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connect-windows-vm

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UpdatedMay 4, 2026 at 20:29

Use when the user wants to RDP into a Windows GCE VM through IAP — open an existing saved connection, or set one up from scratch and launch the Microsoft 'Windows App' RDP client. Triggers on phrases like "RDP into <vm>", "open Windows VM", "connect to my Windows server".

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kvysotskyi

kvysotskyi/go-iap-mac

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SKILL.md

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name	connect-windows-vm
description	Use when the user wants to RDP into a Windows GCE VM through IAP — open an existing saved connection, or set one up from scratch and launch the Microsoft 'Windows App' RDP client. Triggers on phrases like "RDP into <vm>", "open Windows VM", "connect to my Windows server".

Connect to a Windows GCE VM via IAP

Preconditions

Confirm auth: call auth_check. If authenticated is false, run auth_login (opens a browser; user must finish the OAuth flow).
Confirm the user has the macOS RDP client: call windows_app_check. If not installed, tell the user to install "Windows App" from the Mac App Store before continuing.

If the user already has a saved connection

connections_list → find the entry by displayName / instanceName.
tunnels_active → if a tunnel for that connection is already running, skip step 3.
tunnels_start_for_connection { connectionId } → wait for status running.
(Optional) windows_reset_password { connectionId, saveToKeychain: true, updateBookmark: true } — only when the user explicitly asks to rotate. Always confirm first — this invalidates the previous password instantly on the VM.
freerdp_launch { connectionId } if FreeRDP is installed (freerdp_check), otherwise windows_app_open and tell the user to click the "IAP Tunnels" group bookmark.

If no saved connection exists yet

projects_list { filter } to locate the GCP project.
vms_list { projectId, filter } to find the VM. Confirm isWindows: true.
connections_add with platform: "windows". Default remotePort: 3389. Use a clear displayName (e.g. "prod-bastion-01 (us-central1-a)").
Continue from step 2 of "saved connection".

Pitfalls

Password rotation is destructive. Anyone who has the old password loses access immediately. Never rotate without explicit user confirmation.
The Windows guest agent reset takes ~30–60s; surface that to the user instead of looking like the call hangs.
tunnels_start_* may report port X is in use by another tunnel. Suggested alternative: Y — call tunnels_free_port and either reuse Y or update the connection's stored port via the desktop UI.

More from this repository

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connect-linux-vm

kvysotskyi/go-iap-mac

Use when the user wants to SSH into a Linux GCE VM through IAP — install their key on the VM if needed, start a tunnel, and either return the ssh command or open Terminal. Triggers on "ssh into <vm>", "give me a shell on", "open Linux VM".

2026-05-0420

debug-tunnel

kvysotskyi/go-iap-mac

Use when the user reports a tunnel that won't start, won't connect, drops, or shows status 'error'. Pulls the tunnel log buffer and walks through likely causes. Triggers on "tunnel broken", "RDP timed out", "ssh hangs", "why isn't my tunnel working".

2026-05-0420

onboard-new-vm

kvysotskyi/go-iap-mac

Use when the user wants to add one or more new GCE VMs as saved connections in IAP Tunnel Manager — including resolving project + zone + platform from natural language and choosing a sensible local port. Triggers on "add a new VM", "save these instances", "bookmark these for IAP".

2026-05-0420

rotate-windows-credentials

kvysotskyi/go-iap-mac

Use ONLY when the user explicitly asks to rotate, regenerate, or reset a Windows account password on a GCE VM. Use also when the user reports the saved password is stale and they consent to a fresh one. Triggers on "rotate password", "reset Administrator password", "I lost the Windows password".

2026-05-0420

name	connect-windows-vm
description	Use when the user wants to RDP into a Windows GCE VM through IAP — open an existing saved connection, or set one up from scratch and launch the Microsoft 'Windows App' RDP client. Triggers on phrases like "RDP into <vm>", "open Windows VM", "connect to my Windows server".

Connect to a Windows GCE VM via IAP

Preconditions

Confirm auth: call auth_check. If authenticated is false, run auth_login (opens a browser; user must finish the OAuth flow).
Confirm the user has the macOS RDP client: call windows_app_check. If not installed, tell the user to install "Windows App" from the Mac App Store before continuing.

If the user already has a saved connection

connections_list → find the entry by displayName / instanceName.
tunnels_active → if a tunnel for that connection is already running, skip step 3.
tunnels_start_for_connection { connectionId } → wait for status running.
(Optional) windows_reset_password { connectionId, saveToKeychain: true, updateBookmark: true } — only when the user explicitly asks to rotate. Always confirm first — this invalidates the previous password instantly on the VM.
freerdp_launch { connectionId } if FreeRDP is installed (freerdp_check), otherwise windows_app_open and tell the user to click the "IAP Tunnels" group bookmark.

If no saved connection exists yet

projects_list { filter } to locate the GCP project.
vms_list { projectId, filter } to find the VM. Confirm isWindows: true.
connections_add with platform: "windows". Default remotePort: 3389. Use a clear displayName (e.g. "prod-bastion-01 (us-central1-a)").
Continue from step 2 of "saved connection".

Pitfalls

Password rotation is destructive. Anyone who has the old password loses access immediately. Never rotate without explicit user confirmation.
The Windows guest agent reset takes ~30–60s; surface that to the user instead of looking like the call hangs.
tunnels_start_* may report port X is in use by another tunnel. Suggested alternative: Y — call tunnels_free_port and either reuse Y or update the connection's stored port via the desktop UI.