$line =~ /(\w+)\s+(.*?)\s{2,9}(.*?)/ ;

(.*?) will match 0 or more anything characters, and as few of them as possible. In other words, 0 characters. My approach to this problem would be to not worry so much about the spaces, but concentrate on the fact that "Last" and "Never" are possible delimiters to use. For example: 

while (my $line=<>)   {
    $line =~ /(\S+)\s+(.+?)\s*((?:Last|Never).+)/;
    print "$1::$2::$3\n";
}

[download]

With your input, this produces: 

flexlm::FlexLM license manag::Never logged in
m12345::Shmoe,Ronald K.::Last login Thu May  1 14:11:54 2003 (160 days
+ ago)
m54321::O'Schmoe,Karen D.::Last login Sun Sep 29 15:39:43 2002 (374 da
+ys ago
m54321::O'Schmoe,Karen D.::Last login Sun Sep 29 15:39:43 2002 (374 da
+ys ago
mresw3::Joe-Schmoe,Mira::Never logged in
mdsjlk::Schmoe, Robert L.::Last login Thu Sep 12 15:41:11 2002 (391 da
+ys ago)
oracle::OraSchmoe Oracle user::Never logged in
sshd::OpenSchmoe Privilege Se::Never logged in
web::suitespot,httpd serv::Never logged in

[download]

..which appears to be split out the way you want.

In reply to Re: more than one whitespace char as word anchor by delirium
in thread more than one whitespace char as word anchor by blink

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