Hi Peter,
just as an addition, this is how I usually approach problems like this. First step is to check the logs of the different messages, and compare if there are any differences in the following details:
- Sendergroup
- Mail Policy
- Anything related to LDAP (masquerading, rerouting, etc).
Also, if the network consits of ESAs running centralized management (cluster), I also check the config for any machine specific configuration.
So basically the same you did already by confirming that the sender IP is always the same. But also check the mail policies the messages hit, especial if they are configured differently for antispam.
Hope that helps,
Andreas