Tailor, Tinker, Soldier, Spy: the Bard as a Spy, Cryptography and the Fantasy Espionage Team

The party stands before the Duke and he gives them a charge: march up the mountain to a nearby kingdom and slay the Arch-Lich who lurks there.  The Duke provides the party with maps to the mountain, a summary overview of what they might find (high level henchmen, nasty guards, a dragon chained in the basement) and offers useful magical equipment for the adventure. And God Speed, the Duke tells the party: the Kingdom and its people depend on you.  Defeat the Arch-Lich and forever be written into the annals of history!

Off they go into the mists of tale.  But this is not a story about the party heading off to grand heroics.

This is the story about the intrepid spies who stole the maps.

Even guards in evil kingdoms need to eat.  It’s a funny thing about the bard driving the food cart.  She spent her life learning to play all the roles for the stage and the role of her life is selling a bag of apples and a barrel of beer to an evil guard quartermaster in charge of feeding the rest of the evil underlings and cultists who surround the Arch Lich.  She must build trust.  She’s all about the confidence game – a natural-born grifter.

This is the core of a bard.  Yes, the bard can sing songs to buff up a team and work support, but what the Knowledge Bard, a graduate of the Bardic College is good at are skills: the languages, the persuasion, the investigation, the perception, the stealth and the performance.  She can carry out a role.  She can track down a mystery.  This knowledge-based bard is a master of languages.  She has no communication barrier, not even with the evil races.  She knows funny stories about everyone.  She can sing a couple of songs.  She is the master of selling roles to her audience of one and persuading them to trust her.  She can run a con like no one’s business.

Outside in the courtyard of the Arch Lich’s compound, the bard and the evil quartermaster get along like lifelong friends.  Next thing she knows, the quartermaster is inviting her in for tea.  Then she bribes guards on the inside with treats.  Evil guards are treat-deprived because they serve an evil Arch Lich and evil Arch Liches don’t go in for tiny sweet cakes.  It’s not a sweet-positive atmosphere.  Who is going to turn down a muffin?  Are you that evil?  Gratis, you know, between us.  And don’t mind my two friends over there – they help to unload the cart.

Then, she has her team in.  The bard schmoozes and builds up her network.  She gets a few people to talk, and they introduce her to bigger people who will know more information.  This is a long con.  Be the role, sell the roll, and don’t get caught.  After a while she’s one of them, part of the trusted inside. She’s always been there.  She’s the one who brings the muffins. Getting caught means jeopardizing the job and blowing cover and possibly getting killed.  Now she needs her team to steal information about the fortress and the Arch Lich’s plans.

This is a high risk, high reward sort of job.

The spy bard works her wits, her skills and her spells. While the bard spell list looks nearly unusable for standard dungeon-crawl murder-hobing, it’s fantastic for gathering human (or in-human) intelligence. She doesn’t have the big boom fireball or lightning bolts but her bardic spell list allows her to survive in the hostile environment beyond enemy lines where compromise is a constant risk. 

The best of the best on the bard spell list:

• Message – The ultimate spy cantrip, Message’s singular ability is its ability to travel through a ceiling to the next floor or around corners.  It’s bounded by 120 feet (12 floors assuming 8 foot ceilings) or 3 feet of wood (about 6 floors, total, assuming joists).  Working with a team, Message can get alerts – I’ve been nabbed! – through a building, a palace or a decent sized compound instantly.
• Illusory Script– Essentially short term “cryptography by magic,” Illusory Script will encode one message that only decodes for the target. Highly useful for making copies of documents before they’re properly encrypted.  This spell assumes the message will not pass through the hands of any creatures with True Seeing like, say, an Arch Lich, so use judiciously.
• Unseen Servant – An easy way to perform a lengthy, repetitive task, like encrypting a message by hand; see below.
• Magic Mouth –  For passing along cryptographic keys, locations of dead drops, names of contacts and warnings, Magic Mouth is the perfect spell for communicating information between team members securely in a close and dangerous locale.
• Non-Detection – Non-Detection is the diviner-busting spell.  For 10 minutes, the target of non-detection can get through any magical scrying or divination defenses.  The perfect spell for that high risk break-in, highly sensitive conversation or that Mission Impossible theft.  Essential for pulling off a job.
• Zone of Truth – Need to get absolutely accurate information out of a contact?  The downside of Zone of Truth is the target knows they’re in a Zone of Truth.  Using the spell will burn a contact, but if the information is critical to the safety of the Kingdom and all those innocent people…
• Sending – More powerful than Message but less easily cast (as it is 3rd level), Sending gets 25 words anywhere, to anyone.  25 words is enough to transmit a key to a much longer bit of ciphertext to a receiver or reveal emergency information.  25 words is a tweet! It’s the SMS of spells.
• Clairvoyance – Clairvoyance is an alarm system.  For 10 minutes, the bard gets a sensor on a door that detects intrusion.  That’s how long she has to meet with her network contact to get information, or commit a quick murder, or perform a little larceny.  10 minutes to get in and get out with a reliable watch. 

Spells aren’t enough to infiltrate and share information about a high risk target.  A good run against a target requires spells and skills – mostly involving data.  Encrypting information by hand has a few strong advantages over the spell Illusory Script or a Sending: it is longer than 25 words, it lasts longer than 10 days, it cannot be detected by a Detect Magic, cannot disappear with Dispel and cannot be instantly broken by a creature with True Sight – which, well, Arch Lich.  Or a high level Diviner in the Lich’s employ. 

The bard is a cryptographer and an a cryptanalyst.  The Linguist feat enables the bard to master most languages and cryptography is manipulating language to make it indecipherable with a secret key – or crack the enemy’s codes. 

This is the essential tension between the game of intrigue and the spy bard. The spy bard’s network needs information to effectively deploy military resources and those being spied on must intercept and break codes to further their interests. It’s information and intelligence providing internal security and external offense against the enemy.  Bards have the skills, the motives, and the creativity to keep one step ahead of the enemy’s current technology. 

The stronger the key, the stronger the algorithm, the more unbreakable the code.  The bard needs unbreakable codes – her life and the lives of others hang in the balance. As the spy bard lacks a computer (it’s fantasy), she has two classes of ciphers she can roll by hand at her disposal: alphabetic ciphers and one-time pads.

Alphabetic ciphers include the classes of substitution ciphers.  The spy bard knows enemy bards on the other side who intercept her messages can trivially crack simple monoalphabetic ciphers with frequency analysis.  She has to assume her messages can – and will – be intercepted by fate or by violence. If the enemy catches and deciphers her messages, the intelligence is lost and she’s probably one dead, or undead, spy bard.  They can’t be deciphered. 

She employs a whole bag of techniques that come with her Linguist feat to slow and befuddle her enemies and increase the difficulty of her ciphers: she can insert random characters, she can encode spaces and ‘nulls,’ she can encode syllables instead of single letters, she can use codes inside her encoded text, and she can layer the cracking process with nasty little traps.  She can get very clever and use variations on the monoalphabetic cipher by using multiple alphabets to encode the message.  If she has time or tools, she can even use the Vigenere Cipher, a nasty polyalphabetic cipher extremely difficult to break by hand without time and a good way to guess the key.  Breakable, yes, but perhaps not before the spy bard and her team can get away.

The other option, and a favorite of spy bards, is one-time pads.  One-time pads are virtually uncrackable without the key because they are completely random – the ciphertext gives no footholds in the sheer, icy cliffs of cryptography for enemy bards to crack with frequency analysis.  It works like so:

1. The bard takes a highly sensitive message and one of her favorite plays or songs. 
2. She works through the work of art and gives every word a number. 
3. She replaces the letters of her message with numbers, each number corresponding to the first letter of a word in the work. 
4. She delivers a big list of numbers on a page.
5. Using Sending or Magic Mouth, she drops a message about the work of art to her teammate or a bag man – in effect exchanging the key in 25 words or less at a time delay.

No Diviner, no enemy secret agent, and no magic spell will crack that code if it’s intercepted.  However, this technique has two major weaknesses: 

1. The bard somehow give the key to the intended target of the ciphertext.  If she cannot cast spells, or is not high enough level to use messaging spells, she will need to rely on a back channel.
2. This work can never be used in another one-time pad so the bard needs a nearly inexhaustible supply of plays and songs.  Luckily, she is still a bard.

As a quick bard hack — Cryptography is a labor-intensive and slow process by hand unless one has unseen servant.  Much of the task of enciphering and deciphering is rote – look up the chart, look up the key, look up the ciphertext, write the ciphertext down. Repeat.  Unseen Servant is a short duration programmable spell which performs a task a human servant can do – like writing down letters or looking up charts.  As difficult as it is, the bard can automate much of the labor for efficient communication and gain critical minutes using magic. 

The bard cannot pull off the entire savage burn on the evil Arch Lich without an infiltration team.  She’s a fantastic cryptographer, she speaks all the languages of evil, she can make friends with the Arch Lich’s closest henchmen and get them to spill their plans.  But she cannot get into the Arch Lich’s inner sanctum to steal the Lich’s phylactery alone.  She cannot get herself out if she gets into a fight.  She’s a Grifter.  She needs an Infiltrator.  She needs a Hitter.  She needs her crew. 

The Infiltrator is a Trickster Rogue.  Fast and intelligent, the trickster rogue is a master of the three finger discount.  The bard is the face of the operation; the trickster rogue is the action.  Her job is to break into bedrooms and steal plans, hide in ducts to overhear conversations, sneak into the dungeons to release high value prisoners, execute a couple of targets with backstab (and True Strike), get in, get out, and get away with the maps in her underwear.  She employs a subset of the Bard’s spy spell list –  she has Message to keep in contact with her party members – “Guard patrol on level 5,”- Disguise Self to meld in with the guards or the servants, a little Charm Person (“These are not the orks you are looking for,”) and, when detected, Sleep.  The Infiltrator uses Illusory Script as the microfilm camera of spells to copy plans and leave the originals behind. 

The Hitter is an Eldritch Knight.  A retrieval expert, her job is to protect the Bard and the Rogue when they get themselves into trouble.  She’s not a hired killer, but she will kill to get her teammates out of a rough situation. Having enough social skills to pass as almost anything, the Eldritch Knight can double up as a Grifter to back up the Spy Bard.  Her Mage Armor and Eldritch Sword means never having to carry weapons into a possible combat zone – she has them when she needs them.  One the job goes bad, the Infiltrator is on the run and the Spy Bard is talking her way out of being hung from the nearest rafter, the Hitter can reach out for her sword and start going to town. Hope the Bard has encrypted all the documents sufficiently when they get spotted while running away…

The three methodically plan out their the savage burn on the Arch Lich because that guy has to go down. He’s bad news.  The bard provides a cover for the team (“I’m a bard and these are my roadies!”), builds up her network of contacts, works a the human side of the intelligence chain, defeats the diviners the Arch Lich may have on his staff, and encrypts the data to smuggle out.  The thief lifts the plans about the Arch Lich’s army, his dragon in the basement, his phylactery, and makes off with the Arch Lich’s inexplicable pair of Boots of Striding and Springing.  The thief also performs a little covert ork and hobgoblin murder.  The Eldritch Knight smacks people in the face when it all goes bad because it always all goes bad.   Getting out is difficult; sometimes she stabs some former ‘friends.’ 

They are a highly trained team.  They work on hire.  They answer to no master – that anyone publicly knows about.  They coordinate on a job through well-placed Message, Sending, Magic Mouth, dead drops, and signals.  The job is to get in and get out.  Preferably without getting caught or setting the Arch Lich’s castle on fire. 

When a Kingdom needs help to deliver them from evil, these are who they call first.

In this particular example, we can assume the run went smoothly. The bard talked the team in under the nose of the Arch Lich and made some friends. The team set up dead drops in secure locations inside the Arch Lich’s compound. The thief bloodily murdered a few orks with death from above.  The team discovered the Arch Lich’s horrible plan. They snuck out by cart — “You’re out of beer!” – in the night.  The Eldritch Knight cleared out patrols on the way home. They smuggled their encrypted information to the Duke, who handed it to his cipher secretary for decryption.

Then the Duke called in the main hitters, the fireball wielders, the combat team and handed them the decrypted intelligence.  Here you go, a ready-made adventure for heroes to go roll an Arch Lich for the good of us all…  

Pre-Build Team:

The focus was mostly on the bard but the bard needs a posse.  To express the complex idea of how to build an infiltration team and how the spy bard works in practice, we put together some example characters. This pre-built 5th level infiltration team is a group of highly trained women operatives and mostly ready for play.  I didn’t write these – all credit for these character sheets goes to my research assistant (and husband!) by Eric Thornber.  

These PDFs are free for download.

• Aglaea the 5th Level Spy Bard: Bard and Bard Spell Sheet
• Euphrosyne the 5th Level Spy Rogue: Trickster Rogue and Trickster Rogue Spell Sheet
• Thalia the 5th Level Eldritch Knight and Eldritch Knight Spell Sheet

Writer’s Note: This started as a discussion on twitter about D&D/Shadowrun cross-over.  This is less socio-economics and more world-building but gets at a long standing issue: the Bard – what good is she good for?  It turns out in D&D5e, she’s the lynchpin in a slightly different class of stories than the standard smash-and-grab murder hoboing.  Then I really enjoyed the idea.  Unfortunately, I ran out of words, so I may continue into a major Crypto Bard vs Diviner Underground War write-up next week.  This is less intrigue than I would have liked.

The team at the latter half of the article is based on Leverage’s Hitter/Grifter/Hacker/Thief combo with the Bard filling the role of the Grifter and the Hacker.  The Bard and Rogue are essential.  The Hitter can be swapped out for a Warlock and a Sorcerer, but the Eldritch Knight was the most fun.

While writing this I came across the Chevalier d’Eon, the best example history could give me of a transgender spy bard because awesomeness.