diff --git a/DuckDuckGo/NetworkProtection/AppTargets/BothAppTargets/NetworkProtectionTunnelController.swift b/DuckDuckGo/NetworkProtection/AppTargets/BothAppTargets/NetworkProtectionTunnelController.swift
index 6a286a4848..cae0efdddd 100644
--- a/DuckDuckGo/NetworkProtection/AppTargets/BothAppTargets/NetworkProtectionTunnelController.swift
+++ b/DuckDuckGo/NetworkProtection/AppTargets/BothAppTargets/NetworkProtectionTunnelController.swift
@@ -274,8 +274,13 @@ final class NetworkProtectionTunnelController: NetworkProtection.TunnelControlle
             // We'll only update to completed if we were showing the onboarding step to
             // allow the system extension.  Otherwise we may override the allow-VPN
             // onboarding step.
+            //
+            // Additionally if the onboarding step was allowing the system extension, we won't
+            // start the tunnel at once, and instead require that the user enables the toggle.
+            //
             if onboardingStatusRawValue == OnboardingStatus.isOnboarding(step: .userNeedsToAllowExtension).rawValue {
                 onboardingStatusRawValue = OnboardingStatus.completed.rawValue
+                return
             }
 #endif
 
diff --git a/DuckDuckGo/NetworkProtection/AppTargets/DeveloperIDTarget/SystemExtensionManager.swift b/DuckDuckGo/NetworkProtection/AppTargets/DeveloperIDTarget/SystemExtensionManager.swift
index 817da6c871..c3198e08d2 100644
--- a/DuckDuckGo/NetworkProtection/AppTargets/DeveloperIDTarget/SystemExtensionManager.swift
+++ b/DuckDuckGo/NetworkProtection/AppTargets/DeveloperIDTarget/SystemExtensionManager.swift
@@ -29,22 +29,76 @@ struct SystemExtensionManager {
         case willActivateAfterReboot
     }
 
-    let bundleID: String
-    let manager: OSSystemExtensionManager
+    private static let systemSettingsSecurityURL = "x-apple.systempreferences:com.apple.preference.security?Security"
+
+    private let bundleID: String
+    private let manager: OSSystemExtensionManager
+    private let workspace: NSWorkspace
 
     init(bundleID: String = NetworkProtectionBundle.extensionBundle().bundleIdentifier!,
-         manager: OSSystemExtensionManager = .shared) {
+         manager: OSSystemExtensionManager = .shared,
+         workspace: NSWorkspace = .shared) {
+
         self.bundleID = bundleID
         self.manager = manager
+        self.workspace = workspace
     }
 
     func activate() -> AsyncThrowingStream<ActivationRequestEvent, Error> {
+        /// Documenting a workaround for the issue discussed in https://app.asana.com/0/0/1205275221447702/f
+        ///     Background: For a lot of users, the system won't show the system-extension-blocked alert if there's a previous request
+        ///         to activate the extension.  You can see active requests in your console using command `systemextensionsctl list`.
+        ///
+        ///     Proposed workaround: Just open system settings into the right section when we detect a previous activation request already exists.
+        ///
+        ///     Tradeoffs: Unfortunately we don't know if the previous request was sent out by the currently runing-instance of this App
+        ///         or if an activation request was made, and then the App was reopened.
+        ///         This means we don't know if we'll be notified when the previous activation request completes or fails.  Because we
+        ///         need to update our UI once the extension is allowed, we can't avoid sending a new activation request every time.
+        ///         For the users that don't see the alert come up more than once this should be invisible.  For users (like myself) that
+        ///         see the alert every single time, they'll see both the alert and system settings being opened automatically.
+        ///
+        if hasPendingActivationRequests() {
+            openSystemSettingsSecurity()
+        }
+
         return SystemExtensionRequest.activationRequest(forExtensionWithIdentifier: bundleID, manager: manager).submit()
     }
 
     func deactivate() async throws {
         for try await _ in SystemExtensionRequest.deactivationRequest(forExtensionWithIdentifier: bundleID, manager: manager).submit() {}
     }
+
+    // MARK: - Activation: Checking if there are pending requests
+
+    /// Checks if there are pending activation requests for the system extension.
+    ///
+    /// This implementation should work well for all macOS 11+ releases.  A better implementation for macOS 12+
+    /// would be to use a properties request, but that option requires bigger changes and some rethinking of these
+    /// classes which I'd rather avoid right now.  In short this solution was picked as a quick solution with the best
+    /// ROI to avoid getting blocked.
+    ///
+    private func hasPendingActivationRequests() -> Bool {
+        let task = Process()
+        let pipe = Pipe()
+
+        task.standardOutput = pipe
+        task.launchPath = "/bin/bash" // Specify the shell to use
+        task.arguments = ["-c", "$(which systemextensionsctl) list | $(which egrep) -c '(?:\(bundleID)).+(?:activated waiting for user)+'"]
+
+        task.launch()
+        task.waitUntilExit()
+
+        let data = pipe.fileHandleForReading.readDataToEndOfFile()
+        let output = String(data: data, encoding: .utf8)?.trimmingCharacters(in: .whitespacesAndNewlines)
+
+        return (Int(output ?? "0") ?? 0) > 0
+    }
+
+    private func openSystemSettingsSecurity() {
+        let url = URL(string: Self.systemSettingsSecurityURL)!
+        workspace.open(url)
+    }
 }
 
 final class SystemExtensionRequest: NSObject {