QuoteDo I need to make 1819808NNNN a Trusted Caller as well?
No. Trusted Caller will just add code to the inbounds routes to route calls to the AA. It will not have the callback feature. You are doing the same thing with the callback feature.
When a call arrives does it ring the phone port?
NNNN is replaced by the actual number?
Recheck the call history.
Sometimes a DigitMap doesn't work. I assume this is caused by a corrupted configuration. This has happened to me twice. A factory reset has always fixed the problem for me, but you already tried a reset.
Try this (parentheses removed):
{1819808NNNN:aa($1)},{ph}
If that doesn't work try:
{(Mcb):aa($1)},{ph}
User Settings -> User Define Digit Maps -> UDDM2
Label: cb
DigitMap: (1819808NNNN)