Hi Nils.  I've never used Windows Live (and I'm not even sure what it is).  The fact that we DON'T use that or "Windows Essentials" is at the direction of our own IT guy (who also built Boxi Software).   If he steers clear, there's a reason.  The fact that "Windows Live" is a discontinued brand name, might be the answer -- perhaps it never worked like it was supposed to.  We use Chrome and Firefox for our browsers and webmail working with gmail for standard e-mail.  To facilitate Outlook, we use Thunderbird (which works like a charm).  I'm going to e-mail Josh with your question and see what he has to say.