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Hi Dan,
There are a couple of things that could have happened. One common one is that the Digest’s cron job goes missing. I’m not sure why, but disabling/re-enabling the plugin usually fixes it. You can check if this is the case by following the steps outlined here: https://usestrict.net/bbpress-notify-no-spam-digests-documentation/#triggering-mailouts
Now, when you say that using the Dry Run tool just makes it spin, that’s a bit harder to troubleshoot. If you open the browser inspector, you’ll see an error in the console. Most likely it’s a 500 error being thrown by the host. You should be able to find the message in the host’s error logs.
Please let me know what you find.
Cheers,
Vinny