Most tricky ordeal in which one is faced with a bit of a dilemma? (9)
I believe the answer is:
thorniest
'most tricky' is the definition.
Both the definition and answer are superlative adjectives. Maybe you can see an association between them that I can't see?
'ordeal in which one is faced with a bit of a dilemma?' is the wordplay.
'ordeal' becomes 'test' (a testing situation).
'in which' is an insertion indicator.
'one' becomes 'i' (Roman numeral).
'is faced with' means one lot of letters go next to another (some letters act as the front or face of the word).
'a bit of a dilemma?' becomes 'horn' (as in the phrase 'on the horns of a dilemma').
'i' after 'horn' is 'horni'.
'test' going around 'horni' is 'THORNIEST'.
Can you help me to learn more?
(Other definitions for thorniest that I've seen before include "most problematic" , "Most troublesome or prickly" .)