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Spamcop error randomly when sending an email to our domain


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Yesterday I was made aware of a user that typically emails us regularly got an "email rejected" message when trying to send an  email to one of my users. Error: Mailserver gave this error: Your server IP address is in the SpamCop database, bye
 

They immediately resent the email and it went through.  The second occurrence happened today when another user from that org was trying to email another user of mine. Instead of instantly resending it, they had the third person in the conversation send it which it went right through again.

I'm not sure what would random error messages like this? Its my understanding if the IP was added to the blacklist it would be there for a minimum of 24 hours and neither my IP or the other domains showed up in the database. Any input would be appreciated!

 

I used MXToolbox to look at the Header of both of the emails that we had issues with and they both showed using blackllisted servers? 

BN8PR07MB6131.namprd07.prod.outlook.com fe80::b316:d552:9807:e223
CH2PR07MB6421.namprd07.prod.outlook.com fe80::8c51:6328:d9f7:ba8d

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fe80:: is the local interface address and is not to be used on the internet. It is used to dynamically acquire an actual IPv6 address.

More likely that one of the server's IPv4 address is on the blacklist and resending the email went through a different outbound server. I have heard that a lot of people get spam from outlook.com/onMicrosoft.com. So I wouldn't be surprised if they had a server on the black list.

Because of this kind of issues with the random blocks, I now lean toward using SpamAssassin instead of just a single blacklist. It takes a combination of various keywords and multiple blacklists in order for me to block inbound email in my server.
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