> cannot see why it does not do an automatic number count
This is a classic problem in sorting. As Stephen has said, it does a string sort. This means that it doesn't see numbers, it only sees characters. it sorts by comparing strings one character position at a time. Thus, it sees 'Now 100' as coming before 'Now 2' ('Now 1' comes before 'Now 2', ignoring the characters that come after).
It's the same reason many media players will list '10 Track10' before '2 Track2', and why it's a good idea to use leading zeroes when naming files prefixed with a track number; '2 Track2' becomes '02 Track2', which will appear before '10 Track10' in a string sort.
Different sort algorithms behave differently. I use cygwin on my PC, and Debian on my NAS. Both are flavours of Unix. If I run the command 'sort' on the same file on each of the two platforms, I get different results.
If you can come up with a robust sort algorithm that can cope with this problem, it would be welcomed by the computer science community...