I'm no great expert, but from time to time I try to help my brother-in-law (nice guy but with the technical expertise of a fencepost).  He is a real old-timer, running Windows Mail (not Windows Live Mail) on a Vista PC.  He doesn't always receive emails that I (and reportedly some others) send to him, and I've been unable to work out why.  For example, I answer his emails to me using 'Reply' which I assume guarantees that there is no error in his address; and  I don't receive any 'failure to deliver' feedback messages, except his verbal ones!  So far as I know, he has no problem with sending emails.

Rather than try to tinker with his creaking email client I thought it might be better to move him to Outlook in the hope of removing this baffling symptom.  However, when I started down that route I was immediately asked for (his) Microsoft account password, which produced a new problem; he vehemently denies having any such thing.   Now I suspect he must have set up an account somewhere along the way, possibly years ago, but I'm afraid he just doesn't recognise the question.

So there seem to be 2 possible ways I can help him.

• One is to try solving the mystery of the failure to receive emails in his present setup.  Is this a known problem with Windows Mail?  (I assume it is no longer supported)

• The other is to persist in setting up Outlook as his email client, which means somehow getting round the admin problem of no recorded Microsoft account.  I'm sure MS themselves could help with that aspect, but is it worth it - is the likely cause deeper, so that moving to Outlook wouldn't improve matters?

Any suggestions welcome.