Macy's AmEx "Welcome Bonus" question

[unsungivy]

So, abiding by "thou shalt not leave any Welcome Bonus on the table", I'm trying to knock out the unexpected Welcome Bonus for the Macy's AmEx that I was notified about when I received my upgraded card in the mail.

Does anyone have experience with this? It's spend $500 outside of Macy's (by a date less than 3 months after I upgraded the card), get $50 Star Money.

I'm trying to determine if I "hit" that or not, and when I called the CSR had no idea what I was talking about, and kept trying use her knowledge of NORMAL Star Money earnings to tell me I'd be notified etc. She was unable to tell me if the purchases I had made thus far were "qualifying" purchases or not.

The flyer for the Welcome Bonus itself states "Spend $500 in purchases on your Macy's American Express Card, less returns and other adjustments, outside of Macy's, Macy's Backstage and macys.com, excluding cash advances. Offer expires 11/30/2021. Bonus points will be issued within 2 billing cycles after offer expiration."

Seeing as I have better cards for pretty much everything, I'm trying to minimize my lost "opportunity cost" and use it for things that I would normally default to a flat-rate card for. I've made a few purchases that should be fine, but the lion's share come from Staples (for gift cards), and Venmo.

Since it's technically an AmEx... will it count the Staples purchase? I know AmEx normally does not for Welcome Bonuses, but is that only true for AmExs via AmEx? What about Venmo? The only thing the wording excludes is cash advances, but since these things are iffy, I was trying to verify if they counted, and as stated, CSR was utterly unhelpful.

Has anyone attained this Welcome Bonus, and what was your experience? Thanks!

[coldfusion]

In this case, American Express is just the servicing payment network.  Citibank Retail Services is the actual issuer and it's up to them to determine if the Staples purchases would or wouldn't count toward the welcome bonus.

I can't directly speak to whether or not Citi will count those Staples purchases but a) as a general rule of thumb relying on gift card purchases to meet the spend requirement of a signup or other spend-incentive bonus is a risky proposition, and b) Citi Retail Services does specifically exclude gift card and similar cash-like transactions from counting toward the spend thresholds set for their Sears Mastercard spend-incentive bonuses.

[FinStar]

OP, as mentioned upthread, if you want no complications with receiving the promotional/upgrade SUB, place organic purchases that won't be as risky. Citi Retail & DSNB can be quirky when it comes to specific promotional offers.

[unsungivy]

Yeah... organic purchases are sort of hard to meet when I'm so set up for much higher, worthwhile points or cashback on most things now! It's a massive opportunity cost to use it for most things right now. Darn you Marriott Brilliant for 10x PayPal and AmEx Plat for 15x Restaurants, etc.! Especially since I discovered that these "outside of Macy's" purchases wouldn't advance my yearly spend for rank; at least that I could have sort of justified. I have had game plans for the other Welcome Bonuses recently, but this opportunity was unexpected so I couldn't/didn't plan for it ahead of time (I never saw anyone mention about a welcome bonus with this upgrade anywhere else on the forums).

Trying to find the few things I would ONLY get 2-3% on... they're few and far between atm! At least within the mere 2 month long window that they gave me... ugh. First world problems!