Cryptic crossword clue
Hung out with old spies tailing fool they’d regularly missed 10

The most common and most likely answer to this crossword clue is the 10 letter word ASSOCIATED

I've seen this crossword clue in Financial Times
A
S
S
O
C
I
A
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D

Buddy explains!

The straight part
We know that "Hung out with" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case hung out with = associated.
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 ASSOCIATED mean?

ASSOCIATED verb
  1. To join in or form a league, union, or association.
  2. To spend time socially; keep company.
  3. (with with) To join as a partner, ally, or friend.
  4. To connect or join together; combine.
  5. To connect evidentially, or in the mind or imagination.
  6. (in deliberative bodies) To endorse.
  7. To be associative.
  8. To accompany; to be in the company of.
ASSOCIATED adjective
  1. (of a person or thing) connected with something or another person.
  2. (of a company) connected or amalgamated with another company.

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