diff --git a/Userland/Applications/Welcome/WelcomeWidget.cpp b/Userland/Applications/Welcome/WelcomeWidget.cpp
index 39442953bdb..439cfc0543a 100644
--- a/Userland/Applications/Welcome/WelcomeWidget.cpp
+++ b/Userland/Applications/Welcome/WelcomeWidget.cpp
@@ -7,10 +7,12 @@
 #include "WelcomeWidget.h"
 #include <AK/Random.h>
 #include <Applications/Welcome/WelcomeWindowGML.h>
+#include <LibConfig/Client.h>
 #include <LibCore/File.h>
 #include <LibCore/Process.h>
 #include <LibGUI/Application.h>
 #include <LibGUI/Button.h>
+#include <LibGUI/CheckBox.h>
 #include <LibGUI/Label.h>
 #include <LibGUI/Painter.h>
 #include <LibGfx/BitmapFont.h>
@@ -66,6 +68,13 @@ WelcomeWidget::WelcomeWidget()
         GUI::Application::the()->quit();
     };
 
+    auto exec_path = Config::read_string("SystemServer", "Welcome", "Executable", {});
+    m_startup_checkbox = *find_descendant_of_type_named<GUI::CheckBox>("startup_checkbox");
+    m_startup_checkbox->set_checked(!exec_path.is_empty());
+    m_startup_checkbox->on_checked = [](bool is_checked) {
+        Config::write_string("SystemServer", "Welcome", "Executable", is_checked ? "/bin/Welcome" : "");
+    };
+
     open_and_parse_readme_file();
     open_and_parse_tips_file();
     set_random_tip();
diff --git a/Userland/Applications/Welcome/WelcomeWidget.h b/Userland/Applications/Welcome/WelcomeWidget.h
index c8d490a1f01..a0853b0d184 100644
--- a/Userland/Applications/Welcome/WelcomeWidget.h
+++ b/Userland/Applications/Welcome/WelcomeWidget.h
@@ -29,6 +29,7 @@ private:
     RefPtr<GUI::Button> m_help_button;
     RefPtr<GUI::Button> m_new_button;
     RefPtr<GUI::Label> m_tip_label;
+    RefPtr<GUI::CheckBox> m_startup_checkbox;
     RefPtr<Web::OutOfProcessWebView> m_web_view;
 
     size_t m_initial_tip_index { 0 };
diff --git a/Userland/Applications/Welcome/WelcomeWindow.gml b/Userland/Applications/Welcome/WelcomeWindow.gml
index bf3ef46c71d..77b7394aa5a 100644
--- a/Userland/Applications/Welcome/WelcomeWindow.gml
+++ b/Userland/Applications/Welcome/WelcomeWindow.gml
@@ -104,8 +104,8 @@
 
         @GUI::CheckBox{
             name: "startup_checkbox"
-            text: "Show this Welcome Screen next time SerenityOS starts"
-            fixed_width: 315
+            text: "Show Welcome the next time SerenityOS starts"
+            autosize: true
         }
 
         @GUI::Widget
diff --git a/Userland/Applications/Welcome/main.cpp b/Userland/Applications/Welcome/main.cpp
index d9391530089..86419ff85c4 100644
--- a/Userland/Applications/Welcome/main.cpp
+++ b/Userland/Applications/Welcome/main.cpp
@@ -5,6 +5,7 @@
  */
 
 #include "WelcomeWidget.h"
+#include <LibConfig/Client.h>
 #include <LibGUI/Application.h>
 #include <LibGUI/Icon.h>
 #include <LibGUI/Window.h>
@@ -19,6 +20,8 @@ int main(int argc, char** argv)
 
     auto app = GUI::Application::construct(argc, argv);
 
+    Config::pledge_domains("SystemServer");
+
     if (unveil("/res", "r") < 0) {
         perror("unveil");
         return 1;