Dealing with flight delays and cancellations is challenging enough for travelers, but for some of us it has an additional complication: How to preserve our upgrades in case of rebooking. My trip to Alaska this week provided a textbook example.

As experienced and creative as I might be in handling flight disruptions, the weather is always my worst enemy. I’ve rarely felt more helpless than I did in Denver on my way to Anchorage. My plane had diverted to Colorado Springs because of a thunderstorm, and my departure time kept being pushed back more times than I cared to count…