diff --git a/Tautulli.py b/Tautulli.py
index aa899189..b08b011b 100755
--- a/Tautulli.py
+++ b/Tautulli.py
@@ -36,7 +36,8 @@ import tzlocal
 
 import plexpy
 from plexpy import config, database, helpers, logger, webstart
-
+if os.name == 'nt':
+    from plexpy import windows
 
 # Register signals, such as CTRL + C
 signal.signal(signal.SIGINT, plexpy.sig_handler)
@@ -240,8 +241,10 @@ def main():
     webstart.start()
 
     # Windows system tray icon
-    if os.name == 'nt' and plexpy.CONFIG.WIN_SYS_TRAY:
-        plexpy.win_system_tray()
+    if os.name == 'nt':
+        windows.set_startup()
+        if plexpy.CONFIG.WIN_SYS_TRAY:
+            windows.win_system_tray()
 
     logger.info("Tautulli is ready!")
 
diff --git a/data/interfaces/default/settings.html b/data/interfaces/default/settings.html
index 20fe51a6..540f09d3 100644
--- a/data/interfaces/default/settings.html
+++ b/data/interfaces/default/settings.html
@@ -455,6 +455,12 @@
                             </label>
                             <p class="help-block">Show Tautulli shortcut in the system tray.</p>
                         </div>
+                        <div class="checkbox">
+                            <label>
+                                <input type="checkbox" name="launch_startup" id="launch_startup" value="1" ${config['launch_startup']}> Launch at System Startup
+                            </label>
+                            <p class="help-block">Start Tautulli automatically after Windows Login.</p>
+                        </div>
                         % endif
                         <div class="checkbox">
                             <label>
diff --git a/plexpy/__init__.py b/plexpy/__init__.py
index 447a8e38..f81216de 100644
--- a/plexpy/__init__.py
+++ b/plexpy/__init__.py
@@ -415,56 +415,6 @@ def launch_browser(host, port, root):
             logger.error("Could not launch browser: %s" % e)
 
 
-def win_system_tray():
-    from systray import SysTrayIcon
-
-    def tray_open(sysTrayIcon):
-        launch_browser(CONFIG.HTTP_HOST, HTTP_PORT, HTTP_ROOT)
-
-    def tray_check_update(sysTrayIcon):
-        versioncheck.check_update()
-
-    def tray_update(sysTrayIcon):
-        global SIGNAL
-        global WIN_SYS_TRAY_ICON
-        if UPDATE_AVAILABLE:
-            SIGNAL = 'update'
-        else:
-            hover_text = common.PRODUCT + ' - No Update Available'
-            WIN_SYS_TRAY_ICON.update(hover_text=hover_text)
-
-    def tray_restart(sysTrayIcon):
-        global SIGNAL
-        SIGNAL = 'restart'
-
-    def tray_quit(sysTrayIcon):
-        global SIGNAL
-        SIGNAL = 'shutdown'
-
-    if UPDATE_AVAILABLE:
-        icon = os.path.join(PROG_DIR, 'data/interfaces/', CONFIG.INTERFACE, 'images/logo_tray-update.ico')
-        hover_text = common.PRODUCT + ' - Update Available!'
-    else:
-        icon = os.path.join(PROG_DIR, 'data/interfaces/', CONFIG.INTERFACE, 'images/logo_tray.ico')
-        hover_text = common.PRODUCT
-
-    menu_options = (('Open Tautulli', None, tray_open, 'default'),
-                    ('', None, 'separator', None),
-                    ('Check for Updates', None, tray_check_update, None),
-                    ('Update', None, tray_update, None),
-                    ('Restart', None, tray_restart, None))
-
-    logger.info("Launching system tray icon.")
-
-    global WIN_SYS_TRAY_ICON
-    try:
-        WIN_SYS_TRAY_ICON = SysTrayIcon(icon, hover_text, menu_options, on_quit=tray_quit)
-        WIN_SYS_TRAY_ICON.start()
-    except Exception as e:
-        logger.error("Unable to launch system tray icon: %s." % e)
-        WIN_SYS_TRAY_ICON = None
-
-
 def initialize_scheduler():
     """
     Start the scheduled background tasks. Re-schedule if interval settings changed.
diff --git a/plexpy/config.py b/plexpy/config.py
index 1856cad3..458abf44 100644
--- a/plexpy/config.py
+++ b/plexpy/config.py
@@ -293,6 +293,7 @@ _CONFIG_DEFINITIONS = {
     'JOIN_ON_NEWDEVICE': (int, 'Join', 0),
     'JOURNAL_MODE': (str, 'Advanced', 'WAL'),
     'LAUNCH_BROWSER': (int, 'General', 1),
+    'LAUNCH_STARTUP': (int, 'General', 1),
     'LOG_BLACKLIST': (int, 'General', 1),
     'LOG_DIR': (str, 'General', ''),
     'LOGGING_IGNORE_INTERVAL': (int, 'Monitoring', 120),
diff --git a/plexpy/webserve.py b/plexpy/webserve.py
index bc2331d9..e99a43fe 100644
--- a/plexpy/webserve.py
+++ b/plexpy/webserve.py
@@ -66,6 +66,7 @@ if plexpy.PYTHON2:
     import versioncheck
     import web_socket
     import webstart
+    import windows
     from api2 import API2
     from helpers import checked, addtoapi, get_ip, create_https_certificates, build_datatables_json, sanitize_out
     from session import get_session_info, get_session_user_id, allow_session_user, allow_session_library
@@ -95,6 +96,7 @@ else:
     from plexpy import versioncheck
     from plexpy import web_socket
     from plexpy import webstart
+    from plexpy import windows
     from plexpy.api2 import API2
     from plexpy.helpers import checked, addtoapi, get_ip, create_https_certificates, build_datatables_json, sanitize_out
     from plexpy.session import get_session_info, get_session_user_id, allow_session_user, allow_session_library
@@ -2939,6 +2941,7 @@ class WebInterface(object):
             "http_proxy": checked(plexpy.CONFIG.HTTP_PROXY),
             "http_plex_admin": checked(plexpy.CONFIG.HTTP_PLEX_ADMIN),
             "launch_browser": checked(plexpy.CONFIG.LAUNCH_BROWSER),
+            "launch_startup": checked(plexpy.CONFIG.LAUNCH_STARTUP),
             "enable_https": checked(plexpy.CONFIG.ENABLE_HTTPS),
             "https_create_cert": checked(plexpy.CONFIG.HTTPS_CREATE_CERT),
             "https_cert": plexpy.CONFIG.HTTPS_CERT,
@@ -3042,6 +3045,7 @@ class WebInterface(object):
 
         # Check if we should refresh our data
         first_run = False
+        startup_changed = False
         server_changed = False
         reschedule = False
         https_changed = False
@@ -3053,7 +3057,8 @@ class WebInterface(object):
             first_run = True
 
         checked_configs = [
-            "launch_browser", "enable_https", "https_create_cert", "api_enabled", "freeze_db", "check_github",
+            "launch_browser", "launch_startup", "enable_https", "https_create_cert",
+            "api_enabled", "freeze_db", "check_github",
             "grouping_global_history", "grouping_user_history", "grouping_charts", "group_history_tables",
             "pms_url_manual", "week_start_monday",
             "refresh_libraries_on_startup", "refresh_users_on_startup",
@@ -3102,28 +3107,32 @@ class WebInterface(object):
             kwargs[plain_config] = kwargs[use_config]
             del kwargs[use_config]
 
+        if kwargs.get('launch_startup') != plexpy.CONFIG.LAUNCH_STARTUP or \
+                kwargs.get('launch_browser') != plexpy.CONFIG.LAUNCH_BROWSER:
+            startup_changed = True
+
         # If we change any monitoring settings, make sure we reschedule tasks.
         if kwargs.get('check_github') != plexpy.CONFIG.CHECK_GITHUB or \
-            kwargs.get('refresh_libraries_interval') != str(plexpy.CONFIG.REFRESH_LIBRARIES_INTERVAL) or \
-            kwargs.get('refresh_users_interval') != str(plexpy.CONFIG.REFRESH_USERS_INTERVAL) or \
-            kwargs.get('pms_update_check_interval') != str(plexpy.CONFIG.PMS_UPDATE_CHECK_INTERVAL) or \
-            kwargs.get('monitor_pms_updates') != plexpy.CONFIG.MONITOR_PMS_UPDATES or \
-            kwargs.get('monitor_remote_access') != plexpy.CONFIG.MONITOR_REMOTE_ACCESS or \
-            kwargs.get('pms_url_manual') != plexpy.CONFIG.PMS_URL_MANUAL:
+                kwargs.get('refresh_libraries_interval') != str(plexpy.CONFIG.REFRESH_LIBRARIES_INTERVAL) or \
+                kwargs.get('refresh_users_interval') != str(plexpy.CONFIG.REFRESH_USERS_INTERVAL) or \
+                kwargs.get('pms_update_check_interval') != str(plexpy.CONFIG.PMS_UPDATE_CHECK_INTERVAL) or \
+                kwargs.get('monitor_pms_updates') != plexpy.CONFIG.MONITOR_PMS_UPDATES or \
+                kwargs.get('monitor_remote_access') != plexpy.CONFIG.MONITOR_REMOTE_ACCESS or \
+                kwargs.get('pms_url_manual') != plexpy.CONFIG.PMS_URL_MANUAL:
             reschedule = True
 
         # If we change the SSL setting for PMS or PMS remote setting, make sure we grab the new url.
         if kwargs.get('pms_ssl') != str(plexpy.CONFIG.PMS_SSL) or \
-            kwargs.get('pms_is_remote') != str(plexpy.CONFIG.PMS_IS_REMOTE) or \
-            kwargs.get('pms_url_manual') != plexpy.CONFIG.PMS_URL_MANUAL:
+                kwargs.get('pms_is_remote') != str(plexpy.CONFIG.PMS_IS_REMOTE) or \
+                kwargs.get('pms_url_manual') != plexpy.CONFIG.PMS_URL_MANUAL:
             server_changed = True
 
         # If we change the HTTPS setting, make sure we generate a new certificate.
         if kwargs.get('enable_https') and kwargs.get('https_create_cert'):
             if kwargs.get('https_domain') != plexpy.CONFIG.HTTPS_DOMAIN or \
-                kwargs.get('https_ip') != plexpy.CONFIG.HTTPS_IP or \
-                kwargs.get('https_cert') != plexpy.CONFIG.HTTPS_CERT or \
-                kwargs.get('https_key') != plexpy.CONFIG.HTTPS_KEY:
+                    kwargs.get('https_ip') != plexpy.CONFIG.HTTPS_IP or \
+                    kwargs.get('https_cert') != plexpy.CONFIG.HTTPS_CERT or \
+                    kwargs.get('https_key') != plexpy.CONFIG.HTTPS_KEY:
                 https_changed = True
 
         # Remove config with 'hsec-' prefix and change home_sections to list
@@ -3168,6 +3177,11 @@ class WebInterface(object):
         # Write the config
         plexpy.CONFIG.write()
 
+        # Enable or disable system startup
+        if startup_changed:
+            if os.name == 'nt':
+                windows.set_startup()
+
         # Get new server URLs for SSL communications and get new server friendly name
         if server_changed:
             plextv.get_server_resources()
diff --git a/plexpy/windows.py b/plexpy/windows.py
new file mode 100644
index 00000000..03252e65
--- /dev/null
+++ b/plexpy/windows.py
@@ -0,0 +1,110 @@
+# -*- coding: utf-8 -*-
+
+# This file is part of Tautulli.
+#
+#  Tautulli is free software: you can redistribute it and/or modify
+#  it under the terms of the GNU General Public License as published by
+#  the Free Software Foundation, either version 3 of the License, or
+#  (at your option) any later version.
+#
+#  Tautulli is distributed in the hope that it will be useful,
+#  but WITHOUT ANY WARRANTY; without even the implied warranty of
+#  MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+#  GNU General Public License for more details.
+#
+#  You should have received a copy of the GNU General Public License
+#  along with Tautulli.  If not, see <http://www.gnu.org/licenses/>.
+
+import os
+import shlex
+import sys
+import winreg
+
+import plexpy
+if plexpy.PYTHON2:
+    import common
+    import logger
+    import versioncheck
+else:
+    from plexpy import common
+    from plexpy import logger
+    from plexpy import versioncheck
+
+
+def win_system_tray():
+    from systray import SysTrayIcon
+
+    def tray_open(sysTrayIcon):
+        plexpy.launch_browser(plexpy.CONFIG.HTTP_HOST, plexpy.HTTP_PORT, plexpy.HTTP_ROOT)
+
+    def tray_check_update(sysTrayIcon):
+        versioncheck.check_update()
+
+    def tray_update(sysTrayIcon):
+        if plexpy.UPDATE_AVAILABLE:
+            plexpy.SIGNAL = 'update'
+        else:
+            hover_text = common.PRODUCT + ' - No Update Available'
+            plexpy.WIN_SYS_TRAY_ICON.update(hover_text=hover_text)
+
+    def tray_restart(sysTrayIcon):
+        plexpy.SIGNAL = 'restart'
+
+    def tray_quit(sysTrayIcon):
+        plexpy.SIGNAL = 'shutdown'
+
+    if plexpy.UPDATE_AVAILABLE:
+        icon = os.path.join(plexpy.PROG_DIR, 'data/interfaces/', plexpy.CONFIG.INTERFACE, 'images/logo_tray-update.ico')
+        hover_text = common.PRODUCT + ' - Update Available!'
+    else:
+        icon = os.path.join(plexpy.PROG_DIR, 'data/interfaces/', plexpy.CONFIG.INTERFACE, 'images/logo_tray.ico')
+        hover_text = common.PRODUCT
+
+    menu_options = (('Open Tautulli', None, tray_open, 'default'),
+                    ('', None, 'separator', None),
+                    ('Check for Updates', None, tray_check_update, None),
+                    ('Update', None, tray_update, None),
+                    ('Restart', None, tray_restart, None))
+
+    logger.info("Launching system tray icon.")
+
+    try:
+        plexpy.WIN_SYS_TRAY_ICON = SysTrayIcon(icon, hover_text, menu_options, on_quit=tray_quit)
+        plexpy.WIN_SYS_TRAY_ICON.start()
+    except Exception as e:
+        logger.error("Unable to launch system tray icon: %s." % e)
+        plexpy.WIN_SYS_TRAY_ICON = None
+
+
+def set_startup():
+    startup_reg_path = "Software\\Microsoft\\Windows\\CurrentVersion\\Run"
+
+    exe = sys.executable
+    if plexpy.FROZEN:
+        args = [exe]
+    else:
+        args = [exe, plexpy.FULL_PATH]
+
+    if not plexpy.CONFIG.LAUNCH_BROWSER:
+        args += ['--nolaunch']
+
+    cmd = ' '.join(shlex.quote(arg) for arg in args).replace('python.exe', 'pythonw.exe').replace("'", '"')
+
+    if plexpy.CONFIG.LAUNCH_STARTUP:
+        try:
+            winreg.CreateKey(winreg.HKEY_CURRENT_USER, startup_reg_path)
+            registry_key = winreg.OpenKey(winreg.HKEY_CURRENT_USER, startup_reg_path, 0, winreg.KEY_WRITE)
+            winreg.SetValueEx(registry_key, common.PRODUCT, 0, winreg.REG_SZ, cmd)
+            winreg.CloseKey(registry_key)
+            return True
+        except WindowsError:
+            return False
+
+    else:
+        try:
+            registry_key = winreg.OpenKey(winreg.HKEY_CURRENT_USER, startup_reg_path, 0, winreg.KEY_ALL_ACCESS)
+            winreg.DeleteValue(registry_key, common.PRODUCT)
+            winreg.CloseKey(registry_key)
+            return True
+        except WindowsError:
+            return False