So I went back to Goodneighbor to talk with Hancock after saving Kent. Unfortunately I hadn't spoken with him since before the Bobbi mission, so my dialog with him was being rewarded for being loyal. And then instead of allowing me to discuss anything about The Silver Shroud, he just segues into the "companion or not" dialog. Crap! Any workarounds?

Get him as companion, talk to him few times, sleep, repeat, sleep repeat until it works. Took me a bit of attempts but it worked in the end

Great to know, thanks!

This quest does seem buggy. I couldn't progress with the Silver Shroud quest either at this point, but it went the other way for me. During the Big Dig quest I robbed Hancock and killed his pyromaniac lady friend, although he forgave me because I'm awesome. I resolved that quest seemingly with no problem. Hancock asked to be my companion and I turned him down and haven't spoken to him since.

When I returned to do the Silver Shroud quest and got to the part where I had an audience with Hancock as the Shroud, all Hancock would say was remarking about me not killing Bobbi No-Nose. I DID kill Bobbi, and the Big Dig quest was resolved, but now I can't open the dialogue tree with Hancock at all. He doesn't react to me being the Silver Shroud, and I can't interact with him except to shoot him in the face, which--although cathartic--accomplishes nothing. So I can't progress with the Silver Shroud quest.

I actually hadn't started the Silver Shroud quest but been wanting to (because I have all of the Silver Shroud items. Heck, the outfit is my favorite outfit right now and is the one I've been wearing all of this time). How do you start it? I also already did the digging quest and have Hancock at The Castle right now though...

Go talk to the ghoul operating the radio in the Memory Den. You might have heard his broadcast while in the Goodneighbor area.

You should start it, once you turn in the costume and get it back it gets a DR of 42 and Humans do 15% less damage

Confirmed.

All I had to do was lead him to a settlement, tell him to stay, sleep (though I didn't actually test with sleeping and then without, fyi) and then approach him, choose "talk" and he finished the quest.

Spoiler below for this quest...






Has anyone managed to complete this and keep him alive? I had Charisma around 9 and no matter what they always ended up killing him in the standoff. Tried at least 6 or 7 times.

Kent, you mean? Yeah. It took me a couple times but with the right gun (sniper for me), perks and mashing of the 'Q' button I managed to intimidate the rest of the henchmen away and save Kent.

Aye, VATS in on Sinjin's head and execute critical, then VATS on his lady friend. the other two enemies focus their fire on you

You need to fully embrace your persona as the Silver Shroud.

Forget about attempting the persuasion or intimidation options, if you answer every single speech option as the Silver Shroud, then the henchmen will decide that you really are the Silver Shroud, get intimidated and bug out leaving Sinjin all on his lonesome. Then all you need to do is shoot Sinjin in the head with a big gun till he stops arguing.

Additionally, if you have Nick with you for this mission, he really really loves you answering as the Shroud.

Additionally additionally, this causes the henchmen to become non hostile towards you, if you kill them anyway it will be classed as a murder.