If I were your DM, I would have the awaken work on the staff snake, but it wouldn't stay on through turning the snake back into a staff and then into a snake again.
There isn't really a huge benefit to the process as described, and it's a big time and resource sink to do, so I wouldn't shut it down completely, but I'm not keen on letting a spell permanently improve a magic item unless that spell is designed for that purpose.
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what does my Druid casting Awaken on her Staff of the Python do?
Post under the same name at Giant in the Playground, and rarely here.
It is up to the DM to decide how he/she sees the whole thing.
Personally, I would say the spell fails because the snake from the staff is still an item, not an real beast.
If I were your DM, I would have the awaken work on the staff snake, but it wouldn't stay on through turning the snake back into a staff and then into a snake again.
There isn't really a huge benefit to the process as described, and it's a big time and resource sink to do, so I wouldn't shut it down completely, but I'm not keen on letting a spell permanently improve a magic item unless that spell is designed for that purpose.