diff --git a/code/controllers/configuration/entries/general.dm b/code/controllers/configuration/entries/general.dm
index 263201b6846..7bfbe268b6d 100644
--- a/code/controllers/configuration/entries/general.dm
+++ b/code/controllers/configuration/entries/general.dm
@@ -649,3 +649,5 @@
 	default = 50
 
 /datum/config_entry/string/morgue_cadaver_override_species
+
+/datum/config_entry/flag/toast_notification_on_init
diff --git a/code/controllers/master.dm b/code/controllers/master.dm
index 99060e9ae96..5000aa07e30 100644
--- a/code/controllers/master.dm
+++ b/code/controllers/master.dm
@@ -267,6 +267,9 @@ GLOBAL_REAL(Master, /datum/controller/master) = new
 	log_world(msg)
 
 
+	if(world.system_type == MS_WINDOWS && CONFIG_GET(flag/toast_notification_on_init) && !length(GLOB.clients))
+		world.shelleo("start /min powershell -ExecutionPolicy Bypass -File tools/initToast/initToast.ps1 -name \"[world.name]\" -icon %CD%\\icons\\ui_icons\\common\\tg_16.png -port [world.port]")
+
 	// Set world options.
 	world.change_fps(CONFIG_GET(number/fps))
 	var/initialized_tod = REALTIMEOFDAY
diff --git a/config/config.txt b/config/config.txt
index 2f57ba97810..3ac807188ae 100644
--- a/config/config.txt
+++ b/config/config.txt
@@ -648,3 +648,7 @@ PR_ANNOUNCEMENTS_PER_ROUND 5
 
 ## Uncomment to block granting profiling privileges to users with R_DEBUG, for performance purposes
 #FORBID_ADMIN_PROFILING
+
+## Comment to disable sending a toast notification on the host server when initializations complete.
+## Even if this is enabled, a notification will only be sent if there are no clients connected.
+TOAST_NOTIFICATION_ON_INIT
diff --git a/icons/ui_icons/common/tg_16.png b/icons/ui_icons/common/tg_16.png
new file mode 100644
index 00000000000..2b08bdd29cd
Binary files /dev/null and b/icons/ui_icons/common/tg_16.png differ
diff --git a/tools/initToast/initToast.ps1 b/tools/initToast/initToast.ps1
new file mode 100644
index 00000000000..9b7714f3a2c
--- /dev/null
+++ b/tools/initToast/initToast.ps1
@@ -0,0 +1,32 @@
+param([string]$name, [string]$icon, [Int32]$port=80)
+
+$hkcu = [Microsoft.Win32.RegistryKey]::OpenBaseKey('CurrentUser','default')
+
+$amuid_hkey = $hkcu.CreateSubKey('SOFTWARE\Classes\AppUserModelId\Tgstation.Tgstation', $true, [Microsoft.Win32.RegistryOptions]::Volatile)
+
+if ($name) { $amuid_hkey.SetValue('DisplayName', $name) }
+if ($icon) { $amuid_hkey.SetValue('IconUri', $icon) }
+
+[Windows.UI.Notifications.ToastNotificationManager, Windows.UI.Notifications, ContentType = WindowsRuntime] > $null
+$notifier = [Windows.UI.Notifications.ToastNotificationManager]::CreateToastNotifier('Tgstation.Tgstation')
+
+[Windows.Data.Xml.Dom.XmlDocument, Windows.Data.Xml.Dom, ContentType = WindowsRuntime] > $null
+$xml = New-Object Windows.Data.Xml.Dom.XmlDocument
+
+$xml.LoadXml(@"
+<toast>
+	<visual>
+		<binding template="ToastGeneric">
+			<text>Initialization Complete</text>
+		</binding>
+	</visual>
+	<actions>
+		<action content="Launch Dream Seeker" activationType="protocol" arguments="byond://127.0.0.1:$port"/>
+	</actions>
+</toast>
+"@)
+
+[Windows.UI.Notifications.ToastNotification, Windows.UI.Notifications, ContentType = WindowsRuntime] > $null
+$toast = New-Object Windows.UI.Notifications.ToastNotification $xml
+
+$notifier.Show($toast)