diff --git a/CHANGES.md b/CHANGES.md
index f25b3879..f453fc6b 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -4,6 +4,11 @@
 * Change requirements for pure py3
 
 
+### 3.27.4 (2023-02-15 13:30:00 UTC)
+
+* Fix updating with running virtualenv
+
+
 ### 3.27.3 (2023-02-15 02:00:00 UTC)
 
 * Fix reading legacy autoProcessTV.cfg
diff --git a/gui/slick/interfaces/default/config_general.tmpl b/gui/slick/interfaces/default/config_general.tmpl
index 0818e2e6..9f604721 100644
--- a/gui/slick/interfaces/default/config_general.tmpl
+++ b/gui/slick/interfaces/default/config_general.tmpl
@@ -272,7 +272,7 @@
     #end for
 											</tbody>
 										</table>
-										<p class="extras">the above info may help with packages that don't update internally<br>manual installation tip: <code>python -m pip install -U --user package</code></p>
+										<p class="extras">the above info may help with packages that don't update internally<br>manual installation tip: <code>python -m pip install -U #echo $pip_user_arg#package</code></p>
 									</div>
 								</div>
 							</span>
diff --git a/lib/sg_helpers.py b/lib/sg_helpers.py
index e7ad08c1..4601b512 100644
--- a/lib/sg_helpers.py
+++ b/lib/sg_helpers.py
@@ -1733,3 +1733,13 @@ def iterate_chunk(lst, n):
     """
     for i in moves.range(0, len(lst), n):
         yield lst[i:i + n]
+
+
+def is_virtualenv():
+    # type: (...) -> bool
+    """
+    :return: True if virtualenv Python environment is detected
+    """
+    """Get base/real prefix, or `sys.prefix` if there is none."""
+    get_base_prefix_compat = getattr(sys, 'base_prefix', None) or getattr(sys, 'real_prefix', None) or sys.prefix
+    return get_base_prefix_compat != sys.prefix
diff --git a/sickgear/piper.py b/sickgear/piper.py
index 99ee0ee3..65217b8d 100644
--- a/sickgear/piper.py
+++ b/sickgear/piper.py
@@ -8,7 +8,7 @@ import os
 import re
 
 from json_helper import json_loads
-from sg_helpers import cmdline_runner
+from sg_helpers import cmdline_runner, is_virtualenv
 
 from _23 import filter_list, ordered_dict
 from six import iteritems, PY2
@@ -97,7 +97,7 @@ def initial_requirements():
                 run_pip(['uninstall', '-r', 'recommended-remove.txt'])
                 raise ValueError
         except (BaseException, ImportError):
-            run_pip(['install', '-U', '--user', '-r', 'requirements.txt'])
+            run_pip(['install', '-U'] + (['--user'], [])[is_virtualenv()] + ['-r', 'requirements.txt'])
             module = 'Cheetah'
             try:
                 locals()[module] = __import__(module)
@@ -319,7 +319,8 @@ def pip_update(loading_msg, updates_todo, data_dir):
         # exclude Cheetah3 to prevent `No matching distro found` and fallback to its legacy setup.py installer
         output, err, exit_status = run_pip(['install', '-U']
                                            + ([], ['--only-binary=:all:'])[cur_project_name not in ('Cheetah3', )]
-                                           + ['--user', '-r', piper_path, '--extra-index-url',
+                                           + (['--user'], [])[is_virtualenv()]
+                                           + ['-r', piper_path, '--extra-index-url',
                                               'https://gitlab+deploy-token-1599941:UNupqjtDab_zxNzvP2gA@gitlab.com/api/'
                                               'v4/projects/279215/packages/pypi/simple'])
         pip_version = None
diff --git a/sickgear/webserve.py b/sickgear/webserve.py
index cfbafc7a..b26ec8ff 100644
--- a/sickgear/webserve.py
+++ b/sickgear/webserve.py
@@ -39,7 +39,7 @@ from exceptions_helper import ex, MultipleShowObjectsException
 import exceptions_helper
 from json_helper import json_dumps, json_loads
 import sg_helpers
-from sg_helpers import remove_file, scantree
+from sg_helpers import remove_file, scantree, is_virtualenv
 
 import sickgear
 from . import classes, clients, config, db, helpers, history, image_cache, logger, name_cache, naming, \
@@ -7934,6 +7934,7 @@ class ConfigGeneral(Config):
         t.request_host = helpers.xhtml_escape(self.request.host_name, False)
         api_keys = '|||'.join([':::'.join(a) for a in sickgear.API_KEYS])
         t.api_keys = api_keys and sickgear.API_KEYS or []
+        t.pip_user_arg = ('--user ', '')[is_virtualenv()]
         if 'git' == sickgear.update_software_scheduler.action.install_type:
             # noinspection PyProtectedMember
             sickgear.update_software_scheduler.action.updater._find_installed_version()