diff --git a/Dalamud/Interface/Internal/ManagedAsserts/ImGuiContextOffsets.cs b/Dalamud/Interface/Internal/ManagedAsserts/ImGuiContextOffsets.cs
new file mode 100644
index 000000000..5c76854d2
--- /dev/null
+++ b/Dalamud/Interface/Internal/ManagedAsserts/ImGuiContextOffsets.cs
@@ -0,0 +1,22 @@
+namespace Dalamud.Interface.Internal.ManagedAsserts
+{
+    /// <summary>
+    /// Offsets to various data in ImGui context.
+    /// </summary>
+    /// <remarks>
+    /// Last updated for ImGui 1.83.
+    /// </remarks>
+    [System.Diagnostics.CodeAnalysis.SuppressMessage("StyleCop.CSharp.DocumentationRules", "SA1600:Elements should be documented", Justification = "Document the unsage instead.")]
+    internal static class ImGuiContextOffsets
+    {
+        public const int CurrentWindowStackOffset = 0x73A;
+
+        public const int ColorStackOffset = 0x79C;
+
+        public const int StyleVarStackOffset = 0x7A0;
+
+        public const int FontStackOffset = 0x7A4;
+
+        public const int BeginPopupStackOffset = 0x7B8;
+    }
+}
diff --git a/Dalamud/Interface/Internal/ManagedAsserts/ImGuiManagedAsserts.cs b/Dalamud/Interface/Internal/ManagedAsserts/ImGuiManagedAsserts.cs
new file mode 100644
index 000000000..b0df91162
--- /dev/null
+++ b/Dalamud/Interface/Internal/ManagedAsserts/ImGuiManagedAsserts.cs
@@ -0,0 +1,136 @@
+using System.Diagnostics;
+
+using ImGuiNET;
+
+using static Dalamud.NativeFunctions;
+
+namespace Dalamud.Interface.Internal.ManagedAsserts
+{
+    /// <summary>
+    /// Report ImGui problems with a MessageBox dialog.
+    /// </summary>
+    internal static class ImGuiManagedAsserts
+    {
+        /// <summary>
+        /// Gets a value indicating whether asserts are enabled for ImGui.
+        /// </summary>
+        public static bool AssertsEnabled { get; private set; }
+
+        /// <summary>
+        /// Create a snapshot of the current ImGui context.
+        /// Should be called before rendering an ImGui frame.
+        /// </summary>
+        /// <returns>A snapshot of the current context.</returns>
+        public static unsafe ImGuiContextSnapshot GetSnapshot()
+        {
+            var contextPtr = ImGui.GetCurrentContext();
+
+            var styleVarStack = *((int*)contextPtr + ImGuiContextOffsets.StyleVarStackOffset); // ImVector.Size
+            var colorStack = *((int*)contextPtr + ImGuiContextOffsets.ColorStackOffset); // ImVector.Size
+            var fontStack = *((int*)contextPtr + ImGuiContextOffsets.FontStackOffset); // ImVector.Size
+            var popupStack = *((int*)contextPtr + ImGuiContextOffsets.BeginPopupStackOffset); // ImVector.Size
+            var windowStack = *((int*)contextPtr + ImGuiContextOffsets.CurrentWindowStackOffset); // ImVector.Size
+
+            return new ImGuiContextSnapshot
+            {
+                StyleVarStackSize = styleVarStack,
+                ColorStackSize = colorStack,
+                FontStackSize = fontStack,
+                BeginPopupStackSize = popupStack,
+                WindowStackSize = windowStack,
+            };
+        }
+
+        /// <summary>
+        /// Compare a snapshot to the current post-draw state and report any errors in a MessageBox dialog.
+        /// </summary>
+        /// <param name="source">The source of any problems, something to blame.</param>
+        /// <param name="before">ImGui context snapshot.</param>
+        public static void ReportProblems(string source, ImGuiContextSnapshot before)
+        {
+            if (!AssertsEnabled)
+            {
+                return;
+            }
+
+            var cSnap = GetSnapshot();
+
+            if (before.StyleVarStackSize != cSnap.StyleVarStackSize)
+            {
+                ShowAssert(source, $"You forgot to pop a style var!\n\nBefore: {before.StyleVarStackSize}, after: {cSnap.StyleVarStackSize}");
+                return;
+            }
+
+            if (before.ColorStackSize != cSnap.ColorStackSize)
+            {
+                ShowAssert(source, $"You forgot to pop a color!\n\nBefore: {before.ColorStackSize}, after: {cSnap.ColorStackSize}");
+                return;
+            }
+
+            if (before.FontStackSize != cSnap.FontStackSize)
+            {
+                ShowAssert(source, $"You forgot to pop a font!\n\nBefore: {before.FontStackSize}, after: {cSnap.FontStackSize}");
+                return;
+            }
+
+            if (before.BeginPopupStackSize != cSnap.BeginPopupStackSize)
+            {
+                ShowAssert(source, $"You forgot to end a popup!\n\nBefore: {before.BeginPopupStackSize}, after: {cSnap.BeginPopupStackSize}");
+                return;
+            }
+
+            if (cSnap.WindowStackSize != 1)
+            {
+                if (cSnap.WindowStackSize > 1)
+                {
+                    ShowAssert(source, $"Mismatched Begin/BeginChild vs End/EndChild calls: did you forget to call End/EndChild?\n\ncSnap.WindowStackSize = {cSnap.WindowStackSize}");
+                }
+                else
+                {
+                    ShowAssert(source, $"Mismatched Begin/BeginChild vs End/EndChild calls: did you call End/EndChild too much?\n\ncSnap.WindowStackSize = {cSnap.WindowStackSize}");
+                }
+            }
+        }
+
+        private static void ShowAssert(string source, string message)
+        {
+            var caption = $"You fucked up";
+            message = $"{message}\n\nSource: {source}\n\nAsserts are now disabled. You may re-enable them.";
+            var flags = MessageBoxType.Ok | MessageBoxType.IconError;
+
+            _ = MessageBoxW(Process.GetCurrentProcess().MainWindowHandle, message, caption, flags);
+            AssertsEnabled = false;
+        }
+
+        /// <summary>
+        /// A snapshot of various ImGui context properties.
+        /// </summary>
+        public class ImGuiContextSnapshot
+        {
+            /// <summary>
+            /// Gets the ImGui style var stack size.
+            /// </summary>
+            public int StyleVarStackSize { get; init; }
+
+            /// <summary>
+            /// Gets the ImGui color stack size.
+            /// </summary>
+            public int ColorStackSize { get; init; }
+
+            /// <summary>
+            /// Gets the ImGui font stack size.
+            /// </summary>
+            public int FontStackSize { get; init; }
+
+            /// <summary>
+            /// Gets the ImGui begin popup stack size.
+            /// </summary>
+            public int BeginPopupStackSize { get; init; }
+
+            /// <summary>
+            /// Gets the ImGui window stack size.
+            /// </summary>
+            public int WindowStackSize { get; init; }
+        }
+    }
+}
diff --git a/Dalamud/Interface/UiBuilder.cs b/Dalamud/Interface/UiBuilder.cs
index 3e3694407..5ff2fac4c 100644
--- a/Dalamud/Interface/UiBuilder.cs
+++ b/Dalamud/Interface/UiBuilder.cs
@@ -6,6 +6,7 @@ using Dalamud.Configuration.Internal;
 using Dalamud.Game.ClientState.Conditions;
 using Dalamud.Game.Gui;
 using Dalamud.Interface.Internal;
+using Dalamud.Interface.Internal.ManagedAsserts;
 using Dalamud.Interface.Internal.Notifications;
 using ImGuiNET;
 using ImGuiScene;
@@ -275,6 +276,12 @@ namespace Dalamud.Interface
                 ImGui.End();
             }
 
+            ImGuiManagedAsserts.ImGuiContextSnapshot? snapshot = null;
+            if (this.Draw != null)
+            {
+                snapshot = ImGuiManagedAsserts.GetSnapshot();
+            }
+
             try
             {
                 this.Draw?.Invoke();
@@ -288,6 +295,12 @@ namespace Dalamud.Interface
                 this.hasErrorWindow = true;
             }
 
+            // Only if Draw was successful
+            if (this.Draw != null && snapshot != null)
+            {
+                ImGuiManagedAsserts.ReportProblems(this.namespaceName, snapshot);
+            }
+
             this.FrameCount++;
 
             if (DoStats)
diff --git a/Dalamud/Interface/Windowing/WindowSystem.cs b/Dalamud/Interface/Windowing/WindowSystem.cs
index 4d3a03a0d..5f6334e8e 100644
--- a/Dalamud/Interface/Windowing/WindowSystem.cs
+++ b/Dalamud/Interface/Windowing/WindowSystem.cs
@@ -2,6 +2,7 @@ using System;
 using System.Collections.Generic;
 using System.Linq;
 
+using Dalamud.Interface.Internal.ManagedAsserts;
 using ImGuiNET;
 using Serilog;
 
@@ -98,8 +99,12 @@ namespace Dalamud.Interface.Windowing
 #if DEBUG
                 // Log.Verbose($"[WS{(hasNamespace ? "/" + this.Namespace : string.Empty)}] Drawing {window.WindowName}");
 #endif
+                var snapshot = ImGuiManagedAsserts.GetSnapshot();
 
                 window.DrawInternal();
+
+                var source = ($"{this.Namespace}::" ?? string.Empty) + window.WindowName;
+                ImGuiManagedAsserts.ReportProblems(source, snapshot);
             }
 
             var focusedWindow = this.windows.FirstOrDefault(x => x.IsFocused && x.RespectCloseHotkey);