Theorycrafting: The Most Skilled?

[Grey Watcher]

So, what are some ways you can pad an ability check? How high can you get?

Obvious things are


Proficiency,as of 17th Level (+6)
Expertise, as of 17th Level (+6)
Maxed out ability score (+5)


If you have access to magical items, the ability score can go higher, theoretically up to +10.

Guidance and Bardic Inspiration can get you +1d4 and +1d12, respectively.

Certain abilities and spells give out specific bonuses, like Pass Without Trace granting +10 (!) to Stealth.

What other things are out there?

[Bahamut7]

So, what are some ways you can pad an ability check? How high can you get?

Obvious things are


Proficiency,as of 17th Level (+6)
Expertise, as of 17th Level (+6)
Maxed out ability score (+5)


If you have access to magical items, the ability score can go higher, theoretically up to +10.

Guidance and Bardic Inspiration can get you +1d4 and +1d12, respectively.

Certain abilities and spells give out specific bonuses, like Pass Without Trace granting +10 (!) to Stealth.

What other things are out there?

Certain key items can boost ability scores beyond their maximum and increase it. the Manuals and Tomes of *insert ability score fluff* will not only increase your score by 2 but raise its cap by 2. Now how often these items can be found in a campaign and used are up to the DM. So for basic theorycrafting I would include the appropriate Manual or Tome at least once for a Maxed out ability score (+6).

On a sidenote, the Giant Belts override your score and maximum and set your score at 21 - 29. They will not work with the Manual of Gainful Exercise.

[Arenabait]

Well, this is much different than raw bonuses, but you can add in 1d12 bardic inspiration, 1d4 guidance, 1d10 Great Ones Own Luck, and 1d10 from Boon of Luck. And then there's stuff like the Lucky feat, Halfling Luck, and advantage from Enhance Ability. If we say stealth only, there's also advantage from invisibility, +10 from Pass Without Trace, and +10 from Boon of Undetectibility.

[Naanomi]

Appropriate Attribute 30: +10
Proficiency Bonus: +6
Ioun Stone of Mastery: +1
Bardic Inspiration: +12
Guidance: +4
Epic Boon of Luck: +10
Dark One's Own Luck: +10
*Expertise: +7* (assuming Ioun Stone of Mastery is applied first)
**Gloves of Thievery: +5
***Pass without Trace: +10
***Epic Boon of Undetectability: +10

A Rogue (or Bard)/Warlock could potentially be rocking...

Tools (besides thieves tool) Total: +53... a beer brewed with a roll of 73!
Skill Total: +60... I know about Bears with a roll of Nature: 80!
Sleight of Hand Total: +65
Stealth Total: +80

Unearthed Arcana offers a few more bonuses if allowed