Multiple Contacts not working

- in a test environment I have setup 3 contacts - made sure the "consent" is checked

- I assign those three contacts to a customer

- mark them to receive AR invoices

- send a single invoice and receive the error Mail delivery failed. Use the Email tab on the Company Profile screen to send a test email and confirm that all settings are correct

- change the test to only include a single contact of the three - send the invocie

- works

-determine it works to each of the contacts but only if I send one at a time

- as per ID:101708 I did the following

- in outlook :  file, options, mail tab, send messages, select the commas can be used to separate multiple messages

- in the a4w.ini in \runtime I change UseCommaAsEmailAddressSeparator=Yes from NO

- send test again

- do not receive error and appears to be working but instead of sending what I requested which is a single page invoice to 3 contacts, it send a handful of emails that were not related to the test I was running.  It was like changing these setting released some old queued emails and it did not solve the issue.  Now I am very nervous to try again.  The reason I know it has something to do with releasing old messages is that one customer was sent a invoice of over 300 pages - 300 invoices and those invoices date back in history farther back then the test data set I have.  IN my test data I have purged out all but the last 5 years.  This email that was sent sent invoices from over 15 years of history.  Needless to say very embarrassing.  

- Have others had issues with getting multiple contacts email sending to work?