Is it possible to short-check part of my baggage in a connecting flight?

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There is a related question here however your situation is slightly different. You are looking to short-check one bag to Lisbon. As the related post says, airlines are often reluctant to do this as they wish to ensure that you are flying the itinerary as sold. People who request to short-check bags are sometimes attempting to take advantages of fare discrepencies to bypass the airline's revenue management, and many airlines have instituted policies to prevent it.

In your case, it is obvious that short-checking only one bag would not allow you to leave the airport at LIS. If the airline personnel are logical, they should understand this and tag only one bag to ORY and one to LIS. Technically, this is entirely possible.

Update: I contacted TAP and they said all you need to do is inform their staff at check-in.

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