Add daemon-owned Tailnet login flow

Apple/Core/Client.swift

@@ -68,6 +68,46 @@ public struct Burrow_TailnetProbeResponse: Sendable {
     public init() {}
 }
 
+public struct Burrow_TailnetLoginStartRequest: Sendable {
+    public var accountName: String = ""
+    public var identityName: String = ""
+    public var hostname: String = ""
+    public var authority: String = ""
+    public var unknownFields = SwiftProtobuf.UnknownStorage()
+
+    public init() {}
+}
+
+public struct Burrow_TailnetLoginStatusRequest: Sendable {
+    public var sessionID: String = ""
+    public var unknownFields = SwiftProtobuf.UnknownStorage()
+
+    public init() {}
+}
+
+public struct Burrow_TailnetLoginCancelRequest: Sendable {
+    public var sessionID: String = ""
+    public var unknownFields = SwiftProtobuf.UnknownStorage()
+
+    public init() {}
+}
+
+public struct Burrow_TailnetLoginStatusResponse: Sendable {
+    public var sessionID: String = ""
+    public var backendState: String = ""
+    public var authURL: String = ""
+    public var running: Bool = false
+    public var needsLogin: Bool = false
+    public var tailnetName: String = ""
+    public var magicDNSSuffix: String = ""
+    public var selfDNSName: String = ""
+    public var tailnetIPs: [String] = []
+    public var health: [String] = []
+    public var unknownFields = SwiftProtobuf.UnknownStorage()
+
+    public init() {}
+}
+
 extension Burrow_TailnetDiscoverRequest: SwiftProtobuf.Message, SwiftProtobuf._MessageImplementationBase, SwiftProtobuf._ProtoNameProviding {
     public static let protoMessageName: String = "burrow.TailnetDiscoverRequest"
     public static let _protobuf_nameMap: SwiftProtobuf._NameMap = [
@@ -195,6 +235,158 @@ extension Burrow_TailnetProbeResponse: SwiftProtobuf.Message, SwiftProtobuf._Mes
     }
 }
 
+extension Burrow_TailnetLoginStartRequest: SwiftProtobuf.Message, SwiftProtobuf._MessageImplementationBase, SwiftProtobuf._ProtoNameProviding {
+    public static let protoMessageName: String = "burrow.TailnetLoginStartRequest"
+    public static let _protobuf_nameMap: SwiftProtobuf._NameMap = [
+        1: .standard(proto: "account_name"),
+        2: .standard(proto: "identity_name"),
+        3: .same(proto: "hostname"),
+        4: .same(proto: "authority"),
+    ]
+
+    public mutating func decodeMessage<D: SwiftProtobuf.Decoder>(decoder: inout D) throws {
+        while let fieldNumber = try decoder.nextFieldNumber() {
+            switch fieldNumber {
+            case 1: try decoder.decodeSingularStringField(value: &self.accountName)
+            case 2: try decoder.decodeSingularStringField(value: &self.identityName)
+            case 3: try decoder.decodeSingularStringField(value: &self.hostname)
+            case 4: try decoder.decodeSingularStringField(value: &self.authority)
+            default: break
+            }
+        }
+    }
+
+    public func traverse<V: SwiftProtobuf.Visitor>(visitor: inout V) throws {
+        if !self.accountName.isEmpty {
+            try visitor.visitSingularStringField(value: self.accountName, fieldNumber: 1)
+        }
+        if !self.identityName.isEmpty {
+            try visitor.visitSingularStringField(value: self.identityName, fieldNumber: 2)
+        }
+        if !self.hostname.isEmpty {
+            try visitor.visitSingularStringField(value: self.hostname, fieldNumber: 3)
+        }
+        if !self.authority.isEmpty {
+            try visitor.visitSingularStringField(value: self.authority, fieldNumber: 4)
+        }
+        try unknownFields.traverse(visitor: &visitor)
+    }
+}
+
+extension Burrow_TailnetLoginStatusRequest: SwiftProtobuf.Message, SwiftProtobuf._MessageImplementationBase, SwiftProtobuf._ProtoNameProviding {
+    public static let protoMessageName: String = "burrow.TailnetLoginStatusRequest"
+    public static let _protobuf_nameMap: SwiftProtobuf._NameMap = [
+        1: .standard(proto: "session_id")
+    ]
+
+    public mutating func decodeMessage<D: SwiftProtobuf.Decoder>(decoder: inout D) throws {
+        while let fieldNumber = try decoder.nextFieldNumber() {
+            switch fieldNumber {
+            case 1: try decoder.decodeSingularStringField(value: &self.sessionID)
+            default: break
+            }
+        }
+    }
+
+    public func traverse<V: SwiftProtobuf.Visitor>(visitor: inout V) throws {
+        if !self.sessionID.isEmpty {
+            try visitor.visitSingularStringField(value: self.sessionID, fieldNumber: 1)
+        }
+        try unknownFields.traverse(visitor: &visitor)
+    }
+}
+
+extension Burrow_TailnetLoginCancelRequest: SwiftProtobuf.Message, SwiftProtobuf._MessageImplementationBase, SwiftProtobuf._ProtoNameProviding {
+    public static let protoMessageName: String = "burrow.TailnetLoginCancelRequest"
+    public static let _protobuf_nameMap: SwiftProtobuf._NameMap = [
+        1: .standard(proto: "session_id")
+    ]
+
+    public mutating func decodeMessage<D: SwiftProtobuf.Decoder>(decoder: inout D) throws {
+        while let fieldNumber = try decoder.nextFieldNumber() {
+            switch fieldNumber {
+            case 1: try decoder.decodeSingularStringField(value: &self.sessionID)
+            default: break
+            }
+        }
+    }
+
+    public func traverse<V: SwiftProtobuf.Visitor>(visitor: inout V) throws {
+        if !self.sessionID.isEmpty {
+            try visitor.visitSingularStringField(value: self.sessionID, fieldNumber: 1)
+        }
+        try unknownFields.traverse(visitor: &visitor)
+    }
+}
+
+extension Burrow_TailnetLoginStatusResponse: SwiftProtobuf.Message, SwiftProtobuf._MessageImplementationBase, SwiftProtobuf._ProtoNameProviding {
+    public static let protoMessageName: String = "burrow.TailnetLoginStatusResponse"
+    public static let _protobuf_nameMap: SwiftProtobuf._NameMap = [
+        1: .standard(proto: "session_id"),
+        2: .standard(proto: "backend_state"),
+        3: .standard(proto: "auth_url"),
+        4: .same(proto: "running"),
+        5: .standard(proto: "needs_login"),
+        6: .standard(proto: "tailnet_name"),
+        7: .standard(proto: "magic_dns_suffix"),
+        8: .standard(proto: "self_dns_name"),
+        9: .standard(proto: "tailnet_ips"),
+        10: .same(proto: "health"),
+    ]
+
+    public mutating func decodeMessage<D: SwiftProtobuf.Decoder>(decoder: inout D) throws {
+        while let fieldNumber = try decoder.nextFieldNumber() {
+            switch fieldNumber {
+            case 1: try decoder.decodeSingularStringField(value: &self.sessionID)
+            case 2: try decoder.decodeSingularStringField(value: &self.backendState)
+            case 3: try decoder.decodeSingularStringField(value: &self.authURL)
+            case 4: try decoder.decodeSingularBoolField(value: &self.running)
+            case 5: try decoder.decodeSingularBoolField(value: &self.needsLogin)
+            case 6: try decoder.decodeSingularStringField(value: &self.tailnetName)
+            case 7: try decoder.decodeSingularStringField(value: &self.magicDNSSuffix)
+            case 8: try decoder.decodeSingularStringField(value: &self.selfDNSName)
+            case 9: try decoder.decodeRepeatedStringField(value: &self.tailnetIPs)
+            case 10: try decoder.decodeRepeatedStringField(value: &self.health)
+            default: break
+            }
+        }
+    }
+
+    public func traverse<V: SwiftProtobuf.Visitor>(visitor: inout V) throws {
+        if !self.sessionID.isEmpty {
+            try visitor.visitSingularStringField(value: self.sessionID, fieldNumber: 1)
+        }
+        if !self.backendState.isEmpty {
+            try visitor.visitSingularStringField(value: self.backendState, fieldNumber: 2)
+        }
+        if !self.authURL.isEmpty {
+            try visitor.visitSingularStringField(value: self.authURL, fieldNumber: 3)
+        }
+        if self.running {
+            try visitor.visitSingularBoolField(value: self.running, fieldNumber: 4)
+        }
+        if self.needsLogin {
+            try visitor.visitSingularBoolField(value: self.needsLogin, fieldNumber: 5)
+        }
+        if !self.tailnetName.isEmpty {
+            try visitor.visitSingularStringField(value: self.tailnetName, fieldNumber: 6)
+        }
+        if !self.magicDNSSuffix.isEmpty {
+            try visitor.visitSingularStringField(value: self.magicDNSSuffix, fieldNumber: 7)
+        }
+        if !self.selfDNSName.isEmpty {
+            try visitor.visitSingularStringField(value: self.selfDNSName, fieldNumber: 8)
+        }
+        if !self.tailnetIPs.isEmpty {
+            try visitor.visitRepeatedStringField(value: self.tailnetIPs, fieldNumber: 9)
+        }
+        if !self.health.isEmpty {
+            try visitor.visitRepeatedStringField(value: self.health, fieldNumber: 10)
+        }
+        try unknownFields.traverse(visitor: &visitor)
+    }
+}
+
 public struct TailnetClient: Client, GRPCClient {
     public let channel: GRPCChannel
     public var defaultCallOptions: CallOptions
@@ -227,4 +419,40 @@ public struct TailnetClient: Client, GRPCClient {
             interceptors: []
         )
     }
+
+    public func loginStart(
+        _ request: Burrow_TailnetLoginStartRequest,
+        callOptions: CallOptions? = nil
+    ) async throws -> Burrow_TailnetLoginStatusResponse {
+        try await self.performAsyncUnaryCall(
+            path: "/burrow.TailnetControl/LoginStart",
+            request: request,
+            callOptions: callOptions ?? self.defaultCallOptions,
+            interceptors: []
+        )
+    }
+
+    public func loginStatus(
+        _ request: Burrow_TailnetLoginStatusRequest,
+        callOptions: CallOptions? = nil
+    ) async throws -> Burrow_TailnetLoginStatusResponse {
+        try await self.performAsyncUnaryCall(
+            path: "/burrow.TailnetControl/LoginStatus",
+            request: request,
+            callOptions: callOptions ?? self.defaultCallOptions,
+            interceptors: []
+        )
+    }
+
+    public func loginCancel(
+        _ request: Burrow_TailnetLoginCancelRequest,
+        callOptions: CallOptions? = nil
+    ) async throws -> Burrow_Empty {
+        try await self.performAsyncUnaryCall(
+            path: "/burrow.TailnetControl/LoginCancel",
+            request: request,
+            callOptions: callOptions ?? self.defaultCallOptions,
+            interceptors: []
+        )
+    }
 }

Apple/UI/BurrowView.swift

@@ -1,6 +1,9 @@
 import BurrowConfiguration
 import Foundation
 import SwiftUI
+#if canImport(AuthenticationServices)
+import AuthenticationServices
+#endif
 #if canImport(UIKit)
 import UIKit
 #elseif canImport(AppKit)
@@ -309,6 +312,7 @@ private struct AccountDraft {
             accountName = "default"
             identityName = "apple"
             authority = TailnetProvider.tailscale.defaultAuthority ?? ""
+            authMode = .web
         }
     }
 }
@@ -329,6 +333,14 @@ private struct ConfigurationSheetView: View {
     @State private var authorityProbeStatus: TailnetAuthorityProbeStatus?
     @State private var authorityProbeError: String?
     @State private var isProbingAuthority = false
+    @State private var tailnetLoginStatus: TailnetLoginStatus?
+    @State private var tailnetLoginError: String?
+    @State private var tailnetLoginSessionID: String?
+    @State private var isStartingTailnetLogin = false
+    @State private var tailnetPresentedAuthURL: URL?
+    @State private var preserveTailnetLoginSession = false
+    @State private var browserAuthenticator = TailnetBrowserAuthenticator()
+    @State private var tailnetLoginPollTask: Task<Void, Never>?
     @State private var didRunAutomation = false
 
     init(
@@ -397,7 +409,10 @@ private struct ConfigurationSheetView: View {
             .toolbar {
                 ToolbarItem(placement: .cancellationAction) {
                     Button("Cancel") {
-                        dismiss()
+                        Task { @MainActor in
+                            await cancelTailnetLoginIfNeeded()
+                            dismiss()
+                        }
                     }
                 }
                 #if os(iOS)
@@ -446,14 +461,28 @@ private struct ConfigurationSheetView: View {
         .onChange(of: draft.discoveryEmail) { _, _ in
             resetTailnetDiscoveryFeedback()
         }
+        .onChange(of: draft.authMode) { _, newMode in
+            guard newMode != .web else { return }
+            Task { @MainActor in
+                await cancelTailnetLoginIfNeeded()
+            }
+        }
+        .onDisappear {
+            tailnetLoginPollTask?.cancel()
+            browserAuthenticator.cancel()
+            if !preserveTailnetLoginSession {
+                Task { @MainActor in
+                    await cancelTailnetLoginIfNeeded()
+                }
+            }
+        }
     }
 
     @ViewBuilder
     private var tailnetSections: some View {
         Section("Connection") {
             TextField("Email address", text: $draft.discoveryEmail)
-                .textInputAutocapitalization(.never)
+                .burrowEmailField()
-                .keyboardType(.emailAddress)
                 .burrowLoginField()
                 .autocorrectionDisabled()
 
@@ -507,22 +536,44 @@ private struct ConfigurationSheetView: View {
         }
 
         Section("Authentication") {
-            TextField("Username", text: $draft.username)
-                .burrowLoginField()
-                .autocorrectionDisabled()
             Picker("Authentication", selection: $draft.authMode) {
                 ForEach(availableTailnetAuthModes) { mode in
                     Text(mode.title).tag(mode)
                 }
             }
             .pickerStyle(.menu)
-            if draft.authMode != .none {
+
-                SecureField(
+            if draft.authMode == .web {
-                    draft.authMode == .password ? "Password" : "Preauth Key",
+                Button {
-                    text: $draft.secret
+                    startTailnetLogin()
-                )
+                } label: {
+                    Label {
+                        Text(isStartingTailnetLogin ? "Starting Sign-In" : tailnetSignInActionTitle)
+                    } icon: {
+                        Image(systemName: isStartingTailnetLogin ? "hourglass" : "person.badge.key")
+                    }
+                }
+                .buttonStyle(.borderless)
+                .disabled(isStartingTailnetLogin || normalizedOptional(draft.authority) == nil)
+
+                if let tailnetLoginStatus {
+                    tailnetLoginCard(status: tailnetLoginStatus, failure: nil)
+                } else if let tailnetLoginError {
+                    tailnetLoginCard(status: nil, failure: tailnetLoginError)
+                }
+            } else {
+                TextField("Username", text: $draft.username)
+                    .burrowLoginField()
+                    .autocorrectionDisabled()
+                if draft.authMode != .none {
+                    SecureField(
+                        draft.authMode == .password ? "Password" : "Preauth Key",
+                        text: $draft.secret
+                    )
+                }
             }
-            Text("Tailnet account material stays on-device. Burrow stores the authority and credentials for daemon-managed registration and refresh.")
+
+            Text(tailnetAuthenticationFootnote)
                 .font(.footnote)
                 .foregroundStyle(.secondary)
         }
@@ -583,6 +634,9 @@ private struct ConfigurationSheetView: View {
                 HStack(spacing: 8) {
                     summaryBadge(isManagedTailnetAuthority ? "Managed" : "Custom")
                     summaryBadge(draft.authMode.title)
+                    if tailnetLoginStatus?.running == true {
+                        summaryBadge("Signed In")
+                    }
                 }
             }
         }
@@ -659,6 +713,52 @@ private struct ConfigurationSheetView: View {
         )
     }
 
+    private func tailnetLoginCard(
+        status: TailnetLoginStatus?,
+        failure: String?
+    ) -> some View {
+        VStack(alignment: .leading, spacing: 6) {
+            if let status {
+                Text(status.running ? "Signed In" : status.needsLogin ? "Browser Sign-In Required" : "Checking Sign-In")
+                    .font(.subheadline.weight(.medium))
+                if let tailnetName = status.tailnetName, !tailnetName.isEmpty {
+                    Text("Tailnet: \(tailnetName)")
+                        .font(.footnote)
+                        .foregroundStyle(.secondary)
+                }
+                if let selfDNSName = status.selfDNSName, !selfDNSName.isEmpty {
+                    Text(selfDNSName)
+                        .font(.footnote.monospaced())
+                        .foregroundStyle(.secondary)
+                        .textSelection(.enabled)
+                }
+                if !status.tailnetIPs.isEmpty {
+                    Text(status.tailnetIPs.joined(separator: ", "))
+                        .font(.footnote.monospaced())
+                        .foregroundStyle(.secondary)
+                        .textSelection(.enabled)
+                }
+                if !status.health.isEmpty {
+                    Text(status.health.joined(separator: " • "))
+                        .font(.footnote)
+                        .foregroundStyle(.secondary)
+                }
+            } else if let failure {
+                Text("Sign-In failed")
+                    .font(.subheadline.weight(.medium))
+                    .foregroundStyle(.red)
+                Text(failure)
+                    .font(.footnote)
+                    .foregroundStyle(.secondary)
+            }
+        }
+        .padding(12)
+        .background(
+            RoundedRectangle(cornerRadius: 16)
+                .fill(.thinMaterial)
+        )
+    }
+
     private func summaryBadge(_ label: String) -> some View {
         Text(label)
             .font(.caption.weight(.medium))
@@ -813,6 +913,9 @@ private struct ConfigurationSheetView: View {
             if normalizedOptional(draft.authority) == nil {
                 return true
             }
+            if draft.authMode == .web {
+                return tailnetLoginStatus?.running != true
+            }
             if draft.authMode != .none && normalizedOptional(draft.secret) == nil {
                 return true
             }
@@ -897,8 +1000,9 @@ private struct ConfigurationSheetView: View {
     }
 
     private func submitTailnet() async throws {
-        let secret = draft.authMode == .none ? nil : draft.secret
+        let secret = (draft.authMode == .none || draft.authMode == .web) ? nil : draft.secret
         let username = normalizedOptional(draft.username)
+        preserveTailnetLoginSession = draft.authMode == .web && tailnetLoginStatus?.running == true
         try await saveTailnetAccount(secret: secret, username: username)
         dismiss()
     }
@@ -922,7 +1026,7 @@ private struct ConfigurationSheetView: View {
             switch automation.action {
             case .tailnetLogin:
                 applyTailnetDefaults(for: .tailscale)
-                probeTailnetAuthority()
+                startTailnetLogin()
             case .headscaleProbe:
                 draft.authority = automation.authority ?? TailnetProvider.headscale.defaultAuthority ?? draft.authority
                 probeTailnetAuthority()
@@ -950,6 +1054,10 @@ private struct ConfigurationSheetView: View {
             "Auth: \(draft.authMode.title)",
         ]
 
+        if draft.authMode == .web, tailnetLoginStatus?.running == true {
+            noteParts.append("Browser sign-in complete")
+        }
+
         do {
             let networkID = try await networkViewModel.addTailnetNetwork(payload: payload)
             noteParts.append("Linked to daemon network #\(networkID)")
@@ -1003,7 +1111,36 @@ private struct ConfigurationSheetView: View {
         resetTailnetDiscoveryFeedback()
         draft.authority = provider.defaultAuthority ?? ""
         if !availableTailnetAuthModes.contains(draft.authMode) {
-            draft.authMode = .none
+            draft.authMode = .web
+        }
+    }
+
+    private func startTailnetLogin() {
+        guard let authority = normalizedOptional(draft.authority) else {
+            tailnetLoginStatus = nil
+            tailnetLoginError = "Enter a server URL first."
+            return
+        }
+
+        isStartingTailnetLogin = true
+        tailnetLoginError = nil
+        preserveTailnetLoginSession = false
+
+        Task { @MainActor in
+            defer { isStartingTailnetLogin = false }
+            do {
+                let status = try await networkViewModel.startTailnetLogin(
+                    accountName: normalized(draft.accountName, fallback: "default"),
+                    identityName: normalized(draft.identityName, fallback: "apple"),
+                    hostname: normalizedOptional(draft.hostname),
+                    authority: authority
+                )
+                tailnetLoginSessionID = status.sessionID
+                updateTailnetLoginStatus(status)
+                beginTailnetLoginPolling(sessionID: status.sessionID)
+            } catch {
+                tailnetLoginError = error.localizedDescription
+            }
         }
     }
 
@@ -1031,6 +1168,7 @@ private struct ConfigurationSheetView: View {
     private func resetAuthorityProbe() {
         authorityProbeStatus = nil
         authorityProbeError = nil
+        tailnetLoginError = nil
     }
 
     private func resetTailnetDiscoveryFeedback() {
@@ -1062,6 +1200,76 @@ private struct ConfigurationSheetView: View {
         }
     }
 
+    private func beginTailnetLoginPolling(sessionID: String) {
+        tailnetLoginPollTask?.cancel()
+        tailnetLoginPollTask = Task { @MainActor in
+            while !Task.isCancelled {
+                do {
+                    let status = try await networkViewModel.tailnetLoginStatus(sessionID: sessionID)
+                    updateTailnetLoginStatus(status)
+                    if status.running {
+                        tailnetLoginPollTask = nil
+                        return
+                    }
+                } catch {
+                    tailnetLoginError = error.localizedDescription
+                    tailnetLoginPollTask = nil
+                    return
+                }
+                try? await Task.sleep(for: .seconds(1))
+            }
+        }
+    }
+
+    private func updateTailnetLoginStatus(_ status: TailnetLoginStatus) {
+        tailnetLoginStatus = status
+        tailnetLoginError = nil
+        tailnetLoginSessionID = status.sessionID
+
+        if status.running {
+            browserAuthenticator.cancel()
+            tailnetPresentedAuthURL = nil
+            return
+        }
+
+        guard let authURL = status.authURL else {
+            return
+        }
+
+        if tailnetPresentedAuthURL != authURL {
+            tailnetPresentedAuthURL = authURL
+            browserAuthenticator.start(url: authURL) { [sessionID = status.sessionID] in
+                Task { @MainActor in
+                    if tailnetLoginStatus?.running != true {
+                        tailnetLoginSessionID = sessionID
+                    }
+                }
+            }
+        }
+    }
+
+    private func cancelTailnetLoginIfNeeded() async {
+        tailnetLoginPollTask?.cancel()
+        tailnetLoginPollTask = nil
+        browserAuthenticator.cancel()
+        tailnetPresentedAuthURL = nil
+
+        guard tailnetLoginStatus?.running != true,
+              let sessionID = tailnetLoginSessionID
+        else {
+            return
+        }
+
+        do {
+            try await networkViewModel.cancelTailnetLogin(sessionID: sessionID)
+        } catch {
+            tailnetLoginError = error.localizedDescription
+        }
+
+        tailnetLoginStatus = nil
+        tailnetLoginSessionID = nil
+    }
+
     private func pasteWireGuardConfiguration() {
         guard let clipboardString else { return }
         draft.wireGuardConfig = clipboardString
@@ -1108,7 +1316,28 @@ private struct ConfigurationSheetView: View {
     }
 
     private var availableTailnetAuthModes: [AccountAuthMode] {
-        [.none, .password, .preauthKey]
+        [.web, .none, .password, .preauthKey]
+    }
+
+    private var tailnetSignInActionTitle: String {
+        if tailnetLoginStatus?.running == true {
+            return "Signed In"
+        }
+        if tailnetLoginSessionID != nil {
+            return "Resume Sign-In"
+        }
+        return "Start Sign-In"
+    }
+
+    private var tailnetAuthenticationFootnote: String {
+        switch draft.authMode {
+        case .web:
+            return "Burrow asks the daemon to start a Tailnet browser sign-in session, then closes it locally once the daemon reports the device is running."
+        case .none:
+            return "Save the authority only. Useful when the control plane handles authentication elsewhere."
+        case .password, .preauthKey:
+            return "Tailnet account material stays on-device. Burrow stores the authority and credentials for daemon-managed registration and refresh."
+        }
     }
 
     private var inferredTailnetProvider: TailnetProvider {
@@ -1215,8 +1444,65 @@ private extension View {
         self
         #endif
     }
+
+    @ViewBuilder
+    func burrowEmailField() -> some View {
+        #if os(iOS)
+        textInputAutocapitalization(.never)
+            .keyboardType(.emailAddress)
+        #else
+        self
+        #endif
+    }
 }
 
+#if canImport(AuthenticationServices)
+@MainActor
+private final class TailnetBrowserAuthenticator: NSObject {
+    private var session: ASWebAuthenticationSession?
+
+    func start(url: URL, onDismiss: @escaping @Sendable () -> Void) {
+        cancel()
+        let session = ASWebAuthenticationSession(url: url, callbackURLScheme: nil) { _, _ in
+            onDismiss()
+        }
+        session.presentationContextProvider = self
+        session.prefersEphemeralWebBrowserSession = false
+        self.session = session
+        _ = session.start()
+    }
+
+    func cancel() {
+        session?.cancel()
+        session = nil
+    }
+}
+
+extension TailnetBrowserAuthenticator: ASWebAuthenticationPresentationContextProviding {
+    func presentationAnchor(for session: ASWebAuthenticationSession) -> ASPresentationAnchor {
+        #if canImport(AppKit)
+        return NSApplication.shared.keyWindow
+            ?? NSApplication.shared.windows.first
+            ?? ASPresentationAnchor()
+        #elseif canImport(UIKit)
+        return ASPresentationAnchor()
+        #else
+        return ASPresentationAnchor()
+        #endif
+    }
+}
+#else
+@MainActor
+private final class TailnetBrowserAuthenticator {
+    func start(url: URL, onDismiss: @escaping @Sendable () -> Void) {
+        _ = url
+        onDismiss()
+    }
+
+    func cancel() {}
+}
+#endif
+
 private struct BurrowAutomationConfig {
     enum Action: String {
         case tailnetLogin = "tailnet-login"

Apple/UI/Networks/Network.swift

@@ -40,6 +40,19 @@ struct TailnetAuthorityProbeStatus: Sendable {
     var detail: String?
 }
 
+struct TailnetLoginStatus: Sendable {
+    var sessionID: String
+    var backendState: String
+    var authURL: URL?
+    var running: Bool
+    var needsLogin: Bool
+    var tailnetName: String?
+    var magicDNSSuffix: String?
+    var selfDNSName: String?
+    var tailnetIPs: [String]
+    var health: [String]
+}
+
 enum TailnetDiscoveryClient {
     static func discover(email: String, socketURL: URL) async throws -> TailnetDiscoveryResponse {
         var request = Burrow_TailnetDiscoverRequest()
@@ -74,6 +87,58 @@ enum TailnetAuthorityProbeClient {
     }
 }
 
+enum TailnetLoginClient {
+    static func start(
+        accountName: String,
+        identityName: String,
+        hostname: String?,
+        authority: String,
+        socketURL: URL
+    ) async throws -> TailnetLoginStatus {
+        var request = Burrow_TailnetLoginStartRequest()
+        request.accountName = accountName
+        request.identityName = identityName
+        request.hostname = hostname ?? ""
+        request.authority = authority
+        let response = try await TailnetClient.unix(socketURL: socketURL).loginStart(request)
+        return decode(response)
+    }
+
+    static func status(sessionID: String, socketURL: URL) async throws -> TailnetLoginStatus {
+        var request = Burrow_TailnetLoginStatusRequest()
+        request.sessionID = sessionID
+        let response = try await TailnetClient.unix(socketURL: socketURL).loginStatus(request)
+        return decode(response)
+    }
+
+    static func cancel(sessionID: String, socketURL: URL) async throws {
+        var request = Burrow_TailnetLoginCancelRequest()
+        request.sessionID = sessionID
+        _ = try await TailnetClient.unix(socketURL: socketURL).loginCancel(request)
+    }
+
+    private static func decode(_ response: Burrow_TailnetLoginStatusResponse) -> TailnetLoginStatus {
+        TailnetLoginStatus(
+            sessionID: response.sessionID,
+            backendState: response.backendState,
+            authURL: URL(string: response.authURL.trimmingCharacters(in: .whitespacesAndNewlines)),
+            running: response.running,
+            needsLogin: response.needsLogin,
+            tailnetName: response.tailnetName.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
+                ? nil
+                : response.tailnetName,
+            magicDNSSuffix: response.magicDNSSuffix.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
+                ? nil
+                : response.magicDNSSuffix,
+            selfDNSName: response.selfDNSName.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
+                ? nil
+                : response.selfDNSName,
+            tailnetIPs: response.tailnetIPs,
+            health: response.health
+        )
+    }
+}
+
 @Observable
 @MainActor
 final class NetworkViewModel: Sendable {
@@ -118,6 +183,32 @@ final class NetworkViewModel: Sendable {
         return try await TailnetAuthorityProbeClient.probe(authority: authority, socketURL: socketURL)
     }
 
+    func startTailnetLogin(
+        accountName: String,
+        identityName: String,
+        hostname: String?,
+        authority: String
+    ) async throws -> TailnetLoginStatus {
+        let socketURL = try socketURLResult.get()
+        return try await TailnetLoginClient.start(
+            accountName: accountName,
+            identityName: identityName,
+            hostname: hostname,
+            authority: authority,
+            socketURL: socketURL
+        )
+    }
+
+    func tailnetLoginStatus(sessionID: String) async throws -> TailnetLoginStatus {
+        let socketURL = try socketURLResult.get()
+        return try await TailnetLoginClient.status(sessionID: sessionID, socketURL: socketURL)
+    }
+
+    func cancelTailnetLogin(sessionID: String) async throws {
+        let socketURL = try socketURLResult.get()
+        try await TailnetLoginClient.cancel(sessionID: sessionID, socketURL: socketURL)
+    }
+
     private func addNetwork(type: Burrow_NetworkType, payload: Data) async throws -> Int32 {
         let socketURL = try socketURLResult.get()
         let networkID = nextNetworkID
@@ -317,6 +408,7 @@ enum AccountNetworkKind: String, CaseIterable, Codable, Identifiable, Sendable {
 }
 
 enum AccountAuthMode: String, CaseIterable, Codable, Identifiable, Sendable {
+    case web
     case none
     case password
     case preauthKey
@@ -325,6 +417,7 @@ enum AccountAuthMode: String, CaseIterable, Codable, Identifiable, Sendable {
 
     var title: String {
         switch self {
+        case .web: "Browser Sign-In"
         case .none: "None"
         case .password: "Password"
         case .preauthKey: "Preauth Key"

burrow/src/auth/server/tailscale.rs

@@ -82,11 +82,22 @@ impl TailscaleBridgeManager {
         let key = session_key(&request.account_name, &request.identity_name);
 
         if let Some(existing) = self.sessions.lock().await.get(&key).cloned() {
-            let status = self.fetch_status(existing.as_ref()).await?;
+            match self.fetch_status(existing.as_ref()).await {
-            return Ok(TailscaleLoginStartResponse {
+                Ok(status) => {
-                session_id: existing.session_id.clone(),
+                    return Ok(TailscaleLoginStartResponse {
-                status,
+                        session_id: existing.session_id.clone(),
-            });
+                        status,
+                    });
+                }
+                Err(err) => {
+                    log::warn!(
+                        "tailscale login session {} is stale, restarting: {err}",
+                        existing.session_id
+                    );
+                    self.sessions.lock().await.remove(&key);
+                    let _ = self.shutdown_session(existing.as_ref()).await;
+                }
+            }
         }
 
         let state_dir = state_root().join(session_dir_name(&request));
@@ -155,11 +166,28 @@ impl TailscaleBridgeManager {
         };
 
         match session {
-            Some(session) => self.fetch_status(session.as_ref()).await.map(Some),
+            Some(session) => match self.fetch_status(session.as_ref()).await {
+                Ok(status) => Ok(Some(status)),
+                Err(err) => {
+                    self.remove_session_by_id(session_id).await;
+                    Err(err)
+                }
+            },
             None => Ok(None),
         }
     }
 
+    pub async fn cancel(&self, session_id: &str) -> Result<bool> {
+        let session = self.remove_session_by_id(session_id).await;
+        match session {
+            Some(session) => {
+                self.shutdown_session(session.as_ref()).await?;
+                Ok(true)
+            }
+            None => Ok(false),
+        }
+    }
+
     async fn wait_for_status(&self, session: &ManagedSession) -> Result<TailscaleLoginStatus> {
         let mut last_error = None;
         let mut last_status = None;
@@ -201,6 +229,38 @@ impl TailscaleBridgeManager {
             .await
             .context("invalid tailscale helper status response")
     }
+
+    async fn remove_session_by_id(&self, session_id: &str) -> Option<Arc<ManagedSession>> {
+        let mut sessions = self.sessions.lock().await;
+        let key = sessions
+            .iter()
+            .find_map(|(key, session)| (session.session_id == session_id).then(|| key.clone()))?;
+        sessions.remove(&key)
+    }
+
+    async fn shutdown_session(&self, session: &ManagedSession) -> Result<()> {
+        let _ = self
+            .client
+            .post(format!("{}/shutdown", session.listen_url))
+            .send()
+            .await;
+
+        for _ in 0..10 {
+            let mut child = session.child.lock().await;
+            if child.try_wait()?.is_some() {
+                return Ok(());
+            }
+            drop(child);
+            tokio::time::sleep(Duration::from_millis(100)).await;
+        }
+
+        let mut child = session.child.lock().await;
+        child
+            .start_kill()
+            .context("failed to kill tailscale helper")?;
+        let _ = child.wait().await;
+        Ok(())
+    }
 }
 
 fn helper_command(request: &TailscaleLoginStartRequest, state_dir: &Path) -> Result<Command> {
@@ -249,7 +309,10 @@ fn state_root() -> PathBuf {
             .join("Burrow")
             .join("tailscale");
     }
-    home.join(".local").join("share").join("burrow").join("tailscale")
+    home.join(".local")
+        .join("share")
+        .join("burrow")
+        .join("tailscale")
 }
 
 fn session_dir_name(request: &TailscaleLoginStartRequest) -> String {

burrow/src/daemon/instance.rs

@@ -13,15 +13,19 @@ use tun::tokio::TunInterface;
 
 use super::{
     rpc::grpc_defs::{
-        networks_server::Networks, tailnet_control_server::TailnetControl,
+        networks_server::Networks, tailnet_control_server::TailnetControl, tunnel_server::Tunnel,
-        tunnel_server::Tunnel, Empty, Network, NetworkDeleteRequest, NetworkListResponse,
+        Empty, Network, NetworkDeleteRequest, NetworkListResponse, NetworkReorderRequest,
-        NetworkReorderRequest, State as RPCTunnelState, TailnetDiscoverRequest,
+        State as RPCTunnelState, TailnetDiscoverRequest, TailnetDiscoverResponse,
-        TailnetDiscoverResponse, TailnetProbeRequest, TailnetProbeResponse,
+        TailnetProbeRequest, TailnetProbeResponse, TunnelConfigurationResponse,
-        TunnelConfigurationResponse, TunnelStatusResponse,
+        TunnelStatusResponse,
     },
     runtime::{ActiveTunnel, ResolvedTunnel},
 };
 use crate::{
+    auth::server::tailscale::{
+        TailscaleBridgeManager, TailscaleLoginStartRequest as BridgeLoginStartRequest,
+        TailscaleLoginStatus,
+    },
     control::discovery,
     daemon::rpc::ServerConfig,
     database::{add_network, delete_network, get_connection, list_networks, reorder_network},
@@ -49,6 +53,7 @@ pub struct DaemonRPCServer {
     wg_state_chan: (watch::Sender<RunState>, watch::Receiver<RunState>),
     network_update_chan: (watch::Sender<()>, watch::Receiver<()>),
     active_tunnel: Arc<RwLock<Option<ActiveTunnel>>>,
+    tailnet_login: TailscaleBridgeManager,
 }
 
 impl DaemonRPCServer {
@@ -59,6 +64,7 @@ impl DaemonRPCServer {
             wg_state_chan: watch::channel(RunState::Idle),
             network_update_chan: watch::channel(()),
             active_tunnel: Arc::new(RwLock::new(None)),
+            tailnet_login: TailscaleBridgeManager::default(),
         })
     }
 
@@ -130,6 +136,11 @@ impl DaemonRPCServer {
 
         Ok(())
     }
+
+    fn tailnet_control_url(authority: &str) -> Option<String> {
+        let authority = discovery::normalize_authority(authority);
+        (!discovery::is_managed_tailscale_authority(&authority)).then_some(authority)
+    }
 }
 
 #[tonic::async_trait]
@@ -308,6 +319,60 @@ impl TailnetControl for DaemonRPCServer {
             reachable: status.reachable,
         }))
     }
+
+    async fn login_start(
+        &self,
+        request: Request<super::rpc::grpc_defs::TailnetLoginStartRequest>,
+    ) -> Result<Response<super::rpc::grpc_defs::TailnetLoginStatusResponse>, RspStatus> {
+        let request = request.into_inner();
+        let response = self
+            .tailnet_login
+            .start_login(BridgeLoginStartRequest {
+                account_name: request.account_name,
+                identity_name: request.identity_name,
+                hostname: (!request.hostname.trim().is_empty()).then_some(request.hostname),
+                control_url: Self::tailnet_control_url(&request.authority),
+            })
+            .await
+            .map_err(proc_err)?;
+
+        Ok(Response::new(tailnet_login_rsp(
+            response.session_id,
+            response.status,
+        )))
+    }
+
+    async fn login_status(
+        &self,
+        request: Request<super::rpc::grpc_defs::TailnetLoginStatusRequest>,
+    ) -> Result<Response<super::rpc::grpc_defs::TailnetLoginStatusResponse>, RspStatus> {
+        let request = request.into_inner();
+        let status = self
+            .tailnet_login
+            .status(&request.session_id)
+            .await
+            .map_err(proc_err)?;
+        let Some(status) = status else {
+            return Err(RspStatus::not_found("tailnet login session not found"));
+        };
+        Ok(Response::new(tailnet_login_rsp(request.session_id, status)))
+    }
+
+    async fn login_cancel(
+        &self,
+        request: Request<super::rpc::grpc_defs::TailnetLoginCancelRequest>,
+    ) -> Result<Response<Empty>, RspStatus> {
+        let request = request.into_inner();
+        let canceled = self
+            .tailnet_login
+            .cancel(&request.session_id)
+            .await
+            .map_err(proc_err)?;
+        if !canceled {
+            return Err(RspStatus::not_found("tailnet login session not found"));
+        }
+        Ok(Response::new(Empty {}))
+    }
 }
 
 fn proc_err(err: impl ToString) -> RspStatus {
@@ -327,3 +392,21 @@ fn status_rsp(state: RunState) -> TunnelStatusResponse {
         start: None, // TODO: Add timestamp
     }
 }
+
+fn tailnet_login_rsp(
+    session_id: String,
+    status: TailscaleLoginStatus,
+) -> super::rpc::grpc_defs::TailnetLoginStatusResponse {
+    super::rpc::grpc_defs::TailnetLoginStatusResponse {
+        session_id,
+        backend_state: status.backend_state,
+        auth_url: status.auth_url.unwrap_or_default(),
+        running: status.running,
+        needs_login: status.needs_login,
+        tailnet_name: status.tailnet_name.unwrap_or_default(),
+        magic_dns_suffix: status.magic_dns_suffix.unwrap_or_default(),
+        self_dns_name: status.self_dns_name.unwrap_or_default(),
+        tailnet_ips: status.tailscale_ips,
+        health: status.health,
+    }
+}

proto/burrow.proto

@@ -20,6 +20,9 @@ service Networks {
 service TailnetControl {
     rpc Discover (TailnetDiscoverRequest) returns (TailnetDiscoverResponse);
     rpc Probe (TailnetProbeRequest) returns (TailnetProbeResponse);
+    rpc LoginStart (TailnetLoginStartRequest) returns (TailnetLoginStatusResponse);
+    rpc LoginStatus (TailnetLoginStatusRequest) returns (TailnetLoginStatusResponse);
+    rpc LoginCancel (TailnetLoginCancelRequest) returns (Empty);
 }
 
 message NetworkReorderRequest {
@@ -84,6 +87,34 @@ message TailnetProbeResponse {
     bool reachable = 5;
 }
 
+message TailnetLoginStartRequest {
+    string account_name = 1;
+    string identity_name = 2;
+    string hostname = 3;
+    string authority = 4;
+}
+
+message TailnetLoginStatusRequest {
+    string session_id = 1;
+}
+
+message TailnetLoginCancelRequest {
+    string session_id = 1;
+}
+
+message TailnetLoginStatusResponse {
+    string session_id = 1;
+    string backend_state = 2;
+    string auth_url = 3;
+    bool running = 4;
+    bool needs_login = 5;
+    string tailnet_name = 6;
+    string magic_dns_suffix = 7;
+    string self_dns_name = 8;
+    repeated string tailnet_ips = 9;
+    repeated string health = 10;
+}
+
 enum State {
     Stopped = 0;
     Running = 1;