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I assume you are getting an error for trial ,
In case you do , please refer :- https://helpx.adobe.com/manage-account-membership/cc-reverts-to-trial.html
Hope this answers your query !!!
Yes - several times.
I have an active subscription, and that works partially
the typekit, thinks i have a free account, so can't use any fonts
my account shows that I have two products the paid version and a free
version, it appears that typekit picks the last one.