coder
diff --git a/‎Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift
Lines changed: 9 additions & 6 deletions b/‎Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift
Lines changed: 9 additions & 6 deletions
diff --git a/‎Coder-Desktop/Coder-DesktopTests/VPNMenuTests.swift
Lines changed: 2 additions & 0 deletions b/‎Coder-Desktop/Coder-DesktopTests/VPNMenuTests.swift
Lines changed: 2 additions & 0 deletions
@@ -117,12 +117,15 @@ struct VPNMenu<VPN: VPNService, FS: FileSyncDaemon>: View {
     }
 
     private var vpnDisabled: Bool {
-        vpn.state == .connecting ||
-            vpn.state == .disconnecting ||
-            // Prevent starting the VPN before the user has approved the system extension.
-            vpn.state == .failed(.systemExtensionError(.needsUserApproval)) ||
-            // Prevent starting the VPN without a VPN configuration.
-            vpn.state == .failed(.networkExtensionError(.unconfigured))
+        // Always enabled if signed out, as that will open the sign in window
+        state.hasSession && (
+            vpn.state == .connecting ||
+                vpn.state == .disconnecting ||
+                // Prevent starting the VPN before the user has approved the system extension.
+                vpn.state == .failed(.systemExtensionError(.needsUserApproval)) ||
+                // Prevent starting the VPN without a VPN configuration.
+                vpn.state == .failed(.networkExtensionError(.unconfigured))
+        )
     }
 }
 
 
@@ -59,6 +59,7 @@ struct VPNMenuTests {
     @Test
     func testVPNDisabledWhileConnecting() async throws {
         vpn.state = .disabled
+        state.login(baseAccessURL: URL(string: "https://coder.example.com")!, sessionToken: "fake-token")
 
         try await ViewHosting.host(view) {
             try await sut.inspection.inspect { view in
@@ -79,6 +80,7 @@ struct VPNMenuTests {
     @Test
     func testVPNDisabledWhileDisconnecting() async throws {
         vpn.state = .disabled
+        state.login(baseAccessURL: URL(string: "https://coder.example.com")!, sessionToken: "fake-token")
 
         try await ViewHosting.host(view) {
             try await sut.inspection.inspect { view in