diff --git a/src/SiteMonitor/Constants.cs b/src/SiteMonitor/Constants.cs
index e189039..0cc8052 100644
--- a/src/SiteMonitor/Constants.cs
+++ b/src/SiteMonitor/Constants.cs
@@ -1,4 +1,5 @@
-using System.Reflection;
+using System;
+using System.Reflection;
 
 namespace SiteMonitor;
 
@@ -6,6 +7,16 @@ namespace SiteMonitor;
 ///   Constants used throughout the file.
 /// </summary>
 public class Constants {
+  /// <summary>
+  ///   The maximum amount of time before alerting the user that we aren't getting chat messages.
+  /// </summary>
+  public static readonly TimeSpan MAX_TIME_WITHOUT_CHATS = TimeSpan.FromMinutes(30);
+
+  /// <summary>
+  ///   The maximum amount of time before alerting the user that the APIs are down and not automatically coming back up.
+  /// </summary>
+  public static readonly TimeSpan MAX_TIME_SERVICE_IS_DOWN = TimeSpan.FromMinutes(5);
+
   /// <summary>
   ///   The version of the application being run right now.
   /// </summary>
diff --git a/src/SiteMonitor/ViewModels/MainWindowViewModel.cs b/src/SiteMonitor/ViewModels/MainWindowViewModel.cs
index b32ffa7..db9c818 100644
--- a/src/SiteMonitor/ViewModels/MainWindowViewModel.cs
+++ b/src/SiteMonitor/ViewModels/MainWindowViewModel.cs
@@ -21,6 +21,7 @@ namespace SiteMonitor.ViewModels;
 ///   The view model for the main UI.
 /// </summary>
 public partial class MainWindowViewModel : ViewModelBase {
+  private DateTime? _apiDownSince;
   [ObservableProperty] private bool _apiUp = true;
 
   [ObservableProperty] private string? _chatTimestamp;
@@ -168,7 +169,7 @@ private async Task PingSite() {
           TimeSpan diff = DateTime.Now - time.ToLocalTime();
           timestamp = $"{timestamp} ({diff.Hours}h {diff.Minutes}m {diff.Seconds}s ago)";
           ChatTimestamp = timestamp;
-          chatNotUpdating = diff > TimeSpan.FromMinutes(5);
+          chatNotUpdating = diff > Constants.MAX_TIME_WITHOUT_CHATS;
         }
       }
       else {
@@ -176,7 +177,9 @@ private async Task PingSite() {
         chatNotUpdating = true;
       }
 
-      if ((!WebsiteUp || !ApiUp || !NullUp || chatNotUpdating) && IsMinimized) {
+      _apiDownSince = !WebsiteUp || !ApiUp || !NullUp ? _apiDownSince ?? DateTime.Now : null;
+      bool apiNotComingUp = DateTime.Now - _apiDownSince > Constants.MAX_TIME_SERVICE_IS_DOWN;
+      if ((apiNotComingUp || chatNotUpdating) && IsMinimized) {
         WindowState = WindowState.Normal;
       }