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I am playing a Beast Master ranger with a stirge animal companion.

I know that once a stirge is attached to an enemy, it doesn't need to use its action or anything; Blood Drain's damage is passive/automatic, with no action required.

If it attaches to the back of an enemy, does that count as flanking (per the optional rule from the DMG) while it's attached?

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Moving Around Other Creatures

Whether a creature is a friend or an enemy, you can’t willingly end your move in its space.

There is noting in the stirge stat block that changes this. This is in contrast with the stat block for Swarms which specifically state that they can share a space.

The stirge remains in its own square and gives and receives flanking advantage as normal - that is, to creatures on the other side of any adjacent enemy (including but not limited to the one its attached to). Being attached, it will move to remain adjacent the creature its attached to if that creature moves - whether it keeps the same 'orientation' or can choose a different adjacent square is up to the DM.

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    \$\begingroup\$ The stat block says clearly, “and the stirge attaches to the target”. Being attached means it’s well within the space controlled by its victim. \$\endgroup\$
    – SevenSidedDie
    Commented Apr 15, 2019 at 6:15
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    \$\begingroup\$ @SevenSidedDie and when you grapple you are also attached but you don’t share a space. AFAIK only swarms can share a space. \$\endgroup\$
    – Dale M
    Commented Apr 15, 2019 at 6:46

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