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The Redcap is a Small creature, but it has an ability called Outsize Strength:

While grappling, the redcap is considered to be Medium.

The spell enlarge/reduce, when using the enlarge effect, says:

The target's size doubles in all dimensions, and its weight is multiplied by eight. This growth increases its size by one category-- from Medium to Large, for example.

So while grappling, the Redcap's size is considered to be Medium. Then suppose one of his allies casts enlarge on him. Is his size now considered to be Large? And if so, what happens to his size when he is no longer grappling, but still under the effect of enlarge?

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A grappling Redcap is considered Medium regardless of its size

You have quoted the relevant text. Outsize Strength is unconditional. If the Redcap were instead made Tiny (through the Reduce part of enlarge/reduce), it would still be considered to be Medium while grappling.

For an example that does synergize with enlarge/reduce, we have the goliath race (EEPC, p. 11):

Powerful Build. You count as one size larger when determining your carrying capacity and the weight you can push, drag, or lift.

A Medium goliath made Large by enlarge/reduce would count as Huge for carrying capacity, and the weight they can push, drag, or lift.

Doesn't the name "Outsize Strength" matter?

D&D 5e doesn't distinguish between rules and flavor in the text of abilities, but names are a different story. The Sage Advice Compendium PDF says (p. 16):

I find it confusing that the mage armor spell is named that when it doesn't count as armor. Some spells and class features have figurative, not literal, names. The text of the spell or class feature explains what it does.

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    \$\begingroup\$ Note that while this is the correct interpretation RAW, as a DM I would probably overrule this, and cause Outsize Strength to be interpreted similar to Powerful Build (simply because that's what my players would expect to happen). \$\endgroup\$ Sep 5 '20 at 0:55
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    \$\begingroup\$ @Spitemaster: I'd concur; I suspect the reason for the trait just saying "Medium" is simplicity. The PC's trait is more precisely worded because they're more likely to be in a situation where enlarge/reduce is cast on them; the redcap can't cast spells, so it's easier to just say "the redcap is considered to be Medium" than it is to say "the redcap is considered to be Medium" (forcing to the DM to then double-check the creature's listed size every time this might be relevant). \$\endgroup\$
    – V2Blast
    Sep 5 '20 at 3:39
  • \$\begingroup\$ @V2Blast I agree, this is almost certainly a convenience thing. It does mean that a Redcap reduced to Tiny still counts as Medium while grappling, which is kinda fun, if not particularly sensible. \$\endgroup\$
    – Red Orca
    Sep 5 '20 at 15:02

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