Check out with short question and get something back (9)
I believe the answer is:
reconquer
'get something back' is the definition.
I can't tell whether this definition defines the answer.
'check out with short question' is the wordplay.
'check out with' becomes 'recon' (I can't explain this - if you can you should believe this answer much more).
'short' means to remove the last letter.
'question' becomes 'query' (synonyms).
'query' with its last letter taken off is 'quer'.
'recon'+'quer'='RECONQUER'
'and' is the link.
Can you help me to learn more?
(Another definition for reconquer that I've seen is " Once more defeat".)