diff --git a/CHANGELOG.md b/CHANGELOG.md
index 57e3e6d000..d0a72d1bea 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -39,6 +39,7 @@ And please only add new entries to the top of this list, right below the `# Unre
 - **Breaking:** Bump `ndk` version to `0.8.0`, ndk-sys to `0.5.0`, `android-activity` to `0.5.0`.
 - Make `WindowBuilder` `Send + Sync`.
 - On macOS, fix assertion when pressing `Globe` key.
+- On Windows, updated `WM_MOUSEMOVE` to detect when cursor Enter or Leave window client area while captured and send the corresponding events. (#3153)
 
 # 0.29.1-beta
 
diff --git a/src/platform_impl/windows/event_loop.rs b/src/platform_impl/windows/event_loop.rs
index 0abd9b1798..43b162afae 100644
--- a/src/platform_impl/windows/event_loop.rs
+++ b/src/platform_impl/windows/event_loop.rs
@@ -49,8 +49,8 @@ use windows_sys::Win32::{
             RAWINPUT, RIM_TYPEKEYBOARD, RIM_TYPEMOUSE,
         },
         WindowsAndMessaging::{
-            CreateWindowExW, DefWindowProcW, DestroyWindow, DispatchMessageW, GetCursorPos,
-            GetMenu, GetMessageW, KillTimer, LoadCursorW, PeekMessageW, PostMessageW,
+            CreateWindowExW, DefWindowProcW, DestroyWindow, DispatchMessageW, GetClientRect,
+            GetCursorPos, GetMenu, GetMessageW, KillTimer, LoadCursorW, PeekMessageW, PostMessageW,
             RegisterClassExW, RegisterWindowMessageA, SetCursor, SetTimer, SetWindowPos,
             TranslateMessage, CREATESTRUCTW, GIDC_ARRIVAL, GIDC_REMOVAL, GWL_STYLE, GWL_USERDATA,
             HTCAPTION, HTCLIENT, MINMAXINFO, MNC_CLOSE, MSG, NCCALCSIZE_PARAMS, PM_REMOVE, PT_PEN,
@@ -1438,48 +1438,63 @@ unsafe fn public_window_callback_inner<T: 'static>(
         }
 
         WM_MOUSEMOVE => {
-            use crate::event::WindowEvent::{CursorEntered, CursorMoved};
-            let mouse_was_outside_window = {
+            use crate::event::WindowEvent::{CursorEntered, CursorLeft, CursorMoved};
+
+            let x = super::get_x_lparam(lparam as u32) as i32;
+            let y = super::get_y_lparam(lparam as u32) as i32;
+            let position = PhysicalPosition::new(x as f64, y as f64);
+
+            let cursor_moved;
+            {
                 let mut w = userdata.window_state_lock();
+                let mouse_was_inside_window =
+                    w.mouse.cursor_flags().contains(CursorFlags::IN_WINDOW);
 
-                let was_outside_window = !w.mouse.cursor_flags().contains(CursorFlags::IN_WINDOW);
-                w.mouse
-                    .set_cursor_flags(window, |f| f.set(CursorFlags::IN_WINDOW, true))
-                    .ok();
-                was_outside_window
-            };
+                match get_pointer_move_kind(window, mouse_was_inside_window, x, y) {
+                    PointerMoveKind::Enter => {
+                        w.mouse
+                            .set_cursor_flags(window, |f| f.set(CursorFlags::IN_WINDOW, true))
+                            .ok();
 
-            if mouse_was_outside_window {
-                userdata.send_event(Event::WindowEvent {
-                    window_id: RootWindowId(WindowId(window)),
-                    event: CursorEntered {
-                        device_id: DEVICE_ID,
-                    },
-                });
+                        userdata.send_event(Event::WindowEvent {
+                            window_id: RootWindowId(WindowId(window)),
+                            event: CursorEntered {
+                                device_id: DEVICE_ID,
+                            },
+                        });
 
-                // Calling TrackMouseEvent in order to receive mouse leave events.
-                unsafe {
-                    TrackMouseEvent(&mut TRACKMOUSEEVENT {
-                        cbSize: mem::size_of::<TRACKMOUSEEVENT>() as u32,
-                        dwFlags: TME_LEAVE,
-                        hwndTrack: window,
-                        dwHoverTime: HOVER_DEFAULT,
-                    })
-                };
-            }
+                        // Calling TrackMouseEvent in order to receive mouse leave events.
+                        unsafe {
+                            TrackMouseEvent(&mut TRACKMOUSEEVENT {
+                                cbSize: mem::size_of::<TRACKMOUSEEVENT>() as u32,
+                                dwFlags: TME_LEAVE,
+                                hwndTrack: window,
+                                dwHoverTime: HOVER_DEFAULT,
+                            })
+                        };
+                    }
+                    PointerMoveKind::Leave => {
+                        w.mouse
+                            .set_cursor_flags(window, |f| f.set(CursorFlags::IN_WINDOW, false))
+                            .ok();
+
+                        userdata.send_event(Event::WindowEvent {
+                            window_id: RootWindowId(WindowId(window)),
+                            event: CursorLeft {
+                                device_id: DEVICE_ID,
+                            },
+                        });
+                    }
+                    PointerMoveKind::None => (),
+                }
 
-            let x = super::get_x_lparam(lparam as u32) as f64;
-            let y = super::get_y_lparam(lparam as u32) as f64;
-            let position = PhysicalPosition::new(x, y);
-            let cursor_moved;
-            {
                 // handle spurious WM_MOUSEMOVE messages
                 // see https://devblogs.microsoft.com/oldnewthing/20031001-00/?p=42343
                 // and http://debugandconquer.blogspot.com/2015/08/the-cause-of-spurious-mouse-move.html
-                let mut w = userdata.window_state_lock();
                 cursor_moved = w.mouse.last_position != Some(position);
                 w.mouse.last_position = Some(position);
             }
+
             if cursor_moved {
                 update_modifiers(window, userdata);
 
@@ -2562,3 +2577,38 @@ unsafe fn handle_raw_input<T: 'static>(userdata: &ThreadMsgTargetData<T>, data:
         });
     }
 }
+
+enum PointerMoveKind {
+    /// Pointer enterd to the window.
+    Enter,
+    /// Pointer leaved the window client area.
+    Leave,
+    /// Pointer is inside the window or `GetClientRect` failed.
+    None,
+}
+
+fn get_pointer_move_kind(
+    window: HWND,
+    mouse_was_inside_window: bool,
+    x: i32,
+    y: i32,
+) -> PointerMoveKind {
+    let rect: RECT = unsafe {
+        let mut rect: RECT = mem::zeroed();
+        if GetClientRect(window, &mut rect) == false.into() {
+            return PointerMoveKind::None; // exit early if GetClientRect failed
+        }
+        rect
+    };
+
+    let x = (rect.left..rect.right).contains(&x);
+    let y = (rect.top..rect.bottom).contains(&y);
+
+    if !mouse_was_inside_window && x && y {
+        PointerMoveKind::Enter
+    } else if mouse_was_inside_window && !(x && y) {
+        PointerMoveKind::Leave
+    } else {
+        PointerMoveKind::None
+    }
+}