" - don't use it's value
+
+* **"--b"** "B" - it's a "'thing'" to see
+"""
+    )
+    assert not warning.getvalue()
+
+
 @pytest.mark.sphinx(buildername="text", testroot="suppressed-action")
 def test_suppressed_action(build_outcome: str) -> None:
     assert "--activities-since" not in build_outcome
@@ -183,13 +204,17 @@ def test_suppressed_action(build_outcome: str) -> None:
 @pytest.mark.parametrize(
     ("example", "output"),
     [
-        ("", ""),
-        ("{", "{"),
-        ('"', '"'),
-        ("'", "'"),
-        ("{a}", "``{a}``"),
-        ('"a"', '``"a"``'),
-        ("'a'", "``'a'``"),
+        pytest.param("", "", id="empty"),
+        pytest.param("{", "{", id="lone-brace"),
+        pytest.param('"', '"', id="lone-double-quote"),
+        pytest.param("'", "'", id="lone-single-quote"),
+        pytest.param("{a}", "``{a}``", id="braces"),
+        pytest.param('"a"', '``"a"``', id="double-quoted"),
+        pytest.param("'a'", "``'a'``", id="single-quoted"),
+        pytest.param("don't use it's value", "don't use it's value", id="apostrophes"),
+        pytest.param("it's a 'thing' to see", "it's a ``'thing'`` to see", id="apostrophe-and-quoted"),
+        pytest.param("'a' and 'b'", "``'a'`` and ``'b'``", id="two-quoted"),
+        pytest.param('say "hi" or "bye"', 'say ``"hi"`` or ``"bye"``', id="two-double-quoted"),
     ],
 )
 def test_help_loader(example: str, output: str) -> None: