diff --git a/src/openrct2-ui/UiContext.cpp b/src/openrct2-ui/UiContext.cpp
index 4bce4325bb..cb42b5335e 100644
--- a/src/openrct2-ui/UiContext.cpp
+++ b/src/openrct2-ui/UiContext.cpp
@@ -980,7 +980,7 @@ private:
 
             w = it->get();
 
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
             {
                 continue;
             }
diff --git a/src/openrct2-ui/WindowManager.cpp b/src/openrct2-ui/WindowManager.cpp
index d3d6ec6c45..6ad62a773f 100644
--- a/src/openrct2-ui/WindowManager.cpp
+++ b/src/openrct2-ui/WindowManager.cpp
@@ -665,9 +665,9 @@ public:
     {
         for (auto& w : gWindowList)
         {
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
-            if (w->flags & WF_STICK_TO_BACK)
+            if (w->flags.has(WindowFlag::stickToBack))
                 continue;
 
             if (loc.x + windowSize.width <= w->windowPos.x)
@@ -759,9 +759,9 @@ public:
         // Place window next to another
         for (auto& w : gWindowList)
         {
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
-            if (w->flags & WF_STICK_TO_BACK)
+            if (w->flags.has(WindowFlag::stickToBack))
                 continue;
 
             const ScreenCoordsXY offsets[] = {
@@ -788,9 +788,9 @@ public:
         // Overlap
         for (auto& w : gWindowList)
         {
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
-            if (w->flags & WF_STICK_TO_BACK)
+            if (w->flags.has(WindowFlag::stickToBack))
                 continue;
 
             const ScreenCoordsXY offsets[] = {
@@ -839,9 +839,9 @@ public:
     {
         windowSize.height += wp->getTitleBarDiffTarget();
 
-        if (flags & WF_AUTO_POSITION)
+        if (flags.has(WindowFlag::autoPosition))
         {
-            if (flags & WF_CENTRE_SCREEN)
+            if (flags.has(WindowFlag::centreScreen))
             {
                 pos = GetCentrePositionForNewWindow(windowSize);
             }
@@ -860,9 +860,9 @@ public:
             // Close least recently used window
             for (auto& w : gWindowList)
             {
-                if (w->flags & WF_DEAD)
+                if (w->flags.has(WindowFlag::dead))
                     continue;
-                if (!(w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT | WF_NO_AUTO_CLOSE)))
+                if (!(w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront, WindowFlag::noAutoClose)))
                 {
                     Close(*w.get());
                     break;
@@ -872,25 +872,25 @@ public:
 
         // Find right position to insert new window
         auto itDestPos = gWindowList.end();
-        if (flags & WF_STICK_TO_BACK)
+        if (flags.has(WindowFlag::stickToBack))
         {
             for (auto it = gWindowList.begin(); it != gWindowList.end(); it++)
             {
-                if ((*it)->flags & WF_DEAD)
+                if ((*it)->flags.has(WindowFlag::dead))
                     continue;
-                if (!((*it)->flags & WF_STICK_TO_BACK))
+                if (!((*it)->flags.has(WindowFlag::stickToBack)))
                 {
                     itDestPos = it;
                 }
             }
         }
-        else if (!(flags & WF_STICK_TO_FRONT))
+        else if (!(flags.has(WindowFlag::stickToFront)))
         {
             for (auto it = gWindowList.rbegin(); it != gWindowList.rend(); it++)
             {
-                if ((*it)->flags & WF_DEAD)
+                if ((*it)->flags.has(WindowFlag::dead))
                     continue;
-                if (!((*it)->flags & WF_STICK_TO_FRONT))
+                if (!((*it)->flags.has(WindowFlag::stickToFront)))
                 {
                     itDestPos = it.base();
                     break;
@@ -903,9 +903,9 @@ public:
         wp->flags = flags;
 
         // Play sounds and flash the window
-        if (!(flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT)))
+        if (!(flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront)))
         {
-            wp->flags |= WF_WHITE_BORDER_MASK;
+            wp->flash();
             OpenRCT2::Audio::Play(OpenRCT2::Audio::SoundId::WindowOpen, 0, pos.x + (windowSize.width / 2));
         }
 
@@ -947,7 +947,7 @@ public:
         // Invalidate the window (area)
         w.invalidate();
 
-        w.flags |= WF_DEAD;
+        w.flags |= WindowFlag::dead;
     }
 
     void CloseSurplus(int32_t cap, WindowClass avoid_classification) override
@@ -962,9 +962,9 @@ public:
             WindowBase* foundW{};
             for (auto& w : gWindowList)
             {
-                if (w->flags & WF_DEAD)
+                if (w->flags.has(WindowFlag::dead))
                     continue;
-                if (!(w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT | WF_NO_AUTO_CLOSE)))
+                if (!(w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront, WindowFlag::noAutoClose)))
                 {
                     foundW = w.get();
                     break;
@@ -991,7 +991,7 @@ public:
         for (auto it = gWindowList.rbegin(); it != gWindowList.rend(); ++it)
         {
             auto& wnd = *(*it);
-            if (wnd.flags & WF_DEAD)
+            if (wnd.flags.has(WindowFlag::dead))
                 continue;
 
             if (pred(&wnd))
@@ -1007,7 +1007,7 @@ public:
         // Now close the collected windows
         for (auto* wnd : windowsToClose)
         {
-            if (!(wnd->flags & WF_DEAD))
+            if (!(wnd->flags.has(WindowFlag::dead)))
             {
                 Close(*wnd);
             }
@@ -1053,7 +1053,7 @@ public:
                 return;
         }
 
-        auto pred = [](WindowBase* w) -> bool { return !(w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT)); };
+        auto pred = [](WindowBase* w) -> bool { return !(w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront)); };
         CloseByCondition(pred, WindowCloseFlags::CloseSingle);
     }
 
@@ -1065,14 +1065,15 @@ public:
     void CloseAll() override
     {
         CloseByClass(WindowClass::dropdown);
-        CloseByCondition([](WindowBase* w) -> bool { return !(w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT)); });
+        CloseByCondition(
+            [](WindowBase* w) -> bool { return !(w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront)); });
     }
 
     void CloseAllExceptClass(WindowClass cls) override
     {
         CloseByClass(WindowClass::dropdown);
         CloseByCondition([cls](WindowBase* w) -> bool {
-            return w->classification != cls && !(w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT));
+            return w->classification != cls && !(w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront));
         });
     }
 
@@ -1081,7 +1082,7 @@ public:
      */
     void CloseAllExceptFlags(WindowFlags flags) override
     {
-        CloseByCondition([flags](WindowBase* w) -> bool { return !(w->flags & flags); });
+        CloseByCondition([flags](WindowBase* w) -> bool { return !(w->flags.hasAny(flags)); });
     }
 
     /**
@@ -1091,7 +1092,9 @@ public:
     {
         CloseByClass(WindowClass::dropdown);
         CloseByCondition([cls, number](WindowBase* w) -> bool {
-            return (!(w->number == number && w->classification == cls) && !(w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT)));
+            return (
+                !(w->number == number && w->classification == cls)
+                && !(w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront)));
         });
     }
 
@@ -1116,7 +1119,7 @@ public:
     {
         for (auto& w : gWindowList)
         {
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
             if (w->classification == cls)
             {
@@ -1135,7 +1138,7 @@ public:
     {
         for (auto& w : gWindowList)
         {
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
             if (w->classification == cls && w->number == number)
             {
@@ -1160,14 +1163,14 @@ public:
         for (auto it = gWindowList.rbegin(); it != gWindowList.rend(); it++)
         {
             auto& w = *it;
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
 
             if (screenCoords.x < w->windowPos.x || screenCoords.x >= w->windowPos.x + w->width
                 || screenCoords.y < w->windowPos.y || screenCoords.y >= w->windowPos.y + w->height)
                 continue;
 
-            if (w->flags & WF_NO_BACKGROUND)
+            if (w->flags.has(WindowFlag::noBackground))
             {
                 auto widgetIndex = FindWidgetFromPoint(*w.get(), screenCoords);
                 if (widgetIndex == kWidgetIndexNull)
@@ -1324,7 +1327,7 @@ public:
      */
     WindowBase* BringToFront(WindowBase& w) override
     {
-        if (!(w.flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT)))
+        if (!(w.flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront)))
         {
             auto itSourcePos = WindowGetIterator(&w);
             if (itSourcePos != gWindowList.end())
@@ -1334,11 +1337,11 @@ public:
                 for (auto it = gWindowList.rbegin(); it != gWindowList.rend(); it++)
                 {
                     auto& w2 = *it;
-                    if (w2->flags & WF_DEAD)
+                    if (w2->flags.has(WindowFlag::dead))
                     {
                         continue;
                     }
-                    if (!(w2->flags & WF_STICK_TO_FRONT))
+                    if (!(w2->flags.has(WindowFlag::stickToFront)))
                     {
                         // base() returns the next element in the list, so we need to decrement it.
                         itDestPos = std::prev(it.base());
@@ -1365,12 +1368,12 @@ public:
         return &w;
     }
 
-    WindowBase* BringToFrontByClassWithFlags(WindowClass cls, WindowFlags flags) override
+    WindowBase* BringToFrontByClass(WindowClass cls) override
     {
         WindowBase* w = FindByClass(cls);
         if (w != nullptr)
         {
-            w->flags |= flags;
+            w->flash();
             w->invalidate();
             w = BringToFront(*w);
         }
@@ -1378,11 +1381,6 @@ public:
         return w;
     }
 
-    WindowBase* BringToFrontByClass(WindowClass cls) override
-    {
-        return BringToFrontByClassWithFlags(cls, WF_WHITE_BORDER_MASK);
-    }
-
     /**
      *
      *  rct2: 0x006ED78A
@@ -1392,7 +1390,7 @@ public:
         WindowBase* w = FindByNumber(cls, number);
         if (w != nullptr)
         {
-            w->flags |= WF_WHITE_BORDER_MASK;
+            w->flash();
             w->invalidate();
             w = BringToFront(*w);
         }
diff --git a/src/openrct2-ui/input/MouseInput.cpp b/src/openrct2-ui/input/MouseInput.cpp
index 2a5a67015f..6ab8f9ee73 100644
--- a/src/openrct2-ui/input/MouseInput.cpp
+++ b/src/openrct2-ui/input/MouseInput.cpp
@@ -492,7 +492,7 @@ namespace OpenRCT2
     {
         int32_t snapProximity;
 
-        snapProximity = (w.flags & WF_NO_SNAPPING) ? 0 : Config::Get().general.WindowSnapProximity;
+        snapProximity = (w.flags.has(WindowFlag::noSnapping)) ? 0 : Config::Get().general.WindowSnapProximity;
         WindowMoveAndSnap(w, newScreenCoords - lastScreenCoords, snapProximity);
     }
 
@@ -540,7 +540,7 @@ namespace OpenRCT2
 
     static void InputViewportDragBegin(WindowBase& w)
     {
-        w.flags &= ~WF_SCROLLING_TO_LOCATION;
+        w.flags.unset(WindowFlag::scrollingToLocation);
         _inputState = InputState::ViewportRight;
         _dragWidget.windowClassification = w.classification;
         _dragWidget.windowNumber = w.number;
@@ -591,7 +591,7 @@ namespace OpenRCT2
         }
         else if (differentialCoords.x != 0 || differentialCoords.y != 0)
         {
-            if (!(w->flags & WF_NO_SCROLLING))
+            if (!(w->flags.has(WindowFlag::noScrolling)))
             {
                 // User dragged a scrollable viewport
 
@@ -1076,7 +1076,7 @@ namespace OpenRCT2
         {
             case WidgetType::frame:
             case WidgetType::resize:
-                if (WindowCanResize(*w)
+                if (w->canBeResized()
                     && (screenCoords.x >= w->windowPos.x + w->width - 19 && screenCoords.y >= w->windowPos.y + w->height - 19))
                     InputWindowResizeBegin(*w, widgetIndex, screenCoords);
                 break;
@@ -1597,7 +1597,7 @@ namespace OpenRCT2
         mainWindow = WindowGetMain();
         if (mainWindow == nullptr)
             return;
-        if ((mainWindow->flags & WF_NO_SCROLLING)
+        if ((mainWindow->flags.has(WindowFlag::noScrolling))
             || (gLegacyScene == LegacyScene::trackDesignsManager || gLegacyScene == LegacyScene::titleSequence))
             return;
         if (mainWindow->viewport == nullptr)
@@ -1704,7 +1704,7 @@ namespace OpenRCT2
             return;
         }
 
-        if (targetWindow->flags & WF_NO_SCROLLING)
+        if (targetWindow->flags.has(WindowFlag::noScrolling))
         {
             return;
         }
diff --git a/src/openrct2-ui/interface/Theme.cpp b/src/openrct2-ui/interface/Theme.cpp
index 1e7c7826b1..84198b8c89 100644
--- a/src/openrct2-ui/interface/Theme.cpp
+++ b/src/openrct2-ui/interface/Theme.cpp
@@ -938,6 +938,6 @@ static constexpr UIThemeWindowEntry PredefinedThemeRCT1_Entries[] =
         }
         // Some windows need to be transparent even if the colours aren't.
         // There doesn't seem to be any side-effects for all windows being transparent
-        window->flags |= WF_TRANSPARENT;
+        window->flags |= WindowFlag::transparent;
     }
 } // namespace OpenRCT2::Ui
diff --git a/src/openrct2-ui/interface/Widget.cpp b/src/openrct2-ui/interface/Widget.cpp
index 4e75c5d0e6..f7fd73bdd0 100644
--- a/src/openrct2-ui/interface/Widget.cpp
+++ b/src/openrct2-ui/interface/Widget.cpp
@@ -141,7 +141,7 @@ namespace OpenRCT2::Ui
         int32_t b = w.windowPos.y + widget.bottom;
 
         //
-        uint8_t press = ((w.flags & WF_10) ? INSET_RECT_FLAG_FILL_MID_LIGHT : 0);
+        uint8_t press = (w.flags.has(WindowFlag::higherContrastOnPress) ? INSET_RECT_FLAG_FILL_MID_LIGHT : 0);
 
         auto colour = w.colours[widget.colour];
 
@@ -537,7 +537,7 @@ namespace OpenRCT2::Ui
         auto colour = w.colours[widget->colour];
 
         uint8_t press = INSET_RECT_F_60;
-        if (w.flags & WF_10)
+        if (w.flags.has(WindowFlag::higherContrastOnPress))
             press |= INSET_RECT_FLAG_FILL_MID_LIGHT;
 
         GfxFillRectInset(rt, { topLeft, bottomRight }, colour, press);
@@ -593,7 +593,7 @@ namespace OpenRCT2::Ui
 
         // Check if the button is pressed down
         uint8_t press = 0;
-        if (w.flags & WF_10)
+        if (w.flags.has(WindowFlag::higherContrastOnPress))
             press |= INSET_RECT_FLAG_FILL_MID_LIGHT;
         if (widgetIsPressed(w, widgetIndex) || isToolActive(w, widgetIndex))
             press |= INSET_RECT_FLAG_BORDER_INSET;
diff --git a/src/openrct2-ui/interface/Window.cpp b/src/openrct2-ui/interface/Window.cpp
index f2b3cef84a..447b1ca27c 100644
--- a/src/openrct2-ui/interface/Window.cpp
+++ b/src/openrct2-ui/interface/Window.cpp
@@ -532,7 +532,7 @@ namespace OpenRCT2::Ui::Windows
         for (auto it = gWindowList.rbegin(); it != gWindowList.rend(); it++)
         {
             auto& w = **it;
-            if (w.flags & WF_DEAD)
+            if (w.flags.has(WindowFlag::dead))
                 continue;
 
             auto viewport = w.viewport;
@@ -925,7 +925,7 @@ namespace OpenRCT2::Ui::Windows
             // Work out if the window requires moving
             if (w->windowPos.x + 10 < width)
             {
-                if (w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT))
+                if (w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront))
                 {
                     if (w->windowPos.y - 22 < height)
                     {
@@ -994,11 +994,6 @@ namespace OpenRCT2::Ui::Windows
         return false;
     }
 
-    bool WindowCanResize(const WindowBase& w)
-    {
-        return (w.flags & WF_RESIZABLE) && (w.minWidth != w.maxWidth || w.minHeight != w.maxHeight);
-    }
-
     /**
      *
      *  rct2: 0x006EA73F
@@ -1026,7 +1021,7 @@ namespace OpenRCT2::Ui::Windows
      */
     void WindowDrawWidgets(WindowBase& w, RenderTarget& rt)
     {
-        if ((w.flags & WF_TRANSPARENT) && !(w.flags & WF_NO_BACKGROUND))
+        if ((w.flags.has(WindowFlag::transparent)) && !(w.flags.has(WindowFlag::noBackground)))
             GfxFilterRect(
                 rt, { w.windowPos, w.windowPos + ScreenCoordsXY{ w.width - 1, w.height - 1 } }, FilterPaletteID::Palette51);
 
@@ -1051,7 +1046,7 @@ namespace OpenRCT2::Ui::Windows
 
         // todo: something missing here too? Between 006EC32B and 006EC369
 
-        if (w.flags & WF_WHITE_BORDER_MASK)
+        if (w.flashTimer > 0)
         {
             GfxFillRectInset(
                 rt, { w.windowPos, w.windowPos + ScreenCoordsXY{ w.width - 1, w.height - 1 } }, { COLOUR_WHITE },
diff --git a/src/openrct2-ui/interface/Window.h b/src/openrct2-ui/interface/Window.h
index df16994ae1..fbdb0b1c50 100644
--- a/src/openrct2-ui/interface/Window.h
+++ b/src/openrct2-ui/interface/Window.h
@@ -83,7 +83,6 @@ namespace OpenRCT2::Ui::Windows
     void WindowRelocateWindows(int32_t width, int32_t height);
 
     bool WindowSetResize(WindowBase& w, ScreenSize minSize, ScreenSize maxSize);
-    bool WindowCanResize(const WindowBase& w);
 
     void InvalidateAllWindowsAfterInput();
 
diff --git a/src/openrct2-ui/scripting/CustomWindow.cpp b/src/openrct2-ui/scripting/CustomWindow.cpp
index 4c4b54905a..723b7a209f 100644
--- a/src/openrct2-ui/scripting/CustomWindow.cpp
+++ b/src/openrct2-ui/scripting/CustomWindow.cpp
@@ -813,7 +813,7 @@ namespace OpenRCT2::Ui::Windows
                     if (viewport == nullptr)
                     {
                         ViewportCreate(*this, { left, top }, wwidth, wheight, Focus(CoordsXYZ(0, 0, 0)));
-                        flags |= WF_NO_SCROLLING;
+                        flags |= WindowFlag::noScrolling;
                         invalidate();
                     }
                     else
@@ -1131,7 +1131,7 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* WindowCustomOpen(std::shared_ptr<Plugin> owner, DukValue dukDesc)
     {
         auto desc = CustomWindowDesc::FromDukValue(dukDesc);
-        uint16_t windowFlags = WF_RESIZABLE | WF_TRANSPARENT;
+        WindowFlags windowFlags = { WindowFlag::resizable, WindowFlag::transparent };
         auto* windowMgr = GetWindowManager();
 
         CustomWindow* window{};
diff --git a/src/openrct2-ui/scripting/ScViewport.hpp b/src/openrct2-ui/scripting/ScViewport.hpp
index 89a8580e22..2d38793127 100644
--- a/src/openrct2-ui/scripting/ScViewport.hpp
+++ b/src/openrct2-ui/scripting/ScViewport.hpp
@@ -276,7 +276,7 @@ namespace OpenRCT2::Scripting
                 {
                     viewport->viewPos.x = left;
                     viewport->viewPos.y = top;
-                    w->flags &= ~WF_SCROLLING_TO_LOCATION;
+                    w->flags.unset(WindowFlag::scrollingToLocation);
                     w->savedViewPos.x = viewport->viewPos.x;
                     w->savedViewPos.y = viewport->viewPos.y;
                     viewport->Invalidate();
diff --git a/src/openrct2-ui/scripting/ScWindow.hpp b/src/openrct2-ui/scripting/ScWindow.hpp
index 8d11943e71..93abaafb9e 100644
--- a/src/openrct2-ui/scripting/ScWindow.hpp
+++ b/src/openrct2-ui/scripting/ScWindow.hpp
@@ -97,7 +97,7 @@ namespace OpenRCT2::Scripting
             auto w = GetWindow();
             if (w != nullptr)
             {
-                if (WindowCanResize(*w))
+                if (w->canBeResized())
                 {
                     WindowResizeByDelta(*w, value - w->width, 0);
                 }
@@ -122,7 +122,7 @@ namespace OpenRCT2::Scripting
             if (w != nullptr)
             {
                 value += w->getTitleBarDiffNormal();
-                if (WindowCanResize(*w))
+                if (w->canBeResized())
                 {
                     WindowResizeByDelta(*w, 0, value - w->height);
                 }
@@ -207,7 +207,7 @@ namespace OpenRCT2::Scripting
             auto w = GetWindow();
             if (w != nullptr)
             {
-                return (w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT)) != 0;
+                return (w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront));
             }
             return false;
         }
@@ -334,7 +334,7 @@ namespace OpenRCT2::Scripting
             {
                 auto* windowMgr = Ui::GetWindowManager();
                 w = windowMgr->BringToFront(*w);
-                w->flags |= WF_WHITE_BORDER_MASK;
+                w->flash();
             }
         }
 
diff --git a/src/openrct2-ui/windows/About.cpp b/src/openrct2-ui/windows/About.cpp
index 8e6ee5d46e..09f3cce5ad 100644
--- a/src/openrct2-ui/windows/About.cpp
+++ b/src/openrct2-ui/windows/About.cpp
@@ -288,6 +288,6 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* AboutOpen()
     {
         auto* windowMgr = GetWindowManager();
-        return windowMgr->FocusOrCreate<AboutWindow>(WindowClass::about, kWindowSize, WF_CENTRE_SCREEN);
+        return windowMgr->FocusOrCreate<AboutWindow>(WindowClass::about, kWindowSize, WindowFlag::centreScreen);
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/AssetPacks.cpp b/src/openrct2-ui/windows/AssetPacks.cpp
index 38cb3ad0de..ad8602fc6e 100644
--- a/src/openrct2-ui/windows/AssetPacks.cpp
+++ b/src/openrct2-ui/windows/AssetPacks.cpp
@@ -341,7 +341,7 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* AssetPacksOpen()
     {
         auto* windowMgr = GetWindowManager();
-        auto flags = WF_AUTO_POSITION | WF_CENTRE_SCREEN;
+        WindowFlags flags = { WindowFlag::autoPosition, WindowFlag::centreScreen };
 
         return windowMgr->FocusOrCreate<AssetPacksWindow>(WindowClass::assetPacks, kWindowSize, flags);
     }
diff --git a/src/openrct2-ui/windows/Banner.cpp b/src/openrct2-ui/windows/Banner.cpp
index 5dd9d01809..3cf07e3fb2 100644
--- a/src/openrct2-ui/windows/Banner.cpp
+++ b/src/openrct2-ui/windows/Banner.cpp
@@ -322,7 +322,7 @@ namespace OpenRCT2::Ui::Windows
         if (w != nullptr)
             return w;
 
-        w = windowMgr->Create<BannerWindow>(WindowClass::banner, kWindowSize, 0);
+        w = windowMgr->Create<BannerWindow>(WindowClass::banner, kWindowSize, {});
 
         if (w != nullptr)
             w->initialise(number);
diff --git a/src/openrct2-ui/windows/Changelog.cpp b/src/openrct2-ui/windows/Changelog.cpp
index f622aabf54..6e2aa2d371 100644
--- a/src/openrct2-ui/windows/Changelog.cpp
+++ b/src/openrct2-ui/windows/Changelog.cpp
@@ -286,7 +286,7 @@ namespace OpenRCT2::Ui::Windows
             int32_t width = (ContextGetWidth() * 4) / 5;
             int32_t height = (ContextGetHeight() * 4) / 5;
             auto* newWindow = windowMgr->Create<ChangelogWindow>(
-                WindowClass::changelog, { width, height }, WF_CENTRE_SCREEN | WF_RESIZABLE);
+                WindowClass::changelog, { width, height }, { WindowFlag::centreScreen, WindowFlag::resizable });
             newWindow->SetPersonality(personality);
             return newWindow;
         }
diff --git a/src/openrct2-ui/windows/ClearScenery.cpp b/src/openrct2-ui/windows/ClearScenery.cpp
index 12484881c9..5286ee8aa8 100644
--- a/src/openrct2-ui/windows/ClearScenery.cpp
+++ b/src/openrct2-ui/windows/ClearScenery.cpp
@@ -369,7 +369,7 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<CleanSceneryWindow>(
-            WindowClass::clearScenery, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, 0);
+            WindowClass::clearScenery, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, {});
     }
 
     /**
diff --git a/src/openrct2-ui/windows/CustomCurrency.cpp b/src/openrct2-ui/windows/CustomCurrency.cpp
index 7005f75988..2f0f5aff70 100644
--- a/src/openrct2-ui/windows/CustomCurrency.cpp
+++ b/src/openrct2-ui/windows/CustomCurrency.cpp
@@ -223,6 +223,7 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* CustomCurrencyOpen()
     {
         auto* windowMgr = GetWindowManager();
-        return windowMgr->FocusOrCreate<CustomCurrencyWindow>(WindowClass::customCurrencyConfig, kWindowSize, WF_CENTRE_SCREEN);
+        return windowMgr->FocusOrCreate<CustomCurrencyWindow>(
+            WindowClass::customCurrencyConfig, kWindowSize, WindowFlag::centreScreen);
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/DebugPaint.cpp b/src/openrct2-ui/windows/DebugPaint.cpp
index cf4dfa3f41..ac5924bcae 100644
--- a/src/openrct2-ui/windows/DebugPaint.cpp
+++ b/src/openrct2-ui/windows/DebugPaint.cpp
@@ -156,7 +156,7 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = GetWindowManager();
         auto* window = windowMgr->FocusOrCreate<DebugPaintWindow>(
             WindowClass::debugPaint, { 16, ContextGetHeight() - 16 - 33 - kWindowSize.height }, kWindowSize,
-            WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_NO_TITLE_BAR);
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::noTitleBar });
 
         return window;
     }
diff --git a/src/openrct2-ui/windows/DemolishRidePrompt.cpp b/src/openrct2-ui/windows/DemolishRidePrompt.cpp
index 18324134b9..dc4219a39f 100644
--- a/src/openrct2-ui/windows/DemolishRidePrompt.cpp
+++ b/src/openrct2-ui/windows/DemolishRidePrompt.cpp
@@ -104,12 +104,12 @@ namespace OpenRCT2::Ui::Windows
             windowMgr->Close(*w);
 
             newWindow = windowMgr->Create<DemolishRidePromptWindow>(
-                WindowClass::demolishRidePrompt, windowPos, kWindowSize, WF_TRANSPARENT);
+                WindowClass::demolishRidePrompt, windowPos, kWindowSize, WindowFlag::transparent);
         }
         else
         {
             newWindow = windowMgr->Create<DemolishRidePromptWindow>(
-                WindowClass::demolishRidePrompt, kWindowSize, WF_CENTRE_SCREEN | WF_TRANSPARENT);
+                WindowClass::demolishRidePrompt, kWindowSize, { WindowFlag::centreScreen, WindowFlag::transparent });
         }
 
         newWindow->SetRide(ride);
diff --git a/src/openrct2-ui/windows/Dropdown.cpp b/src/openrct2-ui/windows/Dropdown.cpp
index b54ba2ed06..169d8616c7 100644
--- a/src/openrct2-ui/windows/Dropdown.cpp
+++ b/src/openrct2-ui/windows/Dropdown.cpp
@@ -229,7 +229,7 @@ namespace OpenRCT2::Ui::Windows
             UpdateSizeAndPosition(screenPos, extraY);
 
             if (colour.hasFlag(ColourFlag::translucent))
-                flags |= WF_TRANSPARENT;
+                flags |= WindowFlag::transparent;
             colours[0] = colour;
         }
 
@@ -262,7 +262,7 @@ namespace OpenRCT2::Ui::Windows
             UpdateSizeAndPosition(screenPos, extraY);
 
             if (colour.hasFlag(ColourFlag::translucent))
-                flags |= WF_TRANSPARENT;
+                flags |= WindowFlag::transparent;
             colours[0] = colour;
         }
 
@@ -394,7 +394,7 @@ namespace OpenRCT2::Ui::Windows
         // Create the window (width/height position are set later)
         auto* windowMgr = GetWindowManager();
         auto* w = windowMgr->Create<DropdownWindow>(
-            WindowClass::dropdown, { width, customItemHeight }, WF_STICK_TO_FRONT | WF_NO_TITLE_BAR);
+            WindowClass::dropdown, { width, customItemHeight }, { WindowFlag::stickToFront, WindowFlag::noTitleBar });
         if (w != nullptr)
         {
             auto numRowsPerColumn = prefRowsPerColumn > 0 ? static_cast<int32_t>(prefRowsPerColumn) : Dropdown::kItemsMaxSize;
@@ -438,7 +438,7 @@ namespace OpenRCT2::Ui::Windows
 
         // Create the window (width/height position are set later)
         auto* windowMgr = GetWindowManager();
-        auto* w = windowMgr->Create<DropdownWindow>(WindowClass::dropdown, { itemWidth, itemHeight }, WF_STICK_TO_FRONT);
+        auto* w = windowMgr->Create<DropdownWindow>(WindowClass::dropdown, { itemWidth, itemHeight }, WindowFlag::stickToFront);
         if (w != nullptr)
         {
             w->setImageItems({ x, y }, extray, colour, numItems, itemWidth, itemHeight, numColumns);
diff --git a/src/openrct2-ui/windows/EditorBottomToolbar.cpp b/src/openrct2-ui/windows/EditorBottomToolbar.cpp
index 29b0d14693..09bc868a0c 100644
--- a/src/openrct2-ui/windows/EditorBottomToolbar.cpp
+++ b/src/openrct2-ui/windows/EditorBottomToolbar.cpp
@@ -452,7 +452,8 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = GetWindowManager();
         auto* window = windowMgr->Create<EditorBottomToolbarWindow>(
             WindowClass::bottomToolbar, ScreenCoordsXY(0, ContextGetHeight() - kToolbarHeight),
-            { ContextGetWidth(), kToolbarHeight }, WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_NO_BACKGROUND | WF_NO_TITLE_BAR);
+            { ContextGetWidth(), kToolbarHeight },
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::noBackground, WindowFlag::noTitleBar });
 
         return window;
     }
diff --git a/src/openrct2-ui/windows/EditorInventionsList.cpp b/src/openrct2-ui/windows/EditorInventionsList.cpp
index ebefe7584f..0d7e76813f 100644
--- a/src/openrct2-ui/windows/EditorInventionsList.cpp
+++ b/src/openrct2-ui/windows/EditorInventionsList.cpp
@@ -588,7 +588,8 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<InventionListWindow>(
-            WindowClass::editorInventionList, kWindowSize, WF_NO_SCROLLING | WF_RESIZABLE | WF_CENTRE_SCREEN);
+            WindowClass::editorInventionList, kWindowSize,
+            { WindowFlag::noScrolling, WindowFlag::resizable, WindowFlag::centreScreen });
     }
 #pragma endregion
 
@@ -686,7 +687,8 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = Ui::GetWindowManager();
         windowMgr->CloseByClass(WindowClass::editorInventionListDrag);
         auto* wnd = windowMgr->Create<InventionDragWindow>(
-            WindowClass::editorInventionListDrag, { 10, 14 }, WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_NO_SNAPPING);
+            WindowClass::editorInventionListDrag, { 10, 14 },
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::noSnapping });
         if (wnd != nullptr)
         {
             wnd->init(*researchItem, editorPos, objectSelectionScrollWidth);
diff --git a/src/openrct2-ui/windows/EditorObjectSelection.cpp b/src/openrct2-ui/windows/EditorObjectSelection.cpp
index 99e9d8f3f9..96b5403f11 100644
--- a/src/openrct2-ui/windows/EditorObjectSelection.cpp
+++ b/src/openrct2-ui/windows/EditorObjectSelection.cpp
@@ -1630,7 +1630,8 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<EditorObjectSelectionWindow>(
-            WindowClass::editorObjectSelection, kWindowSize, WF_10 | WF_RESIZABLE | WF_CENTRE_SCREEN);
+            WindowClass::editorObjectSelection, kWindowSize,
+            { WindowFlag::higherContrastOnPress, WindowFlag::resizable, WindowFlag::centreScreen });
     }
 
     // Used for forced closure
diff --git a/src/openrct2-ui/windows/EditorParkEntrance.cpp b/src/openrct2-ui/windows/EditorParkEntrance.cpp
index 304e4fe374..d45f84ec48 100644
--- a/src/openrct2-ui/windows/EditorParkEntrance.cpp
+++ b/src/openrct2-ui/windows/EditorParkEntrance.cpp
@@ -403,7 +403,8 @@ namespace OpenRCT2::Ui::Windows
         if (window != nullptr)
             return window;
 
-        window = windowMgr->Create<EditorParkEntrance>(WindowClass::editorParkEntrance, kWindowSize, WF_10 | WF_RESIZABLE);
+        window = windowMgr->Create<EditorParkEntrance>(
+            WindowClass::editorParkEntrance, kWindowSize, { WindowFlag::higherContrastOnPress, WindowFlag::resizable });
 
         return window;
     }
diff --git a/src/openrct2-ui/windows/EditorScenarioOptions.cpp b/src/openrct2-ui/windows/EditorScenarioOptions.cpp
index 323d33ea26..635135ad2b 100644
--- a/src/openrct2-ui/windows/EditorScenarioOptions.cpp
+++ b/src/openrct2-ui/windows/EditorScenarioOptions.cpp
@@ -2385,6 +2385,6 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<EditorScenarioOptionsWindow>(
-            WindowClass::editorScenarioOptions, { 280, 148 }, WF_NO_SCROLLING | WF_CENTRE_SCREEN);
+            WindowClass::editorScenarioOptions, { 280, 148 }, { WindowFlag::noScrolling, WindowFlag::centreScreen });
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/Error.cpp b/src/openrct2-ui/windows/Error.cpp
index 4ea518b4aa..a0c98c0ae4 100644
--- a/src/openrct2-ui/windows/Error.cpp
+++ b/src/openrct2-ui/windows/Error.cpp
@@ -144,7 +144,7 @@ namespace OpenRCT2::Ui::Windows
 
         return windowMgr->Create(
             std::move(errorWindow), WindowClass::error, windowPosition, { width, height },
-            WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_NO_TITLE_BAR);
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::noTitleBar });
     }
 
     WindowBase* ErrorOpen(StringId title, StringId message, const Formatter& args, bool autoClose)
diff --git a/src/openrct2-ui/windows/Finances.cpp b/src/openrct2-ui/windows/Finances.cpp
index a31ef49d80..7918d12bde 100644
--- a/src/openrct2-ui/windows/Finances.cpp
+++ b/src/openrct2-ui/windows/Finances.cpp
@@ -487,19 +487,19 @@ namespace OpenRCT2::Ui::Windows
             {
                 width = kWindowSizeResearch.width;
                 height = kWindowSizeResearch.height;
-                flags &= ~WF_RESIZABLE;
+                flags.unset(WindowFlag::resizable);
             }
             else if (p == WINDOW_FINANCES_PAGE_SUMMARY)
             {
                 width = kWindowSizeSummary.width;
                 height = kWindowSizeSummary.height;
-                flags &= ~WF_RESIZABLE;
+                flags.unset(WindowFlag::resizable);
             }
             else if (
                 p == WINDOW_FINANCES_PAGE_VALUE_GRAPH || p == WINDOW_FINANCES_PAGE_PROFIT_GRAPH
                 || p == WINDOW_FINANCES_PAGE_FINANCIAL_GRAPH)
             {
-                flags |= WF_RESIZABLE;
+                flags |= WindowFlag::resizable;
 
                 // We need to compensate for the enlarged title bar for windows that do not
                 // constrain the window height between tabs (e.g. chart tabs)
@@ -511,7 +511,7 @@ namespace OpenRCT2::Ui::Windows
             {
                 width = kWindowSizeGraphsMarketing.width;
                 height = kWindowSizeGraphsMarketing.height;
-                flags &= ~WF_RESIZABLE;
+                flags.unset(WindowFlag::resizable);
             }
 
             setWidgets(_windowFinancesPageWidgets[p]);
@@ -879,7 +879,8 @@ namespace OpenRCT2::Ui::Windows
     static FinancesWindow* FinancesWindowOpen(uint8_t page)
     {
         auto* windowMgr = Ui::GetWindowManager();
-        auto* window = windowMgr->FocusOrCreate<FinancesWindow>(WindowClass::finances, kWindowSizeSummary, WF_10);
+        auto* window = windowMgr->FocusOrCreate<FinancesWindow>(
+            WindowClass::finances, kWindowSizeSummary, WindowFlag::higherContrastOnPress);
 
         if (window != nullptr && page != WINDOW_FINANCES_PAGE_SUMMARY)
             window->setPage(page);
@@ -890,7 +891,8 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* FinancesOpen()
     {
         auto* windowMgr = Ui::GetWindowManager();
-        return windowMgr->FocusOrCreate<FinancesWindow>(WindowClass::finances, kWindowSizeSummary, WF_10);
+        return windowMgr->FocusOrCreate<FinancesWindow>(
+            WindowClass::finances, kWindowSizeSummary, WindowFlag::higherContrastOnPress);
     }
 
     WindowBase* FinancesResearchOpen()
diff --git a/src/openrct2-ui/windows/Footpath.cpp b/src/openrct2-ui/windows/Footpath.cpp
index a489a0510d..1b1b72bf1b 100644
--- a/src/openrct2-ui/windows/Footpath.cpp
+++ b/src/openrct2-ui/windows/Footpath.cpp
@@ -1567,7 +1567,7 @@ namespace OpenRCT2::Ui::Windows
         }
 
         auto* windowMgr = GetWindowManager();
-        return windowMgr->FocusOrCreate<FootpathWindow>(WindowClass::footpath, kWindowSize, 0);
+        return windowMgr->FocusOrCreate<FootpathWindow>(WindowClass::footpath, kWindowSize, {});
     }
 
     void WindowFootpathResetSelectedPath()
diff --git a/src/openrct2-ui/windows/GameBottomToolbar.cpp b/src/openrct2-ui/windows/GameBottomToolbar.cpp
index df0eca8d17..729e4b99cd 100644
--- a/src/openrct2-ui/windows/GameBottomToolbar.cpp
+++ b/src/openrct2-ui/windows/GameBottomToolbar.cpp
@@ -693,7 +693,7 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = GetWindowManager();
         auto* window = windowMgr->Create<GameBottomToolbar>(
             WindowClass::bottomToolbar, ScreenCoordsXY(0, screenHeight - toolbarHeight), { screenWidth, toolbarHeight },
-            WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_NO_BACKGROUND | WF_NO_TITLE_BAR);
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::noBackground, WindowFlag::noTitleBar });
 
         return window;
     }
diff --git a/src/openrct2-ui/windows/Guest.cpp b/src/openrct2-ui/windows/Guest.cpp
index 4ca183112e..098f734a92 100644
--- a/src/openrct2-ui/windows/Guest.cpp
+++ b/src/openrct2-ui/windows/Guest.cpp
@@ -771,7 +771,7 @@ namespace OpenRCT2::Ui::Windows
                 {
                     viewport->flags = origViewportFlags;
                 }
-                flags |= WF_NO_SCROLLING;
+                flags |= WindowFlag::noScrolling;
                 invalidate();
             }
             invalidate();
@@ -1924,7 +1924,7 @@ namespace OpenRCT2::Ui::Windows
             if (Config::Get().general.DebuggingTools)
                 windowSize.width += kTabWidth;
 
-            window = windowMgr->Create<GuestWindow>(WindowClass::peep, windowSize, WF_RESIZABLE);
+            window = windowMgr->Create<GuestWindow>(WindowClass::peep, windowSize, WindowFlag::resizable);
             if (window == nullptr)
             {
                 return nullptr;
diff --git a/src/openrct2-ui/windows/GuestList.cpp b/src/openrct2-ui/windows/GuestList.cpp
index a87009ef9f..be520e6fb0 100644
--- a/src/openrct2-ui/windows/GuestList.cpp
+++ b/src/openrct2-ui/windows/GuestList.cpp
@@ -951,7 +951,8 @@ namespace OpenRCT2::Ui::Windows
         auto* window = windowMgr->BringToFrontByClass(WindowClass::guestList);
         if (window == nullptr)
         {
-            window = windowMgr->Create<GuestListWindow>(WindowClass::guestList, kWindowSize, WF_10 | WF_RESIZABLE);
+            window = windowMgr->Create<GuestListWindow>(
+                WindowClass::guestList, kWindowSize, { WindowFlag::higherContrastOnPress, WindowFlag::resizable });
         }
         return window;
     }
diff --git a/src/openrct2-ui/windows/InstallTrack.cpp b/src/openrct2-ui/windows/InstallTrack.cpp
index 0312cd4657..357204b6de 100644
--- a/src/openrct2-ui/windows/InstallTrack.cpp
+++ b/src/openrct2-ui/windows/InstallTrack.cpp
@@ -423,7 +423,7 @@ namespace OpenRCT2::Ui::Windows
         _currentTrackPieceDirection = 2;
 
         auto* window = windowMgr->FocusOrCreate<InstallTrackWindow>(
-            WindowClass::installTrack, kWindowSize, WF_AUTO_POSITION | WF_CENTRE_SCREEN);
+            WindowClass::installTrack, kWindowSize, { WindowFlag::autoPosition, WindowFlag::centreScreen });
         window->setupTrack(path, std::move(trackDesign));
 
         return window;
diff --git a/src/openrct2-ui/windows/Land.cpp b/src/openrct2-ui/windows/Land.cpp
index 957bc812b2..441ca812d6 100644
--- a/src/openrct2-ui/windows/Land.cpp
+++ b/src/openrct2-ui/windows/Land.cpp
@@ -876,7 +876,7 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<LandWindow>(
-            WindowClass::land, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, 0);
+            WindowClass::land, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, {});
     }
 
     /**
diff --git a/src/openrct2-ui/windows/LandRights.cpp b/src/openrct2-ui/windows/LandRights.cpp
index c5dd69576c..cebdd001d6 100644
--- a/src/openrct2-ui/windows/LandRights.cpp
+++ b/src/openrct2-ui/windows/LandRights.cpp
@@ -595,6 +595,6 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<LandRightsWindow>(
-            WindowClass::landRights, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, 0);
+            WindowClass::landRights, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, {});
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/LoadSave.cpp b/src/openrct2-ui/windows/LoadSave.cpp
index 8b05e93c17..581b4d4e95 100644
--- a/src/openrct2-ui/windows/LoadSave.cpp
+++ b/src/openrct2-ui/windows/LoadSave.cpp
@@ -1179,8 +1179,9 @@ namespace OpenRCT2::Ui::Windows
             ScreenSize windowSize = { config.FileBrowserWidth, config.FileBrowserHeight };
 
             w = windowMgr->Create<LoadSaveWindow>(
-                WindowClass::loadsave, windowSize, WF_STICK_TO_FRONT | WF_RESIZABLE | WF_AUTO_POSITION | WF_CENTRE_SCREEN,
-                action, type);
+                WindowClass::loadsave, windowSize,
+                { WindowFlag::stickToFront, WindowFlag::resizable, WindowFlag::autoPosition, WindowFlag::centreScreen }, action,
+                type);
         }
 
         bool isSave = action == LoadSaveAction::save;
diff --git a/src/openrct2-ui/windows/Main.cpp b/src/openrct2-ui/windows/Main.cpp
index 568309ab2c..785a576aaa 100644
--- a/src/openrct2-ui/windows/Main.cpp
+++ b/src/openrct2-ui/windows/Main.cpp
@@ -78,6 +78,7 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->Create<MainWindow>(
-            WindowClass::mainWindow, { 0, 0 }, { ContextGetWidth(), ContextGetHeight() }, WF_STICK_TO_BACK | WF_NO_TITLE_BAR);
+            WindowClass::mainWindow, { 0, 0 }, { ContextGetWidth(), ContextGetHeight() },
+            { WindowFlag::stickToBack, WindowFlag::noTitleBar });
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/Map.cpp b/src/openrct2-ui/windows/Map.cpp
index ea27e11502..dff2aa6485 100644
--- a/src/openrct2-ui/windows/Map.cpp
+++ b/src/openrct2-ui/windows/Map.cpp
@@ -239,7 +239,7 @@ namespace OpenRCT2::Ui::Windows
             holdDownWidgets = (1uLL << WIDX_MAP_SIZE_SPINNER_Y_UP) | (1uLL << WIDX_MAP_SIZE_SPINNER_Y_DOWN)
                 | (1uLL << WIDX_MAP_SIZE_SPINNER_X_UP) | (1uLL << WIDX_MAP_SIZE_SPINNER_X_DOWN);
 
-            flags |= WF_RESIZABLE;
+            flags |= WindowFlag::resizable;
 
             SetInitialWindowDimensions();
             ResetMaxWindowDimensions();
@@ -1251,7 +1251,7 @@ namespace OpenRCT2::Ui::Windows
         try
         {
             auto* windowMgr = GetWindowManager();
-            auto* w = windowMgr->FocusOrCreate<MapWindow>(WindowClass::map, kWindowSize, WF_10);
+            auto* w = windowMgr->FocusOrCreate<MapWindow>(WindowClass::map, kWindowSize, WindowFlag::higherContrastOnPress);
             w->selectedTab = 0;
             w->listInformationType = 0;
             return w;
diff --git a/src/openrct2-ui/windows/MapGen.cpp b/src/openrct2-ui/windows/MapGen.cpp
index becef83ef2..b8c0e43cc7 100644
--- a/src/openrct2-ui/windows/MapGen.cpp
+++ b/src/openrct2-ui/windows/MapGen.cpp
@@ -1534,7 +1534,8 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<MapGenWindow>(
-            WindowClass::mapgen, kWindowSize, WF_10 | WF_AUTO_POSITION | WF_CENTRE_SCREEN);
+            WindowClass::mapgen, kWindowSize,
+            { WindowFlag::higherContrastOnPress, WindowFlag::autoPosition, WindowFlag::centreScreen });
     }
 
     static void HeightmapLoadsaveCallback(ModalResult result, const utf8* path)
diff --git a/src/openrct2-ui/windows/MapTooltip.cpp b/src/openrct2-ui/windows/MapTooltip.cpp
index abb80f73e8..41c30aca06 100644
--- a/src/openrct2-ui/windows/MapTooltip.cpp
+++ b/src/openrct2-ui/windows/MapTooltip.cpp
@@ -129,7 +129,7 @@ namespace OpenRCT2::Ui::Windows
         {
             w = windowMgr->Create<MapTooltip>(
                 WindowClass::mapTooltip, pos, { width, height },
-                WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_NO_BACKGROUND | WF_NO_TITLE_BAR);
+                { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::noBackground, WindowFlag::noTitleBar });
         }
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/MazeConstruction.cpp b/src/openrct2-ui/windows/MazeConstruction.cpp
index 9ffc27f0ac..8a9ff43dce 100644
--- a/src/openrct2-ui/windows/MazeConstruction.cpp
+++ b/src/openrct2-ui/windows/MazeConstruction.cpp
@@ -446,7 +446,7 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<MazeConstructionWindow>(
-            WindowClass::rideConstruction, ScreenCoordsXY(0, 29), kWindowSize, WF_NO_AUTO_CLOSE);
+            WindowClass::rideConstruction, ScreenCoordsXY(0, 29), kWindowSize, WindowFlag::noAutoClose);
     }
 
     void WindowMazeConstructionUpdatePressedWidgets()
diff --git a/src/openrct2-ui/windows/Multiplayer.cpp b/src/openrct2-ui/windows/Multiplayer.cpp
index ad5faf1cbe..e30f619153 100644
--- a/src/openrct2-ui/windows/Multiplayer.cpp
+++ b/src/openrct2-ui/windows/Multiplayer.cpp
@@ -919,7 +919,8 @@ namespace OpenRCT2::Ui::Windows
         if (window == nullptr)
         {
             window = windowMgr->Create<MultiplayerWindow>(
-                WindowClass::multiplayer, { 320, 144 }, WF_10 | WF_RESIZABLE | WF_AUTO_POSITION);
+                WindowClass::multiplayer, { 320, 144 },
+                { WindowFlag::higherContrastOnPress, WindowFlag::resizable, WindowFlag::autoPosition });
         }
 
         return window;
diff --git a/src/openrct2-ui/windows/NetworkStatus.cpp b/src/openrct2-ui/windows/NetworkStatus.cpp
index 51a8a9d7b5..6f3f63ab64 100644
--- a/src/openrct2-ui/windows/NetworkStatus.cpp
+++ b/src/openrct2-ui/windows/NetworkStatus.cpp
@@ -136,7 +136,9 @@ namespace OpenRCT2::Ui::Windows
         else
         {
             window = windowMgr->Create<NetworkStatusWindow>(
-                WindowClass::networkStatus, kWindowSize, WF_10 | WF_TRANSPARENT | WF_CENTRE_SCREEN | WF_STICK_TO_FRONT);
+                WindowClass::networkStatus, kWindowSize,
+                { WindowFlag::higherContrastOnPress, WindowFlag::transparent, WindowFlag::centreScreen,
+                  WindowFlag::stickToFront });
         }
 
         window->setCloseCallBack(onClose);
@@ -164,7 +166,8 @@ namespace OpenRCT2::Ui::Windows
 
         auto* windowMgr = GetWindowManager();
         auto* window = windowMgr->FocusOrCreate<NetworkStatusWindow>(
-            WindowClass::networkStatus, kWindowSize, WF_10 | WF_TRANSPARENT | WF_CENTRE_SCREEN);
+            WindowClass::networkStatus, kWindowSize,
+            { WindowFlag::higherContrastOnPress, WindowFlag::transparent, WindowFlag::centreScreen });
 
         char password[33]{};
         WindowTextInputRawOpen(window, WIDX_PASSWORD, STR_PASSWORD_REQUIRED, STR_PASSWORD_REQUIRED_DESC, {}, password, 32);
diff --git a/src/openrct2-ui/windows/NewCampaign.cpp b/src/openrct2-ui/windows/NewCampaign.cpp
index 0d7cede249..a84522fcf3 100644
--- a/src/openrct2-ui/windows/NewCampaign.cpp
+++ b/src/openrct2-ui/windows/NewCampaign.cpp
@@ -400,7 +400,7 @@ namespace OpenRCT2::Ui::Windows
             w->close();
         }
 
-        w = windowMgr->Create<NewCampaignWindow>(WindowClass::newCampaign, kWindowSize, 0);
+        w = windowMgr->Create<NewCampaignWindow>(WindowClass::newCampaign, kWindowSize, {});
         if (w != nullptr)
         {
             w->setCampaign(campaignType);
diff --git a/src/openrct2-ui/windows/NewRide.cpp b/src/openrct2-ui/windows/NewRide.cpp
index 1daf11117f..d9dece8636 100644
--- a/src/openrct2-ui/windows/NewRide.cpp
+++ b/src/openrct2-ui/windows/NewRide.cpp
@@ -1079,7 +1079,8 @@ namespace OpenRCT2::Ui::Windows
         windowMgr->CloseByClass(WindowClass::trackDesignList);
         windowMgr->CloseByClass(WindowClass::trackDesignPlace);
 
-        window = windowMgr->Create<NewRideWindow>(WindowClass::constructRide, kWindowSize, WF_10 | WF_AUTO_POSITION);
+        window = windowMgr->Create<NewRideWindow>(
+            WindowClass::constructRide, kWindowSize, { WindowFlag::higherContrastOnPress, WindowFlag::autoPosition });
         return window;
     }
 
diff --git a/src/openrct2-ui/windows/News.cpp b/src/openrct2-ui/windows/News.cpp
index 1a58bb14ef..33a44f35f8 100644
--- a/src/openrct2-ui/windows/News.cpp
+++ b/src/openrct2-ui/windows/News.cpp
@@ -580,6 +580,6 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* NewsOpen()
     {
         auto* windowMgr = GetWindowManager();
-        return windowMgr->FocusOrCreate<NewsWindow>(WindowClass::recentNews, kWindowSize, 0);
+        return windowMgr->FocusOrCreate<NewsWindow>(WindowClass::recentNews, kWindowSize, {});
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/ObjectLoadError.cpp b/src/openrct2-ui/windows/ObjectLoadError.cpp
index 830cc442f0..cfd5dcc105 100644
--- a/src/openrct2-ui/windows/ObjectLoadError.cpp
+++ b/src/openrct2-ui/windows/ObjectLoadError.cpp
@@ -577,7 +577,7 @@ namespace OpenRCT2::Ui::Windows
         auto* window = windowMgr->BringToFrontByClass(WindowClass::objectLoadError);
         if (window == nullptr)
         {
-            window = windowMgr->Create<ObjectLoadErrorWindow>(WindowClass::objectLoadError, kWindowSize, 0);
+            window = windowMgr->Create<ObjectLoadErrorWindow>(WindowClass::objectLoadError, kWindowSize, {});
         }
 
         static_cast<ObjectLoadErrorWindow*>(window)->initialise(path, numMissingObjects, missingObjects);
diff --git a/src/openrct2-ui/windows/Options.cpp b/src/openrct2-ui/windows/Options.cpp
index 3335dac9e9..982b7401cf 100644
--- a/src/openrct2-ui/windows/Options.cpp
+++ b/src/openrct2-ui/windows/Options.cpp
@@ -2427,6 +2427,6 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* OptionsOpen()
     {
         auto* windowMgr = GetWindowManager();
-        return windowMgr->FocusOrCreate<OptionsWindow>(WindowClass::options, kWindowSize, WF_CENTRE_SCREEN);
+        return windowMgr->FocusOrCreate<OptionsWindow>(WindowClass::options, kWindowSize, WindowFlag::centreScreen);
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/OverwritePrompt.cpp b/src/openrct2-ui/windows/OverwritePrompt.cpp
index 6d1bde4169..684ae34c24 100644
--- a/src/openrct2-ui/windows/OverwritePrompt.cpp
+++ b/src/openrct2-ui/windows/OverwritePrompt.cpp
@@ -106,8 +106,9 @@ namespace OpenRCT2::Ui::Windows
         windowMgr->CloseByClass(WindowClass::loadsaveOverwritePrompt);
 
         return windowMgr->Create<OverwritePromptWindow>(
-            WindowClass::loadsaveOverwritePrompt, kWindowSize, WF_TRANSPARENT | WF_STICK_TO_FRONT | WF_CENTRE_SCREEN, name,
-            path, action, type, trackDesignPtr);
+            WindowClass::loadsaveOverwritePrompt, kWindowSize,
+            { WindowFlag::transparent, WindowFlag::stickToFront, WindowFlag::centreScreen }, name, path, action, type,
+            trackDesignPtr);
     }
 
     void WindowLoadSaveOverwritePromptInputKey(WindowBase* w, uint32_t keycode)
diff --git a/src/openrct2-ui/windows/Park.cpp b/src/openrct2-ui/windows/Park.cpp
index f59b738d39..282d3c16a6 100644
--- a/src/openrct2-ui/windows/Park.cpp
+++ b/src/openrct2-ui/windows/Park.cpp
@@ -435,7 +435,7 @@ namespace OpenRCT2::Ui::Windows
 
         void onResizeEntrance()
         {
-            flags |= WF_RESIZABLE;
+            flags |= WindowFlag::resizable;
             WindowSetResize(*this, { 230, 174 + 9 }, { 230 * 3, (274 + 9) * 3 });
             initViewport();
         }
@@ -644,7 +644,7 @@ namespace OpenRCT2::Ui::Windows
                     ViewportCreate(
                         *this, windowPos + ScreenCoordsXY{ viewportWidget->left + 1, viewportWidget->top + 1 },
                         viewportWidget->width() - 1, viewportWidget->height() - 1, focus.value());
-                    flags |= WF_NO_SCROLLING;
+                    flags |= WindowFlag::noScrolling;
                     invalidate();
                 }
             }
@@ -659,7 +659,7 @@ namespace OpenRCT2::Ui::Windows
 #pragma region Rating page
         void onResizeRating()
         {
-            flags |= WF_RESIZABLE;
+            flags |= WindowFlag::resizable;
             WindowSetResize(*this, { 268, 174 + 9 }, kMaxWindowSize);
         }
 
@@ -726,7 +726,7 @@ namespace OpenRCT2::Ui::Windows
 #pragma region Guests page
         void onResizeGuests()
         {
-            flags |= WF_RESIZABLE;
+            flags |= WindowFlag::resizable;
             WindowSetResize(*this, { 268, 174 + 9 }, kMaxWindowSize);
         }
 
@@ -1285,7 +1285,8 @@ namespace OpenRCT2::Ui::Windows
     static ParkWindow* ParkWindowOpen(uint8_t page)
     {
         auto* windowMgr = GetWindowManager();
-        auto* wnd = windowMgr->FocusOrCreate<ParkWindow>(WindowClass::parkInformation, { 230, 174 + 9 }, WF_10);
+        auto* wnd = windowMgr->FocusOrCreate<ParkWindow>(
+            WindowClass::parkInformation, { 230, 174 + 9 }, WindowFlag::higherContrastOnPress);
         if (wnd != nullptr && page != WINDOW_PARK_PAGE_ENTRANCE)
         {
             wnd->onMouseUp(WIDX_TAB_1 + page);
diff --git a/src/openrct2-ui/windows/PatrolArea.cpp b/src/openrct2-ui/windows/PatrolArea.cpp
index 42903d400e..fbbc934fce 100644
--- a/src/openrct2-ui/windows/PatrolArea.cpp
+++ b/src/openrct2-ui/windows/PatrolArea.cpp
@@ -294,7 +294,7 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         auto* w = windowMgr->FocusOrCreate<PatrolAreaWindow>(
-            WindowClass::patrolArea, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, 0);
+            WindowClass::patrolArea, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, {});
         if (w != nullptr)
         {
             w->setStaffId(staffId);
diff --git a/src/openrct2-ui/windows/Player.cpp b/src/openrct2-ui/windows/Player.cpp
index 5386e84af6..05c8393c74 100644
--- a/src/openrct2-ui/windows/Player.cpp
+++ b/src/openrct2-ui/windows/Player.cpp
@@ -235,7 +235,7 @@ namespace OpenRCT2::Ui::Windows
                 {
                     const auto viewportFocus = Focus(TileCoordsXYZ(128, 128, 0).ToCoordsXYZ());
                     ViewportCreate(*this, windowPos, width, height, viewportFocus);
-                    flags |= WF_NO_SCROLLING;
+                    flags |= WindowFlag::noScrolling;
                     onPrepareDraw();
                     UpdateViewport(false);
                 }
@@ -305,7 +305,7 @@ namespace OpenRCT2::Ui::Windows
 
                     if (!scroll || savedViewPos != centreLoc.value())
                     {
-                        flags |= WF_SCROLLING_TO_LOCATION;
+                        flags |= WindowFlag::scrollingToLocation;
                         savedViewPos = centreLoc.value();
                         if (!scroll)
                         {
@@ -633,7 +633,7 @@ namespace OpenRCT2::Ui::Windows
         auto* window = static_cast<PlayerWindow*>(windowMgr->BringToFrontByNumber(WindowClass::player, id));
         if (window == nullptr)
         {
-            window = windowMgr->Create<PlayerWindow>(WindowClass::player, { 240, 170 }, WF_RESIZABLE);
+            window = windowMgr->Create<PlayerWindow>(WindowClass::player, { 240, 170 }, WindowFlag::resizable);
         }
 
         window->init(id);
diff --git a/src/openrct2-ui/windows/ProgressWindow.cpp b/src/openrct2-ui/windows/ProgressWindow.cpp
index 17ff7c4436..2dfbca8cd9 100644
--- a/src/openrct2-ui/windows/ProgressWindow.cpp
+++ b/src/openrct2-ui/windows/ProgressWindow.cpp
@@ -246,7 +246,9 @@ namespace OpenRCT2::Ui::Windows
         else
         {
             window = windowMgr->Create<ProgressWindow>(
-                WindowClass::progressWindow, kWindowSize, WF_10 | WF_TRANSPARENT | WF_CENTRE_SCREEN | WF_STICK_TO_FRONT);
+                WindowClass::progressWindow, kWindowSize,
+                { WindowFlag::higherContrastOnPress, WindowFlag::transparent, WindowFlag::centreScreen,
+                  WindowFlag::stickToFront });
         }
 
         window->setCaption(text);
diff --git a/src/openrct2-ui/windows/RefurbishRidePrompt.cpp b/src/openrct2-ui/windows/RefurbishRidePrompt.cpp
index 39353b6362..3965e914e2 100644
--- a/src/openrct2-ui/windows/RefurbishRidePrompt.cpp
+++ b/src/openrct2-ui/windows/RefurbishRidePrompt.cpp
@@ -103,12 +103,12 @@ namespace OpenRCT2::Ui::Windows
             windowMgr->Close(*w);
 
             newWindow = windowMgr->Create<RefurbishRidePromptWindow>(
-                WindowClass::demolishRidePrompt, windowPos, kWindowSize, WF_TRANSPARENT);
+                WindowClass::demolishRidePrompt, windowPos, kWindowSize, WindowFlag::transparent);
         }
         else
         {
             newWindow = windowMgr->Create<RefurbishRidePromptWindow>(
-                WindowClass::demolishRidePrompt, kWindowSize, WF_CENTRE_SCREEN | WF_TRANSPARENT);
+                WindowClass::demolishRidePrompt, kWindowSize, { WindowFlag::centreScreen, WindowFlag::transparent });
         }
 
         newWindow->SetRide(ride);
diff --git a/src/openrct2-ui/windows/Research.cpp b/src/openrct2-ui/windows/Research.cpp
index 94acf79701..0ba864208d 100644
--- a/src/openrct2-ui/windows/Research.cpp
+++ b/src/openrct2-ui/windows/Research.cpp
@@ -296,7 +296,8 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* ResearchOpen()
     {
         auto* windowMgr = GetWindowManager();
-        auto* window = windowMgr->FocusOrCreate<ResearchWindow>(WindowClass::research, kWindowSizeDevelopment, WF_10);
+        auto* window = windowMgr->FocusOrCreate<ResearchWindow>(
+            WindowClass::research, kWindowSizeDevelopment, WindowFlag::higherContrastOnPress);
         window->setPage(WINDOW_RESEARCH_PAGE_DEVELOPMENT);
         return window;
     }
diff --git a/src/openrct2-ui/windows/Ride.cpp b/src/openrct2-ui/windows/Ride.cpp
index f3dca034b5..975a8f6f8b 100644
--- a/src/openrct2-ui/windows/Ride.cpp
+++ b/src/openrct2-ui/windows/Ride.cpp
@@ -1585,7 +1585,7 @@ namespace OpenRCT2::Ui::Windows
 
                 ViewportCreate(*this, screenPos, viewWidth, viewHeight, focus.value());
 
-                flags |= WF_NO_SCROLLING;
+                flags |= WindowFlag::noScrolling;
                 invalidate();
             }
             if (viewport != nullptr)
@@ -1707,7 +1707,7 @@ namespace OpenRCT2::Ui::Windows
                 newMinHeight += 15;
             }
 
-            flags |= WF_RESIZABLE;
+            flags |= WindowFlag::resizable;
             WindowSetResize(*this, { kMinimumWindowWidth, newMinHeight }, { 500, 450 });
             // Unlike with other windows, the focus needs to be recentred so it’s best to just reset it.
             focus = std::nullopt;
@@ -4998,7 +4998,7 @@ namespace OpenRCT2::Ui::Windows
 
         void MusicResize()
         {
-            flags |= WF_RESIZABLE;
+            flags |= WindowFlag::resizable;
 
             auto ride = GetRide(rideId);
             if (ride == nullptr)
@@ -6760,7 +6760,7 @@ namespace OpenRCT2::Ui::Windows
 
         void CustomerResize()
         {
-            flags |= WF_RESIZABLE;
+            flags |= WindowFlag::resizable;
             WindowSetResize(*this, { kMinimumWindowWidth, 163 }, { kMinimumWindowWidth, 163 });
         }
 
@@ -6940,7 +6940,8 @@ namespace OpenRCT2::Ui::Windows
     static RideWindow* WindowRideOpen(const Ride& ride)
     {
         auto* windowMgr = GetWindowManager();
-        return windowMgr->Create<RideWindow>(WindowClass::ride, kWindowSize, WF_10 | WF_RESIZABLE, ride);
+        return windowMgr->Create<RideWindow>(
+            WindowClass::ride, kWindowSize, { WindowFlag::higherContrastOnPress, WindowFlag::resizable }, ride);
     }
 
     /**
diff --git a/src/openrct2-ui/windows/RideConstruction.cpp b/src/openrct2-ui/windows/RideConstruction.cpp
index 653ede3c0a..95a87a2fc8 100644
--- a/src/openrct2-ui/windows/RideConstruction.cpp
+++ b/src/openrct2-ui/windows/RideConstruction.cpp
@@ -2901,10 +2901,10 @@ namespace OpenRCT2::Ui::Windows
                 return ContextOpenWindowView(WindowView::mazeConstruction);
             case RideConstructionWindowContext::Default:
                 return windowMgr->Create<RideConstructionWindow>(
-                    WindowClass::rideConstruction, ScreenCoordsXY(0, 29), kWindowSize, WF_NO_AUTO_CLOSE);
+                    WindowClass::rideConstruction, ScreenCoordsXY(0, 29), kWindowSize, WindowFlag::noAutoClose);
         }
         return windowMgr->Create<RideConstructionWindow>(
-            WindowClass::rideConstruction, ScreenCoordsXY(0, 29), kWindowSize, WF_NO_AUTO_CLOSE);
+            WindowClass::rideConstruction, ScreenCoordsXY(0, 29), kWindowSize, WindowFlag::noAutoClose);
     }
 
     static void CloseConstructWindowOnCompletion(const Ride& ride)
diff --git a/src/openrct2-ui/windows/RideList.cpp b/src/openrct2-ui/windows/RideList.cpp
index bca4274caf..867eb6506e 100644
--- a/src/openrct2-ui/windows/RideList.cpp
+++ b/src/openrct2-ui/windows/RideList.cpp
@@ -1134,7 +1134,8 @@ namespace OpenRCT2::Ui::Windows
         if (window == nullptr)
         {
             window = windowMgr->Create<RideListWindow>(
-                WindowClass::rideList, ScreenCoordsXY(32, 32), kWindowSize, WF_10 | WF_RESIZABLE);
+                WindowClass::rideList, ScreenCoordsXY(32, 32), kWindowSize,
+                { WindowFlag::higherContrastOnPress, WindowFlag::resizable });
         }
         return window;
     }
diff --git a/src/openrct2-ui/windows/SavePrompt.cpp b/src/openrct2-ui/windows/SavePrompt.cpp
index 81e3d832b1..413f99ffb2 100644
--- a/src/openrct2-ui/windows/SavePrompt.cpp
+++ b/src/openrct2-ui/windows/SavePrompt.cpp
@@ -250,6 +250,6 @@ namespace OpenRCT2::Ui::Windows
         auto savePromptWindow = std::make_unique<SavePromptWindow>(prompt_mode);
         return windowMgr->Create(
             std::move(savePromptWindow), WindowClass::savePrompt, {}, windowSize,
-            WF_TRANSPARENT | WF_STICK_TO_FRONT | WF_CENTRE_SCREEN | WF_AUTO_POSITION);
+            { WindowFlag::transparent, WindowFlag::stickToFront, WindowFlag::centreScreen, WindowFlag::autoPosition });
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/ScenarioSelect.cpp b/src/openrct2-ui/windows/ScenarioSelect.cpp
index ce3fc14bc8..d4b0714a4c 100644
--- a/src/openrct2-ui/windows/ScenarioSelect.cpp
+++ b/src/openrct2-ui/windows/ScenarioSelect.cpp
@@ -867,7 +867,7 @@ namespace OpenRCT2::Ui::Windows
         }
 
         window = windowMgr->Create<ScenarioSelectWindow>(
-            WindowClass::scenarioSelect, {}, kWindowSize, WF_AUTO_POSITION | WF_CENTRE_SCREEN, callback);
+            WindowClass::scenarioSelect, {}, kWindowSize, { WindowFlag::autoPosition, WindowFlag::centreScreen }, callback);
         return window;
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/SceneryScatter.cpp b/src/openrct2-ui/windows/SceneryScatter.cpp
index a16f71d5ec..702aa0b2f4 100644
--- a/src/openrct2-ui/windows/SceneryScatter.cpp
+++ b/src/openrct2-ui/windows/SceneryScatter.cpp
@@ -205,7 +205,7 @@ namespace OpenRCT2::Ui::Windows
         auto* window = windowMgr->FindByClass(WindowClass::sceneryScatter);
         if (window == nullptr)
         {
-            window = windowMgr->Create<SceneryScatterWindow>(WindowClass::sceneryScatter, kWindowSize, 0);
+            window = windowMgr->Create<SceneryScatterWindow>(WindowClass::sceneryScatter, kWindowSize, {});
         }
 
         return window;
diff --git a/src/openrct2-ui/windows/ServerList.cpp b/src/openrct2-ui/windows/ServerList.cpp
index 745aedf921..72c1d20a96 100644
--- a/src/openrct2-ui/windows/ServerList.cpp
+++ b/src/openrct2-ui/windows/ServerList.cpp
@@ -540,7 +540,8 @@ namespace OpenRCT2::Ui::Windows
             return window;
 
         window = windowMgr->Create<ServerListWindow>(
-            WindowClass::serverList, kMinimumWindowSize, WF_10 | WF_RESIZABLE | WF_CENTRE_SCREEN);
+            WindowClass::serverList, kMinimumWindowSize,
+            { WindowFlag::higherContrastOnPress, WindowFlag::resizable, WindowFlag::centreScreen });
 
         return window;
     }
diff --git a/src/openrct2-ui/windows/ServerStart.cpp b/src/openrct2-ui/windows/ServerStart.cpp
index 4892292a57..8f1781e719 100644
--- a/src/openrct2-ui/windows/ServerStart.cpp
+++ b/src/openrct2-ui/windows/ServerStart.cpp
@@ -275,7 +275,7 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* ServerStartOpen()
     {
         auto* windowMgr = GetWindowManager();
-        return windowMgr->FocusOrCreate<ServerStartWindow>(WindowClass::serverStart, kWindowSize, WF_CENTRE_SCREEN);
+        return windowMgr->FocusOrCreate<ServerStartWindow>(WindowClass::serverStart, kWindowSize, WindowFlag::centreScreen);
     }
 } // namespace OpenRCT2::Ui::Windows
 
diff --git a/src/openrct2-ui/windows/ShortcutKeys.cpp b/src/openrct2-ui/windows/ShortcutKeys.cpp
index 3954c958f4..0243992ed2 100644
--- a/src/openrct2-ui/windows/ShortcutKeys.cpp
+++ b/src/openrct2-ui/windows/ShortcutKeys.cpp
@@ -79,7 +79,7 @@ namespace OpenRCT2::Ui::Windows
                 auto* windowMgr = GetWindowManager();
                 windowMgr->CloseByClass(WindowClass::changeKeyboardShortcut);
                 auto* w = windowMgr->Create<ChangeShortcutWindow>(
-                    WindowClass::changeKeyboardShortcut, kWindowSizeChange, WF_CENTRE_SCREEN);
+                    WindowClass::changeKeyboardShortcut, kWindowSizeChange, WindowFlag::centreScreen);
                 if (w != nullptr)
                 {
                     w->_shortcutId = shortcutId;
@@ -554,7 +554,7 @@ namespace OpenRCT2::Ui::Windows
         auto w = windowMgr->BringToFrontByClass(WindowClass::keyboardShortcutList);
         if (w == nullptr)
         {
-            w = windowMgr->Create<ShortcutKeysWindow>(WindowClass::keyboardShortcutList, kWindowSize, WF_RESIZABLE);
+            w = windowMgr->Create<ShortcutKeysWindow>(WindowClass::keyboardShortcutList, kWindowSize, WindowFlag::resizable);
         }
         return w;
     }
@@ -615,7 +615,7 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<ResetShortcutKeysPrompt>(
-            WindowClass::resetShortcutKeysPrompt, kWindowSizeReset, WF_CENTRE_SCREEN | WF_TRANSPARENT);
+            WindowClass::resetShortcutKeysPrompt, kWindowSizeReset, { WindowFlag::centreScreen, WindowFlag::transparent });
     }
 #pragma endregion
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/Sign.cpp b/src/openrct2-ui/windows/Sign.cpp
index 1778449cc2..d55d08138d 100644
--- a/src/openrct2-ui/windows/Sign.cpp
+++ b/src/openrct2-ui/windows/Sign.cpp
@@ -337,7 +337,7 @@ namespace OpenRCT2::Ui::Windows
         if (w != nullptr)
             return w;
 
-        w = windowMgr->Create<SignWindow>(WindowClass::banner, kWindowSize, 0);
+        w = windowMgr->Create<SignWindow>(WindowClass::banner, kWindowSize, {});
 
         if (w == nullptr)
             return nullptr;
@@ -361,7 +361,7 @@ namespace OpenRCT2::Ui::Windows
         if (w != nullptr)
             return w;
 
-        w = windowMgr->Create<SignWindow>(WindowClass::banner, kWindowSize, 0);
+        w = windowMgr->Create<SignWindow>(WindowClass::banner, kWindowSize, {});
 
         if (w == nullptr)
             return nullptr;
diff --git a/src/openrct2-ui/windows/Staff.cpp b/src/openrct2-ui/windows/Staff.cpp
index 28a133cd12..b8465dc462 100644
--- a/src/openrct2-ui/windows/Staff.cpp
+++ b/src/openrct2-ui/windows/Staff.cpp
@@ -1156,7 +1156,7 @@ namespace OpenRCT2::Ui::Windows
                     int32_t viewportHeight = viewWidget.height() - 1;
 
                     ViewportCreate(*this, screenPos, viewportWidth, viewportHeight, focus.value());
-                    flags |= WF_NO_SCROLLING;
+                    flags |= WindowFlag::noScrolling;
                     invalidate();
                 }
             }
@@ -1230,7 +1230,8 @@ namespace OpenRCT2::Ui::Windows
         if (w != nullptr)
             return w;
 
-        w = windowMgr->Create<StaffWindow>(WindowClass::peep, kWindowSize, WF_10 | WF_RESIZABLE);
+        w = windowMgr->Create<StaffWindow>(
+            WindowClass::peep, kWindowSize, { WindowFlag::higherContrastOnPress, WindowFlag::resizable });
         if (w == nullptr)
             return nullptr;
 
diff --git a/src/openrct2-ui/windows/StaffFirePrompt.cpp b/src/openrct2-ui/windows/StaffFirePrompt.cpp
index 6d2a8aa776..8c3a79eb02 100644
--- a/src/openrct2-ui/windows/StaffFirePrompt.cpp
+++ b/src/openrct2-ui/windows/StaffFirePrompt.cpp
@@ -96,7 +96,7 @@ namespace OpenRCT2::Ui::Windows
         // Check if the confirm window already exists
         auto* windowMgr = GetWindowManager();
         auto* window = windowMgr->FocusOrCreate<StaffFirePromptWindow>(
-            WindowClass::firePrompt, kWindowSize, WF_CENTRE_SCREEN | WF_TRANSPARENT);
+            WindowClass::firePrompt, kWindowSize, { WindowFlag::centreScreen, WindowFlag::transparent });
         window->setWindowNumber(peep->Id.ToUnderlying());
         return window;
     }
diff --git a/src/openrct2-ui/windows/StaffList.cpp b/src/openrct2-ui/windows/StaffList.cpp
index b2aaae4074..713984b508 100644
--- a/src/openrct2-ui/windows/StaffList.cpp
+++ b/src/openrct2-ui/windows/StaffList.cpp
@@ -731,7 +731,8 @@ namespace OpenRCT2::Ui::Windows
     WindowBase* StaffListOpen()
     {
         auto* windowMgr = GetWindowManager();
-        return windowMgr->FocusOrCreate<StaffListWindow>(WindowClass::staffList, kWindowSize, WF_10 | WF_RESIZABLE);
+        return windowMgr->FocusOrCreate<StaffListWindow>(
+            WindowClass::staffList, kWindowSize, { WindowFlag::higherContrastOnPress, WindowFlag::resizable });
     }
 
     void WindowStaffListRefresh()
diff --git a/src/openrct2-ui/windows/TextInput.cpp b/src/openrct2-ui/windows/TextInput.cpp
index a3022c41fa..cddd4dc901 100644
--- a/src/openrct2-ui/windows/TextInput.cpp
+++ b/src/openrct2-ui/windows/TextInput.cpp
@@ -373,7 +373,8 @@ namespace OpenRCT2::Ui::Windows
         windowMgr->CloseByClass(WindowClass::textinput);
 
         auto w = windowMgr->Create<TextInputWindow>(
-            WindowClass::textinput, { kWindowSize.width, kWindowSize.height + 10 }, WF_CENTRE_SCREEN | WF_STICK_TO_FRONT);
+            WindowClass::textinput, { kWindowSize.width, kWindowSize.height + 10 },
+            { WindowFlag::centreScreen, WindowFlag::stickToFront });
         if (w != nullptr)
         {
             w->setParentWindow(call_w, call_widget);
@@ -388,7 +389,8 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         auto w = windowMgr->Create<TextInputWindow>(
-            WindowClass::textinput, { kWindowSize.width, kWindowSize.height + 10 }, WF_CENTRE_SCREEN | WF_STICK_TO_FRONT);
+            WindowClass::textinput, { kWindowSize.width, kWindowSize.height + 10 },
+            { WindowFlag::centreScreen, WindowFlag::stickToFront });
         if (w != nullptr)
         {
             w->setTitle(title, description);
diff --git a/src/openrct2-ui/windows/Themes.cpp b/src/openrct2-ui/windows/Themes.cpp
index 4fa1c265a6..3443ca04cb 100644
--- a/src/openrct2-ui/windows/Themes.cpp
+++ b/src/openrct2-ui/windows/Themes.cpp
@@ -905,7 +905,8 @@ namespace OpenRCT2::Ui::Windows
         if (window != nullptr)
             return window;
 
-        window = windowMgr->Create<ThemesWindow>(WindowClass::themes, kWindowSize, WF_10 | WF_RESIZABLE);
+        window = windowMgr->Create<ThemesWindow>(
+            WindowClass::themes, kWindowSize, { WindowFlag::higherContrastOnPress, WindowFlag::resizable });
 
         return window;
     }
diff --git a/src/openrct2-ui/windows/TileInspector.cpp b/src/openrct2-ui/windows/TileInspector.cpp
index ae6ff017c0..d9321d4e82 100644
--- a/src/openrct2-ui/windows/TileInspector.cpp
+++ b/src/openrct2-ui/windows/TileInspector.cpp
@@ -2454,7 +2454,7 @@ static uint64_t PageDisabledWidgets[] = {
         WindowBase* window = windowMgr->BringToFrontByClass(WindowClass::tileInspector);
         if (window == nullptr)
             window = windowMgr->Create<TileInspector>(
-                WindowClass::tileInspector, ScreenCoordsXY(0, 29), kWindowSize, WF_RESIZABLE);
+                WindowClass::tileInspector, ScreenCoordsXY(0, 29), kWindowSize, WindowFlag::resizable);
         return window;
     }
 
diff --git a/src/openrct2-ui/windows/TitleExit.cpp b/src/openrct2-ui/windows/TitleExit.cpp
index 26d2c6100a..548e39a504 100644
--- a/src/openrct2-ui/windows/TitleExit.cpp
+++ b/src/openrct2-ui/windows/TitleExit.cpp
@@ -59,6 +59,6 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = GetWindowManager();
         return windowMgr->Create<TitleExitWindow>(
             WindowClass::titleExit, ScreenCoordsXY(ContextGetWidth() - 40, ContextGetHeight() - 64), kWindowSize,
-            WF_STICK_TO_BACK | WF_TRANSPARENT | WF_NO_TITLE_BAR);
+            { WindowFlag::stickToBack, WindowFlag::transparent, WindowFlag::noTitleBar });
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/TitleLogo.cpp b/src/openrct2-ui/windows/TitleLogo.cpp
index b699360826..e6eb8a3e53 100644
--- a/src/openrct2-ui/windows/TitleLogo.cpp
+++ b/src/openrct2-ui/windows/TitleLogo.cpp
@@ -71,7 +71,8 @@ namespace OpenRCT2::Ui::Windows
         if (window == nullptr)
         {
             window = windowMgr->Create<TitleLogoWindow>(
-                WindowClass::titleLogo, ScreenCoordsXY(0, 0), kWindowSize, WF_STICK_TO_BACK | WF_TRANSPARENT | WF_NO_TITLE_BAR);
+                WindowClass::titleLogo, ScreenCoordsXY(0, 0), kWindowSize,
+                { WindowFlag::stickToBack, WindowFlag::transparent, WindowFlag::noTitleBar });
         }
         return window;
     }
diff --git a/src/openrct2-ui/windows/TitleMenu.cpp b/src/openrct2-ui/windows/TitleMenu.cpp
index b923c281df..a23fcdeeaf 100644
--- a/src/openrct2-ui/windows/TitleMenu.cpp
+++ b/src/openrct2-ui/windows/TitleMenu.cpp
@@ -288,6 +288,6 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = GetWindowManager();
         return windowMgr->Create<TitleMenuWindow>(
             WindowClass::titleMenu, ScreenCoordsXY(0, ContextGetHeight() - 182), { 0, windowHeight },
-            WF_STICK_TO_BACK | WF_TRANSPARENT | WF_NO_BACKGROUND | WF_NO_TITLE_BAR);
+            { WindowFlag::stickToBack, WindowFlag::transparent, WindowFlag::noBackground, WindowFlag::noTitleBar });
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/TitleOptions.cpp b/src/openrct2-ui/windows/TitleOptions.cpp
index 2254ca7cae..29f8b69703 100644
--- a/src/openrct2-ui/windows/TitleOptions.cpp
+++ b/src/openrct2-ui/windows/TitleOptions.cpp
@@ -60,7 +60,7 @@ namespace OpenRCT2::Ui::Windows
         {
             window = windowMgr->Create<TitleOptionsWindow>(
                 WindowClass::titleOptions, ScreenCoordsXY(ContextGetWidth() - 80, 0), kWindowSize,
-                WF_STICK_TO_BACK | WF_TRANSPARENT | WF_NO_TITLE_BAR);
+                { WindowFlag::stickToBack, WindowFlag::transparent, WindowFlag::noTitleBar });
         }
 
         return window;
diff --git a/src/openrct2-ui/windows/TitleVersion.cpp b/src/openrct2-ui/windows/TitleVersion.cpp
index 72f897cddb..3f4b0263c0 100644
--- a/src/openrct2-ui/windows/TitleVersion.cpp
+++ b/src/openrct2-ui/windows/TitleVersion.cpp
@@ -45,7 +45,7 @@ namespace OpenRCT2::Ui::Windows
         {
             window = windowMgr->Create<TitleVersionWindow>(
                 WindowClass::titleVersion, ScreenCoordsXY(kTextOffset, ContextGetHeight() - 30), kWindowSize,
-                WF_STICK_TO_BACK | WF_TRANSPARENT | WF_NO_TITLE_BAR);
+                { WindowFlag::stickToBack, WindowFlag::transparent, WindowFlag::noTitleBar });
         }
         return window;
     }
diff --git a/src/openrct2-ui/windows/Tooltip.cpp b/src/openrct2-ui/windows/Tooltip.cpp
index 0a5989b814..de5bfa3052 100644
--- a/src/openrct2-ui/windows/Tooltip.cpp
+++ b/src/openrct2-ui/windows/Tooltip.cpp
@@ -168,7 +168,7 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = GetWindowManager();
         windowMgr->Create(
             std::move(tooltipWindow), WindowClass::tooltip, windowPos, { width, height },
-            WF_TRANSPARENT | WF_STICK_TO_FRONT | WF_NO_TITLE_BAR);
+            { WindowFlag::transparent, WindowFlag::stickToFront, WindowFlag::noTitleBar });
     }
 
     void WindowTooltipOpen(WindowBase* widgetWindow, WidgetIndex widgetIndex, const ScreenCoordsXY& screenCoords)
diff --git a/src/openrct2-ui/windows/TopToolbar.cpp b/src/openrct2-ui/windows/TopToolbar.cpp
index fea01635ba..55ec19be53 100644
--- a/src/openrct2-ui/windows/TopToolbar.cpp
+++ b/src/openrct2-ui/windows/TopToolbar.cpp
@@ -1510,7 +1510,7 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = GetWindowManager();
         auto* window = windowMgr->Create<TopToolbar>(
             WindowClass::topToolbar, ScreenCoordsXY(0, 0), { ContextGetWidth(), kTopToolbarHeight + 1 },
-            WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_NO_BACKGROUND | WF_NO_TITLE_BAR);
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::noBackground, WindowFlag::noTitleBar });
 
         window->setWidgets(_topToolbarWidgets);
 
diff --git a/src/openrct2-ui/windows/TrackDesignManage.cpp b/src/openrct2-ui/windows/TrackDesignManage.cpp
index e2717f8180..36df5ef85b 100644
--- a/src/openrct2-ui/windows/TrackDesignManage.cpp
+++ b/src/openrct2-ui/windows/TrackDesignManage.cpp
@@ -213,7 +213,7 @@ namespace OpenRCT2::Ui::Windows
 
         auto* window = windowMgr->Create(
             std::move(trackDesignManageWindow), WindowClass::manageTrackDesign, {}, kWindowSize,
-            WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_CENTRE_SCREEN | WF_AUTO_POSITION);
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::centreScreen, WindowFlag::autoPosition });
 
         return window;
     }
@@ -231,6 +231,6 @@ namespace OpenRCT2::Ui::Windows
 
         windowMgr->Create(
             std::move(trackDeletePromptWindow), WindowClass::trackDeletePrompt, {}, kWindowSizeDeletePrompt,
-            WF_STICK_TO_FRONT | WF_TRANSPARENT | WF_AUTO_POSITION | WF_CENTRE_SCREEN);
+            { WindowFlag::stickToFront, WindowFlag::transparent, WindowFlag::autoPosition, WindowFlag::centreScreen });
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/TrackDesignPlace.cpp b/src/openrct2-ui/windows/TrackDesignPlace.cpp
index 1114b57241..bad37ef70c 100644
--- a/src/openrct2-ui/windows/TrackDesignPlace.cpp
+++ b/src/openrct2-ui/windows/TrackDesignPlace.cpp
@@ -755,7 +755,7 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = Ui::GetWindowManager();
         windowMgr->CloseConstructionWindows();
 
-        auto* window = windowMgr->FocusOrCreate<TrackDesignPlaceWindow>(WindowClass::trackDesignPlace, kWindowSize, 0);
+        auto* window = windowMgr->FocusOrCreate<TrackDesignPlaceWindow>(WindowClass::trackDesignPlace, kWindowSize, {});
         if (window != nullptr)
         {
             window->init(std::move(openTrackDesign));
diff --git a/src/openrct2-ui/windows/TrackList.cpp b/src/openrct2-ui/windows/TrackList.cpp
index 21776ed6ad..ae5956b428 100644
--- a/src/openrct2-ui/windows/TrackList.cpp
+++ b/src/openrct2-ui/windows/TrackList.cpp
@@ -756,11 +756,11 @@ namespace OpenRCT2::Ui::Windows
         auto* windowMgr = Ui::GetWindowManager();
         windowMgr->CloseConstructionWindows();
 
-        WindowFlags flags = 0;
+        WindowFlags flags = {};
         ScreenCoordsXY screenPos{};
         if (gLegacyScene == LegacyScene::trackDesignsManager)
         {
-            flags = WF_AUTO_POSITION | WF_CENTRE_SCREEN;
+            flags = { WindowFlag::autoPosition, WindowFlag::centreScreen };
         }
         else
         {
diff --git a/src/openrct2-ui/windows/Viewport.cpp b/src/openrct2-ui/windows/Viewport.cpp
index 6797931c19..8dee649d27 100644
--- a/src/openrct2-ui/windows/Viewport.cpp
+++ b/src/openrct2-ui/windows/Viewport.cpp
@@ -207,6 +207,6 @@ namespace OpenRCT2::Ui::Windows
 
     WindowBase* ViewportOpen()
     {
-        return GetWindowManager()->Create<ViewportWindow>(WindowClass::viewport, kWindowSize, WF_RESIZABLE);
+        return GetWindowManager()->Create<ViewportWindow>(WindowClass::viewport, kWindowSize, WindowFlag::resizable);
     }
 } // namespace OpenRCT2::Ui::Windows
diff --git a/src/openrct2-ui/windows/Water.cpp b/src/openrct2-ui/windows/Water.cpp
index 24a09f8052..79313f9f7f 100644
--- a/src/openrct2-ui/windows/Water.cpp
+++ b/src/openrct2-ui/windows/Water.cpp
@@ -429,7 +429,7 @@ namespace OpenRCT2::Ui::Windows
     {
         auto* windowMgr = GetWindowManager();
         return windowMgr->FocusOrCreate<WaterWindow>(
-            WindowClass::water, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, 0);
+            WindowClass::water, ScreenCoordsXY(ContextGetWidth() - kWindowSize.width, 29), kWindowSize, {});
     }
 
     /**
diff --git a/src/openrct2/core/FlagHolder.hpp b/src/openrct2/core/FlagHolder.hpp
index 94fb4ab86c..b8d443c970 100644
--- a/src/openrct2/core/FlagHolder.hpp
+++ b/src/openrct2/core/FlagHolder.hpp
@@ -50,6 +50,11 @@ struct FlagHolder
         return (holder & EnumsToFlags(types...)) != 0;
     }
 
+    constexpr bool hasAny(const FlagHolder& other) const
+    {
+        return (holder & other.holder) != 0;
+    }
+
     template<typename... TTypes>
     [[nodiscard]] constexpr bool hasAll(TTypes... types) const
     {
@@ -97,4 +102,10 @@ struct FlagHolder
         res.holder |= other.holder;
         return res;
     }
+
+    constexpr FlagHolder& operator|=(const FlagHolder& other) noexcept
+    {
+        holder |= other.holder;
+        return *this;
+    }
 };
diff --git a/src/openrct2/interface/Viewport.cpp b/src/openrct2/interface/Viewport.cpp
index 18edd02e86..fe6279e5b3 100644
--- a/src/openrct2/interface/Viewport.cpp
+++ b/src/openrct2/interface/Viewport.cpp
@@ -340,7 +340,7 @@ namespace OpenRCT2
                 // Get next valid window after.
                 auto itNextWindow = [&]() {
                     auto itNext = std::next(itWindowPos);
-                    while (itNext != gWindowList.end() && (itNext->get()->flags & WF_DEAD))
+                    while (itNext != gWindowList.end() && (itNext->get()->flags.has(WindowFlag::dead)))
                     {
                         ++itNext;
                     }
@@ -442,7 +442,7 @@ namespace OpenRCT2
         for (; it != gWindowList.end(); it++)
         {
             auto w = it->get();
-            if (!(w->flags & WF_TRANSPARENT) || (w->flags & WF_DEAD))
+            if (!(w->flags.has(WindowFlag::transparent)) || (w->flags.has(WindowFlag::dead)))
                 continue;
             if (w->viewport == window->viewport)
                 continue;
@@ -485,30 +485,6 @@ namespace OpenRCT2
         if ((!x_diff) && (!y_diff))
             return;
 
-        if (w->flags & WF_7)
-        {
-            int32_t left = std::max<int32_t>(viewport->pos.x, 0);
-            int32_t top = std::max<int32_t>(viewport->pos.y, 0);
-            int32_t right = std::min<int32_t>(viewport->pos.x + viewport->width, ContextGetWidth());
-            int32_t bottom = std::min<int32_t>(viewport->pos.y + viewport->height, ContextGetHeight());
-
-            if (left >= right)
-                return;
-            if (top >= bottom)
-                return;
-
-            if (DrawingEngineHasDirtyOptimisations())
-            {
-                RenderTarget& rt = DrawingEngineGetDpi();
-                WindowDrawAll(rt, left, top, right, bottom);
-                return;
-            }
-            else
-            {
-                GfxInvalidateScreen();
-            }
-        }
-
         const int32_t left = std::max(viewport->pos.x, 0);
         const int32_t top = std::max(viewport->pos.y, 0);
         const int32_t right = std::min(left + viewport->width + std::min(viewport->pos.x, 0), ContextGetWidth());
@@ -620,7 +596,7 @@ namespace OpenRCT2
         }
 
         auto windowCoords = window->savedViewPos;
-        if (window->flags & WF_SCROLLING_TO_LOCATION)
+        if (window->flags.has(WindowFlag::scrollingToLocation))
         {
             // Moves the viewport if focusing in on an item
             uint8_t flags = 0;
@@ -642,7 +618,7 @@ namespace OpenRCT2
             // If we are at the final zoom position
             if (!windowCoords.x && !windowCoords.y)
             {
-                window->flags &= ~WF_SCROLLING_TO_LOCATION;
+                window->flags.unset(WindowFlag::scrollingToLocation);
             }
             if (flags & 1)
             {
diff --git a/src/openrct2/interface/Window.cpp b/src/openrct2/interface/Window.cpp
index 6cba6c6406..0d42f7ea76 100644
--- a/src/openrct2/interface/Window.cpp
+++ b/src/openrct2/interface/Window.cpp
@@ -85,7 +85,7 @@ static constexpr float kWindowScrollLocations[][2] = {
     {
         for (auto& w : gWindowList)
         {
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
             func(w.get());
         }
@@ -146,7 +146,7 @@ static constexpr float kWindowScrollLocations[][2] = {
             for (auto itOther = std::next(it); itOther != itEnd; ++itOther)
             {
                 const auto& otherWindow = *(*itOther);
-                if (otherWindow.flags & WF_DEAD)
+                if (otherWindow.flags.has(WindowFlag::dead))
                     continue;
 
                 if (otherWindow.windowPos.x <= window.windowPos.x && otherWindow.windowPos.y <= window.windowPos.y
@@ -167,9 +167,10 @@ static constexpr float kWindowScrollLocations[][2] = {
      */
     void WindowUpdateAll()
     {
-        // Remove all windows in gWindowList that have the WF_DEAD flag
+        // Remove all windows in gWindowList that have the WindowFlag::dead flag
         gWindowList.erase(
-            std::remove_if(gWindowList.begin(), gWindowList.end(), [](auto&& w) -> bool { return w->flags & WF_DEAD; }),
+            std::remove_if(
+                gWindowList.begin(), gWindowList.end(), [](auto&& w) -> bool { return w->flags.has(WindowFlag::dead); }),
             gWindowList.end());
 
         // Periodic update happens every second so 40 ticks.
@@ -182,10 +183,10 @@ static constexpr float kWindowScrollLocations[][2] = {
 
         // Border flash invalidation
         WindowVisitEach([](WindowBase* w) {
-            if (w->flags & WF_WHITE_BORDER_MASK)
+            if (w->flashTimer > 0)
             {
-                w->flags -= WF_WHITE_BORDER_ONE;
-                if (!(w->flags & WF_WHITE_BORDER_MASK))
+                w->flashTimer--;
+                if (w->flashTimer == 0)
                 {
                     w->invalidate();
                 }
@@ -244,7 +245,7 @@ static constexpr float kWindowScrollLocations[][2] = {
         WindowVisitEach([&window](WindowBase* w) {
             if (w == &window)
                 return;
-            if (w->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT))
+            if (w->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront))
                 return;
             if (w->windowPos.x >= window.windowPos.x + window.width)
                 return;
@@ -277,7 +278,7 @@ static constexpr float kWindowScrollLocations[][2] = {
             if (&w1 == w2)
                 return;
             // ?
-            if (w2->flags & (WF_STICK_TO_BACK | WF_STICK_TO_FRONT))
+            if (w2->flags.hasAny(WindowFlag::stickToBack, WindowFlag::stickToFront))
                 return;
             // Check if w2 intersects with w1
             if (w2->windowPos.x > (w1.windowPos.x + w1.width) || w2->windowPos.x + w2->width < w1.windowPos.x)
@@ -312,7 +313,7 @@ static constexpr float kWindowScrollLocations[][2] = {
     {
         for (auto& w : gWindowList)
         {
-            if (w->flags & WF_DEAD)
+            if (w->flags.has(WindowFlag::dead))
                 continue;
             if (w->classification == WindowClass::mainWindow)
             {
@@ -371,7 +372,7 @@ static constexpr float kWindowScrollLocations[][2] = {
                 auto it = WindowGetIterator(&w);
                 for (; it != gWindowList.end(); it++)
                 {
-                    if ((*it)->flags & WF_DEAD)
+                    if ((*it)->flags.has(WindowFlag::dead))
                         continue;
 
                     auto w2 = (*it).get();
@@ -403,12 +404,12 @@ static constexpr float kWindowScrollLocations[][2] = {
         // rct2: 0x006E7C76
         if (w.viewportTargetSprite.IsNull())
         {
-            if (!(w.flags & WF_NO_SCROLLING))
+            if (!(w.flags.has(WindowFlag::noScrolling)))
             {
                 w.savedViewPos = screenCoords
                     - ScreenCoordsXY{ static_cast<int32_t>(w.viewport->ViewWidth() * kWindowScrollLocations[i][0]),
                                       static_cast<int32_t>(w.viewport->ViewHeight() * kWindowScrollLocations[i][1]) };
-                w.flags |= WF_SCROLLING_TO_LOCATION;
+                w.flags.set(WindowFlag::scrollingToLocation);
             }
         }
     }
@@ -496,9 +497,9 @@ static constexpr float kWindowScrollLocations[][2] = {
         {
             // Check if this window overlaps w
             auto topwindow = it->get();
-            if (topwindow->flags & WF_TRANSPARENT)
+            if (topwindow->flags.has(WindowFlag::transparent))
                 continue;
-            if (topwindow->flags & WF_DEAD)
+            if (topwindow->flags.has(WindowFlag::dead))
                 continue;
             if (topwindow->windowPos.x >= right || topwindow->windowPos.y >= bottom)
                 continue;
@@ -558,9 +559,9 @@ static constexpr float kWindowScrollLocations[][2] = {
         for (auto it = WindowGetIterator(&w); it != gWindowList.end(); it++)
         {
             auto* v = (*it).get();
-            if (v->flags & WF_DEAD)
+            if (v->flags.has(WindowFlag::dead))
                 continue;
-            if ((&w == v || (v->flags & WF_TRANSPARENT)) && v->isVisible)
+            if ((&w == v || (v->flags.has(WindowFlag::transparent))) && v->isVisible)
             {
                 WindowDrawSingle(rt, *v, left, top, right, bottom);
             }
@@ -857,7 +858,7 @@ static constexpr float kWindowScrollLocations[][2] = {
     {
         auto windowRT = rt.Crop({ left, top }, { right - left, bottom - top });
         WindowVisitEach([&windowRT, left, top, right, bottom](WindowBase* w) {
-            if (w->flags & WF_TRANSPARENT)
+            if (w->flags.has(WindowFlag::transparent))
                 return;
             if (right <= w->windowPos.x || bottom <= w->windowPos.y)
                 return;
@@ -870,7 +871,7 @@ static constexpr float kWindowScrollLocations[][2] = {
     void WindowInitAll()
     {
         auto* windowMgr = Ui::GetWindowManager();
-        windowMgr->CloseAllExceptFlags(0);
+        windowMgr->CloseAllExceptFlags({});
     }
 
     void WindowFollowSprite(WindowBase& w, EntityId spriteIndex)
diff --git a/src/openrct2/interface/Window.h b/src/openrct2/interface/Window.h
index ca417cd85a..0415158f67 100644
--- a/src/openrct2/interface/Window.h
+++ b/src/openrct2/interface/Window.h
@@ -60,39 +60,39 @@ namespace OpenRCT2
 
     struct Viewport;
 
-    enum WINDOW_FLAGS
+    enum class WindowFlag : uint8_t
     {
-        /*
-        WF_TIMEOUT_SHL = 0,
-        WF_TIMEOUT_MASK = 7,
-        WF_DRAGGING = 1 << 3,
-        WF_SCROLLER_UP = 1 << 4,
-        WF_SCROLLER_DOWN = 1 << 5,
-        WF_SCROLLER_MIDDLE = 1 << 6,
-        WF_DISABLE_VP_SCROLL = 1 << 9,
-        */
-
-        WF_STICK_TO_BACK = (1 << 0),
-        WF_STICK_TO_FRONT = (1 << 1),
-        WF_NO_SCROLLING = (1 << 2), // User is unable to scroll this viewport
-        WF_SCROLLING_TO_LOCATION = (1 << 3),
-        WF_TRANSPARENT = (1 << 4),
-        WF_NO_BACKGROUND = (1 << 5), // Instead of half transparency, completely remove the window background
-        WF_DEAD = (1u << 6),         // Window is closed and will be deleted in the next update.
-        WF_7 = (1 << 7),
-        WF_RESIZABLE = (1 << 8),
-        WF_NO_AUTO_CLOSE = (1 << 9), // Don't auto close this window if too many windows are open
-        WF_10 = (1 << 10),
-        WF_WHITE_BORDER_ONE = (1 << 12),
-        WF_WHITE_BORDER_MASK = (1 << 12) | (1 << 13),
-        WF_NO_TITLE_BAR = (1 << 14),
-        WF_NO_SNAPPING = (1 << 15),
+        stickToBack,
+        stickToFront,
+        /**
+         * User is unable to scroll this viewport
+         */
+        noScrolling,
+        scrollingToLocation,
+        transparent,
+        /**
+         * Instead of half transparency, completely remove the window background
+         */
+        noBackground,
+        /**
+         * Window is closed and will be deleted in the next update.
+         */
+        dead,
+        resizable,
+        /**
+         * Don't auto close this window if too many windows are open
+         */
+        noAutoClose,
+        // TODO: investigate why exactly this is used.
+        higherContrastOnPress,
+        noTitleBar,
+        noSnapping,
 
         // *ONLY* create only flags below
-        WF_AUTO_POSITION = (1 << 16),
-        WF_CENTRE_SCREEN = (1 << 17),
+        autoPosition,
+        centreScreen,
     };
-    using WindowFlags = uint32_t;
+    using WindowFlags = FlagHolder<uint16_t, WindowFlag>;
 
     enum class WindowView : uint8_t
     {
diff --git a/src/openrct2/interface/WindowBase.cpp b/src/openrct2/interface/WindowBase.cpp
index 9ea2e81d23..7c3e08c20f 100644
--- a/src/openrct2/interface/WindowBase.cpp
+++ b/src/openrct2/interface/WindowBase.cpp
@@ -11,7 +11,7 @@ namespace OpenRCT2
     void WindowBase::setViewportLocation(const CoordsXYZ& coords)
     {
         WindowScrollToLocation(*this, coords);
-        flags &= ~WF_SCROLLING_TO_LOCATION;
+        flags.unset(WindowFlag::scrollingToLocation);
 
         // Immediately update the viewport position since we are not scrolling.
         if (viewport != nullptr)
@@ -151,7 +151,7 @@ namespace OpenRCT2
 
     int16_t WindowBase::getTitleBarCurrentHeight() const
     {
-        if (!(flags & WF_NO_TITLE_BAR) && widgets.size() > 2)
+        if (!(flags.has(WindowFlag::noTitleBar)) && widgets.size() > 2)
             return widgets[1].height();
         else
             return 0;
diff --git a/src/openrct2/interface/WindowBase.h b/src/openrct2/interface/WindowBase.h
index bd318b90e6..4ea067b3a8 100644
--- a/src/openrct2/interface/WindowBase.h
+++ b/src/openrct2/interface/WindowBase.h
@@ -33,6 +33,8 @@ struct RCTObjectEntry;
 
 namespace OpenRCT2
 {
+    constexpr uint8_t kDefaultWindowFlashCountdown = 3;
+
     // TODO: move to Viewport.h?
     struct Focus
     {
@@ -89,6 +91,10 @@ namespace OpenRCT2
             RideId rideId;
         };
         WindowFlags flags{};
+        /**
+         * Set to 3 when the window should flash and decremented per tick.
+         */
+        uint8_t flashTimer{};
         OpenRCT2::ScrollArea scrolls[3];
         uint16_t numListItems{};    // 0 for no items
         int16_t selectedListItem{}; // -1 for none selected
@@ -128,7 +134,7 @@ namespace OpenRCT2
 
         constexpr bool canBeResized() const
         {
-            return (flags & WF_RESIZABLE) && (minWidth != maxWidth || minHeight != maxHeight);
+            return flags.has(WindowFlag::resizable) && (minWidth != maxWidth || minHeight != maxHeight);
         }
 
         // Events
@@ -221,15 +227,20 @@ namespace OpenRCT2
         {
         }
 
-        int16_t right()
+        constexpr int16_t right()
         {
             return windowPos.x + width;
         }
 
-        int16_t bottom()
+        constexpr int16_t bottom()
         {
             return windowPos.y + height;
         }
+
+        constexpr void flash()
+        {
+            flashTimer = kDefaultWindowFlashCountdown;
+        }
     };
 
 #ifdef __WARN_SUGGEST_FINAL_METHODS__
diff --git a/src/openrct2/scenario/Scenario.cpp b/src/openrct2/scenario/Scenario.cpp
index 8c8adc1eee..e3f89cb3be 100644
--- a/src/openrct2/scenario/Scenario.cpp
+++ b/src/openrct2/scenario/Scenario.cpp
@@ -169,7 +169,7 @@ static void ScenarioEnd()
 
     auto* windowMgr = Ui::GetWindowManager();
     windowMgr->CloseByClass(WindowClass::dropdown);
-    windowMgr->CloseAllExceptFlags(WF_STICK_TO_BACK | WF_STICK_TO_FRONT);
+    windowMgr->CloseAllExceptFlags({ WindowFlag::stickToBack, WindowFlag::stickToFront });
 
     ContextOpenWindowView(WindowView::parkObjective);
 }
diff --git a/src/openrct2/ui/DummyWindowManager.cpp b/src/openrct2/ui/DummyWindowManager.cpp
index d46d2eee41..e37e042156 100644
--- a/src/openrct2/ui/DummyWindowManager.cpp
+++ b/src/openrct2/ui/DummyWindowManager.cpp
@@ -124,10 +124,6 @@ namespace OpenRCT2::Ui
         {
             return nullptr;
         }
-        WindowBase* BringToFrontByClassWithFlags(WindowClass cls, WindowFlags flags) override
-        {
-            return nullptr;
-        }
         WindowBase* BringToFrontByNumber(WindowClass cls, WindowNumber number) override
         {
             return nullptr;
diff --git a/src/openrct2/ui/WindowManager.h b/src/openrct2/ui/WindowManager.h
index 5536a25120..1bd9d6f46c 100644
--- a/src/openrct2/ui/WindowManager.h
+++ b/src/openrct2/ui/WindowManager.h
@@ -51,7 +51,8 @@ namespace OpenRCT2::Ui
             = 0;
 
         template<typename T, typename... TArgs, typename std::enable_if<std::is_base_of<WindowBase, T>::value>::type* = nullptr>
-        T* Create(WindowClass cls, const ScreenCoordsXY& pos = {}, ScreenSize size = {}, WindowFlags flags = 0, TArgs&&... args)
+        T* Create(
+            WindowClass cls, const ScreenCoordsXY& pos = {}, ScreenSize size = {}, WindowFlags flags = {}, TArgs&&... args)
         {
             return static_cast<T*>(Create(std::make_unique<T>(std::forward<TArgs>(args)...), cls, pos, size, flags));
         }
@@ -60,11 +61,11 @@ namespace OpenRCT2::Ui
         T* Create(WindowClass cls, ScreenSize size, WindowFlags flags, TArgs&&... args)
         {
             return static_cast<T*>(
-                Create(std::make_unique<T>(std::forward<TArgs>(args)...), cls, {}, size, flags | WF_AUTO_POSITION));
+                Create(std::make_unique<T>(std::forward<TArgs>(args)...), cls, {}, size, flags | WindowFlag::autoPosition));
         }
 
         template<typename T, typename std::enable_if<std::is_base_of<WindowBase, T>::value>::type* = nullptr>
-        T* FocusOrCreate(WindowClass cls, const ScreenCoordsXY& pos, ScreenSize size, WindowFlags flags = 0)
+        T* FocusOrCreate(WindowClass cls, const ScreenCoordsXY& pos, ScreenSize size, WindowFlags flags = {})
         {
             auto* w = BringToFrontByClass(cls);
             if (w == nullptr)
@@ -75,7 +76,7 @@ namespace OpenRCT2::Ui
         }
 
         template<typename T, typename std::enable_if<std::is_base_of<WindowBase, T>::value>::type* = nullptr>
-        T* FocusOrCreate(WindowClass cls, ScreenSize size, WindowFlags flags = 0)
+        T* FocusOrCreate(WindowClass cls, ScreenSize size, WindowFlags flags = {})
         {
             auto* w = BringToFrontByClass(cls);
             if (w == nullptr)
@@ -113,7 +114,6 @@ namespace OpenRCT2::Ui
 
         virtual WindowBase* BringToFront(WindowBase& w) = 0;
         virtual WindowBase* BringToFrontByClass(WindowClass cls) = 0;
-        virtual WindowBase* BringToFrontByClassWithFlags(WindowClass cls, WindowFlags flags) = 0;
         virtual WindowBase* BringToFrontByNumber(WindowClass cls, WindowNumber number) = 0;
     };