diff --git a/certbot/CHANGELOG.md b/certbot/CHANGELOG.md
index 28a866731..92ceba3fb 100644
--- a/certbot/CHANGELOG.md
+++ b/certbot/CHANGELOG.md
@@ -14,7 +14,8 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
 
 ### Fixed
 
-*
+* Fixed a bug where argument sources weren't correctly detected in abbreviated
+  arguments, short arguments, and some other circumstances
 
 More details about these changes can be found on our GitHub repo.
 
diff --git a/certbot/certbot/_internal/cli/helpful.py b/certbot/certbot/_internal/cli/helpful.py
index f42096ded..6fea1b131 100644
--- a/certbot/certbot/_internal/cli/helpful.py
+++ b/certbot/certbot/_internal/cli/helpful.py
@@ -187,10 +187,12 @@ class HelpfulArgumentParser:
         #   2. config files
         #   3. env vars (shouldn't be any)
         #   4. command line
+
         def update_result(settings_dict: Dict[str, Tuple[configargparse.Action, str]],
                           source: ArgumentSource) -> None:
-            actions = [action for _, (action, _) in settings_dict.items()]
-            result.update({ action.dest: source for action in actions})
+            actions = [self._find_action_for_arg(arg) if action is None else action
+                       for arg, (action, _) in settings_dict.items()]
+            result.update({ action.dest: source for action in actions })
 
         # config file sources look like "config_file|<name of file>"
         for source_key in source_to_settings_dict:
@@ -203,17 +205,59 @@ class HelpfulArgumentParser:
         if 'command_line' in source_to_settings_dict:
             settings_dict: Dict[str, Tuple[None, List[str]]]
             settings_dict = source_to_settings_dict['command_line'] # type: ignore
-            (_, args) = settings_dict['']
-            args = [arg for arg in args if arg.startswith('-')]
+            (_, unprocessed_args) = settings_dict['']
+            args = []
+            for arg in unprocessed_args:
+                # ignore non-arguments
+                if not arg.startswith('-'):
+                    continue
+
+                # special case for config file argument, which we don't have an action for
+                if arg in ['-c', '--config']:
+                    result['config_dir'] = ArgumentSource.COMMAND_LINE
+                    continue
+
+                if '=' in arg:
+                    arg = arg.split('=')[0]
+
+                if arg.startswith('--'):
+                    args.append(arg)
+                # for short args (ones that start with a single hyphen), handle
+                # the case of multiple short args together, e.g. "-tvm"
+                else:
+                    for short_arg in arg[1:]:
+                        args.append(f"-{short_arg}")
+
             for arg in args:
                 # find the action corresponding to this arg
-                for action in self.actions:
-                    if arg in action.option_strings:
-                        result[action.dest] = ArgumentSource.COMMAND_LINE
-                        continue
+                action = self._find_action_for_arg(arg)
+                result[action.dest] = ArgumentSource.COMMAND_LINE
 
         return result
 
+    def _find_action_for_arg(self, arg: str) -> configargparse.Action:
+        # Finds a configargparse Action which matches the given arg, where arg
+        # can either be preceded by hyphens (as on the command line) or not (as
+        # in config files)
+
+        # if the argument doesn't have leading hypens, prefix it so it can be
+        # compared directly w/ action option strings
+        if arg[0] != '-':
+            arg = '--' + arg
+
+        # first, check for exact matches
+        for action in self.actions:
+            if arg in action.option_strings:
+                return action
+
+        # now check for abbreviated (i.e. prefix) matches
+        for action in self.actions:
+            for option_string in action.option_strings:
+                if option_string.startswith(arg):
+                    return action
+
+        raise AssertionError(f"Action corresponding to argument {arg} is None")
+
     def parse_args(self) -> NamespaceConfig:
         """Parses command line arguments and returns the result.
 
diff --git a/certbot/certbot/_internal/tests/cli_test.py b/certbot/certbot/_internal/tests/cli_test.py
index 446b2252f..e4505dbee 100644
--- a/certbot/certbot/_internal/tests/cli_test.py
+++ b/certbot/certbot/_internal/tests/cli_test.py
@@ -552,6 +552,48 @@ class ParseTest(unittest.TestCase):
             ])
             assert_value_and_source(namespace, 'server', COMMAND_LINE_VALUE, ArgumentSource.COMMAND_LINE)
 
+    def test_abbreviated_arguments(self):
+        # Argparse's "allow_abbrev" option (which is True by default) allows
+        # for unambiguous partial arguments (e.g. "--preferred-chal dns" will be
+        # interepreted the same as "--preferred-challenges dns")
+        namespace = self.parse('--preferred-chal dns --no-dir')
+        assert_set_by_user_with_value(namespace, 'pref_challs', ['dns-01'])
+        assert_set_by_user_with_value(namespace, 'directory_hooks', False)
+
+        with tempfile.NamedTemporaryFile() as tmp_config:
+            tmp_config.close()  # close now because of compatibility issues on Windows
+            with open(tmp_config.name, 'w') as file_h:
+                file_h.write('preferred-chal = dns')
+
+            namespace = self.parse([
+                'certonly',
+                '--config', tmp_config.name,
+            ])
+            assert_set_by_user_with_value(namespace, 'pref_challs', ['dns-01'])
+
+    @mock.patch('certbot._internal.hooks.validate_hooks')
+    def test_argument_with_equals(self, unsused_mock_validate_hooks):
+        namespace = self.parse('-d=example.com')
+        assert_set_by_user_with_value(namespace, 'domains', ['example.com'])
+
+        # make sure it doesn't choke on equals signs being present in the argument value
+        plugins = disco.PluginsRegistry.find_all()
+        namespace = cli.prepare_and_parse_args(plugins, ['run', '--pre-hook="foo=bar"'])
+        assert_set_by_user_with_value(namespace, 'pre_hook', '"foo=bar"')
+
+    def test_adjacent_short_args(self):
+        namespace = self.parse('-tv')
+        assert_set_by_user_with_value(namespace, 'text_mode', True)
+        assert_set_by_user_with_value(namespace, 'verbose_count', 1)
+
+        namespace = self.parse('-tvvv')
+        assert_set_by_user_with_value(namespace, 'text_mode', True)
+        assert_set_by_user_with_value(namespace, 'verbose_count', 3)
+
+        namespace = self.parse('-tvm foo@example.com')
+        assert_set_by_user_with_value(namespace, 'text_mode', True)
+        assert_set_by_user_with_value(namespace, 'verbose_count', 1)
+        assert_set_by_user_with_value(namespace, 'email', 'foo@example.com')
 
 if __name__ == '__main__':
     sys.exit(pytest.main(sys.argv[1:] + [__file__]))  # pragma: no cover