diff --git a/picard/coverart/image.py b/picard/coverart/image.py
index 186eab392..70f737969 100644
--- a/picard/coverart/image.py
+++ b/picard/coverart/image.py
@@ -273,9 +273,7 @@ class CoverArtImage:
             metadata.add_unique("coverart_types", cover_type)
         filename = ScriptParser().eval(filename, metadata)
         if config.setting["ascii_filenames"]:
-            if isinstance(filename, str):
-                filename = unaccent(filename)
-            filename = replace_non_ascii(filename)
+            filename = replace_non_ascii(filename, pathsave=True)
         if not filename:
             filename = "cover"
         if not os.path.isabs(filename):
diff --git a/picard/file.py b/picard/file.py
index 0eec71480..50cb32e5e 100644
--- a/picard/file.py
+++ b/picard/file.py
@@ -314,9 +314,7 @@ class File(QtCore.QObject, Item):
         naming_format = naming_format.replace("\t", "").replace("\n", "")
         filename = ScriptParser().eval(naming_format, metadata, self)
         if settings["ascii_filenames"]:
-            if isinstance(filename, str):
-                filename = unaccent(filename)
-            filename = replace_non_ascii(filename)
+            filename = replace_non_ascii(filename, pathsave=True)
         # replace incompatible characters
         if settings["windows_compatibility"] or sys.platform == "win32":
             filename = replace_win32_incompat(filename)
diff --git a/picard/util/textencoding.py b/picard/util/textencoding.py
index 35b095c65..6d09ec4cf 100644
--- a/picard/util/textencoding.py
+++ b/picard/util/textencoding.py
@@ -65,6 +65,8 @@ from functools import partial
 import re
 import unicodedata
 
+from picard.util import sanitize_filename
+
 #########################  LATIN SIMPLIFICATION ###########################
 # The translation tables for punctuation and latin combined-characters are taken from
 # http://unicode.org/repos/cldr/trunk/common/transforms/Latin-ASCII.xml
@@ -175,10 +177,11 @@ _simplify_punctuation = {
     "\u200B": "",  # Zero Width Space
 }
 _re_simplify_punctuation = _re_any(_simplify_punctuation.keys())
+_pathsave_simplify_punctuation = {k: sanitize_filename(v) for k, v in _simplify_punctuation.items()}
 
-
-def unicode_simplify_punctuation(string):
-    return _re_simplify_punctuation.sub(lambda m: _simplify_punctuation[m.group(0)], string)
+def unicode_simplify_punctuation(string, pathsave=False):
+    punctuation = _pathsave_simplify_punctuation if pathsave else _simplify_punctuation
+    return _re_simplify_punctuation.sub(lambda m: punctuation[m.group(0)], string)
 
 
 _simplify_combinations = {
@@ -407,10 +410,12 @@ _simplify_combinations = {
     "\u01BE": "ts",  # LATIN LETTER TS LIGATION (see http://unicode.org/notes/tn27/)
 }
 _re_simplify_combinations = _re_any(_simplify_combinations)
+_pathsave_simplify_combinations = {k: sanitize_filename(v) for k, v in _simplify_combinations.items()}
 
 
-def unicode_simplify_combinations(string):
-    return _re_simplify_combinations.sub(lambda m: _simplify_combinations[m.group(0)], string)
+def unicode_simplify_combinations(string, pathsave=False):
+    combinations = _pathsave_simplify_combinations if pathsave else _simplify_combinations
+    return _re_simplify_combinations.sub(lambda m: combinations[m.group(0)], string)
 
 
 def unicode_simplify_accents(string):
@@ -428,15 +433,15 @@ def unaccent(string):
     return unicode_simplify_accents(string)
 
 
-def replace_non_ascii(string, repl="_"):
+def replace_non_ascii(string, repl="_", pathsave=False):
     """Replace non-ASCII characters from ``string`` by ``repl``."""
-    interim = unicode_simplify_combinations(string)
+    interim = unicode_simplify_combinations(string, pathsave)
     interim = unicode_simplify_accents(interim)
-    interim = unicode_simplify_punctuation(interim)
+    interim = unicode_simplify_punctuation(interim, pathsave)
     interim = unicode_simplify_compatibility(interim)
 
     def error_repl(e, repl="_"):
-        return(repl, e.start + 1)
+        return (repl, e.start + 1)
     codecs.register_error('repl', partial(error_repl, repl=repl))
     # Decoding and encoding to allow replacements
     return interim.encode('ascii', 'repl').decode('ascii')
diff --git a/test/test_textencoding.py b/test/test_textencoding.py
index d81cc1292..7d511e9ad 100644
--- a/test/test_textencoding.py
+++ b/test/test_textencoding.py
@@ -128,6 +128,10 @@ class PunctuationTest(unittest.TestCase):
         self.assertEqual(util.textencoding.unicode_simplify_punctuation(combinations_from), combinations_from)
         self.assertEqual(util.textencoding.unicode_simplify_punctuation(ascii_chars), ascii_chars)
 
+    def test_pathsave(self):
+        self.assertEqual(util.textencoding.unicode_simplify_punctuation('\u2215', True), '_')
+        self.assertEqual(util.textencoding.unicode_simplify_punctuation('/\\\u2215', True), '/\\_')
+
     def test_incorrect(self):
         pass
 
@@ -141,6 +145,10 @@ class CombinationsTest(unittest.TestCase):
         self.assertEqual(util.textencoding.unicode_simplify_combinations(punctuation_from), punctuation_from)
         self.assertEqual(util.textencoding.unicode_simplify_combinations(ascii_chars), ascii_chars)
 
+    def test_pathsave(self):
+        self.assertEqual(util.textencoding.unicode_simplify_combinations('8½', True), '8 1_2')
+        self.assertEqual(util.textencoding.unicode_simplify_combinations('8/\\½', True), '8/\\ 1_2')
+
     def test_incorrect(self):
         pass
 
@@ -191,6 +199,9 @@ class ReplaceNonAsciiTest(unittest.TestCase):
         self.assertEqual(util.textencoding.replace_non_ascii(u"⒈ ⒉ ⒊"), u"1. 2. 3.") # Digit full stop
         self.assertEqual(util.textencoding.replace_non_ascii(u"１２３"), u"123") # Fullwidth digits
 
+    def test_pathsave(self):
+        self.assertEqual(util.textencoding.replace_non_ascii('\u2044/8½\\', pathsave=True), '_/8 1_2\\')
+
     def test_incorrect(self):
         self.assertNotEqual(util.textencoding.replace_non_ascii(u"Lukáš"), u"Lukáš")
         self.assertNotEqual(util.textencoding.replace_non_ascii(u"Lukáš"), u"Luk____")