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If I cast disintegrate and the enemy casts counterspell, would I wait to see the outcome of the enemy's counterspell before I cast counterspell?
Or would I have to just cast it without knowing (like when a Divination wizard uses their divination die with their Portent feature to replace a roll before it's made)?

Do I (the player) choose to cast counterspell before or after the other player or DM has made the ability check for their counterspell?

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You cast the 2nd counterspell before the 1st counterspell's ability check

Counterspell (PHB, 228) is clear in it's mechanics (my emphasis):

You attempt to interrupt a creature in the process of casting a spell.

When using this spell, you are interrupting the casting. No effects are being resolved prior to the counterspell.

In your question, no ability check is made on the first counterspell because it is currently being counterspelled. If for some reason that second counterspell fails, then the ability would check on the first would complete.

This means the following is happening in order:

  1. Creature A begins to cast disintegrate
  2. Creature B sees the spell being cast and casts counterspell. Let's say that they are casting it at 3rd level, so there would have to be an ability check to determine if it's effective. But wait!
  3. Before Creature B's spell is resolved, creature A casts counterspell to stop it. In the case above, Creature B was using a 3rd level slot, so the 3rd level slot spent by Creature A to counter it would be enough to stop it.
  4. Disintegrate now finishes and target makes saving throw.

The key here is that counterspell is interrupting the casting of a spell. In the first counterspell casting, it's interrupting disintegrate. In the second (the attempt to stop the first counterspell), it's interrupting the counterspell against your disintegrate.

To be clear: When you attempt to counterspell the counterspell, you are stopping it from completing. There is no ability check for the first counterspell against disintegrate because you are interrupting the casting.

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  • \$\begingroup\$ Does interrupting my own spell to cast a second spell have an effect on the first spell? \$\endgroup\$
    – aherocalledFrog
    Dec 31, 2019 at 15:26
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    \$\begingroup\$ @aherocalledFrog Nope! Take a look at this question and some of the associated links marked as dupes. \$\endgroup\$
    – NotArch
    Dec 31, 2019 at 15:29
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Counterspell states:

Casting Time: 1 reaction, which you take when you see a creature within 60 feet of you casting a spell

You can choose to counterspell when the other person counterspells. You cannot counterspell after the spell you're trying to interrupt is resolved.

Since counterspell's own effect is to attempt to interrupt another spell, a second counterspell would happen before the effect of the first one takes place - i.e. before the ability check for the first counterspell, as that ability check is part of its effect.

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    \$\begingroup\$ This is an excellent point. Counterspell interrupts another spell by occurring during the spell's casting and before its effect (e.g. before the creature targeted by disintegrate even has to make a save, since that save and resulting effects are part of disintegrate's effects). Since counterspell's own effect is to attempt to interrupt another spell, a second counterspell would happen before the effect of the first one takes place - i.e. before the ability check for the first counterspell, as that is part of its effect. \$\endgroup\$
    – V2Blast
    Dec 31, 2019 at 2:06
  • \$\begingroup\$ @V2Blast That would be a good answer as you stated it. \$\endgroup\$
    – Eternallord66
    Dec 31, 2019 at 14:09
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    \$\begingroup\$ @jgn This doesn't answer the question per se. The answer still leaves it vague based on your wording. Are you saying treat it like the Portent feature where I would counterspell before any roll is made to counterspell my disintegrate? \$\endgroup\$
    – Eternallord66
    Dec 31, 2019 at 14:11
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    \$\begingroup\$ @NautArch This answer is not addressing whether my counterspell would be before or after the ability check of the first counterspell in plain simple english. \$\endgroup\$
    – Eternallord66
    Dec 31, 2019 at 15:00
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    \$\begingroup\$ Rather than basically repeating what other answers have already said, I've simply edited part of my comment into @jgn's answer to clarify the point they're making. Hopefully they don't mind that. \$\endgroup\$
    – V2Blast
    Dec 31, 2019 at 18:20
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Counterspell resolves before the enemy's spellcasting ability check

Counterspell's casting is defined as follows:

Casting Time: 1 reaction, which you take when you see a creature within 60 feet of you casting a spell

Notably, it's a reaction you take while the creature is still casting the spell, meaning the spell has not resolved. This means that a successful Counterspell interrupts the attempt rather than the effect.

This unfortunately (for the players at least) means that, when casting Counterspell, the player only knows that a spell is being cast, and maybe what the spell is. They do not know whether that casting attempt would have succeeded.

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  • \$\begingroup\$ So you are saying it would be like the Portent feature where I would choose to counterspell before the roll is made for the other counterspell? \$\endgroup\$
    – Eternallord66
    Dec 31, 2019 at 14:58
  • \$\begingroup\$ I think so, yes. \$\endgroup\$
    – MrSpudtastic
    Dec 31, 2019 at 19:55

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