The most common and most likely answer to this crossword clue is the 4 plus 3 plus 5 letter word MISS THE POINT
I've seen this crossword clue in The Guardian
M
I
S
S
T
H
E
P
O
I
N
T
More clues leading to the result MISS THE POINT
Buddy explains!

The straight part
We know that "Fail to understand" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case fail to understand = miss the point.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.