diff --git a/phpmon/Domain/App/Startup+Launch.swift b/phpmon/Domain/App/Startup+Launch.swift
index d2213af8..ff370d4c 100644
--- a/phpmon/Domain/App/Startup+Launch.swift
+++ b/phpmon/Domain/App/Startup+Launch.swift
@@ -123,6 +123,9 @@ extension Startup {
         // Mark app as having successfully booted passing all checks
         Startup.hasFinishedBooting = true
 
+        // Enable the main menu item
+        MainMenu.shared.statusItem.button?.isEnabled = true
+
         // Post-launch stats and update check, but only if not running tests
         await performPostLaunchActions()
     }
diff --git a/phpmon/Domain/Menu/MainMenu.swift b/phpmon/Domain/Menu/MainMenu.swift
index b8280d4b..fb61efc1 100644
--- a/phpmon/Domain/Menu/MainMenu.swift
+++ b/phpmon/Domain/Menu/MainMenu.swift
@@ -57,7 +57,6 @@ class MainMenu: NSObject, NSWindowDelegate, NSMenuDelegate, PhpSwitcherDelegate
             })
             statusItem.menu = menu
             statusItem.menu?.delegate = self
-            statusItem.button?.isEnabled = true
         }
     }
 
diff --git a/tests/ui/StartupTest.swift b/tests/ui/StartupTest.swift
index 4f413487..ee2cb0e7 100644
--- a/tests/ui/StartupTest.swift
+++ b/tests/ui/StartupTest.swift
@@ -20,7 +20,10 @@ final class StartupTest: UITestCase {
         var configuration = TestableConfigurations.working
         configuration.filesystem["/opt/homebrew/bin/php"] = nil // PHP binary must be missing
 
-        let app = launch(with: configuration)
+        let app = launch(
+            waitForInitialization: false, // we expect an error during initialization
+            with: configuration
+        )
 
         // Dialog 1: "PHP is not correctly installed"
         assertAllExist([
@@ -50,7 +53,10 @@ final class StartupTest: UITestCase {
         var configuration = TestableConfigurations.working
         configuration.filesystem["/opt/homebrew/etc/php/8.4/php-fpm.d/valet-fpm.conf"] = nil
 
-        let app = launch(with: configuration)
+        let app = launch(
+            waitForInitialization: false, // we expect an error during initialization
+            with: configuration
+        )
 
         assertExists(app.staticTexts["alert.php_fpm_broken.title".localized], 3.0)
         click(app.buttons["generic.ok".localized])
@@ -60,7 +66,10 @@ final class StartupTest: UITestCase {
         var configuration = TestableConfigurations.working
         configuration.shellOutput["valet --version"] = .instant("Laravel Valet 5.0")
 
-        let app = launch(with: configuration)
+        let app = launch(
+            waitForInitialization: false, // we expect an error during initialization
+            with: configuration
+        )
 
         assertExists(app.staticTexts["startup.errors.valet_version_not_supported.title".localized], 3.0)
         click(app.buttons["generic.ok".localized])
diff --git a/tests/ui/UITestCase.swift b/tests/ui/UITestCase.swift
index 248d600b..8160fce5 100644
--- a/tests/ui/UITestCase.swift
+++ b/tests/ui/UITestCase.swift
@@ -9,31 +9,41 @@
 import XCTest
 
 class UITestCase: XCTestCase {
-    /** Launches the app and opens the menu. */
+    /**
+     Launches the app and opens the menu.
+     Defaults to waiting for the app to finish initialization.
+
+     - Parameter waitForInitialization: Waits for the PHP Monitor to pass the environment checks (startup).
+     - Parameter openMenu: Attempts to open the status menu when ready; requires passing environment checks.
+     - Parameter configuration: The TestableConfiguration to include when launching PHP Monitor.
+     */
     public func launch(
+        waitForInitialization: Bool = true,
         openMenu: Bool = false,
-        with configuration: TestableConfiguration? = nil
+        with configuration: TestableConfiguration? = nil,
     ) -> XCPMApplication {
         let app = XCPMApplication()
         let config = configuration ?? TestableConfigurations.working
         app.withConfiguration(config)
         app.launch()
 
-        let statusItem = app.statusItems.firstMatch
-        let isEnabled = NSPredicate(format: "isEnabled == true")
-        let expectation = expectation(for: isEnabled, evaluatedWith: statusItem, handler: nil)
-        let result = XCTWaiter().wait(for: [expectation], timeout: 15)
+        if waitForInitialization || openMenu {
+            let statusItem = app.statusItems.firstMatch
+            let isEnabled = NSPredicate(format: "isEnabled == true")
+            let expectation = expectation(for: isEnabled, evaluatedWith: statusItem, handler: nil)
+            let result = XCTWaiter().wait(for: [expectation], timeout: 15)
 
-        if result == .timedOut {
-            XCTFail("PHP Monitor did not initialize with an available UI element within 15 seconds.")
+            if result == .timedOut {
+                XCTFail("PHP Monitor did not initialize with an available UI element within 15 seconds.")
+            }
+
+            if openMenu {
+                statusItem.click()
+            }
         }
 
         // Note: If this fails here, make sure the menu bar item can be displayed
         // If you use Bartender or something like this, this item may be hidden and tests will fail
-        if openMenu {
-            statusItem.click()
-        }
-
         return app
     }