Dropping Some Eaves

Achievements
I have run CoS over 20 times on multiple toons trying to get this achievement. I have killed all the sentries before they could alert anyone, i have disabled all the beacons, i have only used enforcers to draw away bodyguards from second boss. I have also picked the spy correctly on the first try on almost every single attempt. Yet i still have yet to see the correct dialogue needed to get this achievement. Is this achievement RNG based? Or just bugged? I know a GM hinted at it being RNG based but I just talked to one today who said there were specific steps to take. If so what are they?
I have had same issue....waited for one of the quests to be up as indicated in wowhead post on how to do achieve....killed all 5 sentries...disable all beacons before killing first boss....did the enforcer thing to get the 3 mini-boss kills before 2nd boss....talked to all the chatty rumormongers...got spy on first attempt...and still squaddush….I won't bother trying to get a gm to help...they always say "game is working as intended"...or I cannot help you plz look at wowhead…..it would be nice to know if it is rng
Only thing you didn't mention was whether you opened the door before the role play was over or not. I typically don't open the door until I hear the role play over. Some say it doesn't matter - some say it does.

Some say as long as you don't run into the room - did you open the door and run into the room?

Never heard about needing a quest to be up.

Also, even with not opening the door, it may be RNG.
I would love to get a blue post about this!
I struggled with this for weeks also. Wasn't sure what I was doing wrong. I'm still not sure honestly.

Not sure if if actually matters but I killed all the sentries and disabled the beacons. There is so much misinformation out there about this achievement a blue post about it would be nice.
There's a great post in WoWhead that explains how to do it.

I pulled several times solo and nothing, but then I did it in the specific way highlighted and I got it straight away.

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