diff --git a/Dalamud/Game/ChatHandlers.cs b/Dalamud/Game/ChatHandlers.cs
index 90a399d4c..836fb5ec8 100644
--- a/Dalamud/Game/ChatHandlers.cs
+++ b/Dalamud/Game/ChatHandlers.cs
@@ -2,6 +2,7 @@ using System.Collections.Generic;
 using System.Linq;
 using System.Reflection;
 using System.Text.RegularExpressions;
+using System.Threading;
 using System.Threading.Tasks;
 
 using CheapLoc;
@@ -14,9 +15,9 @@ using Dalamud.Interface.Internal;
 using Dalamud.Interface.Internal.Notifications;
 using Dalamud.Interface.Internal.Windows;
 using Dalamud.Interface.Internal.Windows.PluginInstaller;
+using Dalamud.Logging.Internal;
 using Dalamud.Plugin.Internal;
 using Dalamud.Utility;
-using Serilog;
 
 namespace Dalamud.Game;
 
@@ -60,6 +61,8 @@ internal class ChatHandlers : IServiceType
     //     { XivChatType.Echo, Color.Gray },
     // };
 
+    private static readonly ModuleLog Log = new("CHATHANDLER");
+
     private readonly Regex rmtRegex = new(
         @"4KGOLD|We have sufficient stock|VPK\.OM|[Gg]il for free|[Gg]il [Cc]heap|5GOLD|www\.so9\.com|Fast & Convenient|Cheap & Safety Guarantee|【Code|A O A U E|igfans|4KGOLD\.COM|Cheapest Gil with|pvp and bank on google|Selling Cheap GIL|ff14mogstation\.com|Cheap Gil 1000k|gilsforyou|server 1000K =|gils_selling|E A S Y\.C O M|bonus code|mins delivery guarantee|Sell cheap|Salegm\.com|cheap Mog|Off Code:|FF14Mog.com|使用する5％オ|[Oo][Ff][Ff] [Cc]ode( *)[:;]|offers Fantasia",
         RegexOptions.Compiled | RegexOptions.IgnoreCase);
@@ -110,6 +113,7 @@ internal class ChatHandlers : IServiceType
 
     private bool hasSeenLoadingMsg;
     private bool startedAutoUpdatingPlugins;
+    private CancellationTokenSource deferredAutoUpdateCts = new();
 
     [ServiceManager.ServiceConstructor]
     private ChatHandlers(ChatGui chatGui)
@@ -165,16 +169,19 @@ internal class ChatHandlers : IServiceType
         if (clientState == null)
             return;
 
-        if (type == XivChatType.Notice && !this.hasSeenLoadingMsg)
-            this.PrintWelcomeMessage();
+        if (type == XivChatType.Notice)
+        {
+            if (!this.hasSeenLoadingMsg)
+                this.PrintWelcomeMessage();
+            
+            if (!this.startedAutoUpdatingPlugins)
+                this.AutoUpdatePluginsWithRetry();
+        }
 
         // For injections while logged in
         if (clientState.LocalPlayer != null && clientState.TerritoryType == 0 && !this.hasSeenLoadingMsg)
             this.PrintWelcomeMessage();
 
-        if (!this.startedAutoUpdatingPlugins)
-            this.AutoUpdatePlugins();
-
 #if !DEBUG && false
             if (!this.hasSeenLoadingMsg)
                 return;
@@ -264,24 +271,42 @@ internal class ChatHandlers : IServiceType
         this.hasSeenLoadingMsg = true;
     }
 
-    private void AutoUpdatePlugins()
+    private void AutoUpdatePluginsWithRetry()
+    {
+        var firstAttempt = this.AutoUpdatePlugins();
+        if (!firstAttempt)
+        {
+            Task.Run(() =>
+            {
+                Task.Delay(30_000, this.deferredAutoUpdateCts.Token);
+                this.AutoUpdatePlugins();
+            });
+        }
+    }
+
+    private bool AutoUpdatePlugins()
     {
         var chatGui = Service<ChatGui>.GetNullable();
         var pluginManager = Service<PluginManager>.GetNullable();
         var notifications = Service<NotificationManager>.GetNullable();
 
         if (chatGui == null || pluginManager == null || notifications == null)
-            return;
+        {
+            Log.Warning("Aborting auto-update because a required service was not loaded.");
+            return false;
+        }
 
         if (!pluginManager.ReposReady || !pluginManager.InstalledPlugins.Any() || !pluginManager.AvailablePlugins.Any())
         {
             // Plugins aren't ready yet.
             // TODO: We should retry. This sucks, because it means we won't ever get here again until another notice.
-            return;
+            Log.Warning("Aborting auto-update because plugins weren't loaded or ready.");
+            return false;
         }
 
         this.startedAutoUpdatingPlugins = true;
 
+        Log.Debug("Beginning plugin auto-update process...");
         Task.Run(() => pluginManager.UpdatePluginsAsync(true, !this.configuration.AutoUpdatePlugins, true)).ContinueWith(task =>
         {
             this.IsAutoUpdateComplete = true;
@@ -320,5 +345,7 @@ internal class ChatHandlers : IServiceType
                 }
             }
         });
+
+        return true;
     }
 }
diff --git a/Dalamud/Interface/Utility/ImGuiHelpers.cs b/Dalamud/Interface/Utility/ImGuiHelpers.cs
index 85f81b203..ad151ec4e 100644
--- a/Dalamud/Interface/Utility/ImGuiHelpers.cs
+++ b/Dalamud/Interface/Utility/ImGuiHelpers.cs
@@ -31,7 +31,8 @@ public static class ImGuiHelpers
     /// This does not necessarily mean you can call drawing functions.
     /// </summary>
     public static unsafe bool IsImGuiInitialized =>
-        ImGui.GetCurrentContext() is not 0 && ImGui.GetIO().NativePtr is not null;
+        ImGui.GetCurrentContext() is not (nint)0  // KW: IDEs get mad without the cast, despite being unnecessary
+        && ImGui.GetIO().NativePtr is not null; 
 
     /// <summary>
     /// Gets the global Dalamud scale; even available before drawing is ready.<br />
diff --git a/Dalamud/Plugin/Internal/PluginManager.cs b/Dalamud/Plugin/Internal/PluginManager.cs
index 0ef3d49f8..020abf437 100644
--- a/Dalamud/Plugin/Internal/PluginManager.cs
+++ b/Dalamud/Plugin/Internal/PluginManager.cs
@@ -958,7 +958,7 @@ internal partial class PluginManager : IDisposable, IServiceType
             autoUpdate ? PluginListInvalidationKind.AutoUpdate : PluginListInvalidationKind.Update,
             updatedList.Select(x => x.InternalName));
 
-        Log.Information("Plugin update OK.");
+        Log.Information("Plugin update OK. {updateCount} plugins updated.", updatedList.Length);
 
         return updatedList;
     }
@@ -1581,6 +1581,8 @@ internal partial class PluginManager : IDisposable, IServiceType
 
     private void DetectAvailablePluginUpdates()
     {
+        Log.Debug("Starting plugin update check...");
+        
         lock (this.pluginListLock)
         {
             this.updatablePluginsList.Clear();
@@ -1615,10 +1617,12 @@ internal partial class PluginManager : IDisposable, IServiceType
                 }
             }
         }
+        
+        Log.Debug("Update check found {updateCount} available updates.", this.updatablePluginsList.Count);
     }
 
     private void NotifyAvailablePluginsChanged()
-    {
+    { 
         this.DetectAvailablePluginUpdates();
 
         this.OnAvailablePluginsChanged?.InvokeSafely();