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SharePoint 2013 Sharing notifications not sent

We recently upgraded to SharePoint 2013 and we want to take advantage of the Share feature for documents.
When I click on Share the document is correctly shared with the user selected. However; some users are not receiving email alerts while others are.
I have set up an SMTP relay to Office 365 and when I monitor the Queue folder and the logs I can see messages generated for the users that receive the messages but nothing for the other users. This tells me SharePoint is not even trying to send them messages.

The interesting thing is that these same users can create Alerts on a library or document and they will receive the emails meaning SharePoint has the email addresses (at first I thought it may be a sync issue).

I cannot find any common thread between the users. I checked if they had access their personal sites in case a "My Site" was required. Some have, some haven't.

Has anybody seen this behavior before?
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