“It’s Because You…Paid With Miles” – Delta’s New Excuse for Reservation Problems?

My family recently returned from our first Delta Air Lines trip of 2025. (We visited Grand Cayman for the first time. What a beautiful place!)

Our flights were terrific, the cabin crews were fantastic, and the LAX T3 Sky Club was a treat, as always. (The E Concourse Sky Clubs in Atlanta was a different story; lines were out the door in the F Concourse.)

There were a couple of interesting hiccups. When I questioned Delta reps, both gave me answers I’d never heard in my four decades of flying the airline: it seems SkyMiles bookings are the new scapegoats.

I talked with other longtime Delta flyers and some Delta contacts to see if there was something I was missing. All of this was news to them.

Checked Luggage at LAX

I am a Platinum Medallion and my wife is a Gold (after dropping down from Platinum, thanks to late-2024 snafu with upgrading one of her Delta Amexes). Most of our Delta flights are domestic trips. We’re used to having up to a three-bag, 70 pounds per piece luggage allowance per passenger on our itineraries. (For the record, we’ve never come close to maxing out either one of those figures.)

My wife, daughter, and I had four checked bags for our week-long trip to the island. Mrs. Carley and our kiddo were on one itinerary, and I was on the second.

We used SkyMiles to pay for the airfares and booked Main Cabin. We moved to Comfort+ shortly after we purchased the trip last fall.

I selected two checked bags at the LAX check-in kiosk. I was asked to pay $45 or 4,500 SkyMiles for the second bag. (The first was complimentary.)

Huh?

I figured between holding Platinum status and three Delta SkyMiles® American Express Cards that I’d receive more than that. But OK. Maybe it’s a system error. We are, after all, talking about Delta IT. (Which reared its ugly head several times during this trip.) Plus, I thought Delta considered the Caribbean as part of North America — where the three-bag allowance applies.

So, we went to the Sky Priority passenger agent assist line.

The rep told me my second bag wasn’t complimentary because “the trip was partially paid for with (Sky)Miles.”

That’s a new one. For an airline bragging that its cobranded credit cards account for 1% of the United States’ gross domestic product — and that its miles can be used to pay for practically anything — blaming the loyalty currency doesn’t really make much sense.

I wasn’t too worried because 1) it was “only” $45 and 2) my wife and daughter’s bags were still free, and 3) Delta is my The Platinum Card® from American Express’s selected airline for my airline incidental reimbursement. (Terms apply.)

I checked the Delta site for baggage allowances. Sure enough, Grand Cayman isn’t within the North American baggage rules (which is just the United States and Canada). It falls under international rules: one free checked bag (up to 50 pounds) per passenger in Main Cabin. The second bag is $45.

But why wouldn’t the agent just tell us that? Why blame the luggage allowance on an award booking?

Upgrade Ineligibility

I received an upgrade to First Class on our Atlanta to Grand Cayman flight. She and my daughter were way down the upgrade list.

I told my wife to enjoy the comfy seat, free meal, and cocktail refills (especially since that’s no longer a thing for me). But she wanted me to use the alone time and extra space to knock out some work — so I wouldn’t have to do as much during our vacation week.

CUT TO: several days later. I used the Fly Delta app to check in my wife and daughter’s return trip. I was asked if they wanted to request an upgrade to First Class.

Uh, sure?

I thought I’d already done that. After all, they were on the upgrade list for our previous flights.

When I tried requesting the upgrade, the Fly Delta app gave me an error.

I was pretty far down the upgrade list and knew I wouldn’t get upgraded. So, Mrs. Carley and Kiddo Carley most definitely would lose out, too. I didn’t want to spend our last vacation day in the Cayman Islands arguing with Delta or messaging them on the app.

A wonderful Delta rep checked us in at Owen Roberts International Airport in Grand Cayman (GCM). I asked her about the upgrade snag. She grinned and lifted her eyebrows before saying, “It’s because you paid for the trip with miles.”

I smiled back and said, “Really?”

She laughed and said yes. In other words, she seemed to know it was something other than an award booking issue. And she knew that I knew it was something other than an award booking issue.

Final Approach

Delta talks up its SkyMiles program as if it were the next great world currency. To be sure, SkyMiles does have its good qualities.

But does Delta instruct its employees to throw SkyMiles under the (Air)bus when problems arise? Is it poor training on upper management’s part?

Is this something you’ve experienced? Please share your experiences and thoughts in the Comments section below.

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