Only just realized this quest exist, as I did the Butcher's Bill quests ages ago and it never appeared. I thought if I at least did the Mercer Safehouse quest along with the first Randolph Safehouse it would get me somewhere, but so far, nothing. Even did the the first Jackpot quest moments ago and I'm still getting nothing.

So uh, am I not understanding something or is this some sort of bug?

Yeah, figured I wasn't going to get an answer. I've looked up this side quest near and far and there is absolutely no mention of anyone having an issue getting this to trigger. Guess I'll finish off the other Railroad radiant crap in hopes it shows. If not, well, I'll just have to sit with a thumb up my ass until it pops up I guess.

You need to complete the Butcher's Bill 2 quest (find Agent Blackbird), otherwise the quest does not trigger. Keep doing Railroad stuff.

I already said I did those quests ages ago. A lot of time has passed since then and it has never shown up since then. All I have left are a few more Randolph Safehouse quest, Concierge (which is just another boring radiant designed quest), and the Jackpot quests. Hell, I can't even get the second and third Jackpot quests because PAM isn't telling me anything.

Seriously, what the hell is wrong with these Railroad quests. They're almost as bad as the Minutemen quest, only that the Railroad leaves you staring at an NPC waiting indefinitely until you get a quest. Again, thumb up my ass.