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Missing email attachment began happening recently with a sender I frequently exchange emails with.
For experimental purpose I let him send the same email with the same attachment(pdf file) to my address I normally use(earthlink) and to my gmail address. The one received at gmail came with the attachment but the one received at earthlink did not. I forwarded the mail received at gmail to my earthlink address and the attachment came with it. Note that I am using web mail and not using any mailer software.

What could be wring?

Maybe EarthLink filtering of some sort? Especially if it's a single message sent with two To or Cc targets to both EarthLink and Gmail. Check the headers in the raw email to see if there's any indication, and try other file formats.

And see these old threads on EarthLink missing attachments:
http://mailblog.earthlink.net/webmail/2 ... mail_1.php
http://forums.macresource.com/read.php?1,767933

Sounds like Earthlink is blacklisting attachments from the sender's ISP. Probably a response to a flood of malware originating at the ISP in question.

The email is sent from iPhone 6 via gmail server. The experiment as in my thread starter post appears to points earthlink mail server but not all mail from iPhone has this problem.
I contacted earthlink tech support and my browser settings were changed through remote control session. I was told that cache and cookies were erased for possible remedy. The problem email sender has not send me test email yet to confirm. I am not sure if that would fix this problem.

Edit: The test email with an attachment has been received and the problem is found to be resolved.
I wonder how the cache or cookies could be the cause of the problem.

It was confirmed with Earthlink that the solution by clearing Cache and Cookies is temporary fix and they are working on a permanent solution.

The forum links above suggest they've been working on a fix for years.

With all the free cloud sharing options these days why not just send a link to those? It is not like if you are sending via email, the files are super secret anyways.

Flying Fox wrote:

With all the free cloud sharing options these days why not just send a link to those? It is not like if you are sending via email, the files are super secret anyways.

Are you suggesting placing file(s) in a cloud storage and emailing the link to it?

churin wrote:

Flying Fox wrote:

With all the free cloud sharing options these days why not just send a link to those? It is not like if you are sending via email, the files are super secret anyways.

Are you suggesting placing file(s) in a cloud storage and emailing the link to it?

Yes, that is exactly what he's suggesting.