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I am running a LTI tool for my university LMS on a Windows 12 Server and it was failing today. It turned out that the server time was about 20 minutes ahead of the correct time and my tool was timing out.

It was synched with the windows.com time service, which was 20 minutes ahead, and so were the NIST time services available. I ended up unsynching and adjusting. I don't see anyone else with the same issue anywhere, and the NIST internet clocks all look correct.

What could possibly be the issue here?

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Aha. My Windows Server is a VPS, so it does not really connect to any of the time services, but the time is probably set at the backend. So I contacted my VPS provider. Fortunately, it was not the timer service apocalypse.