Practice scenario

VPN will not connect

A student cannot reach a department file share from home. Work out what to collect, what to test, and when to escalate.

IntroductoryVPN

Updated 6 Aug 2026

HD-10482Student · emailMacBook Air (personal)

VPN keeps failing

“I've tried connecting three times and it keeps failing. I need to get to my research group's shared drive for a meeting tomorrow morning. It worked fine last week.”

Working from home
Meeting tomorrow at 9am

Decision 1 of 4

What is the most useful first question to ask?

What is the exact wording of the error, and at what point does it appear?
Have you tried reinstalling the VPN client?
Have you restarted your computer?
What version of macOS are you running?

This scenario is fictional. Ticket references, requesters, and messages are invented for training and do not correspond to any real request.