Has anyone experienced situations where the SPG Crossover Rewards are not showing up for individual flights on Delta.com?

I am SPG Plat and so far have had good luck with upgrades (flying mostly RJ flights on fairly quiet routes) since obtaining Plat in August 2014. For each flight, pre-flight on Delta.com would show "Crossover Rewards Upgrade Requested" (or something to the effect) on the flight info/status page prior to checking in for the flight (i.e. T-1 and earlier). Once checked in, I would automatically be put on the upgrade list. Recently booked a flight directly with DL and this message does not show up when I look at the status/info page within my DL profile. Spoke with Delta and was told that it should automatically put me on the upgrade list upon checking in, but not 100% confident.

Curious to see if anyone else has experienced this recently, and, if so what success they've had in still getting the associated benefits (fee waiver, upgrade, etc.) once they fly? FWIW I've been upgraded as recently as May so it seems to be a new glitch?