diff --git a/CHANGELOG.md b/CHANGELOG.md
index ccb5059bb..e5c3fac3c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -31,6 +31,7 @@
 - Minor: Added the `--incognito/--no-incognito` options to the `/openurl` command, allowing you to override the "Open links in incognito/private mode" setting. (#5149)
 - Minor: Added support for the `{input.text}` placeholder in the **Split** -> **Run a command** hotkey. (#5130)
 - Minor: Add a new Channel API for experimental plugins feature. (#5141)
+- Minor: Added the ability to change the top-most status of a window regardless of the _Always on top_ setting (right click the notebook). (#5135)
 - Bugfix: Fixed an issue where certain emojis did not send to Twitch chat correctly. (#4840)
 - Bugfix: Fixed capitalized channel names in log inclusion list not being logged. (#4848)
 - Bugfix: Trimmed custom streamlink paths on all platforms making sure you don't accidentally add spaces at the beginning or end of its path. (#4834)
diff --git a/src/widgets/BaseWindow.cpp b/src/widgets/BaseWindow.cpp
index 592f2b97e..20bb911f1 100644
--- a/src/widgets/BaseWindow.cpp
+++ b/src/widgets/BaseWindow.cpp
@@ -1,6 +1,7 @@
 #include "widgets/BaseWindow.hpp"
 
 #include "Application.hpp"
+#include "common/QLogging.hpp"
 #include "singletons/Settings.hpp"
 #include "singletons/Theme.hpp"
 #include "singletons/WindowManager.hpp"
@@ -207,37 +208,52 @@ void BaseWindow::init()
 //    }
 #endif
 
-#ifdef USEWINSDK
-    // fourtf: don't ask me why we need to delay this
-    if (!this->flags_.has(TopMost))
-    {
-        QTimer::singleShot(1, this, [this] {
-            getSettings()->windowTopMost.connect(
-                [this](bool topMost, auto) {
-                    ::SetWindowPos(HWND(this->winId()),
-                                   topMost ? HWND_TOPMOST : HWND_NOTOPMOST, 0,
-                                   0, 0, 0,
-                                   SWP_NOMOVE | SWP_NOSIZE | SWP_NOACTIVATE);
-                },
-                this->connections_);
-        });
-    }
-#else
     // TopMost flag overrides setting
     if (!this->flags_.has(TopMost))
     {
         getSettings()->windowTopMost.connect(
-            [this](bool topMost, auto) {
-                auto isVisible = this->isVisible();
-                this->setWindowFlag(Qt::WindowStaysOnTopHint, topMost);
-                if (isVisible)
-                {
-                    this->show();
-                }
+            [this](bool topMost) {
+                this->setTopMost(topMost);
             },
             this->connections_);
     }
+}
+
+void BaseWindow::setTopMost(bool topMost)
+{
+    if (this->flags_.has(TopMost))
+    {
+        qCWarning(chatterinoWidget)
+            << "Called setTopMost on a window with the `TopMost` flag set.";
+        return;
+    }
+
+    if (this->isTopMost_ == topMost)
+    {
+        return;
+    }
+
+#ifdef USEWINSDK
+    ::SetWindowPos(reinterpret_cast<HWND>(this->winId()),
+                   topMost ? HWND_TOPMOST : HWND_NOTOPMOST, 0, 0, 0, 0,
+                   SWP_NOMOVE | SWP_NOSIZE | SWP_NOACTIVATE);
+
+#else
+    auto isVisible = this->isVisible();
+    this->setWindowFlag(Qt::WindowStaysOnTopHint, topMost);
+    if (isVisible)
+    {
+        this->show();
+    }
 #endif
+
+    this->isTopMost_ = topMost;
+    this->topMostChanged(this->isTopMost_);
+}
+
+bool BaseWindow::isTopMost() const
+{
+    return this->isTopMost_ || this->flags_.has(TopMost);
 }
 
 void BaseWindow::setActionOnFocusLoss(ActionOnFocusLoss value)
@@ -559,6 +575,15 @@ void BaseWindow::showEvent(QShowEvent *)
     {
         this->moveTo(this->pos(), widgets::BoundsChecking::CursorPosition);
     }
+
+    if (!this->flags_.has(TopMost))
+    {
+        QTimer::singleShot(1, this, [this] {
+            ::SetWindowPos(reinterpret_cast<HWND>(this->winId()),
+                           this->isTopMost_ ? HWND_TOPMOST : HWND_NOTOPMOST, 0,
+                           0, 0, 0, SWP_NOMOVE | SWP_NOSIZE | SWP_NOACTIVATE);
+        });
+    }
 #endif
 }
 
diff --git a/src/widgets/BaseWindow.hpp b/src/widgets/BaseWindow.hpp
index d55b5bd6d..aafb3555e 100644
--- a/src/widgets/BaseWindow.hpp
+++ b/src/widgets/BaseWindow.hpp
@@ -68,10 +68,20 @@ public:
     float scale() const override;
     float qtFontScale() const;
 
+    /// @returns true if the window is the top-most window.
+    ///          Either #setTopMost was called or the `TopMost` flag is set which overrides this
+    bool isTopMost() const;
+    /// Updates the window's top-most status
+    /// If the `TopMost` flag is set, this is a no-op
+    void setTopMost(bool topMost);
+
     pajlada::Signals::NoArgSignal closing;
 
     static bool supportsCustomWindowFrame();
 
+signals:
+    void topMostChanged(bool topMost);
+
 protected:
 #if QT_VERSION >= QT_VERSION_CHECK(6, 0, 0)
     bool nativeEvent(const QByteArray &eventType, void *message,
@@ -131,6 +141,7 @@ private:
     FlagsEnum<Flags> flags_;
     float nativeScale_ = 1;
     bool isResizeFixing_ = false;
+    bool isTopMost_ = false;
 
     struct {
         QLayout *windowLayout = nullptr;
diff --git a/src/widgets/Notebook.cpp b/src/widgets/Notebook.cpp
index 3b9536199..4ae8b22f3 100644
--- a/src/widgets/Notebook.cpp
+++ b/src/widgets/Notebook.cpp
@@ -59,6 +59,28 @@ Notebook::Notebook(QWidget *parent)
     });
     this->updateTabVisibilityMenuAction();
 
+    this->toggleTopMostAction_ = new QAction("Top most window", this);
+    this->toggleTopMostAction_->setCheckable(true);
+    auto *window = dynamic_cast<BaseWindow *>(this->window());
+    if (window)
+    {
+        auto updateTopMost = [this, window] {
+            this->toggleTopMostAction_->setChecked(window->isTopMost());
+        };
+        updateTopMost();
+        QObject::connect(this->toggleTopMostAction_, &QAction::triggered,
+                         window, [window] {
+                             window->setTopMost(!window->isTopMost());
+                         });
+        QObject::connect(window, &BaseWindow::topMostChanged, this,
+                         updateTopMost);
+    }
+    else
+    {
+        qCWarning(chatterinoApp)
+            << "Notebook must be created within a BaseWindow";
+    }
+
     this->addNotebookActionsToMenu(&this->menu_);
 
     // Manually resize the add button so the initial paint uses the correct
@@ -1181,6 +1203,8 @@ void Notebook::addNotebookActionsToMenu(QMenu *menu)
     menu->addAction(this->showTabsAction_);
 
     menu->addAction(this->lockNotebookLayoutAction_);
+
+    menu->addAction(this->toggleTopMostAction_);
 }
 
 NotebookButton *Notebook::getAddButton()
diff --git a/src/widgets/Notebook.hpp b/src/widgets/Notebook.hpp
index 3dcabf82d..9aa694c66 100644
--- a/src/widgets/Notebook.hpp
+++ b/src/widgets/Notebook.hpp
@@ -196,6 +196,7 @@ private:
     NotebookTabLocation tabLocation_ = NotebookTabLocation::Top;
     QAction *lockNotebookLayoutAction_;
     QAction *showTabsAction_;
+    QAction *toggleTopMostAction_;
 
     // This filter, if set, is used to figure out the visibility of
     // the tabs in this notebook.
@@ -224,7 +225,6 @@ private:
 
     // Main window on Windows has basically a duplicate of this in Window
     NotebookButton *streamerModeIcon_{};
-
     void updateStreamerModeIcon();
 };