It’s been a good run, but my streak is broken. I have a Southwest flight this weekend and for the first time, I was not able to upgrade for free to the extra legroom seats at 48 hours before departure. So far this year, I was 7 for 7 in being able to do that.
To be fair, this flight was almost sold out even before the 48 hour mark, so it could be that people had no choice but to buy Choice Extra fares to get those seats assigned anyway. I will also note that when I first checked, there were 2 open middle seats in the first few rows and I would prefer a standard aisle seat and to keep the 3 of us traveling together in the same row. That, plus my son being under 15 years old and ineligible to sit in the exit rows further stacked the deck against us.

Still, I have been quite happy with my success year to date. While clearly a stop down from domestic first class, I would take a Southwest extra legroom seat experience over other US carriers’ extra legroom offerings.
It’s still possible some seats open up before takeoff, and I will continue to monitor it. Perhaps publishing this now will jinx some seats to become available!