reply 550 This mail server requires authentication (1) when

[neildt]

I'm trying to configure a MailEnable Standard Edition 8.04 so that my clients who have local postoffices on the server can relay mail via the SMTP service. Also I need our external mail scanning company to be able to deliver mail directly to our server and the local post offices once it has been scanned.

At the moment I've configured the following;

Under Inbound > Port Settings > Settings
I enabled 'Require connections to authenticate before sending

This means that any one trying to send email through this server need to provide authentication details. This works fine.

However, I need my email virus/spam scanning company to be able to deliver mail directly to he server. At the moment

Under Relay > Privileged IPs

I added all of their IP addresses in which they deliver mail from.

However, when they try to deliver the mail they are getting the message 'reply 550 This mail server requires authentication (1) when attempting to send via this SMTP (submission) port.;'

Why is this and how can I over come this problem. We are considering upgrading to Professional Edition, but if this feature isn't available in Standard, I think we will need to look for an alternative.

[MailEnable-Ian]

Hi

The option for "'Require connections to authenticate before sending" means that any remote mail server or SMTP application will be enforced to authenticate on that specific port number you have enabled the option for. If this is not enabled it does not mean that it will open the server for relay and allow anyone to relay through. It is for inbound connections only on that submission port. Therefore you need to disable this option and only use the SMTP relay options.

1. Allow relay for authenticated senders - This will allow your locally hosted mailboxes to relay via authentication.
2. Allow privileged IP's to relay and add the external applications IP address.

[neildt]

Thanks for your response. Even if I don't enter any more Privileged IPs, the external application is still able to deliver to my local mail boxes ? Is that correct ? Our mail filtering company informed us to perform the following;

"To avoid hackers and spammers bypassing our system and delivering directly to your server, we recommend you configure your network to ONLY accept emails from our IP ranges. To achieve this, please configure your firewall or mail servers to accept connections on port 25 from the following IP address ranges:"...

[MailEnable-Ian]

Hi,

Sounds like this is what you need: http://www.mailenable.com/kb/Content/Ar ... D=me020450

[neildt]

Hi Ian,

Yes that is what I was looking for. However even though I enabled it as below;

Require authentication for all connections:
This setting will enforce authentication for all inbound connections. Any remote server that tries to send to a locally hosted address within MailEnable will require authentication.

It appears that our mail filtering company were still able to deliver the email, despite the fact that I had not enabled their IP addresses for relaying. Do you know why this is ?

Thanks.

[MailEnable-Ian]

Hi,

Check the SMTP activity and debug log files to see what relaying criteria was met in order to relay (debug log).

[neildt]

Hi Ian,

Here is the information from both the log files;

SMTP Activity Log

05/06/14 09:07:14 SMTP-IN AED097877A734EC389B6C626504D1CDB.MAI 632 217.146.191.18 220 mail.mydomain.com ESMTP MailEnable Service, Version: 8.04-- ready at 05/06/14 09:07:14 0 0
05/06/14 09:07:14 SMTP-IN AED097877A734EC389B6C626504D1CDB.MAI 632 217.146.191.18 EHLO EHLO mx-gate01.antispamdomain.com 250-mydomain.com [217.146.191.18], this server offers 4 extensions 146 39
05/06/14 09:07:14 SMTP-IN AED097877A734EC389B6C626504D1CDB.MAI 632 217.146.191.18 MAIL MAIL FROM: <neildt@hotmail.com> 250 Requested mail action okay, completed 43 51
05/06/14 09:07:14 SMTP-IN AED097877A734EC389B6C626504D1CDB.MAI 632 217.146.191.18 RCPT RCPT TO: <postmaster@mydomain.com> 550 This mail server requires authentication (1) when attempting to send via this SMTP (submission) port. 107 53

SMTP Debug Log

05/06/14 09:07:14 ME-I0070: [AED097877A734EC389B6C626504D1CDB.MAI] (recv) socket [632] was gracefully closed during [RCPT] command by the remote client 217.146.191.18.
05/06/14 09:07:14 ME-I0074: [632] (Debug) End of conversation

The IP address in this sample data, 217.146.191.18 does have relay rights set using wildcard like 217.146.191.* for privileged IP's

Please let me know if you need any more information to diagnose this problem.

[neildt]

Do you need me to provide any more information? I would be greatful for a response

[MailEnable-Ian]

Hi,

From looking at the error in the SMTP log: This mail server requires authentication (1) when attempting to send via this SMTP (submission) port. It would seem to indicate that you have ticked the option within the SMTP port settings window for port 25 to require authentication on that submission port. If this is the case, untick the option and ensure that the inbound authentication option selected is the one under the SMTP > Advanced SMTP tab.

[neildt]

Hi

Yes that is correct. I've changed the settings as per your information below, and enabled 'all inbound connections require authentication' on the Advanced SMTP tab. I think I see what the problem is. When I've been testing I have been using the only email address I set-up (the postmaster email) for the primary domain.

I just checked in the log file and found

05/09/14 07:07:55 ME-IXXXX: [672] Recipient is SMTP notification address, so authentication requirement ignored.

I created another email address for this primary domain, and it is prevented me from sending to that email as I wasn't authenticated.

05/09/14 07:14:42 ME-I0101: [672] Local Delivery: Address ([SMTP:neil@primarydomain.com]) is local and sender must meet relay requirements.
05/09/14 07:14:42 ME-E0109: [672] Relay Denied: Failed to meet all relay criteria. Attempt to relay to [SMTP:neil@primarydomain.com] was denied

So it seems even if you aren't authenticated you can still send to this email ??

[MailEnable-Ian]

Hi,

Its because it was the SMTP notification address. It does not require auth.

[neildt]

Thanks Ian. That was confusing me... Might be worth adding this in your documentation somewhere, as I couldn't see it.