Most VPN troubleshooting goes wrong in the same predictable way: three things get changed at once, and whatever happens next, nothing has been learned. The alternative is boring and effective — check one layer at a time, in an order that rules things out, and write down what each layer shows.
One boundary before starting: troubleshooting means finding where a problem lives, not working against anyone's rules. On a network you don't control, or a device your organization manages, the policies in place stay in place. If a managed device is part of the picture, your organization's IT function is part of the troubleshooting — and switching off device security tooling is never a troubleshooting step.
1. Device basics first
Start embarrassingly simple, because this layer resolves more than anyone likes to admit.
Restart the VPN client.
