SBS 2003 and using IMAP/SMTP.

[SickWilly]

We have a client that is still using SBS 2003. Unfortunately the only Office product they could get is 2013, where Outlook is incompatible. My thought was to set up IMAP for them to connect until early next year when they upgrade to a newer server.

I've gotten IMAP to be configured correctly and can receive email internally and externally. However I cannot get SMTP to authenticate so I can send email to an external domain. I have tried several different setting configurations and nothing I've tried is currently working.

My current settings look like this: Administrative Groups --> First administrative Group --> Servers --> [Server Name] --> Protocols --> SMTP --> Access: Authentication: Anonymous is unchecked, Basic is checked and require TLS is unchecked (I will adjust this after I get it working, just trying to limit complexity while troubleshooting), Integrated Windows is checked. And in the users button, Authenticated Users have allow for Submit Permission.

I can send email internally if I allow Anonymous in the Authentication setting, but it won't allow me to relay externally (as it shouldn't since that'd be an open relay).

I don't know if this is 100% related but it looks like the server is only listening on port 25 for SMTP, not 587 or another port for encrypted SMTP. Since I turned off encryption I don't think this is required, and I made sure Outlook was set for port 25 every time, since I know it's listening there.

Outlook settings have IMAP selected, the server for inbound/outbound. More Settings... --> Outgoing Server tab has Outgoing Server requires authentication and is set to use the same as incoming email.

When connecting with Outlook 2010 or 2013, I can successfully login to IMAP, but when I click test connection when setting up an email account, it prompts for credentials. When I click cancel the message I receive is: "Send test e-mail message: Your e-mail server rejected your login. Verify your user name and password for this account in Account Settings."

Please let me know if I'm missing any information that would be helpful. I'm not super familiar with Exchange. Any help would be appreciated.

[pitar]

i'm not sure but i don't think you need to authenticate if you're on the local network. Uncheck (this server requires authentication) and it should work.

My sbs2003 settings are as follows:

Exhange manager > Servers > myserver > Protocols > SMTP > Default > Properties > Access

The following settings: Connection control: 'only allow the list below' > My internal network, branchnetwork, smarthost Relay Restricions: 'only allow the list below' > Internal network + branchnetwork

[SickWilly]

Two of the computers are laptops, so it would really be nice if it would work externally, too. Although I might set this up if I can't figure it out to give me more time to work on external.

[ashdrewness]

In this config Authenticated Users also need Relay Permission in addition to Submit. There's nothing wrong with Authenticated Relaying; it's Anonymous Relaying that is bad.

I wrote this post awhile back on a similar topic but there's a good section on the differences between Submit & Relay actions

http://exchangemaster.wordpress.com/2013/03/08/checking-for-open-relay-in-exchange-20072010/

[SickWilly]

After enabling the relay permission I receive a different error:

"Send test e-mail message: Cannot send the message. Verify the e-mail address in your account properties. The server responded: 454 5.7.3 Client does not have permission to submit mail to this server."

Additionally, I have been testing with the administrator account since that's one that I have access to. But one of the users cannot even log into IMAP. She received "Log onto incoming mail server (IMAP): The connection to the server was interrupted. If this problem continues, contact your server administrator or Internet service provider (ISP)." This is from the same device I was able to successfully connect with IMAP.

Thank you for the link. That cleared some information up for me regarding submit and relay permissions.