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I have a question about the damage type of a leaping Chaos Bolt (XGtE, p. 151; GGtR, p. 67).

The first step of the spell description is rather clear as to choosing damage type:

the target takes 2d8 damage. Choose one of the d8s. The number it rolled determines the type of damage

and following that, it adds

If you roll the same number on both d8s, the chaotic energy leaps from the target to a different creature

Finally, it adds

Make a new attack roll against the new target, and make a new damage roll, which could cause the chaotic energy to leap again.

It is clear that this 2nd (or later) damage roll follows the same rule about leaping on doubles. It's not perfectly clear to me, because it's not restated, whether you also re-apply the "choose damage type from one of the d8s" mechanic from the first target.

I'm thinking you probably choose a new damage type each time, but I'm not sure if that's RAW or RAI or just what I'm thinking.

Basically, do you choose the damage type randomly once per casting, or once per target?

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Yes, you choose a new damage type per target/leap

The spell description for Chaos Bolt contains the following (emphasis mine):

Make a ranged spell attack against the target. On a hit, the target takes 2d8 + 1d6 damage. Choose one of the d8s....

It goes on to describe the damage choice as you've mentioned above.

Since we already know the following (emphasis mine):

If you roll the same number on both d8s, the chaotic energy leaps from the target to a different creature.... Make a new attack roll against the new target, and make a new damage roll, which could cause the chaotic energy to leap again.

We can then interpolate that the values of the d8s do indeed matter beyond how much damage they represent, since they need to match in order for the spell to leap.

It seems to me that if the values of the d8s matter such that it could cause the spell to jump additional times, then they should matter in their original capacity as well, which in this case is determining damage type.

Support for this, as user Sdjz pointed out in a comment on this answer, can be found in the way the spell described determining a damage type in the first place:

Choose one of the d8s. The number rolled on that die determines the attack’s damage type...

That line, coupled with:

Make a new attack roll against the new target, and make a new damage roll...

Implies that as part of rolling the damage you must determine its type. And since we roll again for each leap of our spell, we are determining a new damage type each time.

Interestingly enough, in the case you roll two matching values on your d8s, you don't actually seem to get a choice in your damage type, so it wouldn't matter for the first bolt in this example.

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    \$\begingroup\$ Further support for this: When making the first attack, "The number rolled on that die determines the attack’s damage type" so this only determines the damage for that particular attack. If you make a new attack, how else are you going to determine damage? \$\endgroup\$ – Sdjz Jun 26 at 21:32

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