diff --git a/novelwriter/gui/dochighlight.py b/novelwriter/gui/dochighlight.py
index c70d30d0..8103fd79 100644
--- a/novelwriter/gui/dochighlight.py
+++ b/novelwriter/gui/dochighlight.py
@@ -505,7 +505,7 @@ class TextBlockData(QTextBlockUserData):
                     text = f"{text[:s]}{pad}{text[e:]}"
                     self._metaData.append((s, e, res.group(0), "url"))
 
-        self._text = text
+        self._text = text.replace("\u02bc", "'")
         self._offset = offset
 
         return
diff --git a/novelwriter/text/patterns.py b/novelwriter/text/patterns.py
index d592b70c..a5d2b3e9 100644
--- a/novelwriter/text/patterns.py
+++ b/novelwriter/text/patterns.py
@@ -93,7 +93,7 @@ class RegExPatterns:
             if CONFIG.dialogStyle in (1, 3):
                 qO = CONFIG.fmtSQuoteOpen.strip()[:1]
                 qC = CONFIG.fmtSQuoteClose.strip()[:1]
-                if qO == qC:
+                if qO == qC or qC in self.AMBIGUOUS:
                     rx.append(f"(?:\\B{qO}.+?{qC}\\B)")
                 else:
                     rx.append(f"(?:{qO}[^{qO}]+{qC})")
@@ -102,7 +102,7 @@ class RegExPatterns:
             if CONFIG.dialogStyle in (2, 3):
                 qO = CONFIG.fmtDQuoteOpen.strip()[:1]
                 qC = CONFIG.fmtDQuoteClose.strip()[:1]
-                if qO == qC:
+                if qO == qC or qC in self.AMBIGUOUS:
                     rx.append(f"(?:\\B{qO}.+?{qC}\\B)")
                 else:
                     rx.append(f"(?:{qO}[^{qO}]+{qC})")
diff --git a/tests/test_text/test_text_patterns.py b/tests/test_text/test_text_patterns.py
index ee938e10..e6a8b599 100644
--- a/tests/test_text/test_text_patterns.py
+++ b/tests/test_text/test_text_patterns.py
@@ -310,11 +310,11 @@ def testTextPatterns_DialogueStyle():
     assert allMatches(regEx, 'one "two" three') == []
 
     # Check with no whitespace, single quote
-    assert allMatches(regEx, "one\u2018two\u2019three") == [
-        [("\u2018two\u2019", 3, 8)]
-    ]
-    assert allMatches(regEx, "one\u2018two\u2019 three") == [
-        [("\u2018two\u2019", 3, 8)]
+    # The apostrophe ambiguity rule should kick in here
+    assert allMatches(regEx, "one\u2018two\u2019three") == []
+    assert allMatches(regEx, "one\u2018two\u2019 three") == []
+    assert allMatches(regEx, "one \u2018two\u02bc three\u2019 four") == [
+        [("\u2018two\u02bc three\u2019", 4, 16)],
     ]
 
     # Check with no whitespace, double quote