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Good question.

Two checks, that is it: once when you activate the key, and once when the menu bar app launches. Nothing in between, no background beacon, no check when you open a Pro feature. The CLI does not check at all unless you run whatcable --activate. What gets sent is the licence key and your Mac's hardware UUID, nothing else. The UUID is what enforces the two-Mac limit.

The grace period works off a single date: the last time a check succeeded. Pro stays unlocked while that date is less than 30 days old, and every launch with internet refreshes it. A check that fails because you are offline or my server is down changes nothing, it just does not refresh the date, so a spell offline…

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