diff --git a/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncConfig.swift b/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncConfig.swift
index 345928b6..dc946c83 100644
--- a/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncConfig.swift
+++ b/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncConfig.swift
@@ -103,15 +103,6 @@ struct FileSyncConfig<VPN: VPNService, FS: FileSyncDaemon>: View {
                     // Opens the log file in Console
                     NSWorkspace.shared.open(fileSync.logFile)
                 }
-            }.task {
-                // When the Window is visible, poll for session updates every
-                // two seconds.
-                while !Task.isCancelled {
-                    if !fileSync.state.isFailed {
-                        await fileSync.refreshSessions()
-                    }
-                    try? await Task.sleep(for: .seconds(2))
-                }
             }.onAppear {
                 isVisible = true
             }.onDisappear {
diff --git a/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncSessionModal.swift b/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncSessionModal.swift
index d3981723..0e42ea0c 100644
--- a/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncSessionModal.swift
+++ b/Coder-Desktop/Coder-Desktop/Views/FileSync/FileSyncSessionModal.swift
@@ -8,7 +8,7 @@ struct FileSyncSessionModal<VPN: VPNService, FS: FileSyncDaemon>: View {
     @EnvironmentObject private var fileSync: FS
 
     @State private var localPath: String = ""
-    @State private var workspace: Agent?
+    @State private var remoteHostname: String?
     @State private var remotePath: String = ""
 
     @State private var loading: Bool = false
@@ -37,12 +37,12 @@ struct FileSyncSessionModal<VPN: VPNService, FS: FileSyncDaemon>: View {
                     }
                 }
                 Section {
-                    Picker("Workspace", selection: $workspace) {
+                    Picker("Workspace", selection: $remoteHostname) {
                         ForEach(agents, id: \.id) { agent in
-                            Text(agent.primaryHost!).tag(agent)
+                            Text(agent.primaryHost!).tag(agent.primaryHost!)
                         }
                         // HACK: Silence error logs for no-selection.
-                        Divider().tag(nil as Agent?)
+                        Divider().tag(nil as String?)
                     }
                 }
                 Section {
@@ -55,15 +55,16 @@ struct FileSyncSessionModal<VPN: VPNService, FS: FileSyncDaemon>: View {
                 Button("Cancel", action: { dismiss() }).keyboardShortcut(.cancelAction)
                 Button(existingSession == nil ? "Add" : "Save") { Task { await submit() }}
                     .keyboardShortcut(.defaultAction)
+                    .disabled(localPath.isEmpty || remotePath.isEmpty || remoteHostname == nil)
             }.padding(20)
         }.onAppear {
             if let existingSession {
                 localPath = existingSession.alphaPath
-                workspace = agents.first { $0.primaryHost == existingSession.agentHost }
+                remoteHostname = agents.first { $0.primaryHost == existingSession.agentHost }?.primaryHost
                 remotePath = existingSession.betaPath
             } else {
                 // Set the picker to the first agent by default
-                workspace = agents.first
+                remoteHostname = agents.first?.primaryHost
             }
         }.disabled(loading)
             .alert("Error", isPresented: Binding(
@@ -76,7 +77,7 @@ struct FileSyncSessionModal<VPN: VPNService, FS: FileSyncDaemon>: View {
 
     func submit() async {
         createError = nil
-        guard let workspace else {
+        guard let remoteHostname else {
             return
         }
         loading = true
@@ -87,7 +88,7 @@ struct FileSyncSessionModal<VPN: VPNService, FS: FileSyncDaemon>: View {
             }
             try await fileSync.createSession(
                 localPath: localPath,
-                agentHost: workspace.primaryHost!,
+                agentHost: remoteHostname,
                 remotePath: remotePath
             )
         } catch {
diff --git a/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift b/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift
index 207f0d96..83757efd 100644
--- a/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift
+++ b/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift
@@ -116,6 +116,12 @@ struct VPNMenu<VPN: VPNService, FS: FileSyncDaemon>: View {
             .environmentObject(vpn)
             .environmentObject(state)
             .onReceive(inspection.notice) { inspection.visit(self, $0) } // ViewInspector
+            .task {
+                while !Task.isCancelled {
+                    await fileSync.refreshSessions()
+                    try? await Task.sleep(for: .seconds(2))
+                }
+            }
     }
 
     private var vpnDisabled: Bool {

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