Email attachments missing (Outlook 2013 / Exchange Server 2010)

I have an internal corporate user who cannot receive PDF attachments (or the email) from an external address but that same external user can send the email & attachment to others inside the company with no problem. We have a spam server and I white listed the external email address and overrode the attachment policy to ensure it was at least making that far. Any ideas on possible Exchange/Outlook settings that I may need to look at?
Shane TaylorAsked:
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Will SzymkowskiSenior Solution ArchitectCommented:
Does this users mailbox accept any attachments? If someone internally or a different external user sends an attachment does this user receive it?

Does the user have any rules in Outlook for attachments?

If you were to create a new mailbox does the email attachment get received?

Shane TaylorAuthor Commented:
Hi Will,

Yes, the external user is sending the email & attachments to another internal user successfully who is forwarding it to the person in question. I had thought he may have some rules in Outlook preventing attachments but he says he can receive PDF's from others just not this external address. I have not tried creating another mailbox but may try that.
Can you trace the message to see if Exchange received the email for the user?

If yes, can the user see the email in OWA or in Outlook if you disable cached mode?  If yes, to this then delete the user's profile then recreate it for Exchange to rebuild the local email cache.
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Will SzymkowskiSenior Solution ArchitectCommented:
If it is from ANOTHER external user with an attachment does the user receive it?

Shane TaylorAuthor Commented:
Hey Wayne,

I do not see the message using EMC Message Tracking. I can however see emails he has received without attachments from the external user.
Hi Shane,

Ok, so we have the following situation:

1. Other users in your company don't have any problems from receiving the same email with attachment
2. The user received the email but no attachment.

Do you see the attachment in OWA?
Shane TaylorAuthor Commented:
Hey Will,

Yes he can receive attachments from another external user.
Hi Shane,

If you see the email with attachment in OWA then we know it's not the server that's stripping the attachment for this specific user but it's a local issue on the user's computer.  We need to know how the email arrived on the server.


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Shane TaylorAuthor Commented:
Hey Wayne,

Yes to #1

No to #2. he is not even receiving the email.

No attachment or email in OWA.
Shane TaylorAuthor Commented:
I thought I would update this. I am not sure what the root cause of the issue was but I went in to the spam server and whitelisted the entire domain from where the attachments were originating (instead of just whitelisting the specific user email address) and apparently the manager can now receive attachments.
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