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A druid can shapechange into animal, and limited stuff changes together:

the clothing and one item held in each hand.

Can a backpack (preferrably loaded) count as an item held in one hand?

Assume the druid is strong enough in human form to lift several such backpacks.

Thing is, a backpack on the back is not a clothing item. So the DM has already ruled that the druid's backpack falls to the ground when they transform.

Druid's player then said he will take it off and hold the backpack in his hand when transforming, so the backpack transforms together with the druid.

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  • \$\begingroup\$ @HeyICanChan clarified in the Q text. \$\endgroup\$ – Mindwin Sep 21 '17 at 20:57
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    \$\begingroup\$ So the important part isn't the kind of container but whether the magic of changing shape discerns between the container—and everything within—being one thing (hence transforming with the druid) or as being a workaround to merge more stuff (hence failing outright, spilling the contents, sending the contents to wherever your extra or reduced mass comes from or goes to, or whatever), correct? \$\endgroup\$ – Hey I Can Chan Sep 21 '17 at 21:04
  • \$\begingroup\$ @HeyICanChan yeah. but I don't think the stuff on the druid's pockets fall off anyway, so either the backpack goes wholly or is left behind. \$\endgroup\$ – Mindwin Sep 21 '17 at 22:50
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    \$\begingroup\$ If we're already trying to interpret around the DM's rejection of a worn backpack, this reads like trying to read the DM's mind about a held backpack. The answer is ask your DM or change their mind. \$\endgroup\$ – okeefe Oct 12 '17 at 1:04
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A worn backpack should be treated as clothing. Since it's not, it's quite possible that additional things that should let your backpack be wild shaped won't work by GM fiat anyways.

That said, yes, a loaded backpack held in one hand should be treated as an item held in one hand and the pack should shift with you. Containers and the objects in them-- as well as other multi-part objects like thieves' tools, rations, boots, and necklaces-- generally should be treated as a single object for such effects, unless there's some reason to have it work otherwise (like someone specifically cutting a boot's laces shouldn't have the sole fall off, for example, and a cutpurse shouldn't destroy his desired loot when he slits the bag).

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With the DM already ruling, the likelihood is that they will have that ruling stand. Technically I would side with the DM, this is clothing not really something that can be interacted with outside of retrieval and storage. What is the purpose of not having the backpack transform. If this is outside of a fight, have the Druid take off the backpack and hand it to another player, and then have that player affix it to the animal form of the druid. Therefore you can still have the use of whatever you needed the backpack for, but aren't riding so close to the line to allow the DM to shrug it off.

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    \$\begingroup\$ I think you've misread the question; the druid player wants the pack to transform, but the DM does not. \$\endgroup\$ – user17995 Oct 11 '17 at 22:04
  • \$\begingroup\$ You are correct, I did misread that. Did the DM provide reasons as to why this isn't clothing? Essentially, it sounds as if the DM is trying to prevent something, like the Druid travelling as an animal for increased land speed or something like that. Otherwise I can't grasp why a loaded pack would be something to say isn't able to be transformed with. Either way, sounds like the DM will either need to be convinced or the Druid will need a work around, such as having another party member grabbing the pack. \$\endgroup\$ – Cyrus Knyghtbane Oct 16 '17 at 18:40

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