diff --git a/youtube_dl/compat.py b/youtube_dl/compat.py
index c75ab131b..d1b86bd13 100644
--- a/youtube_dl/compat.py
+++ b/youtube_dl/compat.py
@@ -2754,6 +2754,17 @@ else:
         compat_expanduser = os.path.expanduser
 
 
+if compat_os_name == 'nt' and sys.version_info < (3, 8):
+    # os.path.realpath on Windows does not follow symbolic links
+    # prior to Python 3.8 (see https://bugs.python.org/issue9949)
+    def compat_realpath(path):
+        while os.path.islink(path):
+            path = os.path.abspath(os.readlink(path))
+        return path
+else:
+    compat_realpath = os.path.realpath
+
+
 if sys.version_info < (3, 0):
     def compat_print(s):
         from .utils import preferredencoding
@@ -2998,6 +3009,7 @@ __all__ = [
     'compat_os_name',
     'compat_parse_qs',
     'compat_print',
+    'compat_realpath',
     'compat_setenv',
     'compat_shlex_quote',
     'compat_shlex_split',
diff --git a/youtube_dl/update.py b/youtube_dl/update.py
index 002ea7f33..84c964617 100644
--- a/youtube_dl/update.py
+++ b/youtube_dl/update.py
@@ -9,6 +9,7 @@ import subprocess
 import sys
 from zipimport import zipimporter
 
+from .compat import compat_realpath
 from .utils import encode_compat_str
 
 from .version import __version__
@@ -84,7 +85,9 @@ def update_self(to_screen, verbose, opener):
     print_notes(to_screen, versions_info['versions'])
 
     # sys.executable is set to the full pathname of the exe-file for py2exe
-    filename = sys.executable if hasattr(sys, 'frozen') else sys.argv[0]
+    # though symlinks are not followed so that we need to do this manually
+    # with help of realpath
+    filename = compat_realpath(sys.executable if hasattr(sys, 'frozen') else sys.argv[0])
 
     if not os.access(filename, os.W_OK):
         to_screen('ERROR: no write permissions on %s' % filename)