I was bored, so I decided to try to calculate what could be the highest total result one could obtain for a skill check.

Answers can include officially published material, including magic items - but no Unearthed Arcana. Wish is also not to be included.

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    \$\begingroup\$ Are you allowing for variant rules to be used? For example, proficiency dice (which results in a 1d12 instead of a +6 for a high level proficiency) \$\endgroup\$ – David Coffron Apr 2 '19 at 14:45
  • \$\begingroup\$ Oh? I never heard of that before. I should check it out. \$\endgroup\$ – Gael L Apr 2 '19 at 15:13
  • \$\begingroup\$ Unearthed arcana is a no, but any official magic item is a yes. And I guess I will do that, ok. \$\endgroup\$ – Gael L Apr 2 '19 at 15:27
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    \$\begingroup\$ @GaelL: It's an optional rule in the DMG (among other options for changes/replacements to proficiency bonuses). \$\endgroup\$ – V2Blast Apr 3 '19 at 1:13

The maximum result for a skill check is at least 169

The Rules

In order to maximize a skill check, we must use the following variant rules:

The Party

Our party, from Theros, consists of four characters:

  • A bard 15 -------------------------------------------------------- (for guidance via Magical Secrets and Bardic Inspiration)
  • A Circle of the Dreams druid 6/ Wild Magic sorcerer 6 ---- (for pass without trace, Bend Luck, Hearth of Moonlight and Shadow)
  • An artificer 7 ----------------------------------------------------- (for Flash of Genius)
  • A hobgoblin Oracle rogue 1/ranger 10/The Fiend warlock 6/any 3 ------- (for Oracle's Insight, Expertise, Save Face, Hide in Plain Sight, Dark One's Own Luck, Boon of Luck, and Boon of Undetectability)

The Gear

  • A luckstone
  • An Ioun Stone of mastery
  • The Lost Crown of Besilmer
  • 5 manuals of quickness of action
  • 5 tomes of clear thought (read by the artificer)
  • fresh mud, dirt, plants, soot, and other naturally occurring materials

The Calculation

  • Dexterity score is 30 (or a +10 modifier)
  • Flash of Genius adds 10 (Intelligence)
  • a Hero Point adds 1d6 (maximum 6)
  • Bardic Inspiration adds 1d12 (maximum 12)
  • Bend Luck adds 1d4 (maximum 4)
  • pass without trace adds 10
  • guidance adds 1d4 (maximum 4)
  • Hearth of Moonlight and Shadow adds 5
  • Hide in Plain Sight adds 10
  • Expertise results in doubled 1d12 (maximum of 24)
  • Dark One's Own Luck adds 1d10 (maximum 10)
  • Oracle's Insight adds 1d10 (maximum 10)
  • Save Face adds 5
  • Boon of Luck adds 1d10 (maximum 10)
  • Boon of Undetectability adds 10
  • luckstone adds 1
  • Ioun Stone of mastery adds 2 (thanks to expertise)
  • The Lost Crown of Besilmer adds 1d6 (maximum 6)
  • Roll a 20

Grand total: 169

Epic Boons of Fate

Finally, there is an epic boon called Boon of Fate which lets you add 1d10 to an ability check of any creature you can see. With enough creatures that have this epic boon you can make the total check immense. So basically, add 10 for each character with the Boon of Fate within 60 feet. Since you could use the Minimus Containment imprisonment spell to place them in extremely small spaces, there is effectively no limit to the amount of creatures you can fit in that 1.7 million cubic feet.

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    \$\begingroup\$ Step 16: How is hobby failing any check with a roll of 118? The highest DC given by the game is 30 which is labelled as "nearly impossible" \$\endgroup\$ – illustro Apr 2 '19 at 18:25
  • \$\begingroup\$ @illustro That's why I made it a contested check. Someone rolled 119 on Perception. Also, adventure modules have been known to have higher DCs \$\endgroup\$ – David Coffron Apr 2 '19 at 18:25
  • \$\begingroup\$ You should also include the chance of the character making that contested check rolling the maximum on all of their dice when working out the chance of a 123. \$\endgroup\$ – illustro Apr 2 '19 at 18:27
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    \$\begingroup\$ @illustro The chance is not calculable. That other character may have just used Divine Intervention, wish, or something to gain a ridiculous bonus on their next Perception check. It is not factored into my analysis \$\endgroup\$ – David Coffron Apr 2 '19 at 18:28

Arbitrarily Large

The Stealth skill has special rules that allow you to reuse the total for one check on the next so long as you aren't discovered. Combined with the Epic Boon of Fate and the simulacrum spell this allows a character to simply achieve arbitrarily large Stealth skill checks with a sufficient investment of time. Banning Wish makes this also take an arbitrarily large amount of cash, but that isn't a problem with the constraints in this question. No other skill does better than this.

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