On May 31, 2020, a Windows certificate for Toggl Track Desktop expired and caused the app to stop working. Immediately after, we released a new version that fixed the problem.
If your Windows Desktop app is still failing to sync, please update it to the latest version and make sure you're on the "Stable" release channel.
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Please click on the chat bubble in the bottom right corner and start a conversation with Toggl Track Support if the Toggl Track desktop app refuses to work even after the update.