The green examples should break at all their hyphens; the red ones should not.

T-shirt

billy-o

tally-
ho

co-
author

hi-
de-
hi

far-
sighted

hocus-
pocus

Nanki-
Poo

Miami-
Dade

Wells-
next-
the-
Sea

Lee-
on-
the-
Solent

\\/^-_-^\//

(''')-.-(''')

:-">

<{^-^}>

:-D