From 646217784a0f0c297dac05c73a475a86cd3fb779 Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Thu, 10 Apr 2025 16:42:34 +1000
Subject: [PATCH 01/10] feat: use the deployment's hostname suffix in the UI

---
 .../Coder-Desktop/Coder_DesktopApp.swift      |  4 +-
 Coder-Desktop/Coder-Desktop/State.swift       | 46 +++++++++++++++++--
 .../Coder-Desktop/Views/VPN/VPNMenuItem.swift | 11 +++--
 Coder-Desktop/CoderSDK/Deployment.swift       | 14 ++++++
 4 files changed, 67 insertions(+), 8 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift b/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
index 30ea7e7..cf0624e 100644
--- a/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
+++ b/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
@@ -65,10 +65,12 @@ class AppDelegate: NSObject, NSApplicationDelegate {
             title: "Coder Desktop",
             image: "MenuBarIcon",
             onAppear: {
-                // If the VPN is enabled, it's likely the token isn't expired
+                // If the VPN is enabled, it's likely the token hasn't expired,
+                // and the deployment config is up to date.
                 guard case .disabled = self.vpn.state, self.state.hasSession else { return }
                 Task { @MainActor in
                     await self.state.handleTokenExpiry()
+                    await self.state.refreshDeploymentConfig()
                 }
             }, content: {
                 VPNMenu<CoderVPNService, MutagenDaemon>().frame(width: 256)
diff --git a/Coder-Desktop/Coder-Desktop/State.swift b/Coder-Desktop/Coder-Desktop/State.swift
index aea2fe9..b1aba95 100644
--- a/Coder-Desktop/Coder-Desktop/State.swift
+++ b/Coder-Desktop/Coder-Desktop/State.swift
@@ -25,6 +25,15 @@ class AppState: ObservableObject {
         }
     }
 
+    @Published private(set) var hostnameSuffix: String {
+        didSet {
+            guard persistent else { return }
+            UserDefaults.standard.set(hostnameSuffix, forKey: Keys.hostnameSuffix)
+        }
+    }
+
+    static let defaultHostnameSuffix: String = "coder"
+
     // Stored in Keychain
     @Published private(set) var sessionToken: String? {
         didSet {
@@ -33,6 +42,8 @@ class AppState: ObservableObject {
         }
     }
 
+    var client: Client?
+
     @Published var useLiteralHeaders: Bool = UserDefaults.standard.bool(forKey: Keys.useLiteralHeaders) {
         didSet {
             reconfigure()
@@ -80,7 +91,7 @@ class AppState: ObservableObject {
     private let keychain: Keychain
     private let persistent: Bool
 
-    let onChange: ((NETunnelProviderProtocol?) -> Void)?
+    private let onChange: ((NETunnelProviderProtocol?) -> Void)?
 
     // reconfigure must be called when any property used to configure the VPN changes
     public func reconfigure() {
@@ -94,6 +105,10 @@ class AppState: ObservableObject {
         self.onChange = onChange
         keychain = Keychain(service: Bundle.main.bundleIdentifier!)
         _hasSession = Published(initialValue: persistent ? UserDefaults.standard.bool(forKey: Keys.hasSession) : false)
+        _hostnameSuffix = Published(
+            initialValue: persistent ? UserDefaults.standard
+                .string(forKey: Keys.hostnameSuffix) ?? Self.defaultHostnameSuffix : Self.defaultHostnameSuffix
+        )
         _baseAccessURL = Published(
             initialValue: persistent ? UserDefaults.standard.url(forKey: Keys.baseAccessURL) : nil
         )
@@ -107,6 +122,11 @@ class AppState: ObservableObject {
             if sessionToken == nil || sessionToken!.isEmpty == true {
                 clearSession()
             }
+            client = Client(
+                url: baseAccessURL!,
+                token: sessionToken!,
+                headers: useLiteralHeaders ? literalHeaders.map { $0.toSDKHeader() } : []
+            )
         }
     }
 
@@ -114,14 +134,18 @@ class AppState: ObservableObject {
         hasSession = true
         self.baseAccessURL = baseAccessURL
         self.sessionToken = sessionToken
+        client = Client(
+            url: baseAccessURL,
+            token: sessionToken,
+            headers: useLiteralHeaders ? literalHeaders.map { $0.toSDKHeader() } : []
+        )
         reconfigure()
     }
 
     public func handleTokenExpiry() async {
         if hasSession {
-            let client = Client(url: baseAccessURL!, token: sessionToken!)
             do {
-                _ = try await client.user("me")
+                _ = try await client!.user("me")
             } catch let SDKError.api(apiErr) {
                 // Expired token
                 if apiErr.statusCode == 401 {
@@ -135,9 +159,24 @@ class AppState: ObservableObject {
         }
     }
 
+    public func refreshDeploymentConfig() async {
+        if hasSession {
+            do {
+                let config = try await client!.sshConfiguration()
+                hostnameSuffix = config.hostname_suffix ?? Self.defaultHostnameSuffix
+            } catch {
+                // If fetching the config fails, there's likely a bigger issue.
+                // We'll show an error in the UI if they try and do something
+                logger.error("failed to refresh deployment config: \(error)")
+                return
+            }
+        }
+    }
+
     public func clearSession() {
         hasSession = false
         sessionToken = nil
+        client = nil
         reconfigure()
     }
 
@@ -159,6 +198,7 @@ class AppState: ObservableObject {
         static let hasSession = "hasSession"
         static let baseAccessURL = "baseAccessURL"
         static let sessionToken = "sessionToken"
+        static let hostnameSuffix = "hostnameSuffix"
 
         static let useLiteralHeaders = "UseLiteralHeaders"
         static let literalHeaders = "LiteralHeaders"
diff --git a/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift b/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift
index af7e6bb..804828a 100644
--- a/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift
+++ b/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift
@@ -42,6 +42,8 @@ enum VPNMenuItem: Equatable, Comparable, Identifiable {
 }
 
 struct MenuItemView: View {
+    @EnvironmentObject var state: AppState
+
     let item: VPNMenuItem
     let baseAccessURL: URL
     @State private var nameIsSelected: Bool = false
@@ -49,14 +51,15 @@ struct MenuItemView: View {
 
     private var itemName: AttributedString {
         let name = switch item {
-        case let .agent(agent): agent.primaryHost ?? "\(item.wsName).coder"
-        case .offlineWorkspace: "\(item.wsName).coder"
+        case let .agent(agent): agent.primaryHost ?? "\(item.wsName).\(state.hostnameSuffix)"
+        case .offlineWorkspace: "\(item.wsName).\(state.hostnameSuffix)"
         }
 
         var formattedName = AttributedString(name)
         formattedName.foregroundColor = .primary
-        if let range = formattedName.range(of: ".coder") {
-            formattedName[range].foregroundColor = .secondary
+
+        if let lastDot = formattedName.range(of: ".", options: .backwards) {
+            formattedName[lastDot.lowerBound ..< formattedName.endIndex].foregroundColor = .secondary
         }
         return formattedName
     }
diff --git a/Coder-Desktop/CoderSDK/Deployment.swift b/Coder-Desktop/CoderSDK/Deployment.swift
index b88029f..cca6f04 100644
--- a/Coder-Desktop/CoderSDK/Deployment.swift
+++ b/Coder-Desktop/CoderSDK/Deployment.swift
@@ -8,6 +8,14 @@ public extension Client {
         }
         return try decode(BuildInfoResponse.self, from: res.data)
     }
+
+    func sshConfiguration() async throws(SDKError) -> SSHConfigResponse {
+        let res = try await request("/api/v2/deployment/ssh", method: .get)
+        guard res.resp.statusCode == 200 else {
+            throw responseAsError(res)
+        }
+        return try decode(SSHConfigResponse.self, from: res.data)
+    }
 }
 
 public struct BuildInfoResponse: Codable, Equatable, Sendable {
@@ -20,3 +28,9 @@ public struct BuildInfoResponse: Codable, Equatable, Sendable {
             .flatMap { Range($0.range(at: 1), in: version).map { String(version[$0]) } }
     }
 }
+
+public struct SSHConfigResponse: Codable, Equatable, Sendable {
+    public let hostname_prefix: String?
+    public let hostname_suffix: String?
+    public let ssh_config_options: [String: String]
+}

From f141a7478b2d5e4e1406e82faf434604d6e7e372 Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Thu, 10 Apr 2025 16:58:08 +1000
Subject: [PATCH 02/10] fixup

---
 Coder-Desktop/Coder-Desktop/State.swift | 13 +++----------
 1 file changed, 3 insertions(+), 10 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/State.swift b/Coder-Desktop/Coder-Desktop/State.swift
index b1aba95..ee3c047 100644
--- a/Coder-Desktop/Coder-Desktop/State.swift
+++ b/Coder-Desktop/Coder-Desktop/State.swift
@@ -25,12 +25,7 @@ class AppState: ObservableObject {
         }
     }
 
-    @Published private(set) var hostnameSuffix: String {
-        didSet {
-            guard persistent else { return }
-            UserDefaults.standard.set(hostnameSuffix, forKey: Keys.hostnameSuffix)
-        }
-    }
+    @Published private(set) var hostnameSuffix: String = defaultHostnameSuffix
 
     static let defaultHostnameSuffix: String = "coder"
 
@@ -105,10 +100,6 @@ class AppState: ObservableObject {
         self.onChange = onChange
         keychain = Keychain(service: Bundle.main.bundleIdentifier!)
         _hasSession = Published(initialValue: persistent ? UserDefaults.standard.bool(forKey: Keys.hasSession) : false)
-        _hostnameSuffix = Published(
-            initialValue: persistent ? UserDefaults.standard
-                .string(forKey: Keys.hostnameSuffix) ?? Self.defaultHostnameSuffix : Self.defaultHostnameSuffix
-        )
         _baseAccessURL = Published(
             initialValue: persistent ? UserDefaults.standard.url(forKey: Keys.baseAccessURL) : nil
         )
@@ -127,6 +118,7 @@ class AppState: ObservableObject {
                 token: sessionToken!,
                 headers: useLiteralHeaders ? literalHeaders.map { $0.toSDKHeader() } : []
             )
+            Task { await refreshDeploymentConfig() }
         }
     }
 
@@ -139,6 +131,7 @@ class AppState: ObservableObject {
             token: sessionToken,
             headers: useLiteralHeaders ? literalHeaders.map { $0.toSDKHeader() } : []
         )
+        Task { await refreshDeploymentConfig() }
         reconfigure()
     }
 

From 5dea75fdc1f238466667fa925832bf9228425448 Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Thu, 10 Apr 2025 17:09:00 +1000
Subject: [PATCH 03/10] fixup

---
 Coder-Desktop/Coder-Desktop/State.swift | 7 +++++--
 1 file changed, 5 insertions(+), 2 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/State.swift b/Coder-Desktop/Coder-Desktop/State.swift
index ee3c047..fade6cc 100644
--- a/Coder-Desktop/Coder-Desktop/State.swift
+++ b/Coder-Desktop/Coder-Desktop/State.swift
@@ -37,7 +37,7 @@ class AppState: ObservableObject {
         }
     }
 
-    var client: Client?
+    private var client: Client?
 
     @Published var useLiteralHeaders: Bool = UserDefaults.standard.bool(forKey: Keys.useLiteralHeaders) {
         didSet {
@@ -118,7 +118,10 @@ class AppState: ObservableObject {
                 token: sessionToken!,
                 headers: useLiteralHeaders ? literalHeaders.map { $0.toSDKHeader() } : []
             )
-            Task { await refreshDeploymentConfig() }
+            Task {
+                await handleTokenExpiry()
+                await refreshDeploymentConfig()
+            }
         }
     }
 

From e04f61ae99667db24ab92e93ac140928f593e1ed Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Fri, 11 Apr 2025 12:30:45 +1000
Subject: [PATCH 04/10] thinking

---
 Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift | 11 +++++++----
 Coder-Desktop/Coder-Desktop/VPN/VPNService.swift   |  3 +++
 2 files changed, 10 insertions(+), 4 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift b/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
index cf0624e..369c48b 100644
--- a/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
+++ b/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
@@ -41,10 +41,15 @@ class AppDelegate: NSObject, NSApplicationDelegate {
 
     override init() {
         vpn = CoderVPNService()
-        state = AppState(onChange: vpn.configureTunnelProviderProtocol)
+        let state = AppState(onChange: vpn.configureTunnelProviderProtocol)
+        vpn.onStart = {
+            // We don't need this to have finished before the VPN actually starts
+            Task { await state.refreshDeploymentConfig() }
+        }
         if state.startVPNOnLaunch {
             vpn.startWhenReady = true
         }
+        self.state = state
         vpn.installSystemExtension()
         #if arch(arm64)
             let mutagenBinary = "mutagen-darwin-arm64"
@@ -65,12 +70,10 @@ class AppDelegate: NSObject, NSApplicationDelegate {
             title: "Coder Desktop",
             image: "MenuBarIcon",
             onAppear: {
-                // If the VPN is enabled, it's likely the token hasn't expired,
-                // and the deployment config is up to date.
+                // If the VPN is enabled, it's likely the token isn't expired
                 guard case .disabled = self.vpn.state, self.state.hasSession else { return }
                 Task { @MainActor in
                     await self.state.handleTokenExpiry()
-                    await self.state.refreshDeploymentConfig()
                 }
             }, content: {
                 VPNMenu<CoderVPNService, MutagenDaemon>().frame(width: 256)
diff --git a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
index 50078d5..f1b6ef5 100644
--- a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
+++ b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
@@ -76,6 +76,7 @@ final class CoderVPNService: NSObject, VPNService {
 
     // Whether the VPN should start as soon as possible
     var startWhenReady: Bool = false
+    var onStart: (() -> Void)?
 
     // systemExtnDelegate holds a reference to the SystemExtensionDelegate so that it doesn't get
     // garbage collected while the OSSystemExtensionRequest is in flight, since the OS framework
@@ -96,6 +97,8 @@ final class CoderVPNService: NSObject, VPNService {
             return
         }
 
+        onStart?()
+
         menuState.clear()
         await startTunnel()
         logger.debug("network extension enabled")

From cbd8ce499972dead256b9f7580bf10b7c820d31f Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Fri, 11 Apr 2025 15:21:37 +1000
Subject: [PATCH 05/10] move on start

---
 Coder-Desktop/Coder-Desktop/VPN/VPNService.swift | 7 ++++---
 1 file changed, 4 insertions(+), 3 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
index f1b6ef5..211bb28 100644
--- a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
+++ b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
@@ -97,8 +97,6 @@ final class CoderVPNService: NSObject, VPNService {
             return
         }
 
-        onStart?()
-
         menuState.clear()
         await startTunnel()
         logger.debug("network extension enabled")
@@ -185,8 +183,11 @@ extension CoderVPNService {
         // Connected -> Connected: no-op
         case (.connected, .connected):
             break
-        // Non-connecting -> Connecting: Establish XPC
+        // Non-connecting -> Connecting:
+        // - Establish XPC
+        // - Run `onStart` closure
         case (_, .connecting):
+            onStart?()
             xpc.connect()
             xpc.ping()
             tunnelState = .connecting

From a354ebebc32e6704048bb67c81db552c19f251c9 Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Mon, 14 Apr 2025 12:25:37 +1000
Subject: [PATCH 06/10] review

---
 Coder-Desktop/Coder-Desktop/State.swift       | 13 +++-------
 .../Coder-Desktop/Views/VPN/VPNMenuItem.swift |  4 +--
 Coder-Desktop/CoderSDK/Deployment.swift       | 16 +-----------
 Coder-Desktop/CoderSDK/Util.swift             | 25 +++++++++++++++++++
 Coder-Desktop/CoderSDK/WorkspaceAgents.swift  | 16 ++++++++++++
 5 files changed, 48 insertions(+), 26 deletions(-)
 create mode 100644 Coder-Desktop/CoderSDK/Util.swift
 create mode 100644 Coder-Desktop/CoderSDK/WorkspaceAgents.swift

diff --git a/Coder-Desktop/Coder-Desktop/State.swift b/Coder-Desktop/Coder-Desktop/State.swift
index fade6cc..b617940 100644
--- a/Coder-Desktop/Coder-Desktop/State.swift
+++ b/Coder-Desktop/Coder-Desktop/State.swift
@@ -157,15 +157,11 @@ class AppState: ObservableObject {
 
     public func refreshDeploymentConfig() async {
         if hasSession {
-            do {
-                let config = try await client!.sshConfiguration()
-                hostnameSuffix = config.hostname_suffix ?? Self.defaultHostnameSuffix
-            } catch {
-                // If fetching the config fails, there's likely a bigger issue.
-                // We'll show an error in the UI if they try and do something
-                logger.error("failed to refresh deployment config: \(error)")
-                return
+            let res = try? await retry(floor: .milliseconds(100), ceil: .seconds(10)) {
+                let config = try await client!.agentConnectionInfoGeneric()
+                return config.hostname_suffix
             }
+            hostnameSuffix = res ?? Self.defaultHostnameSuffix
         }
     }
 
@@ -194,7 +190,6 @@ class AppState: ObservableObject {
         static let hasSession = "hasSession"
         static let baseAccessURL = "baseAccessURL"
         static let sessionToken = "sessionToken"
-        static let hostnameSuffix = "hostnameSuffix"
 
         static let useLiteralHeaders = "UseLiteralHeaders"
         static let literalHeaders = "LiteralHeaders"
diff --git a/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift b/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift
index 804828a..0b231de 100644
--- a/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift
+++ b/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenuItem.swift
@@ -58,8 +58,8 @@ struct MenuItemView: View {
         var formattedName = AttributedString(name)
         formattedName.foregroundColor = .primary
 
-        if let lastDot = formattedName.range(of: ".", options: .backwards) {
-            formattedName[lastDot.lowerBound ..< formattedName.endIndex].foregroundColor = .secondary
+        if let range = formattedName.range(of: ".\(state.hostnameSuffix)", options: .backwards) {
+            formattedName[range].foregroundColor = .secondary
         }
         return formattedName
     }
diff --git a/Coder-Desktop/CoderSDK/Deployment.swift b/Coder-Desktop/CoderSDK/Deployment.swift
index cca6f04..d39a2a7 100644
--- a/Coder-Desktop/CoderSDK/Deployment.swift
+++ b/Coder-Desktop/CoderSDK/Deployment.swift
@@ -8,14 +8,6 @@ public extension Client {
         }
         return try decode(BuildInfoResponse.self, from: res.data)
     }
-
-    func sshConfiguration() async throws(SDKError) -> SSHConfigResponse {
-        let res = try await request("/api/v2/deployment/ssh", method: .get)
-        guard res.resp.statusCode == 200 else {
-            throw responseAsError(res)
-        }
-        return try decode(SSHConfigResponse.self, from: res.data)
-    }
 }
 
 public struct BuildInfoResponse: Codable, Equatable, Sendable {
@@ -27,10 +19,4 @@ public struct BuildInfoResponse: Codable, Equatable, Sendable {
             .firstMatch(in: version, range: NSRange(version.startIndex ..< version.endIndex, in: version))
             .flatMap { Range($0.range(at: 1), in: version).map { String(version[$0]) } }
     }
-}
-
-public struct SSHConfigResponse: Codable, Equatable, Sendable {
-    public let hostname_prefix: String?
-    public let hostname_suffix: String?
-    public let ssh_config_options: [String: String]
-}
+}
\ No newline at end of file
diff --git a/Coder-Desktop/CoderSDK/Util.swift b/Coder-Desktop/CoderSDK/Util.swift
new file mode 100644
index 0000000..4eab2db
--- /dev/null
+++ b/Coder-Desktop/CoderSDK/Util.swift
@@ -0,0 +1,25 @@
+import Foundation
+
+public func retry<T>(
+    floor: Duration,
+    ceil: Duration,
+    rate: Double = 1.618,
+    operation: @Sendable () async throws -> T
+) async throws -> T {
+    var delay = floor
+
+    while !Task.isCancelled {
+        do {
+            return try await operation()
+        } catch let error as CancellationError {
+            throw error
+        } catch {
+            try Task.checkCancellation()
+
+            delay = min(ceil, delay * rate)
+            try await Task.sleep(for: delay)
+        }
+    }
+
+    throw CancellationError()
+}
diff --git a/Coder-Desktop/CoderSDK/WorkspaceAgents.swift b/Coder-Desktop/CoderSDK/WorkspaceAgents.swift
new file mode 100644
index 0000000..3420af7
--- /dev/null
+++ b/Coder-Desktop/CoderSDK/WorkspaceAgents.swift
@@ -0,0 +1,16 @@
+import Foundation
+
+
+public extension Client {
+        func agentConnectionInfoGeneric() async throws(SDKError) -> AgentConnectionInfo {
+        let res = try await request("/api/v2/workspaceagents/connection", method: .get)
+        guard res.resp.statusCode == 200 else {
+            throw responseAsError(res)
+        }
+        return try decode(AgentConnectionInfo.self, from: res.data)
+    }
+}
+
+public struct AgentConnectionInfo: Codable, Sendable {
+    public let hostname_suffix: String?
+}

From 75f17caaac1786cfdca642d2205350a7ea820a7c Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Mon, 14 Apr 2025 12:26:46 +1000
Subject: [PATCH 07/10] fmt

---
 Coder-Desktop/CoderSDK/Deployment.swift      | 2 +-
 Coder-Desktop/CoderSDK/WorkspaceAgents.swift | 3 +--
 2 files changed, 2 insertions(+), 3 deletions(-)

diff --git a/Coder-Desktop/CoderSDK/Deployment.swift b/Coder-Desktop/CoderSDK/Deployment.swift
index d39a2a7..b88029f 100644
--- a/Coder-Desktop/CoderSDK/Deployment.swift
+++ b/Coder-Desktop/CoderSDK/Deployment.swift
@@ -19,4 +19,4 @@ public struct BuildInfoResponse: Codable, Equatable, Sendable {
             .firstMatch(in: version, range: NSRange(version.startIndex ..< version.endIndex, in: version))
             .flatMap { Range($0.range(at: 1), in: version).map { String(version[$0]) } }
     }
-}
\ No newline at end of file
+}
diff --git a/Coder-Desktop/CoderSDK/WorkspaceAgents.swift b/Coder-Desktop/CoderSDK/WorkspaceAgents.swift
index 3420af7..4144a58 100644
--- a/Coder-Desktop/CoderSDK/WorkspaceAgents.swift
+++ b/Coder-Desktop/CoderSDK/WorkspaceAgents.swift
@@ -1,8 +1,7 @@
 import Foundation
 
-
 public extension Client {
-        func agentConnectionInfoGeneric() async throws(SDKError) -> AgentConnectionInfo {
+    func agentConnectionInfoGeneric() async throws(SDKError) -> AgentConnectionInfo {
         let res = try await request("/api/v2/workspaceagents/connection", method: .get)
         guard res.resp.statusCode == 200 else {
             throw responseAsError(res)

From ba2d732bb092457795a82060cdd8276ffe5edda8 Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Mon, 14 Apr 2025 18:02:59 +1000
Subject: [PATCH 08/10] fixup

---
 Coder-Desktop/Coder-Desktop/VPN/VPNService.swift | 10 +++++-----
 1 file changed, 5 insertions(+), 5 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
index 211bb28..c3c1773 100644
--- a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
+++ b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
@@ -183,16 +183,16 @@ extension CoderVPNService {
         // Connected -> Connected: no-op
         case (.connected, .connected):
             break
-        // Non-connecting -> Connecting:
-        // - Establish XPC
-        // - Run `onStart` closure
+        // Non-connecting -> Connecting: Establish XPC
         case (_, .connecting):
-            onStart?()
             xpc.connect()
             xpc.ping()
             tunnelState = .connecting
-        // Non-connected -> Connected: Retrieve Peers
+        // Non-connected -> Connected:
+        // - Retrieve Peers
+        // - Run `onStart` closure
         case (_, .connected):
+            onStart?()
             xpc.connect()
             xpc.getPeerState()
             tunnelState = .connected

From 26d2eb8169a967a445788ce71bd2efa916b3acf8 Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Mon, 14 Apr 2025 21:17:25 +1000
Subject: [PATCH 09/10] single cancelable refresh task

---
 Coder-Desktop/Coder-Desktop/State.swift | 19 ++++++++++++++-----
 1 file changed, 14 insertions(+), 5 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/State.swift b/Coder-Desktop/Coder-Desktop/State.swift
index b617940..3c1d1d3 100644
--- a/Coder-Desktop/Coder-Desktop/State.swift
+++ b/Coder-Desktop/Coder-Desktop/State.swift
@@ -155,19 +155,28 @@ class AppState: ObservableObject {
         }
     }
 
+    private var refreshTask: Task<String?, Never>?
     public func refreshDeploymentConfig() async {
-        if hasSession {
-            let res = try? await retry(floor: .milliseconds(100), ceil: .seconds(10)) {
-                let config = try await client!.agentConnectionInfoGeneric()
-                return config.hostname_suffix
+        // Client is non-nil if there's a sesssion
+        if hasSession, let client {
+            refreshTask?.cancel()
+
+            refreshTask = Task {
+                let res = try? await retry(floor: .milliseconds(100), ceil: .seconds(10)) {
+                    let config = try await client.agentConnectionInfoGeneric()
+                    return config.hostname_suffix
+                }
+                return res
             }
-            hostnameSuffix = res ?? Self.defaultHostnameSuffix
+
+            self.hostnameSuffix = await refreshTask?.value ?? Self.defaultHostnameSuffix
         }
     }
 
     public func clearSession() {
         hasSession = false
         sessionToken = nil
+        refreshTask?.cancel()
         client = nil
         reconfigure()
     }

From b6218fc55d1f64ca8c7de849d6c410075fef2922 Mon Sep 17 00:00:00 2001
From: Ethan Dickson <ethan@coder.com>
Date: Mon, 14 Apr 2025 21:21:49 +1000
Subject: [PATCH 10/10] logs

---
 Coder-Desktop/Coder-Desktop/State.swift | 11 ++++++++---
 1 file changed, 8 insertions(+), 3 deletions(-)

diff --git a/Coder-Desktop/Coder-Desktop/State.swift b/Coder-Desktop/Coder-Desktop/State.swift
index 3c1d1d3..3aa8842 100644
--- a/Coder-Desktop/Coder-Desktop/State.swift
+++ b/Coder-Desktop/Coder-Desktop/State.swift
@@ -163,13 +163,18 @@ class AppState: ObservableObject {
 
             refreshTask = Task {
                 let res = try? await retry(floor: .milliseconds(100), ceil: .seconds(10)) {
-                    let config = try await client.agentConnectionInfoGeneric()
-                    return config.hostname_suffix
+                    do {
+                        let config = try await client.agentConnectionInfoGeneric()
+                        return config.hostname_suffix
+                    } catch {
+                        logger.error("failed to get agent connection info (retrying): \(error)")
+                        throw error
+                    }
                 }
                 return res
             }
 
-            self.hostnameSuffix = await refreshTask?.value ?? Self.defaultHostnameSuffix
+            hostnameSuffix = await refreshTask?.value ?? Self.defaultHostnameSuffix
         }
     }