On the Monday before Thanksgiving, Delta sent a cheery email with an upbeat headline: Big News: Complimentary Upgrades Are Expanding.  The short embedded message read: “Starting April 1, 2018, you’ll be eligible for Unlimited Complimentary Upgrades to Delta One on all domestic flights. You’ll be notified of your Complimentary Upgrade within hours of your departure time.”

I took it at face value.  After all, no asterisks or small print appeared to spoil the supposed happy news.  Good old Delta, always doing nice things for Five Million Miler Lifetime Platinums like me.  This Delta One upgrade goodie on top of being eligible for domestic First Class and Comfort+ with no catch?

Of course there’s always a catch, which I learned of on Tuesday when I checked in for my family’s flight on Wednesday RDU/MSP at 6:00 AM.  I am traveling with my wife and 14 year old daughter.  Plenty of Comfort+ and First Class seats were still available even on the Wednesday before Thanksgiving, usually the busiest travel day of the year, and my status as a Lifetime Platinum hasn’t changed.

The Delta system asked me as I was checking the three of us in whether I wanted to upgrade to Comfort+ for $29 each, or $87 altogether—on top of paying a steep fare of more than $400 each for the short round trip Raleigh to the Twin Cities, tickets I had purchased months before.

I recalled that Delta doesn’t allow comp upgrades for more than two (the elite flyer plus one other person), not even to Comfort+, and thus I expected to pay for my daughter’s Comfort+ upgrade.  But I didn’t expect to pay for all three.  I phoned the elite line to help me understand.

Turns out that Delta has a marvelous Catch-22 rule built into its upgrade program:  If more than two are on the record, then Delta doesn’t recognize even the Five Million Miler for upgrades of any kind, not even to Comfort+, which is why the system asked me to pay for all three Comfort+ upgrades.  It is blind to my status if my wife and daughter are both on the record with me.

The nice Delta agent offered to divide me, or me plus one other, out of the record which would have signaled the Delta system to “see” my status and perhaps offer an upgrade.  However, that leaves the third traveler—either my wife or daughter—stranded in a single seat somewhere back in coach.

Of course we might lucky and find three seats together if I paid $29 each way for the single traveler to be in Comfort+.  But there’s no guarantee of that, and you don’t know until you agree to divide out the records and try to seat everyone together.  By then it’s too late to revert to the original threesome if no seats are available for the single upgrade.  That’s not a risk I wish to take when my family is traveling together, especially not on the busiest travel day of the year.  I get the Delta message: Don’t travel with your family if you want upgrade perks.

So we will remain together seated tightly-confined way back behind Comfort+, where Delta has assured me and my family of an uncomfortable start to our Thanksgiving holiday.