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Our emails with attachments being rejected by oulook.com only.

Hi,

Our emails with attachments are being rejected by oulook.com only for the past few months..

It is very strange because outlook.com would accept our emails if it's without an attachment but
rejects if it's with an attachment.

And we are not having any issue with anyone except when sending mail to outlook.com.

 outlook.com doesn't give any reason except code 554 5.4.0. and google search for the error returned:

"Mail error 554 5.4. 0 can be caused due to improper mail server configuration or anti-spam tool configuration."

which is indicating that there is a problem on our end. But if there is a problem on our end,
why do we not have a problem sending mail to anyone except when sending to outlook.com?

Thanks!
Avatar of David Favor
David Favor
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This suggests Outlook.com might be classifying your message as SPAM.

Attach a copy of your entire message, with all headers + attachments intact.

Likely something will stand out when people run your message through test tools.
What sort of attachment?  Have you tried attaching a very simple text file, for example?
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COCO3515

ASKER

If outlook.com is classifying our email as spam, it would reject every single email from us. But it isn't rejecting every single email from us. It is rejecting emails with attachments only. And They are rejecting all types of attachments (pdf, docx, xlsx, txt & csv).
If these same attachments are forwarded to gmail and then forwarded to outlook.com from gmail, it works.
It just doesn't make any sense. Any ideas?

It may be that outlook.com considers your domain questionable and an attachment puts it over the threshold of what is allowed.

Do you have SPF, DMARC, and DKIM implemented and correctly configured?
No I haven't configured SPF, DMARC or DKIM because every one is able to receive our emails except outlook.com.

check if this helps :  Can not send emails with attachments using Outlook 2019 - Microsoft Community 
this says to put your files in onedrive - and mail the link - not the file :  Blocked attachments in Outlook - Outlook (microsoft.com) 
Without even having SPF implemented, I'm surprised that you're not having more problems than just outlook.com.  I've found gmail to be picky about that.  As time goes on you'll likely see more rejections.  SPF is very easy to implement; you should be able to get the exact string to put in DNS from your email host.
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Scott Fell
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Thank you, Scott Fell and CompProbSolv.
Just tested it on  https://www.mail-tester.com/  and they complained about spf and demarc, just like you had mentioned.
I'll try to set these up and see if the problem goes away. Thanks again!