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Keeping the checkbox checked would be somewhat misleading, as it would imply that any update on the Gravatar side would get synced to pretalx. That is not the case – due to privacy concerns, we retrieve the image from Gravatar once, and then serve it ourselves. Checking the box again will start the sync again.
I can see a case for an interface that isn't a checkbox next to the "Retrieve profile picture", and instead something like a button, and I'd merge a PR making this change, but other than that, I'd consider this out of scope for now.
I don't see how this would violate the TOS of Automattic, who (as far as I can tell) do not have separate TOS for Gravatar. If, however, you can point out where pretalx violates the TOS of Gravatar/Automattic, I'd of course stop doing so immediately and disable our Gravatar integration! As that's a topic of legal bearing, please contact info at pretalx.com for further discussion.
Problem and impact
Editing our profile a second time shows the Gravitar button has oddly become unchecked.
Yes, there is a certain logic involved. But I would just keep it checked, once the user has checked it.
That way each time he goes to Edit My Profile, he needn't think "huh, didn't I tell it to use my Gravitar?"
Yes even if lower down it says it is indeed using it.
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