diff --git a/.changes/enter-event.md b/.changes/enter-event.md
new file mode 100644
index 0000000..1b638dc
--- /dev/null
+++ b/.changes/enter-event.md
@@ -0,0 +1,5 @@
+---
+"tray-icon": "patch"
+---
+
+On Windows, fix `Enter` event emitted only once and never emitted again.
diff --git a/src/platform_impl/windows/mod.rs b/src/platform_impl/windows/mod.rs
index b143020..fd52d83 100644
--- a/src/platform_impl/windows/mod.rs
+++ b/src/platform_impl/windows/mod.rs
@@ -439,6 +439,7 @@ unsafe extern "system" fn tray_proc(
 
                 if !in_x || !in_y {
                     KillTimer(hwnd, WM_USER_LEAVE_TIMER_ID as _);
+                    userdata.entered = false;
 
                     TrayIconEvent::send(TrayIconEvent::Leave {
                         id: userdata.id.clone(),