diff --git a/komorebi/src/border_manager/border.rs b/komorebi/src/border_manager/border.rs
index a33b085a..2d0d1e51 100644
--- a/komorebi/src/border_manager/border.rs
+++ b/komorebi/src/border_manager/border.rs
@@ -313,6 +313,11 @@ impl Border {
     }
 
     pub fn destroy(&self) -> color_eyre::Result<()> {
+        // clear user data **BEFORE** closing window
+        // pending messages will see a null pointer and exit early
+        unsafe {
+            SetWindowLongPtrW(self.hwnd(), GWLP_USERDATA, 0);
+        }
         WindowsApi::close_window(self.hwnd)
     }
 
diff --git a/komorebi/src/border_manager/mod.rs b/komorebi/src/border_manager/mod.rs
index f29f55d1..0280164d 100644
--- a/komorebi/src/border_manager/mod.rs
+++ b/komorebi/src/border_manager/mod.rs
@@ -767,6 +767,13 @@ fn remove_border(
 fn destroy_border(border: Box<Border>) -> color_eyre::Result<()> {
     let raw_pointer = Box::into_raw(border);
     unsafe {
+        // release d2d resources **BEFORE** destroying window
+        // this drops render_target and brushes while HWND is still valid
+        // prevents EndDraw() from accessing freed HWND resources
+        (*raw_pointer).render_target = None;
+        (*raw_pointer).brushes.clear();
+
+        // Now safe to destroy window
         (*raw_pointer).destroy()?;
     }
     Ok(())