Lighttpd wont start error 255

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Whenever you see an exit status code other than zero returned, 255 in above case, it means that part failed.
Try run that bit of code next time your experiencing issues, it will give you some more details to look for:

sudo /usr/sbin/lighttpd -tt -f /etc/lighttpd/lighttpd.conf

pi@ph5b:~ $ man lighttpd
[..]
       -f  configfile
               Load configuration file configfile.
[..]
       -tt     Test  the  configuration file for syntax errors, load and
               initialize modules, and exit.

EDIT:

pi@ph5b:~ $ sudo /usr/sbin/lighttpd -tt -f /etc/lighttpd/lighttpd.conf; echo $?
0
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