I was trying to test the newsletter tool under the admin menu, and it seems to be not liking me in the the littlest bit.

I select a role (newletter), which has one user in it at the moment..

and even add an "additional Emails:"

Filled in From, Reply To and Subject

went into advance settings and changed the send actions to synchronous..

I get the following message on postback:

No Messages were sent, maybe due to empty roles.

It seems I've unknownly been having problems with this for a while as no one ever recieved the few news letters I've tried to mail out ...

I've verified that the smtp settings in the host settings is working by clicking on the little test link..

what am I missing?

Currently on 4.08.00

but think this has spanned a couple versions for me, since no one's ever recieved one of the news letters I've sent out... which hasn't been many, but would like to utilize the feature more for sure.

this sounds very weird, do you have any issues reported in your event log?

Did you test SMT Server configuration in Host Settings successfully?