We've implemented domain masquerading as per the managing domains wiki. The issue we now experience is....
When a user sends from firstname.lastname@example.org to external the address is correctly masqd as email@example.com and you can reply from externally fine, if that user sends the same email but cc's in firstname.lastname@example.org and the external recepient then replies to all the cc'd email address is not masq'd so they end up replying correctly to email@example.com but get a bounce on the cc'd address which is still firstname.lastname@example.org
Is there any way to get cc'd internal addresses that are out bound (or in total) to masq to externaldomain.com?
The other option I have (as my client likes to change their mind frequently) us to drop the domain.local and just use the externaldomain.com as the default domain, but from initial research changing the systems domainname is not usually a good idea!
To top it off, we're also using zimbra as LDAP for Samba (which is beautiful) and I don't want to break this by changing domain name and having to re-create users.
Suggestions, pointers, flames welcome.