Outlook Not Sending Attachments

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pjobrent

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Good Morning All,

I came across a strange situation yesterday afternoon, we have a user that is trying to send an email to a user and regardless of the attachment (pdf, jpeg, doc, etc.) the recipient cannot receive the attachment, but they still do receive the email and no errors about a missing attachment. I think that it sounds like the issue is on the recipients end, but our user said that she had this issue with one of the recipients previous email and now that he changed and has a new one the error came back, but we resolved it on our end the first go around? It has me stumped and I would greatly appreciate any insight on where to even begin, please let me know if you need any more information.

Also FYI, I had our user send the email to my work email and personal email and both of them came across fine with the attachment included, so it appears to be just the one recipient.

Thanks,
Brent
 
I'm guessing it is the recipient's side too, but there are some things you can check.

Does the message size indicate the attachment is still on the message, just not accessible?
Assuming she used HTML, is the received message HTML or plain text? Plain text indicates it's a problems with RTF formatting and winmail.dat.
Delete the recipients name from the autocomplete cache. Do attachments work now? If so, another indication the problem with with RTF/winmail.dat files.
 
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