OK, so I went back to .bomb and cancelled the UDU upgrade request for the two segments in question, and then attempted to request a mileage upgrade. Only one choice in the drop-down menu: e500 upgrade!! Seemed to be the right procedure, but .bomb struck again.

Called the ICC to request mileage upgrade. After making sure I didn't need a rental car at a special discount, and noting such in my record , agent was ready to assist. I already knew RDU-ORD was NF2, so that was confirmed on request. Agent said she would waitlist me for the ORD-SFO segment which was NF0. Seeing that the flight is F9 A9, I'm feeling okay about chances at this point.

Inquired with agent about how upgrades would clear vs. UDU etc, and she said Oh, yes, you're on the priority waitlist!!

Just went back to check My Itin, and lo and behold original agent hadn't even placed me on the second segment waitlist at all...

Called India again and learned that You're upgrade is confirmed!! Um, sorry to be a bother, that's only for one of two segments, could you please finish the job of the first agent and waitlist me for the rest of the one-way upgrade...

Thanks for letting me vent.
higher_flyer

Should have predicted this one: second agent now has me waitlisted on the second segment but also withdrew another 15,000 miles as if to process a new upgrade request. The ICC is such a joke.