Have you logged a call with Sage Support?

Yes. It has gone all the way up to a technical application specialist from Alchamex/Sage

Everyone says it should work, but across 3 different servers and 2 fresh installs, it still doesn't work. The ticket has been ongoing for over a month now. Everyone seems stumped. For right now I am waiting for them to "test the problem on their end" but I figured in the meantime I can see if anyone else has experienced issues with 64 bit Outlook.

Have you tried using the SMTP / Exchange Server setup instead of the Outlook option?

That works for sending mail, but not for the address book, which is pretty important. Not to mention multiple users use it, and if I set the SMTP settings for one person, it actually sets it for all users, so that doesn't work for us. I appreciate the suggestion though!

How are you handling it now?

For now we have a second server setup with 32 bit. The problem with 32 bit, is it can only use >4gb of memory. Some of the reports they run are very large and crash/take up to 30 minutes to run. On 64 bit excel, it can utilize the entire 16gb of memory on the server, and reports run much, much faster, and don't crash. They just cannot email them using BI tools.

Catch 22

It's an error with the software, not a catch 22. It's not supposed to operate this way. Hence the support case, and my posting here. Thanks for trying to help.