I began riding Amtrak regularly in January 2003. I take the Texas Eagle, Lakeshore Ltd, Capitol Ltd, and the Crescent to get to Houston, TX several times a year.
For the last couple of years I have always traveled in a reserved roomette. But on my first few trips with Amtrak I traveled in coach. On all of these trips, I attempted to upgrade to a roommette. I asked the conductor when he came around collecting tickets if there were any roomettes available.
He always said he would check and get back to me. In each case, the conductor never returned with an answer. This happened on about 12 different trips in 2003 & 2004. I was never, ever able to upgrade on any trip. I of course asked repeatedly, and no one ever came back with an answer.So, I now just reserve a roommette. I'm glad other had better luck than me.
Bill B)
I've often encountered the same thing. In my experience, it seems that most conductors are annoyed by on board upgrades, but that's just my impression. In a few cases, I've had them actually encourage the upgrade, but in most cases, I'll mention something to the conductor when he collects the ticket, and I usually have to go track him down in the cafe car about 30 mins to an hour later to "seal the deal," as it were. In once case on the Capitol, he was "holding" a deluxe bedroom "in case of complaints about other rooms." I don't know if that's technically allowed, but he was doing it, until I asked, "so you're deadheading a room indefinitely as a contingency when someone is willing to pay for it now?" I was in the room in short order. ;-)
But in all cases, I've been able to get a yay or nay as to room availability simply by doing the following:
1). Ask the conductor about upgrading when he collects the ticket
2). He'll most likely say that he has to take care of some paperwork first, so I'll ask when I should check back with him. He'll usually say about 30 minutes.
3). 30-60 minutes later I'll head into the cafe to track him down.
And that usually works for me.
-Rafi