Email woes after installing a new domain controller/exchange server. Help? >.<

[dana tassler]

Good evening all,

We're using a freeBSD server to host a production Ruby on Rails application. This application uses sendmail to hand emails off to an exchange server, and then those emails leave our facility.

The domain controller/exchange server's IP address changed, as did our local domain. It used to be "company.local" and it's now "company.priv."

I did replace occurrences of the old domain in /etc/hosts, /etc/resolv.conf and in the /etc/mail directory. Of course, after each change, I restarted sendmail.

Without getting into detail, our email is not working properly. Most recently it's failed to properly handshake with external mail relays/servers.

Anyway, would any of you happen to know anyone who's good with freeBSD, sendmail and getting those two to work well in an active directory environment with exchange? I surely would appreciate any help or leads.

[Efrem R. Jasso]

Tass--silly question but if you're talking about a globally accessible
domain name, have you waited for at least 24-48 hours for propagation of
the name to the root servers around the world?

-Efrem

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[dana tassler]

Efrem!

Not a silly question at all. I've been reading up about the
horribleness which is DNS, so I now know that's a by-product.

We did install the server last week Thursday.

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"One way is to make it so simple that there are obviously no
deficiencies and the other way is to make it so complicated that there
are no obvious deficiencies."

- C.A.R. Hoare, in talking about designing software.

[Anthony Hook]

From the FreeBSD server, can you ping it by it's FQDN (company.priv)?  If so, it's likely the Exchange server.  I would check out the receive connectors on the exchange server.

Is your sendmail attempting to relay anonymously, or is it authenticating?  If it is attempting to 'relay' anonymously, the exchange server is likely blocking it, and it will need to be 'whitelisted' by IP to use the Exchange to relay out.

This may help, http://technet.microsoft.com/en-us/library/bb124327(v=exchg.80).aspx.  You could also attempt to telnet from the FreeBSD server to the Exchange server and manually have an SMTP convo.  I often use http://en.wikipedia.org/wiki/Simple_Mail_Transfer_Protocol#SMTP_transport_example (type the black stuffs).  If it tells you that you cannot relay, then for sure you know it's the receive connector.

I hope this may help, let us know!

Thanks,

Anthony Hook

- Anthony Hook