Originally Posted by DZykan

I purchase Southwest and Marriott gift cards regularly from Staples.com for business travel and have not had a problem receiving both the 3x UR mall points and the 5x office supply points. I've seen a lot of people mentioning that one of the key flags for Chase is when there are many purchases right at $506.95 or a similar amount ($500 gift card plus the fee), so whenever I buy my gift cards I always buy a small random item to go along with my order, for example a pack of paper, pens, etc. I also buy different amounts each time, for example on my last order I purchased $650 in Southwest gift cards so that I'd have a purchase that wasn't right around an even hundred dollar mark, plus a $5 and change allen wrench set that I actually needed

Anyone have insight into whether this is a worthy strategy or if I just haven't been flagged yet? I put about $1k-$2k of gift cards on my Ink Plus card each month, but also about $1k or more of other spend...thoughts?