Sorry to dig up an old thread, but I didn't see much point in starting a new one.
I didn't actually realise that you couldn't load railcards onto contactless; I asked someone at the station to do it with my Gold Card last week (I swapped my usual season ticket for a cheap one to retain the benefits, but now I need to pay for London travel individually for the first time in years, so I'm a bit rusty on this!).
They told me to phone TFL. So I phoned TFL, and they said it was not possible and I'd have to get an Oyster card. So this morning on my now-weekly visit to London I purchased an Oystercard, and they said I needed to register it. So I registered it on the site on my phone there and then, but this rejected me as I hadn't used it yet. So I went back to the staff member who said that it takes 48 hours from purchase to register (I don't understand that?). Thus after wasting so much time going through all of this, I'm still nowhere near getting a discount loaded onto my fares in London.
Does anybody know if TFL are going to make this any more user-friendly anytime soon? Or am I missing a trick somewhere?