diff --git a/chatterino.pro b/chatterino.pro
index bee2ef08..b984da7d 100644
--- a/chatterino.pro
+++ b/chatterino.pro
@@ -225,7 +225,8 @@ SOURCES += \
     src/singletons/Theme.cpp \
     src/controllers/moderationactions/ModerationActionModel.cpp \
     src/widgets/settingspages/LookPage.cpp \
-    src/widgets/settingspages/FeelPage.cpp
+    src/widgets/settingspages/FeelPage.cpp \
+    src/widgets/dialogs/UpdatePromptDialog.cpp
 
 HEADERS  += \
     src/Application.hpp \
@@ -398,7 +399,8 @@ HEADERS  += \
     src/common/Singleton.hpp \
     src/controllers/moderationactions/ModerationActionModel.hpp \
     src/widgets/settingspages/LookPage.hpp \
-    src/widgets/settingspages/FeelPage.hpp
+    src/widgets/settingspages/FeelPage.hpp \
+    src/widgets/dialogs/UpdatePromptDialog.hpp
 
 RESOURCES += \ 
     resources/resources.qrc \
diff --git a/resources/images/download_update.png b/resources/images/download_update.png
new file mode 100644
index 00000000..92519418
Binary files /dev/null and b/resources/images/download_update.png differ
diff --git a/resources/resources.qrc b/resources/resources.qrc
index b930ed4b..146c2c66 100644
--- a/resources/resources.qrc
+++ b/resources/resources.qrc
@@ -72,6 +72,7 @@
         <file>contributors.txt</file>
         <file>avatars/fourtf.png</file>
         <file>avatars/pajlada.png</file>
+        <file>images/download_update.png</file>
     </qresource>
     <qresource prefix="/qt/etc">
         <file>qt.conf</file>
diff --git a/src/widgets/BaseWindow.cpp b/src/widgets/BaseWindow.cpp
index af776185..d0c4a8cc 100644
--- a/src/widgets/BaseWindow.cpp
+++ b/src/widgets/BaseWindow.cpp
@@ -318,8 +318,8 @@ void BaseWindow::mouseMoveEvent(QMouseEvent *event)
     BaseWidget::mouseMoveEvent(event);
 }
 
-void BaseWindow::addTitleBarButton(const TitleBarButton::Style &style,
-                                   std::function<void()> onClicked)
+TitleBarButton *BaseWindow::addTitleBarButton(const TitleBarButton::Style &style,
+                                              std::function<void()> onClicked)
 {
     TitleBarButton *button = new TitleBarButton;
     button->setScaleIndependantSize(30, 30);
@@ -329,6 +329,8 @@ void BaseWindow::addTitleBarButton(const TitleBarButton::Style &style,
     button->setButtonStyle(style);
 
     QObject::connect(button, &TitleBarButton::clicked, this, [onClicked] { onClicked(); });
+
+    return button;
 }
 
 RippleEffectLabel *BaseWindow::addTitleBarLabel(std::function<void()> onClicked)
diff --git a/src/widgets/BaseWindow.hpp b/src/widgets/BaseWindow.hpp
index 883cf0a4..77fcc818 100644
--- a/src/widgets/BaseWindow.hpp
+++ b/src/widgets/BaseWindow.hpp
@@ -36,7 +36,8 @@ public:
 
     QWidget *getLayoutContainer();
     bool hasCustomWindowFrame();
-    void addTitleBarButton(const TitleBarButton::Style &style, std::function<void()> onClicked);
+    TitleBarButton *addTitleBarButton(const TitleBarButton::Style &style,
+                                      std::function<void()> onClicked);
     RippleEffectLabel *addTitleBarLabel(std::function<void()> onClicked);
 
     void setStayInScreenRect(bool value);
diff --git a/src/widgets/Window.cpp b/src/widgets/Window.cpp
index 99bc9ce6..28638ef0 100644
--- a/src/widgets/Window.cpp
+++ b/src/widgets/Window.cpp
@@ -10,6 +10,7 @@
 #include "widgets/AccountSwitchPopupWidget.hpp"
 #include "widgets/Notebook.hpp"
 #include "widgets/dialogs/SettingsDialog.hpp"
+#include "widgets/dialogs/UpdatePromptDialog.hpp"
 #include "widgets/dialogs/WelcomeDialog.hpp"
 #include "widgets/helper/Shortcut.hpp"
 #include "widgets/splits/Split.hpp"
@@ -52,10 +53,23 @@ Window::Window(WindowType _type)
     });
 
     if (this->hasCustomWindowFrame() && _type == Window::Main) {
+        // settings
         this->addTitleBarButton(TitleBarButton::Settings, [app] {
             app->windows->showSettingsDialog();  //
         });
 
+        // updates
+        auto update = this->addTitleBarButton(TitleBarButton::None, [] {});
+        update->setPixmap(QPixmap(":/images/download_update.png"));
+        QObject::connect(update, &TitleBarButton::clicked, this, [this, update] {
+            auto dialog = new UpdatePromptDialog();
+            dialog->setAttribute(Qt::WA_DeleteOnClose);
+            dialog->move(update->mapToGlobal(QPoint(-100 * this->getScale(), update->height())));
+            dialog->show();
+            dialog->raise();
+        });
+
+        // account
         this->userLabel = this->addTitleBarLabel([this, app] {
             app->windows->showAccountSelectPopup(
                 this->userLabel->mapToGlobal(this->userLabel->rect().bottomLeft()));  //
diff --git a/src/widgets/dialogs/UpdatePromptDialog.cpp b/src/widgets/dialogs/UpdatePromptDialog.cpp
new file mode 100644
index 00000000..2cc4df2a
--- /dev/null
+++ b/src/widgets/dialogs/UpdatePromptDialog.cpp
@@ -0,0 +1,30 @@
+#include "UpdatePromptDialog.hpp"
+
+#include "util/LayoutCreator.hpp"
+#include "widgets/Label.hpp"
+
+#include <QDialogButtonBox>
+#include <QPushButton>
+#include <QVBoxLayout>
+
+namespace chatterino {
+
+UpdatePromptDialog::UpdatePromptDialog()
+    : BaseWindow(nullptr, BaseWindow::Flags(BaseWindow::Frameless | BaseWindow::TopMost |
+                                            BaseWindow::EnableCustomFrame))
+{
+    auto layout = LayoutCreator<UpdatePromptDialog>(this).setLayoutType<QVBoxLayout>();
+
+    layout.emplace<Label>("An update is available!");
+    layout.emplace<Label>("Do you want to download and install it?");
+    layout.emplace<Label>("This doesn't work yet!");
+
+    auto buttons = layout.emplace<QDialogButtonBox>();
+    auto install = buttons->addButton("Install", QDialogButtonBox::AcceptRole);
+    auto dismiss = buttons->addButton("Dismiss", QDialogButtonBox::RejectRole);
+
+    QObject::connect(install, &QPushButton::clicked, this, [this] { this->close(); });
+    QObject::connect(dismiss, &QPushButton::clicked, this, [this] { this->close(); });
+}
+
+}  // namespace chatterino
diff --git a/src/widgets/dialogs/UpdatePromptDialog.hpp b/src/widgets/dialogs/UpdatePromptDialog.hpp
new file mode 100644
index 00000000..e4afffdc
--- /dev/null
+++ b/src/widgets/dialogs/UpdatePromptDialog.hpp
@@ -0,0 +1,19 @@
+#pragma once
+
+#include "widgets/BaseWindow.hpp"
+#include "widgets/Label.hpp"
+
+namespace chatterino {
+
+class UpdatePromptDialog : public BaseWindow
+{
+public:
+    UpdatePromptDialog();
+
+private:
+    struct {
+        Label *label;
+    } ui_;
+};
+
+}  // namespace chatterino
diff --git a/src/widgets/helper/TitlebarButton.cpp b/src/widgets/helper/TitlebarButton.cpp
index ac32d237..5abc177d 100644
--- a/src/widgets/helper/TitlebarButton.cpp
+++ b/src/widgets/helper/TitlebarButton.cpp
@@ -20,7 +20,7 @@ void TitleBarButton::setButtonStyle(Style _style)
     this->update();
 }
 
-void TitleBarButton::paintEvent(QPaintEvent *)
+void TitleBarButton::paintEvent(QPaintEvent *event)
 {
     QPainter painter(this);
 
@@ -115,9 +115,11 @@ void TitleBarButton::paintEvent(QPaintEvent *)
             painter.restore();
             break;
         }
+        default:;
     }
 
-    this->fancyPaint(painter);
+    RippleEffectButton::paintEvent(event);
+    //    this->fancyPaint(painter);
 }
 
 }  // namespace chatterino
diff --git a/src/widgets/helper/TitlebarButton.hpp b/src/widgets/helper/TitlebarButton.hpp
index 3612e3e3..b77995be 100644
--- a/src/widgets/helper/TitlebarButton.hpp
+++ b/src/widgets/helper/TitlebarButton.hpp
@@ -7,7 +7,15 @@ namespace chatterino {
 class TitleBarButton : public RippleEffectButton
 {
 public:
-    enum Style { Minimize = 1, Maximize = 2, Unmaximize = 4, Close = 8, User = 16, Settings = 32 };
+    enum Style {
+        None = 0,
+        Minimize = 1,
+        Maximize = 2,
+        Unmaximize = 4,
+        Close = 8,
+        User = 16,
+        Settings = 32
+    };
 
     TitleBarButton();