Former pupil caught breaking old fence? (8)
I believe the answer is:
obstacle
'fence?' is the definition.
The answer and definition can be both man-made objects as well as being singular nouns.
Maybe there's a link between them I don't understand?
'former pupil caught breaking old' is the wordplay.
'former pupil' becomes 'OB' (abbreviation for 'Old Boy' - private school pupil).
'caught' becomes 'c' (cricket abbreviation).
'breaking' indicates putting letters inside.
'old' becomes 'stale' (associated in meaning).
'c' placed within 'stale' is 'stacle'.
'ob'+'stacle'='OBSTACLE'
Can you help me to learn more?
(Other definitions for obstacle that I've seen before include "Anything that stands in the way" , "Progress blocker" , "bar" , "A spanner in the works?" , "difficulty" .)