CF2018 Standard Odd Email Behavior

We have a CF2018 Standard server currently running 3 scheduled tasks.  Each task sends an email.  I noticed that, when recently adding the third task, which is scheduled to run first (2:10AM), after a scheduled restart of the CF App Server Service (9PM), it would run, but not send an email.  I decided to bracket this task with two other ones, 1 minute before and 1 minute after, which would send test emails.  With those two tasks in place, the 2:09AM task would run, but not send an email, the 2:10 task would run and would now send an email, and the 2:11 task would also run and send an email.  I disabled the CF App Server Service restart, and now all tasks send an email.  This leads me to think that, after a CF App Server Service restart, the first task to run that sends an email will not, in fact, send and email.

Has anyone seen this behavior in CF before?

TIA,

Scott

A clarification - It's not that the email does not send.  It's that the email isn't created.