Nice find. Do you have an idea for a fix?

@idank please look at my fix which I submitted. It works good and covers below tests.

import logging
import re

if __name__ == "__main__":
    logging.basicConfig(format='%(asctime)s - %(levelname)s: %(message)s',
                        level=logging.DEBUG)
    opt_regex = re.compile(r'''
        (?P<opt>--?(?:\?|\#|(?:\w+-)*\w+))  # option starts with - or -- and can have - in the middle but not at the end, also allow '-?'
        (?:
         (?:\s*((?P<argoptional>(<=|=<|=\[))|=)\s*)  # -a= or -a=< or -a=[ or maybe -a<=
         (?P<arg>
          (?(argoptional)         # if we think we have an arg (we saw [ or <)
           [^\]>]+                # either read everything until the closing ] or >
           |
           (?(2)
            [-a-zA-Z]+             # or if we didn't see [ or < but just saw =, read all letters, e.g. -a=abc
            |
            [A-Z]+                # but if we didn't have =, only allow uppercase letters, e.g. -a FOO
           )
          )
         )
         (?(argoptional)(?P<argoptionalc>[\]>])) # read closing ] or > if we have an arg
        )?                        # the whole arg thing is optional
        (?P<ending>,\s*|\s+|\Z|/|\|)''', re.X)  # read any trailing whitespace or the end of the string

    for i in range(1, 10000):
        s = '-?' + ' ' * i * 1000

        logging.debug('Started with {} spaces'.format(i * 1000))
        opt_regex.match(s, 0)
        logging.debug('Finished with {} spaces'.format(i * 1000))

Output:

2021-12-26 22:01:12,654 - DEBUG: Started with 1000 spaces
2021-12-26 22:01:12,655 - DEBUG: Finished with 1000 spaces
2021-12-26 22:01:12,655 - DEBUG: Started with 2000 spaces
2021-12-26 22:01:12,655 - DEBUG: Finished with 2000 spaces
2021-12-26 22:01:12,655 - DEBUG: Started with 3000 spaces
2021-12-26 22:01:12,655 - DEBUG: Finished with 3000 spaces
2021-12-26 22:01:12,655 - DEBUG: Started with 4000 spaces
2021-12-26 22:01:12,655 - DEBUG: Finished with 4000 spaces
2021-12-26 22:01:12,655 - DEBUG: Started with 5000 spaces
2021-12-26 22:01:12,656 - DEBUG: Finished with 5000 spaces
2021-12-26 22:01:12,656 - DEBUG: Started with 6000 spaces
2021-12-26 22:01:12,656 - DEBUG: Finished with 6000 spaces
2021-12-26 22:01:12,656 - DEBUG: Started with 7000 spaces
2021-12-26 22:01:12,656 - DEBUG: Finished with 7000 spaces
2021-12-26 22:01:12,656 - DEBUG: Started with 8000 spaces
2021-12-26 22:01:12,657 - DEBUG: Finished with 8000 spaces
2021-12-26 22:01:12,657 - DEBUG: Started with 9000 spaces
2021-12-26 22:01:12,657 - DEBUG: Finished with 9000 spaces
2021-12-26 22:01:12,657 - DEBUG: Started with 10000 spaces
2021-12-26 22:01:12,658 - DEBUG: Finished with 10000 spaces
2021-12-26 22:01:12,658 - DEBUG: Started with 11000 spaces
2021-12-26 22:01:12,659 - DEBUG: Finished with 11000 spaces
2021-12-26 22:01:12,659 - DEBUG: Started with 12000 spaces
2021-12-26 22:01:12,659 - DEBUG: Finished with 12000 spaces
2021-12-26 22:01:12,659 - DEBUG: Started with 13000 spaces
2021-12-26 22:01:12,660 - DEBUG: Finished with 13000 spaces
2021-12-26 22:01:12,660 - DEBUG: Started with 14000 spaces
2021-12-26 22:01:12,661 - DEBUG: Finished with 14000 spaces
2021-12-26 22:01:12,661 - DEBUG: Started with 15000 spaces
2021-12-26 22:01:12,662 - DEBUG: Finished with 15000 spaces
2021-12-26 22:01:12,662 - DEBUG: Started with 16000 spaces
2021-12-26 22:01:12,663 - DEBUG: Finished with 16000 spaces
2021-12-26 22:01:12,663 - DEBUG: Started with 17000 spaces
2021-12-26 22:01:12,664 - DEBUG: Finished with 17000 spaces
2021-12-26 22:01:12,664 - DEBUG: Started with 18000 spaces
2021-12-26 22:01:12,665 - DEBUG: Finished with 18000 spaces
2021-12-26 22:01:12,665 - DEBUG: Started with 19000 spaces
2021-12-26 22:01:12,666 - DEBUG: Finished with 19000 spaces
2021-12-26 22:01:12,666 - DEBUG: Started with 20000 spaces
2021-12-26 22:01:12,667 - DEBUG: Finished with 20000 spaces
2021-12-26 22:01:12,667 - DEBUG: Started with 21000 spaces
2021-12-26 22:01:12,668 - DEBUG: Finished with 21000 spaces
2021-12-26 22:01:12,668 - DEBUG: Started with 22000 spaces
2021-12-26 22:01:12,669 - DEBUG: Finished with 22000 spaces
2021-12-26 22:01:12,669 - DEBUG: Started with 23000 spaces
2021-12-26 22:01:12,670 - DEBUG: Finished with 23000 spaces
2021-12-26 22:01:12,670 - DEBUG: Started with 24000 spaces
2021-12-26 22:01:12,671 - DEBUG: Finished with 24000 spaces
2021-12-26 22:01:12,672 - DEBUG: Started with 25000 spaces
2021-12-26 22:01:12,673 - DEBUG: Finished with 25000 spaces

-a=VALUE
-a = VALUE
-a =VALUE
-a<=VALUE
-a <=VALUE
-a <= VALUE
-a<= VALUE
-a=<VALUE
-a=[VALUE

Are the two functionally equivalent? They seem to be but I'm not 100% sure. (:

If we're certain they are, would be happy if you sent me a pull request. I'll merge it and update the backend.

@idank I checked it once again and in my first fix was bug - not all built in tests finished with success. I have made one more commit, which covers sample above file and tests from test-options.py.

The change I made is only limited to the number of spaces before and after = Before:

(?:\s*(=)?\s*)           # -a=
(?P<argoptional>[<\[])?  # -a=< or -a=[
(?:\s*(=)?\s*)           # or maybe -a<=

After:

(?:\s?(=)?\s?)           # -a=
(?P<argoptional>[<\[])?  # -a=< or -a=[
(?:\s?(=)?\s?)           # or maybe -a<=

By answering your question yes, I am sure it is functionally equivalent to the previous version Here You have PR https://github.com/idank/explainshell/pull/290