diff --git a/data/interfaces/default/index.html b/data/interfaces/default/index.html
index 2936c774..29f958e8 100644
--- a/data/interfaces/default/index.html
+++ b/data/interfaces/default/index.html
@@ -212,6 +212,28 @@
         </div>
     </div>
 </div>
+<% from plexpy.helpers import anon_url %>
+<div id="python2-modal" class="modal fade wide" tabindex="-1" role="dialog" aria-labelledby="python2-modal">
+    <div class="modal-dialog" role="document">
+        <div class="modal-content">
+            <div class="modal-header">
+                <button type="button" class="close" data-dismiss="modal" aria-hidden="true"><i class="fa fa-remove"></i></button>
+                <h4 class="modal-title">Unable to Update</h4>
+            </div>
+            <div class="modal-body" style="text-align: center;">
+                <p>Tautulli is still running using Python 2 and cannot be updated past v2.6.3.</p>
+                <p>Python 3 is required to continue receiving updates.</p>
+                <p>
+                    <strong>Please see the <a href="${anon_url('https://github.com/Tautulli/Tautulli-Wiki/wiki/Upgrading-to-Python-3-%28Tautulli-v2.5%29')}" target="_blank" rel="noreferrer">wiki</a>
+                    for instructions on how to upgrade to Python 3.</strong>
+                </p>
+            </div>
+            <div class="modal-footer">
+                <input type="button" class="btn btn-bright" data-dismiss="modal" value="Close">
+            </div>
+        </div>
+    </div>
+</div>
 % endif
 
 <div class="modal fade" id="ip-info-modal" tabindex="-1" role="dialog" aria-labelledby="ip-info-modal">
@@ -1010,4 +1032,16 @@
     });
 </script>
 % endif
+% if _session['user_group'] == 'admin':
+<script>
+    const queryString = window.location.search;
+    const urlParams = new URLSearchParams(queryString);
+    if (urlParams.get('update') === 'python2') {
+        $("#python2-modal").modal({
+                backdrop: 'static',
+                keyboard: false
+        });
+    }
+</script>
+% endif
 </%def>
\ No newline at end of file
diff --git a/plexpy/versioncheck.py b/plexpy/versioncheck.py
index 437941db..1d459d56 100644
--- a/plexpy/versioncheck.py
+++ b/plexpy/versioncheck.py
@@ -274,7 +274,10 @@ def check_github(scheduler=False, notify=False, use_cache=False):
                                      'plexpy_update_commit': plexpy.LATEST_VERSION,
                                      'plexpy_update_behind': plexpy.COMMITS_BEHIND})
 
-        if scheduler and plexpy.CONFIG.PLEXPY_AUTO_UPDATE and \
+        if plexpy.PYTHON2:
+            logger.warn('Tautulli is running using Python 2. Unable to run automatic update.')
+
+        elif scheduler and plexpy.CONFIG.PLEXPY_AUTO_UPDATE and \
                 not plexpy.DOCKER and not plexpy.SNAP and not plexpy.FROZEN:
             logger.info('Running automatic update.')
             plexpy.shutdown(restart=True, update=True)
@@ -286,6 +289,10 @@ def check_github(scheduler=False, notify=False, use_cache=False):
 
 
 def update():
+    if plexpy.PYTHON2:
+        logger.warn('Tautulli is running using Python 2. Unable to update.')
+        return
+
     if not plexpy.UPDATE_AVAILABLE:
         return
 
diff --git a/plexpy/webserve.py b/plexpy/webserve.py
index 9ca07680..5461e67f 100644
--- a/plexpy/webserve.py
+++ b/plexpy/webserve.py
@@ -4351,6 +4351,8 @@ class WebInterface(object):
     @cherrypy.expose
     @requireAuth(member_of("admin"))
     def update(self, **kwargs):
+        if plexpy.PYTHON2:
+            raise cherrypy.HTTPRedirect(plexpy.HTTP_ROOT + "home?update=python2")
         if plexpy.DOCKER or plexpy.SNAP:
             raise cherrypy.HTTPRedirect(plexpy.HTTP_ROOT + "home")