diff --git a/picard/formats/id3.py b/picard/formats/id3.py
index b47a8ae31..130896aa9 100644
--- a/picard/formats/id3.py
+++ b/picard/formats/id3.py
@@ -485,10 +485,13 @@ class ID3File(File):
                     if frameid == 'WCOP':
                         # Only add WCOP if there is only one license URL, otherwise use TXXX:LICENSE
                         if len(values) > 1 or not valid_urls:
+                            tags.delall('WCOP')
                             tags.add(self.build_TXXX(encoding, self.__rtranslate_freetext[name], values))
                         else:
+                            tags.delall('TXXX:' + self.__rtranslate_freetext[name])
                             tags.add(id3.WCOP(url=values[0]))
                     elif frameid == 'WOAR' and valid_urls:
+                        tags.delall('WOAR')
                         for url in values:
                             tags.add(id3.WOAR(url=url))
                 elif frameid.startswith('T') or frameid == 'MVNM':
@@ -574,13 +577,16 @@ class ID3File(File):
                     for key, frame in list(tags.items()):
                         if frame.FrameID == 'UFID' and frame.owner == 'http://musicbrainz.org':
                             del tags[key]
+                elif name == 'license':
+                    tags.delall(real_name)
+                    tags.delall('TXXX:' + self.__rtranslate_freetext[name])
                 elif real_name == 'POPM':
                     user_email = config.setting['rating_user_email']
                     for key, frame in list(tags.items()):
                         if frame.FrameID == 'POPM' and frame.email == user_email:
                             del tags[key]
                 elif real_name in self.__translate:
-                    del tags[real_name]
+                    tags.delall(real_name)
                 elif name.lower() in self.__rtranslate_freetext_ci:
                     delall_ci(tags, 'TXXX:' + self.__rtranslate_freetext_ci[name.lower()])
                 elif real_name in self.__translate_freetext:
diff --git a/test/formats/test_id3.py b/test/formats/test_id3.py
index 6b5291ea1..8e065a355 100644
--- a/test/formats/test_id3.py
+++ b/test/formats/test_id3.py
@@ -454,6 +454,68 @@ class CommonId3Tests:
             self.assertIn('http://example.com/1', loaded_licenses)
             self.assertIn('http://example.com/2', loaded_licenses)
 
+        @skipUnlessTestfile
+        def test_license_upgrade_wcop(self):
+            tags = mutagen.id3.ID3Tags()
+            tags.add(mutagen.id3.WCOP(url='http://example.com/1'))
+            save_raw(self.filename, tags)
+            metadata = load_metadata(self.filename)
+            self.assertEqual('http://example.com/1', metadata['license'])
+            metadata.add('license', 'http://example.com/2')
+            save_metadata(self.filename, metadata)
+            raw_metadata = load_raw(self.filename)
+            self.assertNotIn('WCOP', raw_metadata)
+            loaded_licenses = [url for url in raw_metadata['TXXX:LICENSE']]
+            self.assertEqual(['http://example.com/1', 'http://example.com/2'], loaded_licenses)
+
+        @skipUnlessTestfile
+        def test_license_downgrade_wcop(self):
+            tags = mutagen.id3.ID3Tags()
+            licenses = ['http://example.com/1', 'http://example.com/2']
+            tags.add(mutagen.id3.TXXX(desc='LICENSE', text=licenses))
+            save_raw(self.filename, tags)
+            raw_metadata = load_raw(self.filename)
+            metadata = load_metadata(self.filename)
+            self.assertEqual(licenses, metadata.getall('license'))
+            metadata['license'] = 'http://example.com/1'
+            save_metadata(self.filename, metadata)
+            raw_metadata = load_raw(self.filename)
+            self.assertEqual('http://example.com/1', raw_metadata['WCOP'])
+            self.assertNotIn('TXXX:LICENSE', raw_metadata)
+
+        @skipUnlessTestfile
+        def test_license_delete(self):
+            tags = mutagen.id3.ID3Tags()
+            tags.add(mutagen.id3.WCOP(url='http://example.com/1'))
+            tags.add(mutagen.id3.TXXX(desc='LICENSE', text='http://example.com/2'))
+            save_raw(self.filename, tags)
+            metadata = load_metadata(self.filename)
+            del metadata['license']
+            loaded_metadata = save_and_load_metadata(self.filename, metadata)
+            self.assertNotIn('license', loaded_metadata)
+
+        @skipUnlessTestfile
+        def test_woar_not_duplicated(self):
+            metadata = Metadata({
+                'website': 'http://example.com/1'
+            })
+            loaded_metadata = save_and_load_metadata(self.filename, metadata)
+            self.assertEqual(metadata['website'], loaded_metadata['website'])
+            metadata['website'] = 'http://example.com/2'
+            loaded_metadata = save_and_load_metadata(self.filename, metadata)
+            self.assertEqual(metadata['website'], loaded_metadata['website'])
+
+        @skipUnlessTestfile
+        def test_woar_delete(self):
+            metadata = Metadata({
+                'website': 'http://example.com/1'
+            })
+            loaded_metadata = save_and_load_metadata(self.filename, metadata)
+            self.assertEqual(metadata['website'], loaded_metadata['website'])
+            del metadata['website']
+            loaded_metadata = save_and_load_metadata(self.filename, metadata)
+            self.assertNotIn('website', loaded_metadata)
+
 
 class MP3Test(CommonId3Tests.Id3TestCase):
     testfile = 'test.mp3'