Gig held in digs somehow could be upsetting (13)
I believe the answer is:
disconcerting
'upsetting' is the definition.
(I know that upsetting can be written as disconcerting)
'gig held in digs somehow' is the wordplay.
'gig' becomes 'concert'.
'held' becomes 'in' (I am not sure about this - if you are sure you should give a lot more credence to this answer).
'in' indicates putting letters inside.
'somehow' is an anagram indicator.
'concert'+'in'='concertin'
'digs' anagrammed gives 'disg'.
'concertin' placed inside 'disg' is 'DISCONCERTING'.
'could be' acts as a link.
Can you help me to learn more?
(Other definitions for disconcerting that I've seen before include "Causing one to feel unsettled" , "Unsettling" , "Causing unease" , "Such as will cause anxiety" , "Worrying" .)