The problem here is that the word boundary for the first match is used up, and no longer matches for the second match. Something like the following will fix that: 
while ($doesntCountAll =~ /\s$pattern\s/g) {
    $count++; pos($doesntCountAll) -= 1;
}

[download]
However, the method given by Eimi Metamorphoumai is better.

In reply to Re: while =~ consecutive matching problem by TedPride
in thread while =~ consecutive matching problem by p.s

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