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In 3.5 edition there were hundreds of professions, including Clerk and Lawyer. It was purged, and for a good reason, but now, in 5e, I will have my party fill out the huge piles of forms, which will be checked with scrutiny found only in Mechanus.

I can ask for a Wisdom (Perception) check to note any unusual parts and fine print, and Intelligence (Investigation) to find out what to write to get what they want out of the Mechanus administrates. I will not apply their Charisma in any way because forms are mostly Yes / No questions and will be judged by beings of the pure order or their subordinates.

Are there any abilities, be it class, racial, background, tool or of any other type that would be applicable to this situation? Or things that aren't applicable directly by the rules, but may reasonably grant advantage or disadvantage?

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    \$\begingroup\$ I thought maybe one of the the tool proficiencies might help here, but looking at all of them none seem to fit. Calligraphy comes the closest, but it's about the presentation of writing, not the content \$\endgroup\$ Commented Jul 25 at 11:18
  • \$\begingroup\$ @TreeSpawned thank you, I added tools to the last paragraph. \$\endgroup\$
    – Mołot
    Commented Jul 25 at 11:23
  • \$\begingroup\$ Obligatory: forgottenrealms.fandom.com/wiki/Papers_and_Paychecks \$\endgroup\$ Commented Jul 28 at 1:53

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Let the players do this job.

I would recommend that instead of trying to think of all the possible ways to get a bonus, instead simply open it up to the players and let them suggest what skills or proficiencies they want to apply to filling out these forms. A raw Intelligence check would be a good starting point, if they can't come up with anything, but let the players come up with creative ideas for skill or tool proficiencies they might be able to invoke, or other abilities that they might be able to claim to give them a benefit. You'll save yourself the time spent coming up with ideas that nobody wants to use and take advantage of the players' inventiveness to come up with things you would never have thought of.

That said, in most cases, if no skill applies, it's just a raw ability check. There's nothing wrong with that, it's just the way the system works. Sometimes you can't apply a tool or training to what you're trying to do, and that's okay.

Don't look at skills alone.

Don't limit yourself to looking at skill proficiencies. Feel free to give out advantage if a player has a background or other character element that might apply.

For example, if one of the players has a background as a Watch officer in Waterdeep, maybe they could parley that into advantage by talking about how much paperwork they had to do filling out incident reports and arrest records. Or if one of the players is an infernal warlock, they might claim that they have some familiarity with devilish contracts and are therefore better prepared to handle the intricate (but less aggressively sneaky) documentation of Mechanus.

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    \$\begingroup\$ I like that this also gives the idea that some backgrounds / skills might apply to some forms / form-filling scenarios and not others: If the characters need to meticulously list every item of gear they're carrying, or describe the origin & maintenance of their weapons & armor, then appropriate proficiencies might apply to recall those details. Previously-established individual backstories might also apply, and might dovetail into their individualized reasons for visiting Mechanus. \$\endgroup\$ Commented Jul 26 at 18:19
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There aren’t any explicit rules that give proficiency or advantage for filling out forms correctly, but there are many traits and character options that could reasonably be considered to help.

Consider what is included as part of a broad skill proficiency given your game world and the character’s specific backgrounds

While the forms are of a simple “yes/no” type, understanding what the denizens of Mechanus are asking, and their expectations, involves knowledge of the planes. So I think there’s a case for Intelligence (Arcana) to apply to the roll, or possibly Intelligence (Religion) if the religion includes such knowledge.

Religion might also apply if the character is a member of a church which was quite officious - keeping meticulous parish records, writing indulgences, hand copying manuscripts etc. That could apply to a cleric or a monk.

One tool proficiency might apply: Calligrapher’s supplies

Someone proficient in calligraphy clearly has skill with a variety of writing implements, and as it’s not something that would otherwise come up often, I’d be inclined to allow it to apply. At the very least they’re less likely to make the equivalent of “typos” when filling out the form.

Proficiency with a forgery kit could apply, but I’d only rule that it did if the characters are lying on the forms or trying to copy answers from another source. Even then…maybe not.

Some backgrounds might suggest experience with filling out forms

An Acolyte, Guild Artisan or Merchant, Noble or Sage is very likely to have done a lot of paperwork. While there’s no specific proficiency involved, these backgrounds might suggest a skill they have would include relevant experience, or might justify advantage on a roll.

Other maybe suitable backgrounds could include Charlatan, Entertainer, Sailor, Soldier or Spy. And there are some from beyond the Player’s Handbook that might fit as well, including Archaeologist, City Investigator, Cloistered Scholar, Courtier or many of those available for Strixhaven students or the various Ravnica guilds, especially Azorius Functionary. (Thanks to Kirt for suggesting a few more.)

Order of Scribes Wizards might have an advantage

The Order of Scribes is an Arcane Tradition introduced in Tasha’s Cauldron of Everything. One of its key features is the “Wizardly Quill”, whose noted game effects are that it doesn’t require ink, allows the wizard to write much faster (at least when copying spell scrolls into their spell book), and can magically erase anything it’s written (allowing the wizard to correct mistakes without having to start over). While there aren’t any other concrete effects of the feature, this seems useful enough that I’d be inclined to offer advantage to such a wizard when filling out forms under pressure.

Some game effects can apply a benefit to any ability check

There are many of these, many applying to or supplied by Bards. They include Bardic Inspiration, non-bardic Inspiration, the Bard’s “Jack of All Trades” feature, and the guidance spell.

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    \$\begingroup\$ Would suggest adding a few more backgrounds to those you already have: "Azorius Functionary", "City Investigator", "Courtier". \$\endgroup\$
    – Kirt
    Commented Jul 25 at 22:25
  • \$\begingroup\$ @Kirt good suggestions; I did spot Azorius Functionary, but thought the very world-specific ones might be best lumped into a suggestion, and that Ravnica might not be as well remembered as Strixhaven. But those are good and I’ll add them in! \$\endgroup\$ Commented Jul 25 at 23:28
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Paperwork would certainly be an intelligence check. From PHB, these all apply to filling out bureaucratic forms:

Intelligence

Measures: Mental acuity, information recall, analytical skill

If applicable, a knowledge skill, most probably History would apply to knowing what to answer.

It would be an ability check, so anything which helps with those, helps. Examples:

  • Bard Jack of All Trades would apply (+ half proficiency bonus) if no skill was applicable.

  • Spells Foresight and Enhance Ability (for advantage) and Guidance (for +1d4) would also apply to ability checks.

  • Warlock Pact of the Talisman allows adding d4 to a failed ability check.

  • Divination Wizards Portent Die can be used

  • ...

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Might I suggest the humble Constitution saving throw?

If you've ever had to deal with endless reams of forms, you'll understand that it's often far more of an endurance sport than it is a test of the mental faculties - alright, maybe it's both. But, you'd miss out on a great flavor opportunity by making the ordeal purely mental, and not also somehow physical.

For actually running the encounter, try porting Skill Challenges

It's a fun minigame that is often used to run non-combat encounters. See here: Are skill challenges an official option or homebrewed?

I recommend asking for a Wisdom, an Intelligence, and a Constitution saving throw from in amongst the PCs.

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    \$\begingroup\$ Concentration checks are Constitution checks, so there is precedent for mental endurance requiring Constitution \$\endgroup\$
    – No Name
    Commented Jul 27 at 11:27

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