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Steve will correct me if I am wrong but I do believe that the check is made periodically so maybe it has not performed that lookup yet. Or - maybe your CRON tasks are not working if that is the method it uses...
The alternative, of course, is to download the latest from our downloads page and then manually ftp it up to your site. Same end result just a little slower.
But as to the original question we certainly have successfully been using X rated gravatars in all of our test cases with that updated version.
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SWORDFISH
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As I said - I will need Steve to chime in on how the system works but I don't believe that transient controls anything. There IS a WP CRON task defined named 'wp_update_plugins' scheduled to run twice daily. My guess is that yours is not running at all. But that is just a hunch and based on the fact that WP Cron can fail so apparently easily and regularly.
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