Python : splitting string with multiple characters

What you could do is split it on the spaces, then go through each substring and check if it starts with one of the special delimiters. If it does, start a new string and append subsequent strings until you get to the end delimiter. Then remove those substrings and replace them with the new one.

I think what you want is

import re
re.split(r"(?<=\]) | (?=\$|\[)", "auth-server $na me$ $1n ame$ [position [$pr io$]] xxxx [match-fqdn [[$fq dn$] [all]]]")

This yields

['auth-server', '$na me$', '$1n ame$', '[position', '[$pr io$]]', 'xxxx', '[match-fqdn', '[[$fq dn$]', '[all]]]']

Note however that this is not exactly what you described, but what matches your example. It seems that you want to split on spaces when they are preceded by ] or followed by $ or [.

try re.split and a regex who make someone cry blood

import re
print re.split(r'(\$[^\$]+\$|\[\S+([^\]]+\]\])?|[-0-9a-zA-Z]+)',"auth-server $na me$ $1n ame$ [position [$pr io$]] xxxx [match-fqdn [[$fq dn$] [all]]]")

consider using pyparsing:

from pyparsing import *
enclosed = Forward()
nestedBrackets = nestedExpr('[', ']') 
enclosed << ( Combine(Group(Optional('$') + Word(alphas) + Optional('$'))) | nestedBrackets )
print enclosed.parseString(data).asList()

output:

[['auth-server', '$na', 'me$', '$1n', 'ame$', ['position', ['$pr', 'io$']], 'xxxx', 
 ['match-fqdn', [['$fq', 'dn$'], ['all']]]]]

Not quite a full answer, but I used regexp search...

a = "auth-server $na me$ $1n ame$ [position [$pr io$]] xxxx [match-fqdn [[$fq dn$] [all]]]"
m = re.search('\$.*\$', a)

combine this with a.split() and we can do the math...