darn outgoing email issue for OUTLOOK 2016

after getting extremely frustrated with *** on the live chat, clearly *** doesn't understand the issue, literally told me to contact Outlook. . .   then I call, after 30 minutes I gave up.  

SOMEBODY HELP PLEASE. . . 

My husband is a Boy Scout Leader for his local troop, he is also on many committees.  He sends lots and lots of emails to several people at once.  Imagine how frustrated he is.  

I've tried all the different settings, not a darn one works for outgoing.   so here are questons:

1) is this issue because we are using 2016 MS Outlook??

2) will there be a fix??

grrr thanks!