diff --git a/src/win.c b/src/win.c
index 56bd2ba..7c82ab5 100644
--- a/src/win.c
+++ b/src/win.c
@@ -2038,10 +2038,28 @@ bool destroy_win_start(session_t *ps, struct win *w) {
 	}
 
 	if (w->managed) {
-		// Clear PIXMAP_STALE flag, since the window is destroyed there is no
-		// pixmap available so STALE doesn't make sense.
+		// Clear IMAGES_STALE flags since the window is destroyed: Clear
+		// PIXMAP_STALE as there is no pixmap available anymore, so STALE doesn't
+		// make sense.
+		// XXX Clear SHADOW_STALE as setting/clearing flags on a destroyed window
+		// doesn't work leading to an inconsistent state where the shadow is
+		// refreshed but the flags are stuck in STALE.
 		// Do this before changing the window state to destroying
-		win_clear_flags(mw, WIN_FLAGS_PIXMAP_STALE);
+		win_clear_flags(mw, WIN_FLAGS_IMAGES_STALE);
+
+		// If size/shape/position information is stale, win_process_update_flags
+		// will update them and add the new window extents to damage. Since the
+		// window has been destroyed, we cannot get the complete information at
+		// this point, so we just add what we currently have to the damage.
+		if (win_check_flags_any(mw, WIN_FLAGS_SIZE_STALE | WIN_FLAGS_POSITION_STALE)) {
+			add_damage_from_win(ps, mw);
+		}
+
+		// Clear some flags about stale window information. Because now the window
+		// is destroyed, we can't update them anyway.
+		win_clear_flags(mw, WIN_FLAGS_SIZE_STALE | WIN_FLAGS_POSITION_STALE |
+		                        WIN_FLAGS_PROPERTY_STALE |
+		                        WIN_FLAGS_FACTOR_CHANGED | WIN_FLAGS_CLIENT_STALE);
 
 		// Update state flags of a managed window
 		mw->state = WSTATE_DESTROYING;
diff --git a/tests/configs/issue394.conf b/tests/configs/issue394.conf
new file mode 100644
index 0000000..0e33a1c
--- /dev/null
+++ b/tests/configs/issue394.conf
@@ -0,0 +1,4 @@
+fading = true;
+fade-in-step = 1;
+fade-out-step = 0.01;
+shadow = true;
diff --git a/tests/run_tests.sh b/tests/run_tests.sh
index 26bdb12..6c871de 100755
--- a/tests/run_tests.sh
+++ b/tests/run_tests.sh
@@ -17,3 +17,4 @@ eval `dbus-launch --sh-syntax`
 ./run_one_test.sh $exe /dev/null testcases/issue299.py
 ./run_one_test.sh $exe configs/issue465.conf testcases/issue465.py
 ./run_one_test.sh $exe configs/clear_shadow_unredirected.conf testcases/clear_shadow_unredirected.py
+./run_one_test.sh $exe configs/issue394.conf testcases/issue394.py
diff --git a/tests/testcases/common.py b/tests/testcases/common.py
index 104a108..093b7a8 100644
--- a/tests/testcases/common.py
+++ b/tests/testcases/common.py
@@ -28,6 +28,11 @@ def set_window_class(conn, wid, name):
     str_type = to_atom(conn, "STRING")
     conn.core.ChangePropertyChecked(xproto.PropMode.Replace, wid, prop_name, str_type, 8, len(name), name).check()
 
+def set_window_size(conn, wid, width, height):
+    value_mask = xproto.ConfigWindow.Width | xproto.ConfigWindow.Height
+    value_list = [width, height]
+    conn.core.ConfigureWindowChecked(wid, value_mask, value_list).check()
+
 def find_picom_window(conn):
     prop_name = to_atom(conn, "WM_NAME")
     setup = conn.get_setup()
diff --git a/tests/testcases/issue394.py b/tests/testcases/issue394.py
new file mode 100755
index 0000000..e7cafba
--- /dev/null
+++ b/tests/testcases/issue394.py
@@ -0,0 +1,35 @@
+#!/usr/bin/env python
+
+import xcffib.xproto as xproto
+import xcffib
+import time
+from common import set_window_name, set_window_size
+
+conn = xcffib.connect()
+setup = conn.get_setup()
+root = setup.roots[0].root
+visual = setup.roots[0].root_visual
+depth = setup.roots[0].root_depth
+
+# issue 394 is caused by a window getting a size update just before destroying leading to a shadow update on destroyed window.
+wid = conn.generate_id()
+print("Window id is ", hex(wid))
+
+# Create a window
+conn.core.CreateWindowChecked(depth, wid, root, 0, 0, 100, 100, 0, xproto.WindowClass.InputOutput, visual, 0, []).check()
+
+# Set Window name so it doesn't get a shadow
+set_window_name(conn, wid, "Test Window")
+
+# Map the window
+print("mapping")
+conn.core.MapWindowChecked(wid).check()
+
+time.sleep(0.5)
+
+# Resize the window and destroy
+print("resize and destroy")
+set_window_size(conn, wid, 150, 150)
+conn.core.DestroyWindowChecked(wid).check()
+
+time.sleep(0.5)