diff --git a/pyinst.py b/pyinst.py
index 292f5d7192..d27e565551 100644
--- a/pyinst.py
+++ b/pyinst.py
@@ -5,7 +5,6 @@ import sys
 
 from PyInstaller.__main__ import run as run_pyinstaller
 
-
 OS_NAME, ARCH = sys.platform, platform.architecture()[0][:2]
 
 
diff --git a/yt_dlp/compat/__init__.py b/yt_dlp/compat/__init__.py
index 35875ed20e..3a91fad0e0 100644
--- a/yt_dlp/compat/__init__.py
+++ b/yt_dlp/compat/__init__.py
@@ -55,7 +55,7 @@ if compat_os_name == 'nt' and sys.version_info < (3, 8):
     def compat_realpath(path):
         while os.path.islink(path):
             path = os.path.abspath(os.readlink(path))
-        return path
+        return os.path.realpath(path)
 else:
     compat_realpath = os.path.realpath
 
diff --git a/yt_dlp/update.py b/yt_dlp/update.py
index 85c676e003..68418ce981 100644
--- a/yt_dlp/update.py
+++ b/yt_dlp/update.py
@@ -11,8 +11,8 @@ from .compat import compat_realpath
 from .utils import Popen, traverse_obj, version_tuple
 from .version import __version__
 
-
-RELEASE_JSON_URL = 'https://api.github.com/repos/yt-dlp/yt-dlp/releases/latest'
+REPOSITORY = 'yt-dlp/yt-dlp'
+API_URL = f'https://api.github.com/repos/{REPOSITORY}/releases/latest'
 
 
 @functools.cache
@@ -60,137 +60,176 @@ def is_non_updateable():
     return _NON_UPDATEABLE_REASONS.get(detect_variant(), _NON_UPDATEABLE_REASONS['other'])
 
 
-def run_update(ydl):
-    """
-    Update the program file with the latest version from the repository
-    Returns whether the program should terminate
-    """
+def _sha256_file(path):
+    h = hashlib.sha256()
+    mv = memoryview(bytearray(128 * 1024))
+    with open(os.path.realpath(path), 'rb', buffering=0) as f:
+        for n in iter(lambda: f.readinto(mv), 0):
+            h.update(mv[:n])
+    return h.hexdigest()
 
-    def report_error(msg, expected=False):
-        ydl.report_error(msg, tb=False if expected else None)
 
-    def report_unable(action, expected=False):
-        report_error(f'Unable to {action}', expected)
+class Updater:
+    def __init__(self, ydl):
+        self.ydl = ydl
 
-    def report_permission_error(file):
-        report_unable(f'write to {file}; Try running as administrator', True)
+    @functools.cached_property
+    def _new_version_info(self):
+        self.ydl.write_debug(f'Fetching release info: {API_URL}')
+        return json.loads(self.ydl.urlopen(API_URL).read().decode())
 
-    def report_network_error(action, delim=';'):
-        report_unable(f'{action}{delim} Visit  https://github.com/yt-dlp/yt-dlp/releases/latest', True)
+    @property
+    def current_version(self):
+        """Current version"""
+        return __version__
 
-    def calc_sha256sum(path):
-        h = hashlib.sha256()
-        mv = memoryview(bytearray(128 * 1024))
-        with open(os.path.realpath(path), 'rb', buffering=0) as f:
-            for n in iter(lambda: f.readinto(mv), 0):
-                h.update(mv[:n])
-        return h.hexdigest()
+    @property
+    def new_version(self):
+        """Version of the latest release"""
+        return self._new_version_info['tag_name']
 
-    try:
-        version_info = json.loads(ydl.urlopen(RELEASE_JSON_URL).read().decode())
-    except Exception:
-        return report_network_error('obtain version info', delim='; Please try again later or')
+    @property
+    def has_update(self):
+        """Whether there is an update available"""
+        return version_tuple(__version__) < version_tuple(self.new_version)
 
-    version_id = version_info['tag_name']
-    ydl.to_screen(f'Latest version: {version_id}, Current version: {__version__}')
-    if version_tuple(__version__) >= version_tuple(version_id):
-        ydl.to_screen(f'yt-dlp is up to date ({__version__})')
-        return
+    @functools.cached_property
+    def filename(self):
+        """Filename of the executable"""
+        return compat_realpath(_get_variant_and_executable_path()[1])
 
-    err = is_non_updateable()
-    if err:
-        return report_error(err, True)
-
-    variant, filename = _get_variant_and_executable_path()
-    filename = compat_realpath(filename)  # Absolute path, following symlinks
-
-    label = _FILE_SUFFIXES[variant]
-    if label and platform.architecture()[0][:2] == '32':
-        label = f'_x86{label}'
-    release_name = f'yt-dlp{label}'
-
-    ydl.to_screen(f'Current Build Hash {calc_sha256sum(filename)}')
-    ydl.to_screen(f'Updating to version {version_id} ...')
-
-    def get_file(name, fatal=True):
-        error = report_network_error if fatal else lambda _: None
-        url = traverse_obj(
-            version_info, ('assets', lambda _, v: v['name'] == name, 'browser_download_url'), get_all=False)
+    def _download(self, name=None):
+        name = name or self.release_name
+        url = traverse_obj(self._new_version_info, (
+            'assets', lambda _, v: v['name'] == name, 'browser_download_url'), get_all=False)
         if not url:
-            return error('fetch updates')
-        try:
-            return ydl.urlopen(url).read()
-        except OSError:
-            return error('download latest version')
+            raise Exception('Unable to find download URL')
+        self.ydl.write_debug(f'Downloading {name} from {url}')
+        return self.ydl.urlopen(url).read()
 
-    def verify(content):
-        if not content:
-            return False
-        hash_data = get_file('SHA2-256SUMS', fatal=False) or b''
-        expected = dict(ln.split()[::-1] for ln in hash_data.decode().splitlines()).get(release_name)
-        if not expected:
-            ydl.report_warning('no hash information found for the release')
-        elif hashlib.sha256(content).hexdigest() != expected:
-            return report_network_error('verify the new executable')
+    @functools.cached_property
+    def release_name(self):
+        """The release filename"""
+        label = _FILE_SUFFIXES[detect_variant()]
+        if label and platform.architecture()[0][:2] == '32':
+            label = f'_x86{label}'
+        return f'yt-dlp{label}'
+
+    @functools.cached_property
+    def release_hash(self):
+        """Hash of the latest release"""
+        hash_data = dict(ln.split()[::-1] for ln in self._download('SHA2-256SUMS').decode().splitlines())
+        return hash_data[self.release_name]
+
+    def _report_error(self, msg, expected=False):
+        self.ydl.report_error(msg, tb=False if expected else None)
+
+    def _report_permission_error(self, file):
+        self._report_error(f'Unable to write to {file}; Try running as administrator', True)
+
+    def _report_network_error(self, action, delim=';'):
+        self._report_error(f'Unable to {action}{delim} Visit  https://github.com/{REPOSITORY}/releases/latest', True)
+
+    def check_update(self):
+        """Report whether there is an update available"""
+        try:
+            self.ydl.to_screen(
+                f'Latest version: {self.new_version}, Current version: {self.current_version}')
+        except Exception:
+            return self._report_network_error('obtain version info', delim='; Please try again later or')
+
+        if not self.has_update:
+            return self.ydl.to_screen(f'yt-dlp is up to date ({__version__})')
+
+        if not is_non_updateable():
+            self.ydl.to_screen(f'Current Build Hash {_sha256_file(self.filename)}')
         return True
 
-    directory = os.path.dirname(filename)
-    if not os.access(filename, os.W_OK):
-        return report_permission_error(filename)
-    elif not os.access(directory, os.W_OK):
-        return report_permission_error(directory)
+    def update(self):
+        """Update yt-dlp executable to the latest version"""
+        if not self.check_update():
+            return
+        err = is_non_updateable()
+        if err:
+            return self._report_error(err, True)
+        self.ydl.to_screen(f'Updating to version {self.new_version} ...')
 
-    new_filename, old_filename = f'{filename}.new', f'{filename}.old'
-    if variant == 'zip':  # Can be replaced in-place
-        new_filename, old_filename = filename, None
+        directory = os.path.dirname(self.filename)
+        if not os.access(self.filename, os.W_OK):
+            return self._report_permission_error(self.filename)
+        elif not os.access(directory, os.W_OK):
+            return self._report_permission_error(directory)
 
-    try:
-        if os.path.exists(old_filename or ''):
-            os.remove(old_filename)
-    except OSError:
-        return report_unable('remove the old version')
+        new_filename, old_filename = f'{self.filename}.new', f'{self.filename}.old'
+        if detect_variant() == 'zip':  # Can be replaced in-place
+            new_filename, old_filename = self.filename, None
 
-    newcontent = get_file(release_name)
-    if not verify(newcontent):
-        return
-    try:
-        with open(new_filename, 'wb') as outf:
-            outf.write(newcontent)
-    except OSError:
-        return report_permission_error(new_filename)
+        try:
+            if os.path.exists(old_filename or ''):
+                os.remove(old_filename)
+        except OSError:
+            return self._report_error('Unable to remove the old version')
 
-    try:
-        if old_filename:
-            os.rename(filename, old_filename)
-    except OSError:
-        return report_unable('move current version')
-    try:
-        if old_filename:
-            os.rename(new_filename, filename)
-    except OSError:
-        report_unable('overwrite current version')
-        os.rename(old_filename, filename)
-        return
+        try:
+            newcontent = self._download()
+        except OSError:
+            return self._report_network_error('download latest version')
+        except Exception:
+            return self._report_network_error('fetch updates')
 
-    if variant not in ('win32_exe', 'py2exe'):
-        if old_filename:
-            os.remove(old_filename)
-        ydl.to_screen(f'Updated yt-dlp to version {version_id}; Restart yt-dlp to use the new version')
-        return
+        try:
+            expected_hash = self.release_hash
+        except Exception:
+            self.ydl.report_warning('no hash information found for the release')
+        else:
+            if hashlib.sha256(newcontent).hexdigest() != expected_hash:
+                return self._report_network_error('verify the new executable')
 
-    try:
-        # Continues to run in the background
-        Popen(f'ping 127.0.0.1 -n 5 -w 1000 & del /F "{old_filename}"',
-              shell=True, stdout=subprocess.DEVNULL, stderr=subprocess.DEVNULL)
-        ydl.to_screen(f'Updated yt-dlp to version {version_id}')
-        return True  # Exit app
-    except OSError:
-        report_unable('delete the old version')
+        try:
+            with open(new_filename, 'wb') as outf:
+                outf.write(newcontent)
+        except OSError:
+            return self._report_permission_error(new_filename)
+
+        try:
+            if old_filename:
+                os.rename(self.filename, old_filename)
+        except OSError:
+            return self._report_error('Unable to move current version')
+        try:
+            if old_filename:
+                os.rename(new_filename, self.filename)
+        except OSError:
+            self._report_error('Unable to overwrite current version')
+            return os.rename(old_filename, self.filename)
+
+        if detect_variant() not in ('win32_exe', 'py2exe'):
+            if old_filename:
+                os.remove(old_filename)
+            self.ydl.to_screen(f'Updated yt-dlp to version {self.new_version}; Restart yt-dlp to use the new version')
+            return
+
+        try:
+            # Continues to run in the background
+            Popen(f'ping 127.0.0.1 -n 5 -w 1000 & del /F "{old_filename}"',
+                shell=True, stdout=subprocess.DEVNULL, stderr=subprocess.DEVNULL)
+            self.ydl.to_screen(f'Updated yt-dlp to version {self.new_version}')
+            return True  # Exit app
+        except OSError:
+            self._report_unable('delete the old version')
+
+
+def run_update(ydl):
+    """Update the program file with the latest version from the repository
+    @returns    Whether there was a successfull update (No update = False)
+    """
+    return Updater(ydl).update()
 
 
 # Deprecated
 def update_self(to_screen, verbose, opener):
     import traceback
+
     from .utils import write_string
 
     write_string(
@@ -202,12 +241,10 @@ def update_self(to_screen, verbose, opener):
     class FakeYDL():
         to_screen = printfn
 
-        @staticmethod
-        def report_warning(msg, *args, **kwargs):
+        def report_warning(self, msg, *args, **kwargs):
             return printfn(f'WARNING: {msg}', *args, **kwargs)
 
-        @staticmethod
-        def report_error(msg, tb=None):
+        def report_error(self, msg, tb=None):
             printfn(f'ERROR: {msg}')
             if not verbose:
                 return
@@ -224,6 +261,9 @@ def update_self(to_screen, verbose, opener):
             if tb:
                 printfn(tb)
 
+        def write_debug(self, msg, *args, **kwargs):
+            printfn(f'[debug] {msg}', *args, **kwargs)
+
         def urlopen(self, url):
             return opener.open(url)
 
diff --git a/yt_dlp/utils.py b/yt_dlp/utils.py
index 10bcd5f4ec..dc6894d83d 100644
--- a/yt_dlp/utils.py
+++ b/yt_dlp/utils.py
@@ -991,9 +991,10 @@ def make_HTTPS_handler(params, **kwargs):
 
 
 def bug_reports_message(before=';'):
-    msg = ('please report this issue on  https://github.com/yt-dlp/yt-dlp/issues?q= , '
-           'filling out the appropriate issue template. '
-           'Confirm you are on the latest version using  yt-dlp -U')
+    from .update import REPOSITORY
+
+    msg = (f'please report this issue on  https://github.com/{REPOSITORY}/issues?q= , '
+           'filling out the appropriate issue template. Confirm you are on the latest version using  yt-dlp -U')
 
     before = before.rstrip()
     if not before or before.endswith(('.', '!', '?')):