Email with pdf getting flagged???

[cSalmon]

#1
I have a client that I can email back and forth with just fine, but as soon as I try and send an email with a pdf attachment it immediately gets flagged as spam and I get the Delivery Notification: failure message. Message refused by Heuristic check. This email from IP # has been rejected. The email message was detected as spam.

This has happened with two other employee's of the same company in the past. Is there anything I can do on my end?

I should note I have tried both my apple email address as well as a gmail address

 

[D.T.]

That's the virus scanner on their end getting a hit on the PDF (so it really doesn't matter the source). Assuming you've tried a couple of different PDFs (i.e., it's not a specific one that's got a byte signature that's setting of the heuristics scan), then I'd suggest a few things:

- Compressing them first, sometimes that changes the signature enough to change the scan results (on their end)
- Uploading them to a cloud service and linking out to it - for example, DropBox for Google Drive, create link, put link in email

 

[cSalmon]

Thank you for the informative response very much appreciated.

 

[PaulaAguilar]

Sometimes it happens, unfortunatel I have no idea about the reasons of it.