Using older versions of Outlook for Mac in business environments
Thanks, ArshadKhan19. My wife suggested the same thing, but that was not acceptable to me, as I will be doing regular mailings to this contact group and it would be too difficult to track if in smaller groups. I was sure the size was not the problem.
Unfortunately, Outlook does not identify which email addresses are invalid, which would have saved me about 3.5 hours of frustration. It could have send out the message to all the valid addresses and kicked back the invalid ones, since it obviously knew they were there. They could also color code the invalid address when in the group dialogue box, but not happening!
I recalled that when one types in a name and email in the "To:" box, Outlook will color code the address if it can't use the address. Wish it would do this when in the group contact list!!
I expanded the group and put all 340 names individually into the "To:" box. What I found was two names that came up highlighted in a different color with a question mark next to them. Why it wouldn't do this in the group dialogue, is any ones guess! I was able to closely inspect these names and found out there was an extra blank space after .com. I erased these spaces, re-saved the group, deleted the individual names and put the full group back in (which bcc's the names). This worked and I was able to get my email off, although after considerable research and frustration.
If Outlook knows these two email addresses were bad, it is beyond me to understand why it would hang up on the other 338 names!