diff --git a/Coder Desktop/Coder Desktop/Views/VPNMenu.swift b/Coder Desktop/Coder Desktop/Views/VPNMenu.swift
index 0c70c1a..b41cdbb 100644
--- a/Coder Desktop/Coder Desktop/Views/VPNMenu.swift	
+++ b/Coder Desktop/Coder Desktop/Views/VPNMenu.swift	
@@ -5,6 +5,13 @@ struct VPNMenu<VPN: VPNService, S: Session>: View {
     @EnvironmentObject var session: S
     @Environment(\.openSettings) private var openSettings
 
+    // There appears to be a race between the VPN service reporting itself as disconnected,
+    // and the system extension process exiting. When the VPN is toggled off and on quickly,
+    // an error is shown: "The VPN session failed because an internal error occurred".
+    // This forces the user to wait a few seconds before they can toggle the VPN back on.
+    @State private var waitCleanup = false
+    private var waitCleanupDuration: Duration = .seconds(6)
+
     let inspection = Inspection<Self>()
 
     var body: some View {
@@ -16,7 +23,7 @@ struct VPNMenu<VPN: VPNService, S: Session>: 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 { await vpn.start() } else { await stop() }
                         }
                         }
                     )) {
@@ -86,11 +93,21 @@ struct VPNMenu<VPN: VPNService, S: Session>: View {
     }
 
     private var vpnDisabled: Bool {
-        !session.hasSession ||
+        waitCleanup ||
+            !session.hasSession ||
             vpn.state == .connecting ||
             vpn.state == .disconnecting ||
             vpn.state == .failed(.systemExtensionError(.needsUserApproval))
     }
+
+    private func stop() async {
+        await vpn.stop()
+        waitCleanup = true
+        Task {
+            try? await Task.sleep(for: waitCleanupDuration)
+            waitCleanup = false
+        }
+    }
 }
 
 func openSystemExtensionSettings() {