The Silver Shroud

The Silver Shroud is a side quest in Fallout 4.

Detailed walkthrough
Be warned, going into Hubris Comics and collecting the outfit before activating the quest will cause it to stay inactive until speaking to Kent Connolly in the Memory Den

The Silver Shroud Awakens

 * 1) Listen to Silver Shroud Radio near Goodneighbor 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 Silver Shroud script can be found next to the producer's terminal.  Also on the top floor, in the studio BEHIND the backdrop, the Silver submachine gun prop can be found.
 * 5) Grab the Silver Shroud costume 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 and the Silver Shroud submachine gun back, 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, although you do need to wear the Silver Shroud Costume to get "Speak as the Shroud" response options.
 * 8) While outside in Goodneighbor, 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. Wayne is not immediately hostile and therefore can be spoken to as the Shroud. The player character will have the option of asking Wayne about the murder, which Wayne will confess to if the player character speaks as the superhero, or threatens him. Once Wayne is dead leave a calling card on his corpse.
 * 10) The next target is AJ, near Bobbi No-Nose's place, who is accused of selling drugs to children. AJ has two bodyguards with him, but none are immediately hostile, so he can be spoken to as the Shroud. AJ gives the option to take a bribe to leave him alone. You can kill AJ and leave a calling card or you can accept the bribe (50, 75 or 200 caps, depending on persuasion).
 * 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. All opposition is immediately hostile, except for Kendra herself, who can be spoken to as the Shroud.
 * 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 to 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. Doing so has no negative effects but if the player character has high enough Charisma, more caps are given up front for the job, with more upon completion.
 * 16) At Smiling Kate's quest marker she can be overheard plotting with some of Sinjin's men. None of them are immediately hostile, so it is possible to talk with her as the Shroud. (All will turn hostile once dialogue is complete.) Kill Kate and her accomplices.
 * 17) At Northy's quest marker all targets are immediately hostile. Kill Northy and his accomplices.
 * 18) On the body of whichever of the above two was killed last will be a holotape (Find the silver shroud). Listen to it to learn that Sinjin has targeted Kent.
 * 19) Return to Goodneighbor and follow the quest marker to the Memory Den. Irma will explain that Kent was taken by a group of armed raiders.
 * 20) Tune to Silver Shroud Radio to learn that Sinjin has taken Kent to Milton General hospital. Upon arriving, there may be leveled Super mutant opposition at the adjacent locations, and there is a Random encounter at the rear of the building.
 * 21) Important: It's recommended that you save right before entering the building and be sure to enter dressed as the Silver Shroud. Several users have reported that this portion of the quest may need to be completed without power armor to avoid Kent being killed immediately. It's unknown if this is a bug or intentional, but watch for the (failed) status message upon entry if you wish to save him.
 * 22) Look out 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. If the player approaches cautiously while remaining hidden, Sinjin's men to the left and the right can be killed first without triggering any action on the part of Sinjin or Avery. This allows for a much better chance of saving Kent.

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. However this method will cause Sinjin to immediately target Kent. If playing on survival difficulty it could be difficult for some characters to defeat Sinjin before he has a chance to kill Kent. To remedy this situation use the Syringer rifle along with some Pax Syringes (Yellow Belly will not work) and Jet or V.A.T.S. in order to pacify Sinjin for 30 seconds. Or, if one can manage, activate a critical hit on Sinjin to kill him instantly.

For those with a high charisma and the appropriate perk it is possible to pacify Sinjin and his bodyguards on exiting the lift, before the dialogue options appear. After choosing option 1 or 2 above they will not target Kent, especially if turning the bodyguards against each other. This leaves Sinjin as a target.

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.

Special Option: Killing Kent
Upon exiting the elevator, the player can kill Kent before talking to Sinjin. This will trigger unique dialogue where Sinjin and his gang panic. Wearing Shroud's costume will further allow another unique dialogue where the player can turn Sinjin's gang to their side.

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

24. Go back to Goodneighbor and speak with Hancock to collect the reward. Talking with Kent again, he says that he will work up another job for the Silver Shroud later which will give a better version of the Silver Shroud costume.

Cait

 * Cait approves of assassinating Shelly.
 * Cait dislikes taking care of AJ, but likes it if the Sole Survivor solicits a bribe from him.
 * Cait dislikes if the player character speaks to Kendra as the Shroud, but likes it if saying that Wayne deserved his fate.
 * Cait dislikes when the Sole Survivor encourages Kent to continue fighting crime after saving him.
 * Cait dislikes if the Sole Survivor says that friends are not weakness during conversation with Sinjin.
 * Cait loves if the Sole Survivor threatens Sinjin's men.

Codsworth

 * Codsworth likes when the Sole Survivor threatens Sinjin as the Shroud.(Keep in mind Codsworth disapproval of chem use, as saving Kent will be extremely difficult without a critical and high damage weapon or Jet.)
 * Codsworth likes when the Sole Survivor speaks as the Shroud.
 * Codsworth likes when the Sole Survivor tells Kent to keep fighting crime.
 * Codsworth dislikes if the Sole Survivor intimidates Sinjin's men.
 * Codsworth hates assassinating Shelly.

Curie

 * Curie likes when the Sole Survivor speaks as the Shroud.
 * Curie hates assassinating Shelly.
 * Curie likes when the Sole Survivor says "Friends aren't a weakness" when saving Kent.
 * Curie dislikes if the Sole Survivor intimidates Sinjin's men.
 * Curie likes when the Sole Survivor encourages Kent to continue fighting crime after saving him.

Deacon

 * Deacon loves it when speaking as the Shroud.
 * Deacon loves it when Kent Connolly is rescued
 * Deacon hates assassinating Shelly.

Hancock

 * Hancock likes when having accepted his quest to kill when he is the companion.
 * Hancock hates when you kill Shelly
 * Hancock likes when you intimidate Sinjin's guards.
 * Hancock loves when you intimidate Sinjin's guards as The Shroud.
 * Hancock loves when you spare Kent.
 * Hancock likes when you convince Kent to not give up.

MacCready

 * MacCready dislikes telling Kent that there are "Glimmers of hope" in the new Commonwealth.
 * MacCready likes refusing AJ's bribe.
 * MacCready likes assassinating Shelly.
 * MacCready likes when you threaten Sinjin as The Shroud.
 * MacCready dislikes when you convince Kent to not give up.

Nick

 * Nick Valentine likes it when choosing 'glimmers of hope' when talking to Kent.
 * Nick Valentine likes it when replying as Silver Shroud and refuse AJ's bribe.
 * Nick Valentine hates assassinating Shelly.
 * Nick Valentine likes when the Sole Survivor says "Friends aren't a weakness" when saving Kent.
 * Nick Valentine likes when the Sole Survivor encourages Kent to continue fighting crime after saving him.
 * Nick Valentine loves it when you kill Sinjin without Kent dying.

Paladin Danse

 * Paladin Danse likes refusing AJ's bribe.
 * Paladin Danse likes the "friends aren't a weakness" line and telling Kent he can't quit.
 * Paladin Danse likes speaking to Kendra as the Shroud.
 * Paladin Danse likes if you intimidate Sinjin's men. (persuasion)
 * Paladin Danse dislikes saving Kent.
 * Paladin Danse hates assassinating Shelly.
 * Paladin Danse likes when you convince Kent to not give up.

Piper

 * Piper hates assassinating Shelly Tiller.
 * Piper hates taking the bribe from AJ
 * Piper likes talking as the shroud to AJ
 * Piper likes when the Sole Survivor says "Friends aren't a weakness" when saving Kent.
 * Piper loves saving Kent after speaking as shroud.
 * Piper likes when the Sole Survivor encourages Kent to continue fighting crime after saving him

Preston Garvey

 * Preston Garvey likes telling Kent there's glimmers of hope.
 * Preston Garvey likes telling Kent "Good for you".
 * Preston Garvey likes telling Kent to believe in himself.
 * Preston Garvey dislikes humoring Kent.
 * Preston Garvey dislikes calling Kent crazy.
 * Preston Garvey dislikes refusing to hand over the Shroud costume.
 * Preston Garvey dislikes asking AJ for a bribe.
 * Preston Garvey dislikes the option to walk away after AJ's offer.
 * Preston Garvey hates accepting AJ's bribe.
 * Preston Garvey loves speaking to AJ as the Shroud.
 * Preston Garvey hates assassinating Shelly.
 * Preston Garvey likes telling Sinjin "Friends aren't a weakness."
 * Preston Garvey dislikes telling Sinjin you're only there for his bounty.
 * Preston Garvey likes if you try to intimidate Sinjin's men. (persuasion)
 * Preston Garvey loves if you tell Sinjin to spare Kent. (non-persuasion)
 * Preston Garvey loves if you speak to Sinjin as the Shroud on the final dialogue option.
 * Preston Garvey loves if you save Kent.

Strong

 * Strong dislikes speaking as the Shroud.
 * Strong likes assassinating Shelly.
 * Strong loves threatening Sinjin.
 * Strong dislikes when the Sole Survivor encourages Kent to continue fighting crime after saving him

X6-88

 * X6-88 likes assassinating Shelly.

Behind the scenes

 * The Silver Shroud appears to be based on The Shadow and The Green Hornet. Like the Silver Shroud, they both had popular radio serials and wore a trench coat and fedora.
 * The Silver Shroud, both in name and appearance, also strongly resembles The Gray Ghost from Batman The Animated Series, in which Adam West played a black and white TV and Movie star that was young Bruce Wayne's childhood hero.
 * In regards to the Shadow in particular, the scarf over the Vaultboy's mouth in the quest animation seems like a clear nod, as does the intimidating tone attempted in the "Speak as the Shroud" dialogue option. The darkness motif of the character is also reminiscent of the Shadow.
 * Silver Shroud's Thompson sub-machine gun may be a tribute to World War II hero Mark Tennant, who was nicknamed the 'Green Hornet' by his fellow soldiers based on the radio serial character.
 * While listening to the serial on the radio, Silver Shroud will mention that he has fought the Rogue's Gallery. The Rogue's Gallery is a term used for a police collection of pictures or photographs of criminals and suspects kept for identification purposes, often used in comic books to refer to the hero's collective enemies.
 * When Silver Shroud infiltrates the mobsters hideout, one of the mobsters says "Holy Canoli", famously said by Robin in the 1966 Batman TV series.
 * Emails on the terminals in Hubris Comics mentions that the producer wants to give Silver Shroud an 'English Butler'. This is similar to Alfred Pennyworth in the Batman series.
 * When Silver Shroud and Mistress of Mystery are spying on the robot-mobster meeting through the skylight, it is revealed that the creator of these robot-mobsters calls himself The Mechanist, similar to the Fallout 3 character, the Mechanist.
 * Both Kent and Wayne are the surnames of two well known comic book superheroes: Superman and Batman.

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