Cryptic crossword clue
Spoke to skilled prisoner first 9

The most common and most likely answer to this crossword clue is the 9 letter word CONVERSED

I've seen this crossword clue in The Guardian
C
O
N
V
E
R
S
E
D

Buddy explains!

The straight part
We know that "Spoke to/Spoke to" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case spoke to/spoke to = conversed.
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 CONVERSED mean?

CONVERSED verb
  1. To talk; to engage in conversation
  2. To keep company; to hold intimate intercourse; to commune; followed by with
  3. To have knowledge of (a thing), from long intercourse or study

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