I couldn't reproduce the error from the code given. Can you supply a bit more? Here's what I tested with:

#!/usr/bin/perl

use strict;
use warnings;
use diagnostics;

my %SERVER;
my $key = 1;
$SERVER{$key}{one} = $SERVER{$key}{two} = 1;
print "$SERVER{$key}{one} == 1 && $SERVER{$key}{two} == 1\n";
if($SERVER{$key}{one} == 1 && $SERVER{$key}{two} == 1){
}
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