From 982a23f7496a7b447c33f0b225de1b6bdc52c19f Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Wed, 19 Mar 2025 13:57:14 +1100
Subject: [PATCH] chore: prompt for sign in when turning VPN on if signed out

---
 .../Preview Content/PreviewVPN.swift            |  2 ++
 .../Coder-Desktop/VPN/VPNService.swift          |  1 +
 Coder-Desktop/Coder-Desktop/Views/VPNMenu.swift | 17 ++++++++++++++---
 Coder-Desktop/Coder-DesktopTests/Util.swift     |  1 +
 .../Coder-DesktopTests/VPNMenuTests.swift       |  2 +-
 5 files changed, 19 insertions(+), 4 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/Preview Content/PreviewVPN.swift b/Coder-Desktop/Coder-Desktop/Preview Content/PreviewVPN.swift
index 4faa10fb..a3ef51e5 100644
--- a/Coder-Desktop/Coder-Desktop/Preview Content/PreviewVPN.swift	
+++ b/Coder-Desktop/Coder-Desktop/Preview Content/PreviewVPN.swift	
@@ -78,4 +78,6 @@ final class PreviewVPN: Coder_Desktop.VPNService {
     func configureTunnelProviderProtocol(proto _: NETunnelProviderProtocol?) {
         state = .connecting
     }
+
+    var startWhenReady: Bool = false
 }
diff --git a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
index 22a3ad8b..50078d5f 100644
--- a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
+++ b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
@@ -10,6 +10,7 @@ protocol VPNService: ObservableObject {
     func start() async
     func stop() async
     func configureTunnelProviderProtocol(proto: NETunnelProviderProtocol?)
+    var startWhenReady: Bool { get set }
 }
 
 enum VPNServiceState: Equatable {
diff --git a/Coder-Desktop/Coder-Desktop/Views/VPNMenu.swift b/Coder-Desktop/Coder-Desktop/Views/VPNMenu.swift
index 352123de..c3c44dba 100644
--- a/Coder-Desktop/Coder-Desktop/Views/VPNMenu.swift
+++ b/Coder-Desktop/Coder-Desktop/Views/VPNMenu.swift
@@ -4,6 +4,7 @@ struct VPNMenu<VPN: VPNService>: View {
     @EnvironmentObject var vpn: VPN
     @EnvironmentObject var state: AppState
     @Environment(\.openSettings) private var openSettings
+    @Environment(\.openWindow) private var openWindow
 
     let inspection = Inspection<Self>()
 
@@ -16,7 +17,18 @@ struct VPNMenu<VPN: VPNService>: View {
                     Toggle(isOn: Binding(
                         get: { vpn.state == .connected || vpn.state == .connecting },
                         set: { isOn in Task {
-                            if isOn { await vpn.start() } else { await vpn.stop() }
+                            if isOn {
+                                // Clicking the toggle while logged out should
+                                // open the login window, then start the VPN asap
+                                if !state.hasSession {
+                                    vpn.startWhenReady = true
+                                    openWindow(id: .login)
+                                } else {
+                                    await vpn.start()
+                                }
+                            } else {
+                                await vpn.stop()
+                            }
                         }
                         }
                     )) {
@@ -86,8 +98,7 @@ struct VPNMenu<VPN: VPNService>: View {
     }
 
     private var vpnDisabled: Bool {
-        !state.hasSession ||
-            vpn.state == .connecting ||
+        vpn.state == .connecting ||
             vpn.state == .disconnecting ||
             // Prevent starting the VPN before the user has approved the system extension.
             vpn.state == .failed(.systemExtensionError(.needsUserApproval))
diff --git a/Coder-Desktop/Coder-DesktopTests/Util.swift b/Coder-Desktop/Coder-DesktopTests/Util.swift
index 4b1d0e7c..c41f5c19 100644
--- a/Coder-Desktop/Coder-DesktopTests/Util.swift
+++ b/Coder-Desktop/Coder-DesktopTests/Util.swift
@@ -23,6 +23,7 @@ class MockVPNService: VPNService, ObservableObject {
     }
 
     func configureTunnelProviderProtocol(proto _: NETunnelProviderProtocol?) {}
+    var startWhenReady: Bool = false
 }
 
 extension Inspection: @unchecked Sendable, @retroactive InspectionEmissary {}
diff --git a/Coder-Desktop/Coder-DesktopTests/VPNMenuTests.swift b/Coder-Desktop/Coder-DesktopTests/VPNMenuTests.swift
index c38a062d..616e3c53 100644
--- a/Coder-Desktop/Coder-DesktopTests/VPNMenuTests.swift
+++ b/Coder-Desktop/Coder-DesktopTests/VPNMenuTests.swift
@@ -23,7 +23,7 @@ struct VPNMenuTests {
         try await ViewHosting.host(view) {
             try await sut.inspection.inspect { view in
                 let toggle = try view.find(ViewType.Toggle.self)
-                #expect(toggle.isDisabled())
+                #expect(!toggle.isDisabled())
                 #expect(throws: Never.self) { try view.find(text: "Sign in to use Coder Desktop") }
                 #expect(throws: Never.self) { try view.find(button: "Sign in") }
             }