Originally Posted by JJTNY

I was over here looking for any data points on this tactic - over in one of the Awards FB groups someone reported being successful doing this but I have not had the chance to attempt yet.
With the current 100% bonus for buying points, it gets you decently close to full value of the gift card (to me anyway) while hopefully avoiding the issues people are reporting being able to use the darn cards at Hilton sites.

Of course, by buying points with the GCs one misses the extra points earned by paying with a gift card stacked with being HH Diamond etc, but still, with a 100% bonus I'm thinking I'd rather just get it done than finagle at the front desk.

I will likely try myself later when I have my stack of GCs in hand- but I will have to do a slightly modified version: I was only targeted for 80% points bonus on purchase.

My P2's Hilton account does have the 100% points bonus so I'm going to try on hers. (Can transfer the HH points back to me later if I need to.)
But the FB poster mentioned that the gift card name should match the HH account you are buying on for it to go through, so I may just have to wait until my own account has a better bonus in the future.