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I was watching some Critical Role last night, and one of the players had a -3 modifier to Insight (his Wisdom score of 7 didn't help). And that made me wonder:

What would be the lowest modifier you could create while staying within the normal, official rules?

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    \$\begingroup\$ Similar question, but about CON saves: What is the lowest possible Constitution saving throw modifier for a player character? \$\endgroup\$ Nov 22 '21 at 22:05
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    \$\begingroup\$ Related, in being almost the exact opposite of this: What is the highest total result one can get for a skill check? \$\endgroup\$
    – Someone_Evil
    Nov 22 '21 at 22:05
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    \$\begingroup\$ Lowest for any rolls or do you want to count the lowest with temporary conditions like debuffs? \$\endgroup\$
    – VLAZ
    Nov 22 '21 at 22:18
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    \$\begingroup\$ You used the word normal, but most of these questions rely on all sorts of setup that is far from normal. You might need to define this better. \$\endgroup\$
    – SeriousBri
    Nov 22 '21 at 23:09
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    \$\begingroup\$ Does it have to be applicable for every skill / tool (let's say e.g. Sleight of hand check) or just for whatever skill happens to be able to be pushed the lowest? \$\endgroup\$
    – Tobias F.
    Nov 23 '21 at 8:08
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-28 to all ability checks

I will give this a try and assume for the time being I can bring a nearly unlimited number of friends(or foes). I find it surprisingly hard to really push the modifier down, but this is my shot at it.

Lets start with the easy part, roll unlucky and you get a score of 3 in Dexterity, giving you a -4 for any ability checks you make.

Spells: -10

Now some enemies will cast a number of spells at our target (we assume all possible saves fail):

  • Raise Dead giving you -4 on ability checks

  • Synaptic Static You have to substract 1d6 from every ability check you make during the duration

Magic items: -2

Now we grab ourselves some magic items to even further curse ourselves (quite literally):

Enemies and "friends" abilities: -12

Have a College ot Lore Bard use their cutting words feature on you, giving you a penalty of one roll of their bardic inspiration dice. We assume the bard is at least level 15, so their die is a d12.

End result

With that, we reach a total of -28 to all ability checks.

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  • \$\begingroup\$ Some more options/penalties can be found in this answer to "What is the lowest possible Constitution saving throw modifier for a player character?". \$\endgroup\$ Nov 23 '21 at 11:37
  • \$\begingroup\$ Most of these questions assume the worst possible rolls, not the best \$\endgroup\$
    – SeriousBri
    Nov 23 '21 at 11:40
  • \$\begingroup\$ @SeriousBri well if you want a low score to see how far it can go, I assume you want to maximize any rolls that further lower the score to reach the furthest maximum in the desired direction,hence why I used max rolls on anything that lower the result \$\endgroup\$
    – Tobias F.
    Nov 23 '21 at 11:45
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    \$\begingroup\$ I would assume that too, which is why I voted to close the really unclear question \$\endgroup\$
    – SeriousBri
    Nov 23 '21 at 11:46

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