Subscribe by email not queuing up messages

I am not able to get the plugin to queue up the emails. No logs, nothing failing just not happening. I've deactivated and reactivated. changed the times and am trying to get it to send a digest of the past week. I have had this work but it has been failing for almost a month now. This is a live production site. I had some issues with the email showing shortcodes and html in the past. I really need to get this working, can you help? The site error log has nothing at all pointing to this plugin or mail functionality. I am able to get the test email to send...

Please help, I've granted access already,

Best,
Ian