The Silver Shroud

The Silver Shroud is a quest in Fallout 4.

Detailed walkthrough

 * 1) Listen to Silver Shroud radio east of Diamond City to get the quest.
 * 2) Go to the Memory Den and speak to Kent Connolly and agree to find the suit. A persuasion check can be passed to get some caps up front.
 * 3) Go to Hubris Comics, it has a lot of unique loot, but also a lot of ghouls, so be wary.
 * 4) (Optional) On the second floor, A Silver Shroud photo can be found in a display case next to a baseball bat and ball.  On the top floor, the script for the show can be found next to the producer's terminal.  Also on the top floor, in the studio BEHIND the backdrop, the prop Silver Shroud gun can be found.
 * 5) Grab the suit from the studio and return to Kent.
 * 6) Kent will give the player character the reward, plus a little extra for getting the rest of the items.  After that he will offer the player character the suit and gun, and a few stimpacks after a persuasion check.  the player character can also decline the offer, but that will leave the quest open with instructions to talk to Kent.
 * 7) Once the offer has been accepted, Kent gives the player character the suit back and the Silver Shroud Submachine Gun, and instructions to listen to the Silver Shroud Radio station while in Goodneighbor. The Silver Shroud Submachine Gun is not required for any of the following parts of the mission.
 * 8) While outside in Goodneighbor and wearing the Silver Shroud suit, listen to the radio to get the next few targets.
 * 9) The first target is Wayne DeLancey, behind the Hotel Rexford, who is accused of murder.  The player character will have the option of asking Wayne about the murder, which Wayne will confess to if the player speaks as the superhero, or threatens him.  Once Wayne is dead leave a calling card on his corpse.
 * 10) The next target is AJ the pusher near Bobbi's place behind Guns, Guns, Guns. AJ has been selling drugs to kids.  AJ has two bodyguards with him and gives the player character the option to take a bribe to leave him alone.  Kill AJ and leave a calling card.
 * 11) The next target is Kendra.  To reach her, ask Whitechapel Charlie in The Third Rail where she is.  He'll ask for money but speaking like The Silver Shroud will convince him to give the info for free.
 * 12) Kendra is in Water Street Apartments just south of Goodneighbor.  There will likely be enemies along the way, and there are raiders inside the building.
 * 13) . On reaching Kendra she will tell the player character that the player character is in over their head, and will then attack. Kendra also has a contract on her body once killed.  Leave the calling card on her and head back to Goodneighbor.
 * 14) (Optional) On taking the contract from Kendra the player character can go to the National Guard training yard to kill Shelly Tiller.  Once that's done, the payment can be collected just outside Goodneighbor.
 * 15) On returning to Goodneighbor, the radio station will broadcast that John Hancock wants to meet with The Silver Shroud.  Go the the meeting and he will task the player character with taking down Northy and Smiling Kate. The previous targets were working for them, and they all work for Sinjin.  the player character can pass a couple persuasion checks, but it requires breaking character.  No idea if there's consequences for breaking character with Hancock.
 * 16) Smiling Kate is across the river to the north of Goodneighbor.
 * 17) Smiling Kate is at the quest marker with a few of Sinjin's men, kill them.
 * 18) Go to the next quest marker to find and kill Northy, on his body will be a holotape, listen to it to find out that Sinjin has targeted Kent.
 * 19) Go back to Goodneighbor.  In the Memory Den Kent will be kidnapped, and his door locked, before the player character get there.  Kent is taken by Sinjin to Milton General hospital, go there and beware the Gunners outside.
 * 20) Watch for raiders and traps in the building.  Head down to the basement, then follow the winding path.  Take the last elevator to confront Sinjin.  From here there's several options.

Option 1: Shoot first
It is very difficult to save Kent as both Sinjin and Avery will immediately target him, but it is doable.

Option 2: Intimidation
Speak as The Shroud and Sinjin's bodyguards will run. The same thing can be accomplished with a difficult speech check for more XP.

Option 3: Sacrifice
A difficult persuasion check can make Sinjin target the player character instead of Kent.

Option 4: Begging
Sinjin can be asked to spare Kent, but he just kills Kent immediately.

21. Once Sinjin and his goons are defeated, speak with Kent, if he is alive. He can be persuaded to continuing to work for The Silver Shroud or not, but it doesn't seem to make a difference. Don't forget to grab the steamer trunk in the raised office behind Kent.

22. Go back to Goodneighbor and speak with John Hancock to collect the reward. Talking with Kent again, he says that he will work up another job for the Silver Shroud later.

Bugs

 * After saving Kent from Senjin, he may become stuck in the hospital in the same location he was held prisoner. If this occurs, it appears that he will no longer upgrade the Silver Shroud armor. Speaking to Kent about the upgrades before he returns to Goodneighbor is a possible cause. Possible Fix is pushing him into the elevator and then going up a floor (though just leaving him there might also work). He'll walk himself back to Goodneighbor after that, meeting the player character along with Hancock.
 * The player may not be able to trigger the quest dialogue with Hancock if he is an available companion. Possible fix is to make Hancock the active companion and equip Silver Shroud outfit. Quest dialog starts after using "Talk" choice
 * "Search body for clues" may not check off after searching Northy's body leaving the player with a quest blip over his body. However the player character may progress through the rest of the quest regardless no harm done.
 * "Kill Northy" has been an issue with some computers, where loading Northy crashes the game.
 * The nurse robots may still spawn in Milton General Hospital when going to save Kent, causing Senjin to kill him before the player character gets to them.
 * Player may kill Wayne Delancy and not be able to leave calling card.

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