On my live site, tried sending email to everyone using the Mass Messaging extension to BuddyPress added by plugin ‘Mass Messaging in BuddyPress’. It appeared to send 100 of 132 messages and then stopped. Error log shows as below. Lots of these – looks like one each time an email should have been sent my the queue processor: Also the GD Mail Queue dashboard says: Last Queue Information Queue Started The site is experiencing technical difficulties. Please check your site admin email inbox for instructions. and I got an email from WP 5.2 saying “Your site is experiencing technical difficulty” etc. NB In case it is relevant, the message I sent included a colon, hyphen close bracket smiley, which got converted somewhere to a smiley icon. Amdisbling plugin for now so emails go the old way.