We also had this problem and came here to look for a solution. Does it have to do with a WP Cron setting do you think? We tried searching through settings to see what it could be. We are using Easy WP SMPT and are hosted on WP Engine.
This may be the bug that was fixed in Event Espresso 4.9.16 where selecting large groups of registrations to trigger messages threw an exception. You can update to the latest version of Event Espresso 4 to get that fix.
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