The Assassin's Cake Breaking into a locked room surrounded by guards, in the middle of a castle, all without being seen. A piece of cake... Right?

DM notes. The assassin's cake is a stealth oriented one shot aimed at parties of 3rd-4th level. It is intended to be a difficult encounter but have minimal combat. Players are to plan and execute a reverse heist: placing rather than removing a number of objects. The goal is to place three items in the presence of the target without any evidence of the party being involved, or an apparent means of them being delivered. Due to the minimal combat focus it should be safe, even encouraged, for players to split the party as they each perform their respective roles in the planning and eventual break-in. DMs should discourage the use of familiars to carry out the delivery of the items. The intention is for player characters to do it themselves. The cake itself should be something delecate, such as a sponge or pastry, but players are allowed to store it in a container. It is also assumed to not go stale. Rough times are used such as sunrise and sunset. These are assumed to be around 5am and 8pm respectively. The setting intended to work as part of a larger campaign but due to some plot points an isolated town on a river or other difficult barrier, such as a ravine, would be preferable. Likewise details about significant NPCs are left vague to facilitate this. While set DCs are given these should be changed by the DM as they see fit. while there are options for players to get information from overheard conversations, the DM should first encourage other avenues to find information. "Thieves' cant" rules by Deal Kingsmill (u/DailyDael on reddit) are suggested as a way of introducing players to the challenge. In addition there could be the possibility of having contacts in the town for rogues. Players should not be penalised for discussing the challenge with them, but they will not have much useful information about the target, only the keep layout and should be used as a last resort by he DM. The contact should want reimbursed for 25% of the full reward. Players should start at a farmstead near the outskirts of the town or travel from their current location. In either case the challenge starts outside the town before mid-day. Historical notes. This one-shot is loosely inspired by threat made against Ahmad Sanjar, Sultan of the Seljuq Empire, which spanned much of the middle east in the 11th and 12th century AD. Ahmad had reportedly rebuffed an ambassador sent by Hassan-i Sabbah, leader of the Nuzari Ismaili state. Upon waking the next morning he found a dagger embedded in the ground next to his bed. Accompanying the dagger was a message reading "Did I not wish the sultan well that the dagger which was struck in the hard ground would have been planted on your soft breast". The thread played a part in establishing several decades of peace between the two Nations.

The Nuzari Ismaili state was relatively weak militarily but were renowned for their use of targeted killings, both covert and overt, to gain political influence and are considered to be the original assassins. The contract A wealthy foreign merchant is due to pass through a nearby fortified town called Grassport. While he is relatively unknown locally, his ventures have made him the target of rivals who feel threatened by his encroachment onto their monopolies. While it would be easy to simply have him killed we would prefer that he first has a chance to sell off his assets. This will also help us avoid unwanted scrutiny. Even so far from home the merchant is wary of enemies and so has hired a group of well-trained mercenaries for protection. You are to deliver a discreet "warning" to this merchant while they feel that they are at their least vulnerable: Surrounded by guards, in a keep and far from where anyone knows them. The warning is to be in the form of a cake, a bottle of poison and a simple note, which will be delivered to the party when they depart for grassport. The cake has to be delivered into the merchant's quarters undamaged, along with the bottle of poison and note. These are to be left somewhere clearly visible while the merchant is asleep. You are also not allowed to be seen doing so. If you do this you will be generously rewarded. If, however, a member of the party is seen, someone dies, is injured in an attack or with an obvious trap, or goes missing, you will receive only half payment. If a member of the party is captured in the attempted break-in, the merchant is killed, or the items are not delivered the party will not be rewarded and also incur the wrath of their most generous patrons. Your target will be arriving around mid-day, on the day of your arrival, with a small number of guards, staying in the private rooms in the keep, and leaving on the morning of the third day. The party will be rewarded with 2000gp upon successful delivery of the items, with the above stipulations. You can be assured that your employer will be watching the party and will know how successful they are. Should you succeed it may open up potential for more work in the future. Verbal spell components.

As this is a stealth based challenge, spell components may cause some difficult DM rulings on volume and visibility. The D&D core rules state: Verbal: Most spells require the chanting of mystic words... the particular combination of sounds, with specific pitch and resonance. Somatic: Spellcasting gestures might include a forceful gesticulation or an intricate set of gestures.

A stealth check, using a players spellcasting ability modifier, could be used in situations where the spell caster wants to remain hidden. Cantrips would require a DC 10 check, increasing by 1 per spell level to represent the increasing complexity of the spell.

Grassport. The town itself is a beacon of lawfulness in the region. There is little crime thanks to the well manned watch garrison. Due to the local economy being primarily farming, there are few outsiders in the town. Any that arrive usually arrive by boat and rarely stay longer than is needed to exchange goods, a night or two at the most. To the east, there is a wide river, with a keep built on an island connected to the shore with a drawbridge. On the north, south and westerns sides there is a large defensive wall that extends about 45 feet into the river at its northern and southern ends. Aside from the river there are only three roads into and out of the town. These are on the North, south and west walls, constantly under guard, and closed between sunset and sunrise. The town has a population of about two thousand people. Most are employed in some fields related to farming, whether it is labouring in the fields, blacksmiths making tools, or dock hands exporting food. The party can find some basic facilities as follows: A small library. "Herba bibliotheca," also known as "the book place" by locals. The owner is an enthusiastic old man who instantly assumes anyone entering the shop is interested in the town's primary export: cabbage. He will try and engage the players in deep conversation about the plant. Most of the books here are about growing cabbage. A DC 14 insight or perception check can be made to notice a book (scroll) titled "Make yor own ploughhorse", that contains a 2nd level spell: Find Steed.

A blacksmith. "Smelts of roses" Owned by an intimidating female half orc, she will initially be aggressive to the party, but quickly become friendly if they offer to buy something. They make a good business making ploughs and other farming equipment for the fields and armour and weapons for the guards. They have a total of 5 workers and are willing to make small items, including weapons and medium armour, for the party if they can pay. They have a selection of farming equipment, simple weapons and light and medium armour. Requests for unusual items such as a file will be met with suspicion needing a deception or persuation skill check, although this should be low.

An "Alchemist." "Animal Alchemy" is situated close to, but not next to the Blacksmith. In reality they sell basic salves and a large quantity of fertiliser, which is noticable by the smell of manure. The owner is a Copper-skinned Dragonborn with a dry and cynical sense of humour. Immediately upon entering the party will spot a sign saying "No flames!" The shop will have have a single potion of cure light wounds. They have also somehow acquired a potion of invisibility. They owner will admit they don't know what the potion is but do know that it is valuable. The spell "Identify" can be used to identify it before or after purchase.

Docks. There are docks on the riverbank, to the south of the keep. People here are usually a good source of gossip from the town and the wider region. Most traders live on their boats and so can also be easily found here should the players wish to hire a boat.

The inn. "The sleeping horse" is the only place in town travelers can find to stay. It is a large tavern with two free rooms above the social area. The tavern will be bustling and noisy every evening with castle staff, off-duty guards, farm labourers all enjoying themselves into the early hours. Anyone looking for more than modest accomodation will have their requests accounted for at an appropriate price, but this will raise suspicion with the guards as gossip quickly spreads.

Town square. There is a market in the town square which can provide for most of the general needs of the party. It has an open plaza surrounded by market stalls selling a variety of goods such as food and clothing. It is normal for staff from the keep, particuarly kitchen staff, to collect necesary good from here. Watchful players can use this as a means to identify individuals to learn castle layout or even get a way in. Dock alternatives.

Depending on the setting, docks may not be appropriate. In these circumstances they could be replaced by things like a coach house/stables or a large warehouse for produce.

Grassport keep Grassport keep, originally called Levans Keep, was built to defend the region around what is now Grassport, a plain with fretile soil good for growing crops. A town quickly sprung up around it, using the garrison for protection and the river to quickly get their harvests to larger markets. Raiding and military attacks on the strategic area in centuries past led to the construction of the walls around the town. The keep also acts as the main residence for the local lord. It is built on an island and connected to shore by a drawbridge leading to the Bailey. Grassport keep consists of four main areas: the bailey, prison cells, guard quarters and the lord's chambers. Unless invited, only guards, staff, the lord and the merchant's retinue are allowed into the keep. Anyone else attempting to enter will be forcefully turned away by a guard. The Bailey. The Bailey is the first area any visitor to the keep will enter. It has a large open space and a number of stables along the outer wall. There is a high wall on all sides, with the keep perched atop a rock outcrop that forms the rear wall of the Bailey. Access to the castle walls can be found here, with stairways at the end next to guard quarters, gatehouse and wall end, below keep. Guard quarters. The guard quarters contain most of the facilities at the keep. It has a kitchen, mess hall, an armoury and some barracks. The main entrance to the lords Chambers and and prison cells are accessed from here. The kitchens are always manned, with staff being active until an hour after sunset. They will come and go from town and the prison cells. There are always a few individuals around, although most will be in the mess hall or barracks and not leave these areas unless otherwise stated.

To access the Lords Chambers an individual has to pass through the guard quarters and climb a stairway. There is a reinforced door at the top which is the main entry to the Chambers. This is locked between 10pm and 6am and can be barred from the inside. The guard captain, Lord, and a mercenary all have keys. The lock can be picked with a DC15 check. If the player fails by 5 or more the lock will make a sound audible to the guards in the Lords Chambers. The lord's Chambers. The Lords Chambers consist of a main hall, 3 bed Chambers and privy (toilet), all branching off from a central main hallway. One of the bedchambers and the Lords bedchamber have an attached study, and the main hallway has a high narrow window at one end. There are 5 windows on the wall overlooking the bailey, one for each bedroom and study. All windows in this part of the keep are tall and narrow. Bars make them too narrow for a creature to squeeze through and they do not open. The main hall functions as both a meeting and dining room for the lord. Some silver dining utensils can be found here. There is some damage to the roof tiles over the main hall resulting in a small hole in the roof. A medium creature could squeeze through here as an action but will create an audible noise as loose tiles fall to the floor with them. As layout is important here the order of doorways, from the guard quarters, is: Left hand side. Main hall Right hand side. Merchant's room Wizards room with attached study Privy (toilet) Lord's bedroom. The hallway window is at the end of the hallway, outside the lord's bedroom. There is about 15 feet between each doorway, with 30 between the merchants quarters and the wizards quarters, and the Lords Chambers and the privy. No doors within the Lords Chambers will be locked. Prison cells. The prison cells are carved from a small cave below the keep. Rarely used, they double as a dock using a channel that is hidden from the outside. A small apparently rotting, but usable, boat will be moored here. While some cells are kept empty others are used as a makeshift larder by the kitchen staff to keep food and drink cool. In the roof, over the chanel, is a pipe covered by a grate that connects to the privy. A medium difficulty athletics check can be used to pull off the grate. Loose rubble will fall into the water creating a noise that will be investigated if not sufficiently muffled. This would be a difficult but achievable climb for a small character. There is an s-bend in the pipe and so the lords privy cannot be directly seen from here. These are usually left unguarded but are visited by kitchen staff.

The traget and retinue Around mid-day on the day that the party arrive in the town their target will arrive and make their way directly to the keep. They will arrive concealed in a carriage, with 8 guards and another individual (a wizard). All will be on horseback, with one guard guiding the carriage. Both the wizard and the merchant will stay in separate rooms in the keep. The larger one with the study will have 2 Mercenary Knights posted outside, changing guard every 6 hours from mid-day. Bait and switch. It will be revealed to the party that the individual in the carriage was not, in fact, the merchant, but the wizard acting as a decoy. The merchant hopes that the decoy, alongside the guard presence will help draw assailants away from their real target: himself. Until the deception is discovered the players should be allowed to believe that the individual in the carriage is the merchant. To the knowledge of NPCs, with the exception of the Lord, merchant, wizard and mercenaries, the merchant is staying in the room occupied by the wizard. Sleeping arrangements. Players watching the keep will be able to see individuals moving around in the rooms. The one nearest the guard quarters will have the merchant. Next to this, the wizard will have the room with the attached study. Guards will be posted outside the wizard's rooms. The lord will be in the room furthest from the guard quarters.

The wizard, Lord and merchant will retire to bed around 11pm and wake at around 7am. They will, however, be woken by loud noise or if an alarm is raised. Due to the deception players watching the castle should be allowed to see the character who was on horseback, and assumed to be the wizard in the room nearest the guard quarters. Bored guards. The guards outside the bed chamber will respond to any significant noise they hear and will move to investigate. This can include falling debris, failed lockpicking, objects hitting the hallway window. This also includes any unusual movement.

While investigating, guards will be facing the point of interest and automatically fail sight based perception checks for activities that could be considered to be behind them. Itinerary. The wizard and merchant will spend most of their time in the castle discussing the possibility of routing trade through the town with the Lord. They will enter the town on the second day to browse shops and inspect the docks. They will approach anything that catches their eye such as produce or, perhaps, a display by a street performer. The merchant will be interested in some entertainment that evening.

Mercenary knights. The businessman has hired a company of mercenary knights to act as his personal bodyguard. There are eight of these guards. These use the followng profile: Mercenary Knight Medium human Armor Class 18 (plate)

18 (plate) Hit Points 52(8d8 + 16)

52(8d8 + 16) Speed 30ft. STR DEX CON INT WIS CHA 16 (+3) 11 (+0) 14 (+2) 11(+0) 11 (+0) 15 (+3) Saving throws Constitution +4, Wisdom +2

Constitution +4, Wisdom +2 Senses passive Perception 10

passive Perception 10 Languages Common

Common Challenge 3 (700 XP) Actions Multiattack. The knight makes two melee attacks. Greatsword. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 9 (2d6 + 3) slashing damage. Heavy Crossbow .Ranged Weapon Attack: +2 to hit, range 100/400 ft., one target. Hit: 5 (1d10) piercing damage. Behaviour The mercenary Knights will keep within 10 feet of the merchant whenever possible. The exception to this will be while resting or havig a private conversation, or when the merchant is in his private room. If they or anyone else in their group is attacked then half their number (rounding down, minimum 1) will fight to the death while the others will escort the merchant away from danger. Suspicion of outsiders One way to increase tension and difficulty for higher levels would be to inform the players that the city guards, townsfolk and mercenary knights are suspicious of outsiders. Every time the players do something noticably suspicious, for example inquiring about the Keep layout, guard patterns or identity of the merchant, or committing a crime, increase the perception score of all guards by 1/4. They are also able to remember where and when they see Characters along with the character's appearance. The wizard could also be used to create magical traps, such as Alarm, that can also be used to hinder the party. Likewise, this could also be used to draw the attention of the merchant... Town guards. In addition to the mercenaries the town has a strong garrison that also functions as the town watch. There are 50 guards spread throughout the town. These guards are well trained and so use the stats below: Town Guard Medium human Armor Class 16 (hide shirt, Shield)

16 (hide shirt, Shield) Hit Points 41(6d8 + 14)

41(6d8 + 14) Speed 30ft. STR DEX CON INT WIS CHA 15 (+2) 14 (+2) 14 (+2) 10(+0) 12 (+1) 13 (+1) Saving throws Wisdom +3

Wisdom +3 Senses passive Perception 10

passive Perception 10 Languages any one language (usually Common)

any one language (usually Common) Challenge 1 (200 XP) Actions Multiattack. The town guard makes two melee attacks. Longsword. Melee Weapon Attack: +4 to hit, reach 5 ft., one target. Hit: 6 (1d8 + 2) piercing damage or 7 (1d10 + 2) slashing damage if used with two hands. Light Crossbow .Ranged Weapon Attack: +2 to hit, range 100/400 ft., one target. Hit: 4 (1d8) piercing damage. Behaviour Guards will move towards any obvious threat or sound of fighting. At the end of every round of combat a further 1d4-1 (minimum 1) guards will join the fight from a random direction. They will fight to the death but will not initially attempt to kill players, either attempting to grappel them or knock them unconscious and taking them as a prisoner to the keep. Should this happen they will actively begin searching for the rest of the party if they were previously seen together. Guards protecting the keep will attack a player if seriously provoked but will otherwise follow the above behaviour.

Information sources. The party will require information to get in an out of the keep unseen, as well as to identify their target. Sources of information should be fed to them over the course of the session. Prioritise identifying useful NPCs during the day on the first day, with scouting and gathering information on the first night. The second day can be used for planning the break-in and filling gaps in information. Players should also have some downtime for exploring the town too. Merchant identity. This piece of information can be introduced to the party in a number of ways. To avoid being identified the merchant will be wearing a disguise. A DC 15 investigation or perception check will be enough to tell the party that the appearance is fake as per the effects of the spell "Disguise self". Players can get an oppertunity to see through the disguise whenever they are within 25 feet of the merchant.

Regardless of if the party correctly deduce that the unknown individual is, in fact, the merchant, they can be fed other hints throughout the session. Find a moment for mercenary knights to have a private conversation within earshot of a player character. During the conversation they will question the need for secrecy and deception, hinting at the disguise. This could also be a good opertunity to reveal to the players that the other individual is a wizard, perhaps through a passing comment about them being unable to do "useful stuff" such as throw fireballs. Castle staff. If a player chooses to watch the enterance to the keep a member of the kitchen staff will make their way into town to collect produce from the town square for the kitchens. They can be approached at this point but will state that they are after ingerdients and will brush off the player if they change the subject, or try to engage in deep conversation, as they are in a hurry. The same individual can be found in the sleeping horse later that evening. An attempt can be made to allow a player to help in the kitchens preparing a meal for the lord and his guest. They should describe either a unique culinary skill or recipe that would interest a head chef who is eager to please his lord. The nature of the check (persuation, deception, etc) and DC are up to the DM but it should relate to how convincing the cooking skill sounds. The staff member will ask the head chef and inform them in the morning that they are allowed into the keep if successful. A second check (nature, survival or performance to represent the characters knowledge of ingredients or cooking ability) should be made during the Lords meal to see if the Lord approves. On a failure the head chef will have the player locked in the cells for humiliating them. This should be around DC12. If players do not have a layout of the lord's chambers this NPC or an off-duty guard will give information but the party will only get half reward. Prison enterance. The secret enetrance for the prison can be found by scouting the side of the island farthest from shore but needs a DC 16 check to see it from no more than 20 feet. If a character is seen here in daylight the alarm will be raised. Players can also find out about it by getting arrested and brought to the prison cells. If they carry out a minor offence such as a drunken fight they will only remain in the cells until dawn the following morning without a guard. More serious crimes such as theft or serious violence will result in a longer stay under guard. Anything that displeases or offends the Lord will result in the character being sent to the cells and kept under guard until after the merchant has left the town. If a player is working in the kitchens they will be taken to the prison to collect ingredients and informed that the prison door is left unlocked for the kitchen staff until an hour after sunset. The smell and appearance of the grate should indicate the function of the pipe. Broken roof If a player character is able to view the keep from above they will notice the broken roof on close inspection. Likewise, if an offer is made by the merchant to perform in private on the second night, a player will be asked to perform in the main hall where a low perception check will spot the damage. A player working as kitchen staff can also be allowed into the lord's chambers to deliver their meal. The player should have the option to leave at least 3 hours before midnight to report back to the group, should they wish. In both cases, being escorted to the main hall will allow players to see the layout of the lord's chambers.

Finally, Players will be able to overhear compalints about the broken roof from guards or castle staff. As well as the broken roof, half way down the main hall on the inner wall, there will be a fireplace. A medium creature can squeeze down the chimney but will block it for the duration causing the room to fill with smoke. A small creature will not cause this to happen. The fire will also be lit causing players to take 3d8 fire damage upon entering the room. Smoke will also be grounds to half the final payment if it or the smell is not dealt with before 6am. Joining the guards Asking a guard or the blacksmith about joining the watch will result in them being directed to the west gate and the watch captain. Any character can inquire about joining the watch but will need to pass a deception or persuasion check with a low DC or be turned away by the captain. Martial characters such as barbarians and fighters have advantage on this check and can use their athletics skill as the captain recognise their experience in a fight. He will escort them to the keep to be fitted for a uniform, given a tour of the keep and town. The character will not actually get a uniform until after the merchant has left the town. If a character has been previously arrested they must further convince the captain that they will change their ways. This requires a persuation or deception check of high difficulty. If they break the law after being accepted they are immediately banned from entering the keep unless they are also arrested.