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A Staff of the Woodlands can take the form of a healthy tree (60 feet tall / 5-foot-diameter trunk / branches spread 20-foot radius).

The Awaken spell can give sentience to a tree, potentially turning this item into an Awakened Tree. This would make a really nifty, helpful and interesting magic item for players - and also turn it into an NPC, controlled by the DM in about 30 days time. Win-win.

Would this work - or does the pre-existing magic in the tree-version of the staff repel this spell?

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There is another problem

Awaken does not state that the plant or beast mustn't be magical. It states that Int score must be low or missing. Since the tree has no indicated Int score this is fine.

However, Awaken works in creatures / objects huge and smaller, i.e. fitting in a 15 by 15 feet cube. I would definitely say that the tree is too large, even with the thin trunk. As an aside, Ghosts of Saltmarsh has rules for ships which state that the ship's size category is determined by the greatest length on one axis. It seems reasonable (geometrically) to apply this here as well.

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    \$\begingroup\$ I wonder if there is a way to shrink the tree? \$\endgroup\$ Jul 22 '20 at 15:08
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    \$\begingroup\$ @Anagkai Brilliant! - so cast this upon this Woodlands tree-staff when it is smaller-younger & first enchanted... and let it grow into whatever larger size one wants to over time, thereby giving the item some lore-history. Assuming a magic tree can grow, that is. Time for more questions, it would seem.... \$\endgroup\$ Jul 22 '20 at 15:13
  • \$\begingroup\$ @Pureferret The Staff of the Woodlands does not specify. In fact, even the most common enchanted item in 5e will fit nearly anywhere. Somehow combining Woodlands enchantment into a Pot of Awakening is an excellent idea as well. \$\endgroup\$ Jul 22 '20 at 15:43

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