diff --git a/yt_dlp/update.py b/yt_dlp/update.py
index 4fbe7bd7e7..26f18bddab 100644
--- a/yt_dlp/update.py
+++ b/yt_dlp/update.py
@@ -48,10 +48,10 @@ def detect_variant():
 _NON_UPDATEABLE_REASONS = {
     'exe': None,
     'zip': None,
-    'dir': 'Auto-update is not supported for unpackaged windows executable. Re-download the latest release',
-    'py2exe': 'There is no official release for py2exe executable. Build it again with the latest source code',
-    'source': 'You cannot update when running from source code',
-    'unknown': 'It looks like you installed yt-dlp with a package manager, pip, setup.py or a tarball. Use that to update',
+    'dir': 'Auto-update is not supported for unpackaged windows executable; Re-download the latest release',
+    'py2exe': 'There is no official release for py2exe executable; Build it again with the latest source code',
+    'source': 'You cannot update when running from source code; Use git to pull the latest changes',
+    'unknown': 'It looks like you installed yt-dlp with a package manager, pip, setup.py or a tarball; Use that to update',
 }
 
 
@@ -59,40 +59,6 @@ def is_non_updateable():
     return _NON_UPDATEABLE_REASONS.get(detect_variant(), _NON_UPDATEABLE_REASONS['unknown'])
 
 
-def update_self(to_screen, verbose, opener):
-    ''' Exists for backward compatibility. Use run_update(ydl) instead '''
-
-    printfn = to_screen
-
-    class FakeYDL():
-        _opener = opener
-        to_screen = printfn
-
-        @staticmethod
-        def report_warning(msg, *args, **kwargs):
-            return printfn('WARNING: %s' % msg, *args, **kwargs)
-
-        @staticmethod
-        def report_error(msg, tb=None):
-            printfn('ERROR: %s' % msg)
-            if not verbose:
-                return
-            if tb is None:
-                # Copied from YoutubeDl.trouble
-                if sys.exc_info()[0]:
-                    tb = ''
-                    if hasattr(sys.exc_info()[1], 'exc_info') and sys.exc_info()[1].exc_info[0]:
-                        tb += ''.join(traceback.format_exception(*sys.exc_info()[1].exc_info))
-                    tb += encode_compat_str(traceback.format_exc())
-                else:
-                    tb_data = traceback.format_list(traceback.extract_stack())
-                    tb = ''.join(tb_data)
-            if tb:
-                printfn(tb)
-
-    return run_update(FakeYDL())
-
-
 def run_update(ydl):
     """
     Update the program file with the latest version from the repository
@@ -101,10 +67,17 @@ def run_update(ydl):
 
     JSON_URL = 'https://api.github.com/repos/yt-dlp/yt-dlp/releases/latest'
 
-    def report_error(msg, network=False, expected=False, delim=';'):
-        if network:
-            msg += '%s Visit  https://github.com/yt-dlp/yt-dlp/releases/latest' % delim
-        ydl.report_error(msg, tb='' if network or expected else None)
+    def report_error(msg, expected=False):
+        ydl.report_error(msg, tb='' if expected else None)
+
+    def report_unable(action, expected=False):
+        report_error(f'Unable to {action}', expected)
+
+    def report_permission_error(file):
+        report_unable(f'write to {file}; Try running as administrator', True)
+
+    def report_network_error(action, delim=';'):
+        report_unable(f'{action}{delim} Visit  https://github.com/yt-dlp/yt-dlp/releases/latest', True)
 
     def calc_sha256sum(path):
         h = hashlib.sha256()
@@ -120,7 +93,7 @@ def run_update(ydl):
         version_info = ydl._opener.open(JSON_URL).read().decode('utf-8')
         version_info = json.loads(version_info)
     except Exception:
-        return report_error('can\'t obtain versions info. Please try again later ', True, delim='or')
+        return report_network_error('obtain version info', delim='; Please try again later or')
 
     def version_tuple(version_str):
         return tuple(map(int, version_str.split('.')))
@@ -133,7 +106,7 @@ def run_update(ydl):
     err = is_non_updateable()
     if err:
         ydl.to_screen(f'Latest version: {version_id}, Current version: {__version__}')
-        return report_error(err, expected=True)
+        return report_error(err, True)
 
     # sys.executable is set to the full pathname of the exe-file for py2exe
     # though symlinks are not followed so that we need to do this manually
@@ -163,55 +136,57 @@ def run_update(ydl):
         return dict(ln.split()[::-1] for ln in hash_data.splitlines()).get(filename)
 
     if not os.access(filename, os.W_OK):
-        return report_error('no write permissions on %s' % filename, expected=True)
+        return report_permission_error(filename)
 
     # PyInstaller
     if hasattr(sys, 'frozen'):
         exe = filename
         directory = os.path.dirname(exe)
         if not os.access(directory, os.W_OK):
-            return report_error('no write permissions on %s' % directory, expected=True)
+            return report_permission_error(directory)
         try:
             if os.path.exists(filename + '.old'):
                 os.remove(filename + '.old')
         except (IOError, OSError):
-            return report_error('unable to remove the old version')
+            return report_unable('remove the old version')
 
         try:
             arch = platform.architecture()[0][:2]
             url = get_bin_info('exe', arch).get('browser_download_url')
             if not url:
-                return report_error('unable to fetch updates', True)
+                return report_network_error('fetch updates')
             urlh = ydl._opener.open(url)
             newcontent = urlh.read()
             urlh.close()
-        except (IOError, OSError, StopIteration):
-            return report_error('unable to download latest version', True)
+        except (IOError, OSError):
+            return report_network_error('download latest version')
 
+        if not os.access(exe + '.new', os.W_OK):
+            return report_permission_error(f'{exe}.new')
         try:
             with open(exe + '.new', 'wb') as outf:
                 outf.write(newcontent)
         except (IOError, OSError):
-            return report_error('unable to write the new version')
+            return report_unable('write the new version')
 
         expected_sum = get_sha256sum('exe', arch)
         if not expected_sum:
             ydl.report_warning('no hash information found for the release')
         elif calc_sha256sum(exe + '.new') != expected_sum:
-            report_error('unable to verify the new executable', True)
+            report_network_error('verify the new executable')
             try:
                 os.remove(exe + '.new')
             except OSError:
-                return report_error('unable to remove corrupt download')
+                return report_unable('remove corrupt download')
 
         try:
             os.rename(exe, exe + '.old')
         except (IOError, OSError):
-            return report_error('unable to move current version')
+            return report_unable('move current version')
         try:
             os.rename(exe + '.new', exe)
         except (IOError, OSError):
-            report_error('unable to overwrite current version')
+            report_unable('overwrite current version')
             os.rename(exe + '.old', exe)
             return
         try:
@@ -222,31 +197,31 @@ def run_update(ydl):
             ydl.to_screen('Updated yt-dlp to version %s' % version_id)
             return True  # Exit app
         except OSError:
-            report_error('unable to delete old version')
+            report_unable('delete the old version')
 
     # Zip unix package
     elif isinstance(globals().get('__loader__'), zipimporter):
         try:
             url = get_bin_info('zip', '3').get('browser_download_url')
             if not url:
-                return report_error('unable to fetch updates', True)
+                return report_network_error('fetch updates')
             urlh = ydl._opener.open(url)
             newcontent = urlh.read()
             urlh.close()
-        except (IOError, OSError, StopIteration):
-            return report_error('unable to download latest version', True)
+        except (IOError, OSError):
+            return report_network_error('download the latest version')
 
         expected_sum = get_sha256sum('zip', '3')
         if not expected_sum:
             ydl.report_warning('no hash information found for the release')
         elif hashlib.sha256(newcontent).hexdigest() != expected_sum:
-            return report_error('unable to verify the new zip', True)
+            return report_network_error('verify the new zip')
 
         try:
             with open(filename, 'wb') as outf:
                 outf.write(newcontent)
         except (IOError, OSError):
-            return report_error('unable to overwrite current version')
+            return report_unable('overwrite current version')
 
     ydl.to_screen('Updated yt-dlp to version %s; Restart yt-dlp to use the new version' % version_id)
 
@@ -267,3 +242,41 @@ def print_notes(to_screen, versions, fromVersion=__version__):
         for note in notes:
             to_screen(note)
 '''
+
+
+def update_self(to_screen, verbose, opener):
+    ''' Exists for backward compatibility '''
+
+    printfn = to_screen
+
+    printfn(
+        'WARNING: "yt_dlp.update.update_self" is deprecated and may be removed in a future version. '
+        'Use "yt_dlp.update.run_update(ydl)" instead')
+
+    class FakeYDL():
+        _opener = opener
+        to_screen = printfn
+
+        @staticmethod
+        def report_warning(msg, *args, **kwargs):
+            return printfn('WARNING: %s' % msg, *args, **kwargs)
+
+        @staticmethod
+        def report_error(msg, tb=None):
+            printfn('ERROR: %s' % msg)
+            if not verbose:
+                return
+            if tb is None:
+                # Copied from YoutubeDl.trouble
+                if sys.exc_info()[0]:
+                    tb = ''
+                    if hasattr(sys.exc_info()[1], 'exc_info') and sys.exc_info()[1].exc_info[0]:
+                        tb += ''.join(traceback.format_exception(*sys.exc_info()[1].exc_info))
+                    tb += encode_compat_str(traceback.format_exc())
+                else:
+                    tb_data = traceback.format_list(traceback.extract_stack())
+                    tb = ''.join(tb_data)
+            if tb:
+                printfn(tb)
+
+    return run_update(FakeYDL())