[Preciousss]

Her-ro,

I'm halfway there: managed to get Mail.app (v.1.3.9) to work with our Exchange server (5.5 SP5):

- Configured the Mail account for IMAP.
- Put in the IP address for incoming mail server

The half that works is I'm able to pull email down. The half that doesn't work: I'm unable to send.

Both Mail.app and Entourage v.X return similar error messages. Mail says:

* OK Microsoft Exchange IMAP4rev1 server version 5.5.2654.50 (our server name) ready

You can try to send using a different server. All messages will use this server until you quit or change your network settings.
[Dropdown menu]: send message using: blahblahblah

Entourage says:

A message in your Outbox could not be sent using account "[My Exchange account]." the server did not recognize the recipients or the server refuses to allow you to send mail.

Explanation: Relaying is prohibited. Error 5550

After some research, I found that relaying means trying to send a message through a mail server without being logged into it. Prohibiting relaying is meant to stop spammers from hijacking your mail server for their crap.

Possible solutions I'm wondering about is turning on authentication, both on the server end and within Mail. I tried the latter, no good. Must be the server end, but I can't remember at this point if our IT guy has tried it.

I found this article on Slipstick: http://www.slipstick.com/exs/relay.htm. I'm sure the solution is in there somewhere, but since I don't have access to the server, I'm at a bit of a loss. (Like most, I'm having to do all my Mac troubleshooting on my own here.)

Any ideas or clear directions I should ask the IT guy to perform? Besides upgrading everything, that is. This won't happen for a long time.

Specs on everything: 10.3.5, TiBook, 1GHz, Superdrive, 1GB RAM. Windows NT, Exchange 5.5 SP5. Old and creaky I know. But this is what I have to work with.

Thanks.

[jguidroz]

At the company I work at, our exchange server is also set up to allow pop/smtp accounts using authentication. I can access my exchange account via imap, and then use smtp to send mail, which I have to authenticate myself in order to use. If your administrator doesn't want to do this, then you could try setting up an SMTP server on your laptop to send out mail, but then reverse lookup won't resolve back to your laptop and your mail may get classified as spam.

[legacyb4]

Unless your admin has enabled outgoing mail to be sent through the server, nothing you do will let you get around that.

You also don't mention if you are on the same network as the server (sending from inside the office or from home, for example) which can also affect the way mail is sent.

My guess on how he's protecting his mail server:

a. if you are on the same network and cannot send mail through your mail client, he's probably restricting outgoing SMTP connections through the server by host/client authentication as well as by IP address

b. if you are outside the network (ie. from home), he has hopefully parked the Exchange server behind a mail gateway server so that it isn't even directly exposed to the Internet; in that case, you will have to ask him to set up a way for you to authenticate to the mail gateway and/or the Exchange server

Hope that helps.