diff --git a/SS14.Watchdog/Components/Notifications/NotificationManager.cs b/SS14.Watchdog/Components/Notifications/NotificationManager.cs
index 1ce33b7..d1e9560 100644
--- a/SS14.Watchdog/Components/Notifications/NotificationManager.cs
+++ b/SS14.Watchdog/Components/Notifications/NotificationManager.cs
@@ -1,7 +1,10 @@
 using System;
 using System.Net.Http;
+using System.Net.Http.Headers;
 using System.Net.Http.Json;
+using System.Text;
 using System.Text.Json.Serialization;
+using System.Threading.Tasks;
 using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Options;
 
@@ -16,7 +19,7 @@ public sealed partial class NotificationManager(
     ILogger<NotificationManager> logger,
     IOptions<NotificationOptions> options)
 {
-    public const string DiscordHttpClient = "discord_webhook";
+    public const string NotificationHttpClient = "watchdog_notification";
 
     private readonly HttpClient _httpClient = http.CreateClient();
 
@@ -26,13 +29,26 @@ public void SendNotification(string message)
         var optionsValue = options.Value;
         if (optionsValue.DiscordWebhook == null)
         {
-            logger.LogTrace("Not sending notification: no Discord webhook URL configured");
+            logger.LogTrace("Not sending discord notification: no Discord webhook URL configured");
             return;
         }
 
         SendWebhook(optionsValue, message);
     }
 
+    public async Task SendHttpNotification(string instanceId)
+    {
+        var optionsValue = options.Value;
+
+        if (optionsValue.NotifyUrls.Count == 0)
+        {
+            logger.LogTrace("Not sending HTTP notification: no HTTP URLs configured");
+            return;
+        }
+
+        await SendUpdatePosts(optionsValue, instanceId);
+    }
+
     private async void SendWebhook(NotificationOptions optionsValue, string message)
     {
         logger.LogTrace("Sending notification \"{Message}\" to Discord webhook...", message);
@@ -60,6 +76,49 @@ private async void SendWebhook(NotificationOptions optionsValue, string message)
         }
     }
 
+    private async Task SendUpdatePosts(NotificationOptions optionsValue, string instanceId)
+    {
+        logger.LogTrace("Sending update notification post...");
+
+        try
+        {
+            var data = new UpdatePostExecute
+            {
+                InstanceId = instanceId
+            };
+
+            foreach (var urlString in optionsValue.NotifyUrls)
+            {
+                await SendSpecificUpdatePost(optionsValue, data, new Uri(urlString));
+            }
+        }
+        catch (Exception e)
+        {
+            logger.LogError(e, "Error while sending update notification post!");
+        }
+    }
+
+    private async Task SendSpecificUpdatePost(NotificationOptions optionsValue, UpdatePostExecute data, Uri url)
+    {
+        using var request = new HttpRequestMessage(HttpMethod.Post, url);
+
+        if (!string.IsNullOrWhiteSpace(optionsValue.UpdatePostUser)
+            && !string.IsNullOrWhiteSpace(optionsValue.UpdatePostToken))
+        {
+            var authAsBytes = Encoding.ASCII.GetBytes(optionsValue.UpdatePostUser + ":"  + optionsValue.UpdatePostToken);
+            var authAsBase64 = Convert.ToBase64String(authAsBytes);
+            var authHeader = new AuthenticationHeaderValue("Basic", authAsBase64);
+            request.Headers.Authorization = authHeader;
+        }
+
+        request.Content = JsonContent.Create(data);
+
+        using var response = await _httpClient.SendAsync(request);
+        response.EnsureSuccessStatusCode();
+
+        logger.LogTrace("Succeeded sending update post");
+    }
+
     private sealed class DiscordWebhookExecute
     {
         public string? Content { get; set; }
@@ -76,4 +135,12 @@ private sealed class DiscordAllowedMentions
     [JsonSourceGenerationOptions(PropertyNamingPolicy = JsonKnownNamingPolicy.KebabCaseLower)]
     [JsonSerializable(typeof(DiscordWebhookExecute))]
     private partial class DiscordSourceGenerationContext : JsonSerializerContext;
+
+    private sealed class UpdatePostExecute
+    {
+        /// <summary>
+        ///     The Watchdog instance that was updated.
+        /// </summary>
+        public required string InstanceId { get; set; }
+    }
 }
diff --git a/SS14.Watchdog/Components/Notifications/NotificationOptions.cs b/SS14.Watchdog/Components/Notifications/NotificationOptions.cs
index ed7b36f..063d407 100644
--- a/SS14.Watchdog/Components/Notifications/NotificationOptions.cs
+++ b/SS14.Watchdog/Components/Notifications/NotificationOptions.cs
@@ -1,4 +1,6 @@
-namespace SS14.Watchdog.Components.Notifications;
+using System.Collections.Generic;
+
+namespace SS14.Watchdog.Components.Notifications;
 
 /// <summary>
 /// Options for notifications the watchdog can send via various channels.
@@ -12,4 +14,21 @@ public sealed class NotificationOptions
     /// A Discord webhook URL to send notifications like server crashes to.
     /// </summary>
     public string? DiscordWebhook { get; set; }
+
+    /// <summary>
+    ///     A list of URLs that should be sent a POST request.
+    ///     If specified, each one will be provided <see cref="UpdatePostToken"/> as authentication.
+    /// </summary>
+    /// <remarks>No suffixes or prefixes are added to the URL before sending the POST.</remarks>
+    public List<string> NotifyUrls { get; set; } = [];
+
+    /// <summary>
+    ///     The username that will be passed through to each update URL as BasicAuthentication.
+    /// </summary>
+    public string UpdatePostUser { get; set; } = string.Empty;
+
+    /// <summary>
+    ///     The token that will be passed through to each update URL as BasicAuthentication.
+    /// </summary>
+    public string UpdatePostToken { get; set; } = string.Empty;
 }
diff --git a/SS14.Watchdog/Components/ServerManagement/ServerInstance.Actor.cs b/SS14.Watchdog/Components/ServerManagement/ServerInstance.Actor.cs
index 5237116..cda1d16 100644
--- a/SS14.Watchdog/Components/ServerManagement/ServerInstance.Actor.cs
+++ b/SS14.Watchdog/Components/ServerManagement/ServerInstance.Actor.cs
@@ -191,6 +191,9 @@ private async Task RunCommandUpdateAvailable(CommandUpdateAvailable command, Can
         _updateOnRestart = command.UpdateAvailable;
         if (command.UpdateAvailable)
         {
+            // Should send an update regardless of what the server's state is.
+            await _notificationManager.SendHttpNotification(Key);
+
             if (IsRunning)
             {
                 _logger.LogTrace("Server is running, sending update notification.");
diff --git a/SS14.Watchdog/Components/ServerManagement/ServerInstance.cs b/SS14.Watchdog/Components/ServerManagement/ServerInstance.cs
index e166c80..c09b3a9 100644
--- a/SS14.Watchdog/Components/ServerManagement/ServerInstance.cs
+++ b/SS14.Watchdog/Components/ServerManagement/ServerInstance.cs
@@ -336,6 +336,7 @@ public void HandleUpdateCheck()
                 return;
 
             _logger.LogDebug("Received update notification.");
+
             _taskQueue.QueueTask(async cancel =>
             {
                 var updateAvailable = await _updateProvider.CheckForUpdateAsync(_currentRevision, cancel);
diff --git a/SS14.Watchdog/Startup.cs b/SS14.Watchdog/Startup.cs
index 34375ad..5976367 100644
--- a/SS14.Watchdog/Startup.cs
+++ b/SS14.Watchdog/Startup.cs
@@ -68,7 +68,7 @@ public void ConfigureServices(IServiceCollection services)
 
             services.AddSingleton<NotificationManager>();
 
-            services.AddHttpClient(NotificationManager.DiscordHttpClient);
+            services.AddHttpClient(NotificationManager.NotificationHttpClient);
         }
 
         // This method gets called by the runtime. Use this method to configure the HTTP request pipeline.