diff --git a/ios/MullvadVPNUITests/Pages/TunnelControlPage.swift b/ios/MullvadVPNUITests/Pages/TunnelControlPage.swift
index cf90555e5a5e..f5e59b12e870 100644
--- a/ios/MullvadVPNUITests/Pages/TunnelControlPage.swift
+++ b/ios/MullvadVPNUITests/Pages/TunnelControlPage.swift
@@ -127,31 +127,31 @@ class TunnelControlPage: Page {
 
     /// Verify that the app attempts to connect over UDP before switching to TCP. For testing blocked UDP traffic.
     @discardableResult func verifyConnectingOverTCPAfterUDPAttempts() -> Self {
-        let connectionAttempts = waitForConnectionAttempts(3, timeout: 15)
+        let connectionAttempts = waitForConnectionAttempts(4, timeout: 30)
 
-        // Should do three connection attempts but due to UI bug sometimes only two are displayed, sometimes all three
-        if connectionAttempts.count == 3 { // Expected retries flow
+        // Should do four connection attempts but due to UI bug sometimes only two are displayed, sometimes all four
+        if connectionAttempts.count == 4 { // Expected retries flow
             for (attemptIndex, attempt) in connectionAttempts.enumerated() {
-                if attemptIndex == 0 || attemptIndex == 1 {
+                if attemptIndex == 0 || attemptIndex == 1 || attemptIndex == 2 {
                     XCTAssertEqual(attempt.protocolName, "UDP")
-                } else if attemptIndex == 2 {
+                } else if attemptIndex == 3 {
                     XCTAssertEqual(attempt.protocolName, "TCP")
                 } else {
                     XCTFail("Unexpected connection attempt")
                 }
             }
-        } else if connectionAttempts.count == 2 { // Most of the times this incorrect flow is shown
+        } else if connectionAttempts.count == 3 { // Most of the times this incorrect flow is shown
             for (attemptIndex, attempt) in connectionAttempts.enumerated() {
-                if attemptIndex == 0 {
+                if attemptIndex == 0 || attemptIndex == 1 {
                     XCTAssertEqual(attempt.protocolName, "UDP")
-                } else if attemptIndex == 1 {
+                } else if attemptIndex == 2 {
                     XCTAssertEqual(attempt.protocolName, "TCP")
                 } else {
                     XCTFail("Unexpected connection attempt")
                 }
             }
         } else {
-            XCTFail("Unexpected number of connection attempts")
+            XCTFail("Unexpected number of connection attempts, expected 3~4, got \(connectionAttempts.count)")
         }
 
         return self
@@ -159,35 +159,16 @@ class TunnelControlPage: Page {
 
     /// Verify that connection attempts are made in the correct order
     @discardableResult func verifyConnectionAttemptsOrder() -> Self {
-        let connectionAttempts = waitForConnectionAttempts(4, timeout: 50)
+        let connectionAttempts = waitForConnectionAttempts(4, timeout: 70)
         XCTAssertEqual(connectionAttempts.count, 4)
 
-        if connectionAttempts.last?.protocolName == "UDP" {
-            // If last attempt is over UDP it means we have encountered the UI bug where only one UDP attempt is shown and then the two TCP attempts
-            for (attemptIndex, attempt) in connectionAttempts.enumerated() {
-                if attemptIndex == 0 {
-                    XCTAssertEqual(attempt.protocolName, "UDP")
-                } else if attemptIndex == 1 {
-                    XCTAssertEqual(attempt.protocolName, "TCP")
-                    XCTAssertEqual(attempt.port, "80")
-                } else if attemptIndex == 2 {
-                    XCTAssertEqual(attempt.protocolName, "TCP")
-                    XCTAssertEqual(attempt.port, "5001")
-                } // Ignore the 4th attempt which is the first attempt of new attempt cycle
-            }
-        } else {
-            for (attemptIndex, attempt) in connectionAttempts.enumerated() {
-                if attemptIndex == 0 {
-                    XCTAssertEqual(attempt.protocolName, "UDP")
-                } else if attemptIndex == 1 {
-                    XCTAssertEqual(attempt.protocolName, "UDP")
-                } else if attemptIndex == 2 {
-                    XCTAssertEqual(attempt.protocolName, "TCP")
-                    XCTAssertEqual(attempt.port, "80")
-                } else if attemptIndex == 3 {
-                    XCTAssertEqual(attempt.protocolName, "TCP")
-                    XCTAssertEqual(attempt.port, "5001")
-                }
+        for (attemptIndex, attempt) in connectionAttempts.enumerated() {
+            if attemptIndex < 3 {
+                XCTAssertEqual(attempt.protocolName, "UDP")
+            } else {
+                XCTAssertEqual(attempt.protocolName, "TCP")
+                let validPorts = ["80", "5001"]
+                XCTAssertTrue(validPorts.contains(attempt.port))
             }
         }
 
diff --git a/ios/MullvadVPNUITests/Pages/VPNSettingsPage.swift b/ios/MullvadVPNUITests/Pages/VPNSettingsPage.swift
index 570f32ab080f..7f463069b8a5 100644
--- a/ios/MullvadVPNUITests/Pages/VPNSettingsPage.swift
+++ b/ios/MullvadVPNUITests/Pages/VPNSettingsPage.swift
@@ -102,12 +102,18 @@ class VPNSettingsPage: Page {
         return self
     }
 
-    @discardableResult func tapWireGuardObfuscationOnCell() -> Self {
+    @discardableResult func tapWireGuardObfuscationUdpOverTcpCell() -> Self {
         app.cells[AccessibilityIdentifier.wireGuardObfuscationUdpOverTcp].tap()
 
         return self
     }
 
+    @discardableResult func tapWireGuardObfuscationShadowsocksCell() -> Self {
+        app.cells[AccessibilityIdentifier.wireGuardObfuscationShadowsocks].tap()
+
+        return self
+    }
+
     @discardableResult func tapWireGuardObfuscationOffCell() -> Self {
         app.cells[AccessibilityIdentifier.wireGuardObfuscationOff].tap()
 
diff --git a/ios/MullvadVPNUITests/RelayTests.swift b/ios/MullvadVPNUITests/RelayTests.swift
index b000d2fe50a5..319a1b0a2370 100644
--- a/ios/MullvadVPNUITests/RelayTests.swift
+++ b/ios/MullvadVPNUITests/RelayTests.swift
@@ -151,7 +151,48 @@ class RelayTests: LoggedInWithTimeUITestCase {
 
         VPNSettingsPage(app)
             .tapWireGuardObfuscationExpandButton()
-            .tapWireGuardObfuscationOnCell()
+            .tapWireGuardObfuscationUdpOverTcpCell()
+            .tapBackButton()
+
+        SettingsPage(app)
+            .tapDoneButton()
+
+        TunnelControlPage(app)
+            .tapSecureConnectionButton()
+
+        allowAddVPNConfigurationsIfAsked()
+
+        TunnelControlPage(app)
+            .waitForSecureConnectionLabel()
+
+        try Networking.verifyCanAccessInternet()
+
+        TunnelControlPage(app)
+            .tapDisconnectButton()
+    }
+
+    func testWireGuardOverShadowsocksManually() throws {
+        addTeardownBlock {
+            HeaderBar(self.app)
+                .tapSettingsButton()
+
+            SettingsPage(self.app)
+                .tapVPNSettingsCell()
+
+            VPNSettingsPage(self.app)
+                .tapWireGuardObfuscationExpandButton()
+                .tapWireGuardObfuscationOffCell()
+        }
+
+        HeaderBar(app)
+            .tapSettingsButton()
+
+        SettingsPage(app)
+            .tapVPNSettingsCell()
+
+        VPNSettingsPage(app)
+            .tapWireGuardObfuscationExpandButton()
+            .tapWireGuardObfuscationShadowsocksCell()
             .tapBackButton()
 
         SettingsPage(app)
diff --git a/ios/MullvadVPNUITests/SettingsMigrationTests.swift b/ios/MullvadVPNUITests/SettingsMigrationTests.swift
index 85ab71bafa34..0de0e5931938 100644
--- a/ios/MullvadVPNUITests/SettingsMigrationTests.swift
+++ b/ios/MullvadVPNUITests/SettingsMigrationTests.swift
@@ -116,7 +116,7 @@ class SettingsMigrationTests: BaseUITestCase {
             .enterText(wireGuardPort)
             .dismissKeyboard()
             .tapWireGuardObfuscationExpandButton()
-            .tapWireGuardObfuscationOnCell()
+            .tapWireGuardObfuscationUdpOverTcpCell()
             .tapUDPOverTCPPortExpandButton()
             .tapUDPOverTCPPort80Cell()
             .tapQuantumResistantTunnelExpandButton()