Ok, I’ll try to explain what I have going on:
I am running the most current version of WordPress on HostGator using Portfolio press and all plugins, themes, etc. are up to date.
I was using the Subscribe2 plugin to send notifications but didn’t like it’s functionality, so I switched to your plugin. Subscribe2 is still installed but deactivated.
I am using WP_Members to restrict access to some content on the site. If someone does not have an account, they cannot follow the link emailed to them as it will give them a denied access message and prompt a login. When I ran my last test run that worked, I sent it as “unblocked” as it was a general message saying our system was running again.
I have used the “check email” plugin to test that emails are being sent and received properly, which resulted in a successful test. (it is still active)
I am also running WP missed schedule to help run regular backups as our traffic is a bit low at the moment, but I imagine this would help with any email cron jobs.
I also have WP SMTP running which enables me to bypass the wordpress email engine and instead send from our outlook365 server from a specified email address created for the website.
the last successful email was sent 6/23/15 and I confirmed it went out by talking to recipients and even getting some email bouncebacks to the outlook email account saying some email addresses weren’t entered correctly into user profiles.
please let me know if you need anything more specific. Thanks a lot for your help!