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I did a $15 payment (to test it first) towards mortgage with no problem. No cash advance, did it with my Arrival + and was coded as:
BUSINESS SERVICES NOT ELSEWHERE CLASSIFIED
I talked to chargesmart and they said they send payments to the companies as if there were sent from a checking account...ACH i think it's called.
I will do this only once on my second Venture coming in the mail this week at full mortgage amount to complete my $3k spending and transfer the 40k points to my other Venture to credit $400 to a purchase i did for plane tickets.
Hope this helps.
I feel for you OP, You were just trying to do someone a favor and it didn't work out as you thought it would. I've done this same scenario before, except I helped a friend pay a past due bill that had gone into collections. It was a $540 bill. The whole board on MYFICO said "Hope Your okay with losing a friend!, WHAT A SILLY DECISION!" I did it anyway and because i don't believe the people that I choose to be my friends are innately a**holes, my friend paid me back in a less than 30 days and I gave him 2 months, he also paid the interest included.
Hopefully the person you helped out proves you wrong and pays you back the whole thing, including that nasty fee.
I dropped Barclay's and never looked back. Discover charged me for a cash advance for using it to pay my opening account for DCU. Explained it and they removed it.