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During our session, we ended up debating with our DM over the wording of Insect Plague. Insect Plague's damage occurs under three conditions. Once when the spell is cast, and creatures find themselves within its area. Another if creatures enter its area. Finally, if creatures end their turn within the area.

Essentially, we thought that Insect Plague would apply its damage a maximum of two times per turn, as the first two instances seemed mutually exclusive, at least until the creature exits the area and, for some reason, chooses to re-enter it.

The DM however interprets it differently, as he argues that starting your turn within the effect for the first time is synonymous with "entering" the spell, regardless of receiving the damage when the spell was cast. Which interpretation is correct?

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Starting your turn in the area does not count as entering

This has been explicitly addressed and clarified in a Sage Advice Compendium entry:

Reading the description of any of those spells, you might wonder whether a creature is considered to be entering the spell’s area of effect if the area is created on the creature's space. And if the area of effect can be moved—as the beam of moonbeam can—does moving it into a creature’s space count as the creature entering the area? Our design intent for such spells is this: a creature enters the area of effect when the creature passes into it. Creating the area of effect on the creature or moving it onto the creature doesn’t count. If the creature is still in the area at the start of its turn, it is subjected to the area’s effect.

Insect Plague works like this, too:

When the area appears, each creature in it must make a Constitution saving throw. A creature takes 4d10 piercing damage on a failed save, or half as much damage on a successful one. A creature must also make this saving throw when it enters the spell’s area for the first time on a turn or ends its turn there.

So the creature must make a saving throw when the area appears. It then however already is in the area, and starting its turn there does not count as entering, as it is not passing into it. It must make its next, second, saving throw at the end of the turn, if it is still in the area.

Your reading was correct. Only if during its turn the creature moved out of the swarm and back into it for the first time that turn, that would count as entering and trigger an additional, third saving throw.

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  • \$\begingroup\$ This is the correct reading and citation, but it does seem strange that SAC doesn't mention insect plague on its list of "some spells" that work like this. \$\endgroup\$
    – Kirt
    May 11 at 17:03
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    \$\begingroup\$ @Kirt That is because the list is of spells that have an effect at the beginning of the character's turn, not the end. The logic for what counts as entering however would not suffer from the difference, so the entry applies here too. \$\endgroup\$ May 11 at 17:32
  • \$\begingroup\$ Ah yes, thank you. \$\endgroup\$
    – Kirt
    May 11 at 17:53
  • \$\begingroup\$ Thank you for the confirmation and citation, this is what I believed as well. \$\endgroup\$
    – Menrel
    May 17 at 10:09
  • \$\begingroup\$ @Menrel My pleasure, glad this helped. If you think it answers your question, you can also use the green checkmark. \$\endgroup\$ May 17 at 10:12
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Your language seems confused

Nobody has the right answer and the right citation, but there appears to be something else going on with the language you are using. In the event that this is what is confusing you or your DM, I would like to address that.

Your question title asks: "Would a creature finding itself in the AOE of Insect Plague when it is cast receive damage three times if it were to also end it's turn there?"

No, only twice, and these would not be on the same turn.
1. The caster casts the spell on the caster's turn. The creature takes damage as described by the spell, because "When the area appears, each creature in it must...[take]...piercing damage". However, this is not damage taken when the creature "enters the spell's area for the first time on a turn". The creature has not entered the spell's area; rather, the spell's area has been cast on the creature's space, as the SAC ruling in Nobody's answer explains.
2. The creature starts its turn in the plague. It does not take damage. Starting its turn in the AoE is neither being in the area when the spell is cast, nor is it entering the spell area.
3. The creature ends its turn in the plague. It takes damage, as described by the spell, when it "ends its turn there".

Then you say, "Essentially, we thought that Insect Plague would apply its damage a maximum of two times per turn, as the first two instances seemed mutually exclusive, at least until the creature exits the area and for some reason chooses to re-enter it." There's a lot going on here, some of which is correct and some not.

we thought that Insect Plague would apply its damage a maximum of two times per turn
This is correct. On the caster's turn, the creature can take damage only once. On the creature's turn, it can take damage at most twice, once upon entering and once again if it remains.

the first two instances seemed mutually exclusive
If by the "first two instances" you mean the damage from being in the area when the spell is cast and the damage from entering, then they are mutually exclusive in the sense that they cannot happen the same turn, or apply to the same event. Being in the area when the spell is cast on the caster's turn is in no way entering the spell on your own turn. They are not mutually exclusive in the sense that both things could happen to the same creature, just not at the same time.

we thought that Insect Plague would apply its damage a maximum of two times per turn..at least until the creature exits the area and for some reason chooses to re-enter it
Your "at least" here is incorrect. Insect plague can damage a creature at most two times a turn, even if it chooses to re-enter. A creature with enough movement to enter the plague, leave, then enter again and remain there would only be damaged twice, because the spell says that the damage is taken "when it enters the spell's area for the first time on a turn". Re-entries don't damage because they are not the first time on a turn.

Finally you say "The DM however interprets it differently, as he argues that starting your turn within the effect for the first time is synonymous with "entering" the spell, regardless of receiving the damage when the spell was cast."
This is incorrect. Starting your turn in the area does no damage and does not count as entering the spell. The spell does not 'go away' for you outside your turn and then reappear at the start of your turn. If you ended the turn previous to yours inside the plague, you begin your turn inside the plague, you do not "enter" it.

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    \$\begingroup\$ Cheers, this is indeed in line with my interpretation. Regarding the re-entry as per your example, I would clarify that it would apply the damage the first time the creature crosses into the spell's area, irrespective of whether it started its turn within said space. This would be the first instance of damage the creature would receive from the spell within that given turn, and theoretical subsequent re-entries should not affect it for that turn. The only remaining possible condition for a second instance of damage would be the creature also ending said turn within the spell's area of effect. \$\endgroup\$
    – Menrel
    May 17 at 10:24

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