lost email


I am asking on behalf of my friend who has recently had a stroke and not well enough to ask this question himself.
There seems to be a lost email in his hotmail account - he is confident that the email was sent from his hotmail account - but he can not trace it - it's not in the sent items and not showing in deleted items either. The recipient of the email is also saying that they have not received the email. What would be the best way to ensure that the email is not lost ? is there a system check that he can do to recover any lost emails ? appreciate any advice and please direct me to other groups if this is not the right place to get an answer. Thanks very much.

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