What's the most skilled Infiltrator/Spy you could build?

[Douche]

Race, class, spells. Level 12, let's say.

What combo would you use if you wanted to best impersonate, infiltrate, mislead, etc? Also, assume they have a Hat of Disguise so they don't have to worry about spending spells on Disguise Self

[Aaron Underhand]

Race, class, spells. Level 12, let's say.

What combo would you use if you wanted to best impersonate, infiltrate, mislead, etc? Also, assume they have a Hat of Disguise so they don't have to worry about spending spells on Disguise Self

Don't need magical help, don't need all the levels

5th level vHuman ACTOR feat

GOO warlock with Mask of Many Faces, Misty Visions and One with Shadows

Pact of the Chain with invisible flying familiar

Only gets better as you level up, but really it's fully on stream by 5th

Edited:
Cantrips - Friends, Mage Hand, Minor Illusion

You have Detect Thoughts, Clairvoyance and Sending as spells before you start to pick 5 known...

Add Invisibility, Misty Step, Gaseous Form, Fly, Tongues

[Douche]

Mask of Many Faces

I added the Hat of Disguise so you didn't have to invest in Warlock specifically for this invocation. So, like, want to pick another one?

[Dudewithknives]

Either a level 12 lore bard half elf, just th massive versatility and charisma base to work with is great.

Or if you want the less social and be more sneaky infiltrator, I would go Kobold Scout Rogue. By then max out dex by level 8 and take the skilled feat. Training in just about everything, expertise is 6 skills, and can never roll under a 10 on anything that matters.

[Aaron Underhand]

Either a level 12 lore bard half elf, just th massive versatility and charisma base to work with is great.

Or if you want the less social and be more sneaky infiltrator, I would go Kobold Scout Rogue. By then max out dex by level 8 and take the skilled feat. Training in just about everything, expertise is 6 skills, and can never roll under a 10 on anything that matters.

Agree both Rogue and Lore Bard are strong - Rogue for reliable talent at 11th, and Lore Bard for expertise, skills, spells, and the ability to pass as a minstrel...

For a 12 th level build I would probably add 7 levels of Lore bard - I mean look at options for 4th level spells: Greater Invisibility, Dimension Door, Freedom of movement, Hallucinatory Terrain, Locate Creature and Polymorph

Not to mention expertise in two skills and cutting words


Oh and the extra invocation: Beguiling Influence - after all it's 2/3rd of a feat - though an argument can be made for devil's sight, eldritch sight or eyes of the rune keeper depending upon the setting.

edited:

Of course if you go Warlock to 12th level then you can get all of these AND pick up True Seeing at 11th...

[Biggstick]

A Half Elf who starts three levels Rogue Mastermind and then goes seventeen levels Bard (archetytpe doesn't matter). We're picking up the Actor feat, so we can really take advantage of the Master of Intrigue level 3 ability from Mastermind. Make sure to grab a background that provides two languages, as we need to naturally speak quite a few languages (3 from Half Elf, 2 from background, 2 from Mastermind). We don't need all the languages, just a majority of the commonly spoke ones.

Max out Charisma while picking up the Actor feat. We only need 13 Dexterity for the Rogue multiclass, but you can utilize a 14 or 16 here. I'd recommend grabbing Expertise in Deception, Persuasion, Perception, Stealth, and Insight. Also make sure to grab illusion spells to distract folks, Disguise Self for yourself (in case the hat doesn't work), Invisibility (for getting out when the situation gets hairy), and Enhance Ability.

The big thing with this character though is, that we're completely capable of becoming part of any crew as long as we can spend at least a minute observing someone and consequently removing them from the equation. You always want to utilize your Disguise Kit when you can. Truesight can't see through a physical disguise, as compared to illusion magic from Disguise Self. We're using the actual languages (you can grab Tongues if you want, but speaking the native tongue will make it easier) as well as the actual local accents to better infiltrate.

[Naanomi]

Depends on the magic level of the setting... ironically, a low magic disguise master is better in a high magic setting (when Mastermind's ability to fool mind reading is absolutely irreplaceable); whereas Lore Bard's ability to cutting word down people's Insight/Perception/Investigation checks is more pertinent. Assassin has some disguise abilities as well, but nothing I can't imagine doing without existing skill checks.

Variant Human for quick access to the Actor feat is great; but somehow I've always liked the Lightfoot Halfling that passes herself off as a child of other races.

Backgrounds: Charlatan gives some unique mechanical benefits to Forgery checks, so is hard to pass up unless you have a 'partner in crime' making your paperwork for you

[Mortis_Elrod]

Changeling Bard (whispers or satire) 6/ Rogue (Thief or AT) 6
Background: Custom.
Pick up Actor, and either Stealthy, Empathic, Quick Fingered, Silver-Tongued, Master of Disguise, Burglar, or a boost to Dex or Cha.

It all depends on what you choose your 6 expertise skills to be, and what kind of infiltrating you want to do. But this build nets you to do both pretty well.

Starting Rogue nets you 4 from a pretty nice list of skills, multi-classing into bard gets you 1 more, backgound gives 2 and changeling gives you Deception. You don't even need a hat of disguise but if you have it use it, in case your cover is blown via Hat, you can still be the disguise you want via Shapchanging and then play it off an insult for your simple hat to be handled so roughly. Your background is gonna help some too, make sure to pick the charlatan feature.

Satire gets you tumbling which is amazing, as well as some extra tool/skill proficiency. It also gives you a really nice and safe way to detect peoples thoughts, which is important for social infiltration.

Whispers has a decent combat use, (as long as you aren't infiltrating a people with poison immunity/resistance), a nice way to instill paranoia and have someone leave an area, and anothe form of disguising yourself with the added bonus of knowing their surface thoughts/memories. So is pretty good but no tumbling .

I would pick Whispers myself, even though no tumbling. (yes tumbling is that good. )

Thief Is great for Fast hands which is useful for any type of infiltration, and you also get second story work, which is a nice consolation prize for not having tumbling. Rogue levels themselves net you 4 expertise options, SA, Cunning Action, Thieves Cant (which might be useful for a ribbon if you have to work with other ninja/spys/infiltrators ) and Uncanny Dodge.

Arcane trickster has a little more flair to it of course, giving you spell options would add to your other spell options for having bard levels. Whats really good though is the Mage Hand Legerdemain ability which is kinda of like fast hands but only with your mage hand.

Would take Arcane Trickster here myself. more versatility.

Skills to want are: Deception, Stealth, Persuasion, Insight, Sleight of Hands, Perception. anything else is a bit bonus. Acrobatics might be useful for Ninja warriors, and maybe some knowledge skills for social infiltrators.

Tools to want proffs in: Thieves tools, Disguise kit, Forgery Kit, Poisoners Kit, and maybe a musical instrument or artisan tool. Or gaming set.

You can find the Satire bard in Kits of Old UA (https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&cad=rja&uact=8&ved=0ahUKEwjB28__u7vVAhWFxVQKHdG-ChYQFggoMAA&url=https%3A%2F%2Fmedia.wizards.com%2F2015%2Fdownl oads%2Fdnd%2F04_UA_Classics_Revisited.pdf&usg=AFQjCNE5z7IRQPoi5pWpvvFG9_oxWbirag), the Whispers Bard in the Bard UA (https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&cad=rja&uact=8&ved=0ahUKEwjbos2wvLvVAhWLq1QKHY3VARwQFggoMAA&url=https%3A%2F%2Fmedia.wizards.com%2F2016%2Fdnd%2 Fdownloads%2FUA_Bard.pdf&usg=AFQjCNEmBBZAR_zomqF7FqXTCb-EF3YD5A), the Skill Feats Stealthy, Empathic, Quick Fingered, and Silver-Tongued in the Skill Feats UA (https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&cad=rja&uact=8&ved=0ahUKEwiM_dSdvrvVAhUGzGMKHQtVBTUQFggoMAA&url=https%3A%2F%2Fmedia.wizards.com%2F2017%2Fdnd%2 Fdownloads%2FUA-SkillFeats.pdf&usg=AFQjCNFi3ZWe2520Zxe3PeIdF9T-lMyKVQ), and the tool feats Master of Disguise and Burglar, in the UA Feats (https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&cad=rja&uact=8&ved=0ahUKEwjnteOWv7vVAhWnxFQKHYtbDSAQFggoMAA&url=https%3A%2F%2Fmedia.wizards.com%2F2016%2Fdownl oads%2FDND%2FUA-Feats-V1.pdf&usg=AFQjCNFj5oFkV0Ex0ElMUi_RjADSI6OsXA) articles. Oh and Changeling from Eberron UA (https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=2&cad=rja&uact=8&ved=0ahUKEwj-naeOyLvVAhVM9mMKHaFDA0QQFggxMAE&url=https%3A%2F%2Fmedia.wizards.com%2F2015%2Fdownl oads%2Fdnd%2FUA_Eberron_v1.pdf&usg=AFQjCNGvi4GYkE4BL3bg3mE_9YxnDy25Bw).

[JackPhoenix]

I like the idea of changeling with disguise kit proficiency and Disguise Self spell. You polymorph to look like someone else, then you apply the kit to disguise that new look and apply the spell on top to look like someone else entirely.

If someone think something doesn't fit about you, they may reveal or dispel the illusion. If they find out that the "disguised" person is also fake... and even when they remove that disguise... yes, they still haven't revealed the real "you".

Improve the disguiseception by concealing the as a fake tree, or something, and use Hallucinatory Terrain to look like a boulder or a different terrain feature.

For maximum hilarity, the changeling is actually a Simulacrum possesed through Soul Jar :smallcool:.

Some form of invisibility or True Polymorph should be involved at some point.

[TheUser]

I gotta be that guy to come and say Subtle Sorcerer again don't I....

Imagine being able to use magic without noise or movement.

So while a warlock may be able to disguise themself indefinitely they have to cast and re-cast it in private away from prying ears and eyes.

Imagine not having to worry about persuasion checks and just casting suggestion, or dominate or sleep or any handful of spells (tongues) without needing to invoke incantations and hand movements.

Finally imagine being able to kill anyone using telekinesis to drop masonry on them, or phantasmal force to have them choke on something imaginary and sharp or any number of spells with know discernible visual effects to onlookers.

It's the most dangerous and cheezey infiltrator that exists, reads minds, compels truths, dominates minds and murders adversaries all while nobody is the wiser.

[Zene]

If there's any kind of spellcasting involved, it's gotta be subtle sorcerer. So at least 3 levels in sorcerer.

If this were a L20 theorycraft, I'd say take the other 17 levels in Illusionist, as their ability to warp reality itself at high levels would make them the ultimate spy.

But at 12, I'd probably say Sorc 3 / Lore Bard 9. Maybe exchange one level of the bard for Rogue if you need even more expertise --I'd ideally want expertise in stealth, deception, thieves tools, persuasion, sleight of hand, and intimidation; but not sure if those last two would be worth delaying fourth level bard spells. Probably not, as Dimension Door, Hallucinatory Terrain, and Polymorph could all be pretty sick for a spy.

[Talionis]

Agree in very high magic game you actually want a Rogue either Mastermind or Assassin. Friends is a cantrip that with your hat of disguise allows for a lot of help. I'm away from SCAG right now but Assassin wants nine or 13 levels, so if you won't level past 12 (or for levels after 13) I'd strongly recommend Goo Warlock 3, so much can be done with an invisible pet, the illusion cantrip combined with illusion invocation, and telepathy.

[Citan]

Race, class, spells. Level 12, let's say.

What combo would you use if you wanted to best impersonate, infiltrate, mislead, etc? Also, assume they have a Hat of Disguise so they don't have to worry about spending spells on Disguise Self
Too bad you put the cap at level 12.
At level 13, Assassin Rogue is the one you need. Expert at short-term, but more importantly long-term infiltration, this one can succeed on any mission, unless very hard and short-time ones. Add Ritual Caster for useful rituals and Observant for better spying, and Reliable Talent to stack insult to injury.

For a magic-based infiltration, a Rogue 1 / Lore Bard 3 / Tome Warlock X may be very good at it too, thanks to Invocations, Hex (depending on DM) and other illusions/transmutation spells.
Or play with Subtle spell as a Sorcerer, greater in some situations, but lesser against magically protected people (even if you are not detectable while casting the spell, you still create a magic effect after all ;)).

[Unoriginal]

Never rely on mind-controlling or mind-affecting magic to do the job. If/when the spell break, you have a whole world of troubles waiting for you.

[Talionis]

Never rely on mind-controlling or mind-affecting magic to do the job. If/when the spell break, you have a whole world of troubles waiting for you.

You can do a lot with the friends cantrip and a hat of disguise. Yes they know they were bamboozled, but you can look like anyone so they'll blame someone else for the bamboozling. It's a great trick for getting access to rooms you shouldn't.

It's why a little Warlock goes a long way because the combo of Illusion cantrip and Illusion Invocation, only one is concentration, allows for hiding when things go bad or for a distraction with sound and visuals without expending resources.

Invocations are great for infiltration since they can be recast as needed. And you don't need a huge dip to pick up a couple. Ebon Eyes/ Darkness spell option opens up with a three level dip.

Two levels of Rogue gives cunning action which is helpful, and expertise.

[evolutionXXVII]

I'd say a moon druid. Pass without trace is amazing for infiltration, wild shape means you can turn into a mouse, pigeon, or spider to move around unnoticed. If you're a spy and you need information, use Beast Sense to scout, speak with animals to ask your enemies horses or pet cat what the battle plans are, and animal messenger to send word back to your allies. Got caught and need to get out really quick? Meld with stone into the castle walls and just walk out. Conjure giant owls to cover your escape while you ride one to safety.

[Naanomi]

I'd say a moon druid. Pass without trace is amazing for infiltration, wild shape means you can turn into a mouse, pigeon, or spider to move around unnoticed. If you're a spy and you need information, use Beast Sense to scout, speak with animals to ask your enemies horses or pet cat what the battle plans are, and animal messenger to send word back to your allies. Got caught and need to get out really quick? Meld with stone into the castle walls and just walk out. Conjure giant owls to cover your escape while you ride one to safety.
Definetly a fun route, and don't forget the sensory advantages you have as a bloodhound or giant eagle. I played a Rogue 2/Druid X with the Observant feat for a while and just having passive perception in the 25-37 range was amazing

[BillyBobShorton]

Druid shadow monk. Turn into a mouse and shadow jump. /thread

[Lombra]

Since this is D&D and any high level threat will have anti-magic tools, I'd completely ditch magic users and focus on mundane infiltration, hence, a rogue assassin, probably with the actor feat.

[Naanomi]

Since this is D&D and any high level threat will have anti-magic tools, I'd completely ditch magic users and focus on mundane infiltration, hence, a rogue assassin, probably with the actor feat.
In a high-magic setting, the Mastermind's ability to fool magic lie detection probably beats the Assassin abilities

[Zene]

Never rely on mind-controlling or mind-affecting magic to do the job. If/when the spell break, you have a whole world of troubles waiting for you.


Since this is D&D and any high level threat will have anti-magic tools, I'd completely ditch magic users and focus on mundane infiltration, hence, a rogue assassin, probably with the actor feat.

I find these comments kind of funny. You assume there'd be anti-magic defenses, but no actual magic defenses? So like they're going to put in an anti-magic zone, but they're not going to put a prismatic wall up just behind it? Or like 100 glyphs of warding? Or walls you need to dig through, or pits too wide to jump?

A high-level bard has both the magic, and the skills (4 expertises, same a rogue, plus Jack of All trades for everything else, plus high charisma score for any lying/intimidating/persuading). So performs better than a rogue where magic works, and as well as a rogue (for everything except combat) in areas where magic doesn't work.


In a high-magic setting, the Mastermind's ability to fool magic lie detection probably beats the Assassin abilities

That's a good point. If you are going to go rogue, that seems to be the subclass to do it, as Zone of Truth and mind reading are both pretty easy to do in 5e. Although just making sure you don't get caught seems like a better defense.

[Lombra]

In a high-magic setting, the Mastermind's ability to fool magic lie detection probably beats the Assassin abilities

I just assumed non-playtest material. That mastermind ability is definately top-notch for this problem. Is it pre-level 13 tho?

[Zene]

I just assumed non-playtest material. That mastermind ability is definately top-notch for this problem. Is it pre-level 13 tho?

It's level 17, so yeah not really in scope here. Not playtest though, it's published material. SCAG.

[Lombra]

I find these comments kind of funny. You assume there'd be anti-magic defenses, but no actual magic defenses? So like they're going to put in an anti-magic zone, but they're not going to put a prismatic wall up just behind it? Or like 100 glyphs of warding? Or walls you need to dig through, or pits too wide to jump?

A high-level bard has both the magic, and the skills (4 expertises, same a rogue, plus Jack of All trades for everything else, plus high charisma score for any lying/intimidating/persuading). So performs better than a rogue where magic works, and as well as a rogue (for everything except combat) in areas where magic doesn't work.



That's a good point. If you are going to go rogue, that seems to be the subclass to do it, as Zone of Truth and mind reading are both pretty easy to do in 5e. Although just making sure you don't get caught seems like a better defense.

Disguising among nobles is the first thing that I think about when talking about infiltration, not sneaking in a dungeon, so that's why I proposed a rogue assassin, someone who can go in and out of mostly social encounters without triggering suspects.

If the subject were to infiltrate a dangerousluly trapped and defended place, full of undead and constructs, then I probably will suggest at least some magic.

[Lombra]

It's level 17, so yeah not really in scope here. Not playtest though, it's published material. SCAG.

Oh right, I got confused.