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Problem with sending email with attachments to some recipients

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Last Modified: 2016-08-15
This is a strange one. Recently I upgraded a site from imap email to Office 365 Exchange. The clients use Office 2010. One user is having an issue where he has about 6 people he sends email with Excel and PDF attachments from Outlook and they get the email but no attachment.
Everyone else he sends to work fine. All these people are from different domains. he has sent me the email and it works fine

If he sends the email from www.portal.office.com  mail it sends the email and the attachment fine to those people. If he sends from his iPad it also works fine

What could it possibly be and how do you diagnose this?

Thanks
Andrew
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