Topic: PPTP client can't send mail with outlook 2000

[John Lewis]

When I'm connected to my SME 5.1b4 network via the PPTP VPN, I am unable to send mail using outlook 2000 from my SME accounts.

The Outlook error says the mailserver returned an "unauthorized relaying" error when sending messages to remote addresses.  Sending mail to local addresses works fine, though it takes a long time...

My understanding was that when I'm successfully VPN'd into the network, I should be able to send mail as though I am on the network.

Is there a setting I am unaware of that will allow me to successfully use outlook to send messages through my SME server while logged in via VPN?

I don't want to have to edit the qmail relay files, i'm on the road alot, nor do I really want to have to send all my mail via the web interface.

What else should I be looking at?

[John Lewis]

here is the Outlook error:

The message could not be sent because one of the recipients was rejected by the server. Server Response: '551 Sorry aka1.com(4.21.65.194), I don't allow unauthorized relaying.  Please use another SMTP host to mail from to '. (Account: 'jlewis@arachnerd.org', SMTP Server: 'mail.arachnerd.org', Error Number: 0x800ccc79).

My SME server's network/domain is arachnerd.com

My computer is on the aka1.com network.  I'm logged in to arachnerd.com via pptp vpb, and trying to send a message to the aka1.com domain.

Thanks.

[Charlie Brady]

John Lewis wrote:

> The message could not be sent because one of the recipients
> was rejected by the server. Server Response: '551 Sorry
> aka1.com(4.21.65.194), I don't allow unauthorized relaying.
> Please use another SMTP host to mail from
> to '. (Account:
> 'jlewis@arachnerd.org', SMTP Server: 'mail.arachnerd.org',
> Error Number: 0x800ccc79).
>
> My SME server's network/domain is arachnerd.com
>
> My computer is on the aka1.com network.  I'm logged in to
> arachnerd.com via pptp vpb, and trying to send a message to
> the aka1.com domain.

The problem here is that Outlook is not trying to send the mail through the PPTP tunnel, but just via the Internet. If you use the internal IP address of your server (probably 192.168.x.1, for some x) as the SMTP server, rather than mail.arachnerd.org, then you will probably be able to send your mail.

Regards

Charlie

[John Lewis]

Thanks Charlie, I'll try that today.  I'm annoyed I did not think of that.

However, my understanding was that when a PPTP tunnel is established, and if you have the "use default gateway on remote network" setting enabled, IP traffic from my PC should use the SME server as its gateway, thereby being an approved IP range for the SMTP server...

Am I wrong in this assumption?

[Les Mikesell]

Yes, a pptp connection will pick up an IP address on the local side of the SME server.  However it appears that you aren't using the SME server for your smtp relay - you need to change that in your outlook accounts setup.
There is a generic problem here, though...  If you have an outside ISP account at home with an email account there that only  accepts mail connections when you connect directly, and an office email account on an SMEserver, and a laptop that you carry back and forth, you can't configure outlook to be able to send and receive on both accounts at both places.   Has anyone solved this?