Mail rejected - Error message - 550 Content Rejected; Content Rejected

xuseronline

Verified User
Joined
Jul 10, 2019
Messages
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Several clients on different servers are complaining same issue that the mails that they are sending ( some of the mails) are being bounced back with message:

host-gmail-smtp-in.google.com
SMTP error from remote mail server after end of data:
550 Content Rejected; Content Rejected

Can anybody give any ideas what could be the issues and how to fix it?
 
You have too look at the mails to see what's wrong.
If it says "content rejected" there might be something like only links or too many links, too many words which could be a in a word filter, malware, could be anything.
Could also be dns or mx issues, hard to say.

Send a mail to:
https://www.mail-tester.com/

and see what the results are.
 
My issue ended up being that my emails were getting filtered at the Datacenter level, upstream from my server. So it ended up not being DirectAdmin or Server Configuration related. Posting here as it may be helpful for someone:

Reply from DC:
=========
This is our explanation regarding 550 Content Rejected error:

To help in the global battle of ever-increasing spam, our provider has implemented spam detection procedures on all emails prior to leaving our servers.

Each email is evaluated and rated according to spam rules to determine how likely they are to be actual spam.
Those that fail the test are returned to the original sender with the error message 550 This message was classified as SPAM and may not be delivered.

If you are receiving a bounceback with this error, then the email you sent has not passed the outbound filter.
=========
 
Check the domains and your server IP for blacklist entries and try to fix any that are listed.
 
My issue ended up being that my emails were getting filtered at the Datacenter level, upstream from my server. So it ended up not being DirectAdmin or Server Configuration related. Posting here as it may be helpful for someone:

Reply from DC:
=========
This is our explanation regarding 550 Content Rejected error:

To help in the global battle of ever-increasing spam, our provider has implemented spam detection procedures on all emails prior to leaving our servers.

Each email is evaluated and rated according to spam rules to determine how likely they are to be actual spam.
Those that fail the test are returned to the original sender with the error message 550 This message was classified as SPAM and may not be delivered.

If you are receiving a bounceback with this error, then the email you sent has not passed the outbound filter.
=========

So in other words this datacenter is intercepting SMTP traffic and scanning the content before you send it. Some would call this a great violation of trust/privacy but it's also not hard to understand why they would want to protect themselves.

If it were me, I'd ask for more information about what triggered the filter. They have it, if their system is at all reasonable. If they're not willing to share it, and you're certain the email is clean and of high quality, you might consider that they're not able to meet your needs as a provider.
 
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