Why did the send to my Outlook distribution group fail to go out?

Because PoliteMail does individual tracked sending, it changes the standard Outlook-to-Exchange distribution method. The sender must have permissions to access members of the distribution list.

Depending upon your system configuration, either the Outlook user account (From Address) or the PoliteMail Server Service Account must have access to members of the distribution group.

Sometimes, distribution groups can be “locked down” by your IT or Exchange Administrators, to prevent anyone in the company from sending to those lists, or to prevent the ability for users to expand the list and see the recipients on the list.

If you intend to send to mail-enabled Active Directory objects, please ensure the Exchange Service Account utilized for the PoliteMail Server has adequate permissions to access members of the distribution groups you intend to send to, and that the members of dynamic distribution groups have not been hidden (see below).

PoliteMail for Outlook

You may enable sending to a distribution group using an Alias (without EWS) by unselecting/unchecking Hide group from Exchange address lists.

Now, when the user enters the alias into the To: field, they should see:
[+] Aliasname@domain.com
The plus symbol prefixed to the list name indicates PoliteMail will be able to utilize the user’s credentials to access members and individually track the message, without EWS.