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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?
1 Solution
Hawkeye_11105Author Commented:
So I finally found the problem, SharePoint was setup to map the field proxyAddresses to the profile as the email address.
I went to Central Admin _> App Management -> Manage Service Apps -> User Profile Service -> Manage User Properties and manually changed it to map the "mail" field to the User Profile field Work email.
I started to stumble on this when I tried to create alerts for a few users and received an error message that they had no email addresses.
I forced a full synchronization, waited and then everything began working properly.
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