diff --git a/src/video/windows/SDL_windowsevents.c b/src/video/windows/SDL_windowsevents.c
index 4802303cca..641ff9b272 100644
--- a/src/video/windows/SDL_windowsevents.c
+++ b/src/video/windows/SDL_windowsevents.c
@@ -1473,8 +1473,13 @@ LRESULT CALLBACK WIN_WindowProc(HWND hwnd, UINT msg, WPARAM wParam, LPARAM lPara
                 SDL_SendWindowEvent(data->window, SDL_EVENT_WINDOW_RESTORED, 0, 0);
             }
             SDL_SendWindowEvent(data->window, SDL_EVENT_WINDOW_MAXIMIZED, 0, 0);
+            data->force_resizable = true;
         } else if (data->window->flags & (SDL_WINDOW_MAXIMIZED | SDL_WINDOW_MINIMIZED)) {
             SDL_SendWindowEvent(data->window, SDL_EVENT_WINDOW_RESTORED, 0, 0);
+
+            // If resizable was forced on for the maximized window, clear the style flags now.
+            data->force_resizable = false;
+            WIN_SetWindowResizable(SDL_GetVideoDevice(), data->window, !!(data->window->flags & SDL_WINDOW_RESIZABLE));
         }
 
         if (windowpos->flags & SWP_HIDEWINDOW) {
@@ -1873,14 +1878,14 @@ LRESULT CALLBACK WIN_WindowProc(HWND hwnd, UINT msg, WPARAM wParam, LPARAM lPara
             NCCALCSIZE_PARAMS *params = (NCCALCSIZE_PARAMS *)lParam;
             WINDOWPLACEMENT placement;
             if (GetWindowPlacement(hwnd, &placement) && placement.showCmd == SW_MAXIMIZE) {
-                // Maximized borderless windows should use the full monitor size
+                // Maximized borderless windows should use the monitor work area.
                 HMONITOR hMonitor = MonitorFromWindow(hwnd, MONITOR_DEFAULTTONULL);
                 if (hMonitor) {
                     MONITORINFO info;
                     SDL_zero(info);
                     info.cbSize = sizeof(info);
                     if (GetMonitorInfo(hMonitor, &info)) {
-                        params->rgrc[0] = info.rcMonitor;
+                        params->rgrc[0] = info.rcWork;
                     }
                 }
             } else if (!(window_flags & SDL_WINDOW_RESIZABLE)) {
diff --git a/src/video/windows/SDL_windowswindow.c b/src/video/windows/SDL_windowswindow.c
index b07d7dc0fb..a5d17c0f30 100644
--- a/src/video/windows/SDL_windowswindow.c
+++ b/src/video/windows/SDL_windowswindow.c
@@ -180,13 +180,22 @@ static DWORD GetWindowStyle(SDL_Window *window)
             style |= STYLE_NORMAL;
         }
 
-        if (window->flags & SDL_WINDOW_RESIZABLE) {
+        /* The WS_MAXIMIZEBOX style flag needs to be retained for as long as the window is maximized,
+         * or restoration from minimized can fail, and leaving maximized can result in an odd size.
+         */
+        if ((window->flags & SDL_WINDOW_RESIZABLE) || (window->internal && window->internal->force_resizable)) {
             /* You can have a borderless resizable window, but Windows doesn't always draw it correctly,
                see https://bugzilla.libsdl.org/show_bug.cgi?id=4466
              */
             if (!(window->flags & SDL_WINDOW_BORDERLESS) ||
                 SDL_GetHintBoolean("SDL_BORDERLESS_RESIZABLE_STYLE", false)) {
                 style |= STYLE_RESIZABLE;
+            } else if (window->flags & SDL_WINDOW_BORDERLESS) {
+                /* Even if the resizable style hint isn't set, WS_MAXIMIZEBOX is still needed, or
+                 * maximizing the window will make it fullscreen and cover the taskbar, instead
+                 * of entering a normal maximized state that fills the usable desktop area.
+                 */
+                style |= WS_MAXIMIZEBOX;
             }
         }
 
diff --git a/src/video/windows/SDL_windowswindow.h b/src/video/windows/SDL_windowswindow.h
index ddc3ddd6d9..3a21a1c258 100644
--- a/src/video/windows/SDL_windowswindow.h
+++ b/src/video/windows/SDL_windowswindow.h
@@ -81,6 +81,7 @@ struct SDL_WindowData
     bool skip_update_clipcursor;
     bool windowed_mode_was_maximized;
     bool in_window_deactivation;
+    bool force_resizable;
     RECT cursor_clipped_rect; // last successfully committed clipping rect for this window
     RECT cursor_ctrlock_rect; // this is Windows-specific, but probably does not need to be per-window
     UINT windowed_mode_corner_rounding;