Sometimes, even if an outward port 25 is not blocked, an individual or organisation's normal external IP address has a difficulty in getting SMTP mail accepted. This could be because that IP was assigned in the past to someone who sent spam from it, or appears to be a dynamic address such as typically used for home connection. Whatever the reason for the "poor reputation" or "blacklisting", they can choose to redirect all their email out to an external smarthost for delivery.[3]

This option requires you have a fully qualified domain name but not necessarily full access to modify DNS records for this domain name. You pay for mail service providers or smarthosts to send emails on your behalf and provide a rout / method to delver incoming emails to your machine either by handling the MX and other DNS records for your domain name or by receiving them on their servers and provide you with mail server address, port and credentials so that you can periodically fetch incoming email using different protocols like POP and IMAP.


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Probably closest to your needs is the scenario described as "Postfix on a null client", however there are two things that are not covered. A "null client" in this example is a machine that:a) does not receive any mail from network;b) does not deliver any mail locally - however if you need this, this can be changed (but I'm not covering this here as this answer is already very long);c) sends all outgoing mail to smarthost, ie. a server that processes all mail for the domain you are sending as - in your case it probably will be the Yahoo server, the same you use when sending mail from your mail client.

I will elaborate a bit later on why you need to use smarthost. The one important thing that is missing here is that in your case your Postfix will need to authenticate to the smarthost. This is covered here: _README.html

But sending with email address from yahoo.com domain is also problematic because IP address of your machine does not belong to the pool of addresses assigned to Yahoo. The receiving server may detect it and also reject your mail. And that's why you need to use a smarthost - that's what's happening in options 3 and 4. Your machine will pass all mail to smarthost, and smarthost will send it on further.

However, you cannot just pass the mail to Yahoo server as in the default configuration for "Postfix on a null client", because this example assumes that the smarthost "trusts" your machine and will accept mail from that machine with smarthost's domain in the sender address. But Yahoo server won't just trust your machine and let it send as yahoo.com. It will almost certainly reject such e-mail.

And here comes the third and most complicated part: you need to not send your mail to the smarthost, but submit it. Submission is what mail clients like Outlook or Thunderbird do. They don't connect to the default email port on the server (25), but to the special submission port (587 or 465, depending on the encryption method the client uses), authenticate to the server using your Yahoo login and password, and then proceed to send mail. After the client authenticates to the server, the server trusts it and will accept mail from it.

Similarly, your Postfix needs to authenticate to your smarthost, ie. Yahoo server. To achieve this, you need to install (besides Postfix) the authentication engine (Cyrus SASL) and configure Postfix as outlined in _README.html

I also tried accessing the Sophos console and manually sending an e-mail using telnet and that worked (using port 2025, which is what I had configured smarthost to use as well). I was able to manually authenticate and send an e-mail.

i have a problem to get TLS for email smarthost on port TCP 587 working.

We have to deliver emails to our service provider on tcp port 587 using tls and a special created certificate from an internal pki.

but this is not working in my case because only outbound emails to the smarthost supporting TLS at the moment.

The same relay is forwarding inbound emails to us and this way doesnt support TLS at the moment. Using the net range of the smarthost in "require TLS negotiation" would cause inbound connections from them forcing tls which is not supported yet.

Have i missed something, or is the XG not able to force TLS to the smarthost on port 587?

@Sophos: Why there is not possibility to configure "force tls when using smarthost"? It is a common feature. And no - migrating to sophos central email is not an option for me (due to restrictions from the LSI).

thanks for your feedback. It makes absolutely no sense for me that sending via tcp 587 and TLS is not supported for smarthost. Absolutely no sense...

And why this isn't mentioned anywhere? Why the Sophos Support member want to "get a timeframe" to check the configuration I made although he should know that this isnt possible?

Do i have to replace now all sophos xg firewalls buyed 1 year ago due to incompatibility with SMARTHOST SETTINGS for my service provider because XG only supports native unencrypted smtp over port 25? Is starttls supported for port 25 via smarthost?

Sending a certificate can be configured manually in /static/proxy/smtp/exim.conf. Path of certificate an private key should be added to configuration of smarthost_smtp transport. For example, if certificate and key have been uploaded as smarthostcert then these lines should be added to smarthost_smtp (starting at line ~895):

I need to at minimumreplace the inbound catch all and the outbound ISP smarthost, in order to gainfull control over encrypting emails e.g. in/out partner to partner TLS and keepthe ability of archiving emails with or without the Hexamail software.

After doing someresearch it appears I can replace the inbound and outbound of email by usingExchange Online Protection as an SMTP Relay / smarthost. This would use option3 method here: -gb/article/how-to-set-up-a-multifunction-device-or-application-to-send... Opens a new window

The only way to have the email route to the other SMTP server using smarthost is to have all domains route to the same IP address by setting the overall smarthost setting in the SMTP properties dialog. No matter what settings I put in the remote domain settings, it never uses those settings to send email. Totally ingores them.

If you use a dynamic IP or you are unable to get the proper PTR records set up then you might need to consider using a smarthost. In this case all outgoing messages would be sent to CASG mailserver and the actual recipient would be contacted by CASG mailserver itself. Please note that for smarthost option, email user authorization should be handled on your side, either by IP address or by using SMTP AUTH.

Following on from the previous post Exim4 & DKIM I ran into a problem with no DKIM signature being added to outgoing mail. As I had this working when sending emails directly I figure it has to do with the smarthost config in Exim4. 2351a5e196

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