Breaching Security Breaching Security is a quest available in . Continuing the Dark Brotherhood quest line , this is the next in a series of quests that ultimately will lead to the assassination of the Emperor . Walkthrough . The first step of the quest is for the Dragonborn to speak to Gabriella in the Sanctuary . She says that Commander Maro will be in charge of the Emperor ' s security when he comes to Skyrim , and that the Dark Brotherhood wants Maro distracted during the Emperor ' s visit . The way to achieve this is to kill Commander Maro ' s son , Gaius Maro , and plant false evidence on his body of a plot to assassinate the Emperor . Not only will this cause Commander Maro to be distracted , it will also give the Emperor a false sense of security : since he will believe that an assassination plot has already been foiled , he won ' t be expecting another one . She says that if the deed is done in a major city , Astrid has authorized her to give the Dragonborn a token to give to Olava the Feeble , a friend to the Dark Brotherhood that will enable her to tell the Dragonborn ' s future . An Incriminating Letter will be added to inventory . If she is asked about his schedule , she will say that there is a written copy in the Penitus Oculatus Outpost in Dragon Bridge that can be stolen . Dragon Bridge . The Dragonborn must go to Dragon Bridge for Gaius Maro to start his travels , but killing him there will prevent the bonus from being received . He can be observed in front of the Penitus Oculatus Outpost , saying goodbye to his father . After he leaves , the Dragonborn can steal Gaius Maro ' s Schedule by sneaking inside the outpost and waiting for the guard inside to move away from the table with the schedule . Places and methods for killing Gaius Maro . Riften . After fast traveling to Riften , the alleyway to the left provides an opportunity ( the lock on the gate may need to be picked ) . As Maro leaves ( around 1 : 00 A . M . ) , shooting him with an arrow will avoid detection and any bounty . If the archery skill is at a low level , he may not die with one sneak attack , so there may be a fight . Another option is to wait in the corner of Riften Castle ' s courtyard , behind the small grouping of trees , and wait for him to exit ( he exits that side every time at around 11 : 30 A . M . , although the actual times may vary ) . He will be alone and far enough away from any guards to allow him to be killed without any worry about bounty . Palace of the Kings ( or other Barracks ) . Gaius Maro will sleep in the barracks with the guards in Windhelm . This can be one of the hardest places to get him without being detected . Around 10 : 00 P . M . , in the corner by the sleeping guard , he can be shot with a bow ( preferably after having coated the arrows with poison ) . Each time he is shot , he will get up and look around the room . He can be continually shot without being discovered . Warning : The guards in the beds will sometimes get up and look as well , but will not see the Dragonborn in the shadows . After Maro is dead , once the guards settle down it is possible to creep over to his body and plant the Incriminating Letter . Sneaking back to the corner , then jumping over the beds with the guards in them until the doorway is reached , allows the Dragonborn to sneak out to freedom . The Bannered Mare . In Whiterun , it is extremely easy to sneak into his bedroom in The Bannered Mare , as it seems to be the only time he isn ' t bunking in a castle or in barracks . He can be killed in his sleep with the door shut , and then the letter planted . This does not result in a bounty . However , there is a high chance that Gaius Maro might fall behind on his itinerary schedule and therefore only make a brief stop at The Bannered Mare , for some drinks , before continuing on to Markarth . In this case he normally arrives alone on Turdas evening ( 10 : 00 – 11 : 00 P . M . ) and heads straight to the hearth in the middle of the inn for a drink , whilst enjoying the bard ' s performances . With a high level of Sneak and the Ebony Mail , while sneaking he can be shot using a ranged weapon from the balcony of the room overlooking the hearth ( it ' s the same room rented from Hulda ) . Since this balcony is full of shadowy spots it is possible to hide in one of those and wait for Gaius Maro to charge upstairs looking for his assailant . Once he has touched the shadowy tendrils of poison emitted by the Ebony Mail , it is just a matter of waiting for him to fall lifeless . Then the Incriminating Letter can be planted and the scene left with no alarm raised . Obviously , this technique can also be used in other dark locations as well . A word of caution though : killing him in public usually leads to collateral damage , so there will be some bodies on the way out of the inn . Sometimes , he can be killed in full view of guards and citizens . The guards will do their normal " What was that ? " routine , but won ' t notice him being slaughtered , even though they see the Dragonborn plainly . Citizens , however , will scold and sometimes turn hostile when they see Gaius Maro killed . Approaching him directly . Another alternative method is for the Dragonborn to approach Gaius Maro and use the option of telling him how he will be killed , and then the Emperor . After this , Gaius will begin to attack . Letting him strike the first blow , then fighting back and killing him will not cause a bounty . This method can be used in any major city in order to receive the bonus . If using this method , it ' s best to confront him in view of a guard - so that it is seen that Gaius attacks first . However , if a guard wanders into view of the fight as it ' s proceeding and the first blow he sees is struck by The Dragonborn , a bounty will be earned . If the Dragonborn is a member of the Thieves Guild and happens to encounter Gaius Maro in Riften , if he is provoked , fellow Thieves Guild members ( and even Maven Black - Briar ) will come to the Dragonborn ' s defense . They will finish him off . More generally , if Gaius is attacked in a town or city where friends are present , they will help to kill him . Alternatively , if he is killed anywhere in a city where the Dragonborn is Thane , the Dragonborn ' s position as Thane can be used to remove the bounty . During a Dragon Attack . The bonus can also be received just outside a city . If a dragon attacks just outside a city , he can be killed while the guards are fighting the dragon , resulting in no bounty . The bonus will still be counted . Dragonsreach . An easy way to kill Gaius without good combat skills is when he is in Dragonsreach , in Whiterun . He can be approached and provoked . Once he attacks , the entire court of Whiterun will attack him . However , they will not kill him , but lower his health down to the point as to when he falls to one knee ; he can then be killed with an extra swing or two . Pickpocket . With high enough Pickpocket skill , it is possible to plant the Incriminating Letter on Gaius " before " killing him . This allows him to be killed at range and in the open , and the quest completed without approaching his body . With the pickpocket perk Poisoned , poison can also be placed in his pocket along with the note . The Lotus Extract poison from the mission " Mourning Never Comes " is ideal for this . Beast Form . While in Whiterun , after planting the incriminating letter on Gaius , he can be murdered using Beast Form . Afterwards , escaping to The Companions ' The Underforge , it is possible to wait until returning to normal appearance . Immediate Hostility . Gaius can be attacked while outside a major city but not killed , by running away and losing him . Once he has entered a major hold , he will attack the Dragonborn on sight . Since he attacked first , he can be killed with impunity . The guards will either help the Dragonborn or not do anything . Markarth . At some point , Gaius will go to the guard tower in Markarth . Once he ' s back out of the tower , Unrelenting Force ( preferably all three words ) will launch him off of the high point that the guard tower is on . After following him down , Gaius will attack once he ' s back on his feet , causing the guards to see this as a crime and attack him until he yields . He can then be simply finished off , and the Incriminating Letter planted . Schedule changes . Whenever Gaius sees the Dragonborn he begins taking an alternate route . This can make the quest quite hard as he will turn away from a city if he sees the Dragonborn anywhere near it . If this happens , waiting in a tavern in a city on his route will allow him to eventually resume his normal journey . Conclusion . Upon returning to the Dark Brotherhood Sanctuary , Gabriella approaches , initiating dialogue and congratulating the Dragonborn on completing the mission . She then gives all due rewards . This completes " Breaching Security " and automatically starts " The Cure for Madness , " in which something has gone wrong in the Sanctuary . Also , if the bonus ( Olava ' s Token ) was earned , the miscellaneous quest " Receive a reading from Olava the Feeble " is started . Gaius Maro ' s Schedule . " The guards and Jarl s of the cities have been informed of your arrival , and will leave you to your work . Study the guard patterns , examine any entrances and exits , and make note of any irregularities . " " Talk to no one - the fewer people who know about your mission , the safer the Emperor will ultimately be . "