diff --git a/resources/images/download_update_error.png b/resources/images/download_update_error.png
new file mode 100644
index 00000000..5c1fec10
Binary files /dev/null and b/resources/images/download_update_error.png differ
diff --git a/resources/resources.qrc b/resources/resources.qrc
index 146c2c66..cf41c346 100644
--- a/resources/resources.qrc
+++ b/resources/resources.qrc
@@ -73,6 +73,7 @@
         <file>avatars/fourtf.png</file>
         <file>avatars/pajlada.png</file>
         <file>images/download_update.png</file>
+        <file>images/download_update_error.png</file>
     </qresource>
     <qresource prefix="/qt/etc">
         <file>qt.conf</file>
diff --git a/src/singletons/Updates.cpp b/src/singletons/Updates.cpp
index 4cadf2b1..c9580939 100644
--- a/src/singletons/Updates.cpp
+++ b/src/singletons/Updates.cpp
@@ -141,12 +141,40 @@ void Updates::checkForUpdates()
 #endif
 }
 
-Updates::UpdateStatus Updates::getStatus() const
+Updates::Status Updates::getStatus() const
 {
     return this->status_;
 }
 
-void Updates::setStatus_(UpdateStatus status)
+bool Updates::shouldShowUpdateButton() const
+{
+    switch (this->getStatus()) {
+        case UpdateAvailable:
+        case SearchFailed:
+        case Downloading:
+        case DownloadFailed:
+        case WriteFileFailed:
+            return true;
+
+        default:
+            return false;
+    }
+}
+
+bool Updates::isError() const
+{
+    switch (this->getStatus()) {
+        case SearchFailed:
+        case DownloadFailed:
+        case WriteFileFailed:
+            return true;
+
+        default:
+            return false;
+    }
+}
+
+void Updates::setStatus_(Status status)
 {
     if (this->status_ != status) {
         this->status_ = status;
diff --git a/src/singletons/Updates.hpp b/src/singletons/Updates.hpp
index f760631a..ff3df8bb 100644
--- a/src/singletons/Updates.hpp
+++ b/src/singletons/Updates.hpp
@@ -10,7 +10,7 @@ class Updates
     Updates();
 
 public:
-    enum UpdateStatus {
+    enum Status {
         None,
         Searching,
         UpdateAvailable,
@@ -28,18 +28,21 @@ public:
     const QString &getCurrentVersion() const;
     const QString &getOnlineVersion() const;
     void installUpdates();
-    UpdateStatus getStatus() const;
+    Status getStatus() const;
 
-    pajlada::Signals::Signal<UpdateStatus> statusUpdated;
+    bool shouldShowUpdateButton() const;
+    bool isError() const;
+
+    pajlada::Signals::Signal<Status> statusUpdated;
 
 private:
     QString currentVersion_;
     QString onlineVersion_;
-    UpdateStatus status_ = None;
+    Status status_ = None;
 
     QString updateUrl_;
 
-    void setStatus_(UpdateStatus status);
+    void setStatus_(Status status);
 };
 
 }  // namespace chatterino
diff --git a/src/widgets/BaseWindow.cpp b/src/widgets/BaseWindow.cpp
index c78096c5..dfcd8b8b 100644
--- a/src/widgets/BaseWindow.cpp
+++ b/src/widgets/BaseWindow.cpp
@@ -409,6 +409,11 @@ void BaseWindow::resizeEvent(QResizeEvent *)
     this->calcButtonsSizes();
 }
 
+void BaseWindow::closeEvent(QCloseEvent *)
+{
+    this->closing.invoke();
+}
+
 void BaseWindow::moveIntoDesktopRect(QWidget *parent)
 {
     if (!this->stayInScreenRect_)
diff --git a/src/widgets/BaseWindow.hpp b/src/widgets/BaseWindow.hpp
index 8e6c591e..5baf88b6 100644
--- a/src/widgets/BaseWindow.hpp
+++ b/src/widgets/BaseWindow.hpp
@@ -52,6 +52,8 @@ public:
 
     Flags getFlags();
 
+    pajlada::Signals::NoArgSignal closing;
+
 protected:
     virtual bool nativeEvent(const QByteArray &eventType, void *message, long *result) override;
     virtual void scaleChangedEvent(float) override;
@@ -61,6 +63,7 @@ protected:
     virtual void changeEvent(QEvent *) override;
     virtual void leaveEvent(QEvent *) override;
     virtual void resizeEvent(QResizeEvent *) override;
+    virtual void closeEvent(QCloseEvent *) override;
 
     virtual void themeRefreshEvent() override;
     virtual bool event(QEvent *event) override;
diff --git a/src/widgets/Window.cpp b/src/widgets/Window.cpp
index 23475e9d..5e733abb 100644
--- a/src/widgets/Window.cpp
+++ b/src/widgets/Window.cpp
@@ -6,6 +6,7 @@
 #include "providers/twitch/TwitchServer.hpp"
 #include "singletons/Settings.hpp"
 #include "singletons/Theme.hpp"
+#include "singletons/Updates.hpp"
 #include "singletons/WindowManager.hpp"
 #include "widgets/AccountSwitchPopupWidget.hpp"
 #include "widgets/Notebook.hpp"
@@ -53,27 +54,7 @@ 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->setActionOnFocusLoss(BaseWindow::Delete);
-            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()));  //
-        });
+        this->addCustomTitlebarButtons();
     }
 
     if (_type == Window::Main) {
@@ -194,6 +175,54 @@ Window::Window(WindowType _type)
     this->notebook.setShowAddButton(true);
 }
 
+void Window::addCustomTitlebarButtons()
+{
+    // settings
+    this->addTitleBarButton(TitleBarButton::Settings, [] {
+        getApp()->windows->showSettingsDialog();  //
+    });
+
+    // updates
+    auto update = this->addTitleBarButton(TitleBarButton::None, [] {});
+    update->hide();
+    QObject::connect(update, &TitleBarButton::clicked, this, [this, update] {
+        auto dialog = new UpdatePromptDialog();
+        dialog->setActionOnFocusLoss(BaseWindow::Delete);
+        dialog->move(update->mapToGlobal(QPoint(int(-100 * this->getScale()), update->height())));
+        dialog->show();
+        dialog->raise();
+
+        dialog->buttonClicked.connect([update](auto button) {
+            switch (button) {
+                case UpdatePromptDialog::Dismiss: {
+                    update->hide();
+                } break;
+            }
+        });
+
+        this->updateDialogHandle_.reset(dialog);
+        dialog->closing.connect([this] { this->updateDialogHandle_.release(); });
+    });
+
+    auto updateChange = [update](auto) {
+        update->setVisible(Updates::getInstance().shouldShowUpdateButton());
+
+        auto imageUrl = Updates::getInstance().isError() ? ":/images/download_update_error.png"
+                                                         : ":/images/download_update.png";
+        update->setPixmap(QPixmap(imageUrl));
+    };
+
+    updateChange(Updates::getInstance().getStatus());
+    this->signalHolder.managedConnect(Updates::getInstance().statusUpdated,
+                                      [updateChange](auto status) { updateChange(status); });
+
+    // account
+    this->userLabel = this->addTitleBarLabel([this] {
+        getApp()->windows->showAccountSelectPopup(
+            this->userLabel->mapToGlobal(this->userLabel->rect().bottomLeft()));  //
+    });
+}
+
 Window::WindowType Window::getType()
 {
     return this->type;
diff --git a/src/widgets/Window.hpp b/src/widgets/Window.hpp
index 60bf8be8..60ce046c 100644
--- a/src/widgets/Window.hpp
+++ b/src/widgets/Window.hpp
@@ -10,10 +10,12 @@
 
 #include <pajlada/settings/setting.hpp>
 #include <pajlada/signals/signal.hpp>
+#include <pajlada/signals/signalholder.hpp>
 
 namespace chatterino {
 
 class Theme;
+class UpdatePromptDialog;
 
 class Window : public BaseWindow
 {
@@ -40,15 +42,19 @@ protected:
     bool event(QEvent *event) override;
 
 private:
+    void addCustomTitlebarButtons();
+    void loadGeometry();
+
     RippleEffectLabel *userLabel = nullptr;
+    std::unique_ptr<UpdatePromptDialog> updateDialogHandle_;
 
     WindowType type;
     float dpi;
 
-    void loadGeometry();
-
     SplitNotebook notebook;
 
+    pajlada::Signals::SignalHolder signalHolder;
+
     friend class Notebook;
 
 public:
diff --git a/src/widgets/dialogs/UpdatePromptDialog.cpp b/src/widgets/dialogs/UpdatePromptDialog.cpp
index 2cc4df2a..a8b36c38 100644
--- a/src/widgets/dialogs/UpdatePromptDialog.cpp
+++ b/src/widgets/dialogs/UpdatePromptDialog.cpp
@@ -1,5 +1,6 @@
 #include "UpdatePromptDialog.hpp"
 
+#include "singletons/Updates.hpp"
 #include "util/LayoutCreator.hpp"
 #include "widgets/Label.hpp"
 
@@ -15,16 +16,53 @@ UpdatePromptDialog::UpdatePromptDialog()
 {
     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!");
+    layout.emplace<Label>("You shouldn't be seeing this dialog.").assign(&this->ui_.label);
 
     auto buttons = layout.emplace<QDialogButtonBox>();
     auto install = buttons->addButton("Install", QDialogButtonBox::AcceptRole);
+    this->ui_.installButton = install;
     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(); });
+    QObject::connect(dismiss, &QPushButton::clicked, this, [this] {
+        this->buttonClicked.invoke(Dismiss);
+        this->close();
+    });
+
+    this->updateStatusChanged(Updates::getInstance().getStatus());
+    this->connections_.managedConnect(Updates::getInstance().statusUpdated,
+                                      [this](auto status) { this->updateStatusChanged(status); });
+}
+
+void UpdatePromptDialog::updateStatusChanged(Updates::Status status)
+{
+    this->ui_.installButton->setVisible(status == Updates::UpdateAvailable);
+
+    switch (status) {
+        case Updates::UpdateAvailable: {
+            this->ui_.label->setText(QString("An update (%1) is available.")
+                                         .arg(Updates::getInstance().getOnlineVersion()));
+        } break;
+
+        case Updates::SearchFailed: {
+            this->ui_.label->setText("Failed to load version information.");
+        } break;
+
+        case Updates::Downloading: {
+            this->ui_.label->setText("Downloading updates.");
+            // this->setActionOnFocusLoss(BaseWindow::Nothing);
+        } break;
+
+        case Updates::DownloadFailed: {
+            this->ui_.label->setText("Failed to download the update.");
+        } break;
+
+        case Updates::WriteFileFailed: {
+            this->ui_.label->setText("Failed to save the update to disk.");
+        } break;
+
+        default:;
+    }
 }
 
 }  // namespace chatterino
diff --git a/src/widgets/dialogs/UpdatePromptDialog.hpp b/src/widgets/dialogs/UpdatePromptDialog.hpp
index e4afffdc..48e4eda3 100644
--- a/src/widgets/dialogs/UpdatePromptDialog.hpp
+++ b/src/widgets/dialogs/UpdatePromptDialog.hpp
@@ -1,19 +1,32 @@
 #pragma once
 
+#include "pajlada/signals/signalholder.hpp"
+#include "singletons/Updates.hpp"
 #include "widgets/BaseWindow.hpp"
 #include "widgets/Label.hpp"
 
+class QPushButton;
+
 namespace chatterino {
 
 class UpdatePromptDialog : public BaseWindow
 {
 public:
+    enum Button { Dismiss };
+
     UpdatePromptDialog();
 
+    pajlada::Signals::Signal<Button> buttonClicked;
+
 private:
+    void updateStatusChanged(Updates::Status status);
+
     struct {
-        Label *label;
+        Label *label = nullptr;
+        QPushButton *installButton = nullptr;
     } ui_;
+
+    pajlada::Signals::SignalHolder connections_;
 };
 
 }  // namespace chatterino