Split domain issue with 365

G

GC180

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So my company just bought a MS 365 business subscription with one license for testing. I have that license on my account.
I have set up a split domain with one address hosted by 365 and the rest hosted by Xneelo.
Set up a connector to send all mails destined for @companygroup.co.za to Xneelo (www13.cpt1.host-h.net), except mail for me as I'm on 365 ([email protected]).

Everything works as planned except for mail coming in from our helpdesk ([email protected]). Mail gets to 365, sends via connector to Xneelo, but fails with the reply "Error: ‎550 550 SPF policy prohibits sending from address 40.93.64.85"
My MX is pointed to 365 (companygroup-co-za.mail.protection.outlook.com) and my SPF contains 365 and Xneelo with a soft fail.

This is the complete error when doing a mail trace:
Reason: [{LED=550 SPF policy prohibits sending from address 40.93.64.85};{MSG=};{FQDN=www13.cpt1.host-h.net};{IP=197.221.2.13};{LRT=6/10/2026 10:50:29 AM}]. OutboundProxyTargetIP: 197.221.2.13. OutboundProxyTargetHostName: www13.cpt1.host-h.net

Any ideas?
 
The helpdesk email is coming from spiceworks..com via your xneelo server. I think it is failing the spf check because spiceworks won't have authorized your xneelo ip in their spf.
 
Xneelo says that sending IP 40.93.64.85 is not covered by your SPF record..

You say that it is, because your provided SPF record includes spf.protection.outlook.com which covers the sending IP Xneelo complaints about..

So either Xneelo is not doing the SPF lookup correctly or the email from spiceworks via the connector in 365 to Xneelo ends up with a different Mail-From/return-path/envelope from address..

My money is on the latter, that the Mail-From/return-path/envelope is not your domain but a Spiceworks one.. So Xneelo is doing the SPF lookup against the Spiceworks domain and not yours..

I am not familiar with 365 but see if there is a way to preserve header information when forwarding emails, which should resolve this..
 
Turns out it was something seemingly simple. The error was caused by Xneelo spam filter. If disabled, all mails worked. So I enabled it and added a lot of domains to the allow list. Weird as there were no spam warnings on Xneelo or 365 side :X3:
 
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