diff --git a/Dalamud/Interface/Windowing/Window.cs b/Dalamud/Interface/Windowing/Window.cs
index 032f6e93e..876f9ec63 100644
--- a/Dalamud/Interface/Windowing/Window.cs
+++ b/Dalamud/Interface/Windowing/Window.cs
@@ -41,6 +41,10 @@ public abstract class Window
 
     private bool internalLastIsOpen = false;
     private bool internalIsOpen = false;
+    private bool internalWantsToClose = false;
+    private bool internalLastDrawConditions = true;
+    private bool internalDrawConditions = true;
+
     private bool internalIsPinned = false;
     private bool internalIsClickthrough = false;
     private bool didPushInternalAlpha = false;
@@ -229,7 +233,18 @@ public abstract class Window
     public bool IsOpen
     {
         get => this.internalIsOpen;
-        set => this.internalIsOpen = value;
+        set
+        {
+            if (!value && this.internalIsOpen)
+            {
+                this.internalWantsToClose = true;
+            }
+            else if (value && !this.internalIsOpen)
+            {
+                this.internalWantsToClose = false;
+                this.internalIsOpen = true;
+            }
+        }
     }
 
     private bool CanShowCloseButton => this.ShowCloseButton && !this.internalIsClickthrough;
@@ -360,22 +375,7 @@ public abstract class Window
                     UIGlobals.PlaySoundEffect(this.OnCloseSfxId);
             }
 
-            if (this.fadeOutTexture != null)
-            {
-                this.fadeOutTimer -= ImGui.GetIO().DeltaTime;
-                if (this.fadeOutTimer <= 0f)
-                {
-                    this.fadeOutTexture.Dispose();
-                    this.fadeOutTexture = null;
-                    this.OnSafeToRemove();
-                }
-                else
-                {
-                    this.DrawFakeFadeOutWindow();
-                }
-            }
-
-            this.fadeInTimer = doFades ? 0f : FadeInOutTime;
+            DrawFadeOut();
             return;
         }
 
@@ -384,8 +384,15 @@ public abstract class Window
             this.fadeInTimer = FadeInOutTime;
 
         this.Update();
-        if (!this.DrawConditions())
+        this.internalDrawConditions = this.DrawConditions();
+        if (this.internalDrawConditions == this.internalLastDrawConditions && !this.internalDrawConditions)
+        {
+            DrawFadeOut();
             return;
+        }
+
+        if (this.internalDrawConditions)
+            this.internalLastDrawConditions = this.internalDrawConditions;
 
         var hasNamespace = !string.IsNullOrEmpty(this.Namespace);
 
@@ -607,12 +614,21 @@ public abstract class Window
             this.pushedFadeInAlpha = false;
         }
 
-        if (!this.internalIsOpen && this.fadeOutTexture == null && doFades)
+        if (this.internalDrawConditions != this.internalLastDrawConditions && !this.internalDrawConditions)
         {
-            this.fadeOutTexture = Service<TextureManager>.Get().CreateDrawListTexture(
-                "WindowFadeOutTexture");
-            this.fadeOutTexture.ResizeAndDrawWindow(this.WindowName, Vector2.One);
-            this.fadeOutTimer = FadeInOutTime;
+            this.internalLastDrawConditions = this.internalDrawConditions;
+            SetupFadeOut();
+        }
+
+        if (this.internalWantsToClose)
+        {
+            this.internalIsOpen = false;
+            this.internalWantsToClose = false;
+        }
+
+        if (!this.internalIsOpen)
+        {
+            SetupFadeOut();
         }
 
         if (printWindow)
@@ -632,6 +648,38 @@ public abstract class Window
 
         if (hasNamespace)
             ImGui.PopID();
+        return;
+
+        void SetupFadeOut()
+        {
+            if (this.fadeOutTexture == null && doFades)
+            {
+                this.fadeOutTexture = Service<TextureManager>.Get().CreateDrawListTexture(
+                    "WindowFadeOutTexture");
+                this.fadeOutTexture.ResizeAndDrawWindow(this.WindowName, Vector2.One);
+                this.fadeOutTimer = FadeInOutTime;
+            }
+        }
+
+        void DrawFadeOut()
+        {
+            if (this.fadeOutTexture != null)
+            {
+                this.fadeOutTimer -= ImGui.GetIO().DeltaTime;
+                if (this.fadeOutTimer <= 0f)
+                {
+                    this.fadeOutTexture.Dispose();
+                    this.fadeOutTexture = null;
+                    this.OnSafeToRemove();
+                }
+                else
+                {
+                    this.DrawFakeFadeOutWindow();
+                }
+            }
+
+            this.fadeInTimer = doFades ? 0f : FadeInOutTime;
+        }
     }
 
     private unsafe void ApplyConditionals()