Cryptic crossword clue
Least confident bird bypassing mass on certain days of the year 8

The most common and most likely answer to this crossword clue is the 8 letter word TIMIDEST

T
I
M
I
D
E
S
T

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The straight part
We know that "Least confident" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case least confident = timidest.
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.

What does TIMIDEST mean?

TIMIDEST adjective
  1. Lacking in courage or confidence.

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