Sorting problems when using a list

You are probably sorting them versus ascii string comparisons ('.' <'5', etc.) when you would prefer them sorted numerically. Try converting them to ints tuples and then sorting:

def ipPortToTuple(string):
    """
        '12.34.5.678:910' -> (12,34,5,678,910)
    """
    ip,port = string.strip().split(':')
    return tuple(int(i) for i in ip.split('.')) + (port,)

with open('myfile.txt') as f:
    nonemptyLines = (line for line in f if line.strip()!='')
    sorted(nonemptyLines, key=ipPortToTuple)

      

        
        
        
      

    

edit: The ValueError you are getting is because your text files are not entirely in # format. #. #. #: # as you mean. (There may be comments or blank lines, although in this case the error hints that there is a line with multiple ":".) You can use debugging methods at home in your problem by catching the exception and emitting useful debug data:

def tryParseLines(lines):
    for line in lines:
        try:
            yield ipPortToTuple(line.strip())
        except Exception:
            if __debug__:
                print('line {} did not match #.#.#.#:# format'.format(repr(line)))

with open('myfile.txt') as f:
    sorted(tryParseLines(f))

      

        
        
        
      

    

In the example above, I was a little sloppy as it still allows some invalid IPs (e.g. #. #. #. #. # Or 257.-1. #. #). Below is a more verbose solution to do things like comparing IP addresses with operators <

, as well as the natural job of sorting:

#!/usr/bin/python3

import functools
import re

@functools.total_ordering
class Ipv4Port(object):
    regex = re.compile(r'(\d{1,3})\.(\d{1,3})\.(\d{1,3})\.(\d{1,3}):(\d{1,5})')

    def __init__(self, ipv4:(int,int,int,int), port:int):
        try:
            assert type(ipv4)==tuple and len(ipv4)==4, 'ipv4 not 4-length tuple'
            assert all(0<=x<256 for x in ipv4), 'ipv4 numbers not in valid range (0<=n<256)'
            assert type(port)==int, 'port must be integer'
        except AssertionError as ex:
            print('Invalid IPv4 input: ipv4={}, port={}'.format(repr(ipv4),repr(port)))
            raise ex

        self.ipv4 = ipv4
        self.port = port

        self._tuple = ipv4+(port,)

    @classmethod
    def fromString(cls, string:'12.34.5.678:910'):
        try:
            a,b,c,d,port = cls.regex.match(string.strip()).groups()
            ip = tuple(int(x) for x in (a,b,c,d))
            return cls(ip, int(port))
        except Exception as ex:
            args = list(ex.args) if ex.args else ['']
            args[0] += "\n...indicating ipv4 string {} doesn't match #.#.#.#:# format\n\n".format(repr(string))
            ex.args = tuple(args)
            raise ex

    def __lt__(self, other):
        return self._tuple < other._tuple
    def __eq__(self, other):
        return self._tuple == other._tuple

    def __repr__(self):
        #return 'Ipv4Port(ipv4={ipv4}, port={port})'.format(**self.__dict__)
        return "Ipv4Port.fromString('{}.{}.{}.{}:{}')".format(*self._tuple)

      

        
        
        
      

    

and then:

def tryParseLines(lines):
    for line in lines:
        line = line.strip()
        if line != '':
            try:
                yield Ipv4Port.fromString(line)
            except AssertionError as ex:
                raise ex
            except Exception as ex:
                if __debug__:
                    print(ex)
                raise ex

      

        
        
        
      

    

Demo:

>>> lines = '222.111.22.44:214 \n222.1.1.1:234\n 23.1.35.6:199'.splitlines()
>>> sorted(tryParseLines(lines))
[Ipv4Port.fromString('23.1.35.6:199'), Ipv4Port.fromString('222.1.1.1:234'), Ipv4Port.fromString('222.111.22.44:214')]

      

        
        
        
      

    

Changing the values, for example, 264...

or ...-35...

will result in corresponding errors.