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Jeroen W. Pluimers on .NET, C#, Delphi, databases, and personal interests

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Archive for the ‘SMTP’ Category

‪Dear #lazyweb, can anyone point me to a modern email server setup (just emai…

Posted by jpluimers on 2019/02/01

Summary from [WayBack]‪ Dear #lazyweb, can anyone point me to a modern email server setup (just email) with letsencrypt, some spam filter, multi domain preferably on RHEL/Cent… – Jan Wildeboer – Google+

  • many SMTP servers on the interwebs do not have proper TLS setups, so do not require remote SMTP servers to deliver email with a proper certificate
  • delivering mail via SMTP using STARTTLS with a proper certificate yourself is a good step forward
  • postfix
  • dovecot
  • greylisting (although in practice it does not make much of a difference any more)
  • fail2ban
  • dnsbl (often called rbl)
  • spamassasin
  • rspamd (supports SPF, DKIM and many others)
  • letsencrypt automation can be tough, so here is a small wrapper: [WayBack] GitHub – DrGlitchMX/update-letsencrypt: Tiny script for updating “Let’s Encrypt!” certificates from cron
  • it helps having letsencrypt and the mail server to be on one machine:
    • multidomain let’s encrypt cert that has my webserver name and the mailserver in the Subject Alternative Names field. As both are on the same machine certbot can automatically update it and I just point Postfix and Dovecot to the LE files.
  • Hans-Martin Mosner SMTP as-is is just not suitable for the kind of decentralized mail that you would prefer. You need some mechanism to determine which mail senders to trust and which not. Cryptography is suitable at the MUA level and should be used much more, but at the MTA level, TLS for privacy and SPF(bleh) or DKIM(meh) for sender domain authentication are basically your only weapons -much too weak. The PGP web of trust must be considered a failed experiment – who of your mail contacts uses PGP properly or at all? Ironically the only secure messaging solutions for the masses are centralized.

Things to do:

  • find a proper multi-MX fallback setup guide for postfix


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Posted in *nix, *nix-tools, Communications Development, Development, Internet protocol suite, postfix, Power User, SMTP | Leave a Comment »

Testing SMTP from the console on Linux, BSD and Mac OS: swaks and smtp-cli Perl script clients

Posted by jpluimers on 2019/01/03

Testing SMTP using telnet is tedious as you have to remember the commands and responses in the SMTP protocol. It gets even harder when doing SMTP AUTH, as then you have to base encode a bunch of strings [WayBackHow to Test SMTP AUTH using Telnet [Wiki] | NDCHost

Luckily there is a Perl script swaks: [WayBackSwaks – Swiss Army Knife for SMTP which does ESMTP and LMTP as well as TLS.

The funny thing is that the repository at jetmore/swaks: Swaks – Swiss Army Knife for SMTP only has the readme, but the not the script which you can get from [WayBack]

Despite that, most Linux distributions have an installation package.

[WayBackswaks for OpenSuse is in the [WayBacknetwork repository, so for Tumbleweed (actually: Factory) on Raspberry Pi you need to perform this:

zypper addrepo
zypper refresh
zypper install swaks

On Mac OS X it is even easier: if you have the homebrew package manager installed, you just install the [WayBackswaks formula using the [WayBack] swaks.rb script:

brew install swaks

Note there is also the smtp-cli Perl script which I mentioned before at Fake/Mock SMTP servers and services for use during development, which also does TLS, but few environments have ready built packages for them. If you still want to try it out:


swaks -tls --to --from --server --auth-user username

Which prompts for the password, then outputs like this:

=== Trying
=== Connected to
<- 220 ESMTP ESMTP server ready -> EHLO rmbpro1tbjwp
<- hello [], pleased to meet you
<-  250-HELP
<-  250-SIZE 157286400
<-  250-8BITMIME
<-  250-STARTTLS
<- 250 OK -> STARTTLS
<- 220 Ready to start TLS === TLS started with cipher TLSv1:DHE-RSA-AES256-SHA:256 === TLS no local certificate set === TLS peer DN="/OU=Domain Control Validated/OU=PositiveSSL Wildcard/CN=*" ~> EHLO rmbpro1tbjwp
<~ hello [], pleased to meet you
<~  250-HELP
<~  250-SIZE 157286400
<~  250-8BITMIME
<~ 250 OK ~> AUTH LOGIN
<~ 334 ############ ~> anA=
<~ 334 ############ ~> ############################
<~ 235 ... authentication succeeded ~> MAIL FROM:<>
<~  250 <> sender ok
 ~> RCPT TO:<>
<~  250 <> recipient ok
 ~> DATA
<~ 354 enter mail, end with "." on a line by itself ~> Date: Wed, 19 Jul 2017 09:09:57 +0200
 ~> To:
 ~> From:
 ~> Subject: test Wed, 19 Jul 2017 09:09:57 +0200
 ~> Message-Id: <20170719090957.052207@rmbpro1tbjwp>
 ~> X-Mailer: swaks v20170101.0
 ~> This is a test mailing
 ~> .
<~ 250 accepted mail mXA71v00C4jr6ac01XA9Bo for delivery ~> QUIT
<~  221 ESMTP closing connection
=== Connection closed with remote host.


Posted in *nix, *nix-tools, Communications Development, Development, Hardware Development, Internet protocol suite, Linux, openSuSE, Power User, Raspberry Pi, SMTP, SuSE Linux, Tumbleweed | Leave a Comment »

The part before the @ in email addresses is case sensitive

Posted by jpluimers on 2018/10/16

At [WayBackError when trying to signup using an email address with uppercase letters (#27898) · Issues · / GitLab Community Edition · GitLab, I commented this:

Both the :e-mail and :email_confirmation fields should get the same case processing treatment.

That treatment should consist of this:

  1. The part before the @ should be treated as case sensitive
  2. The part after the @ should be treated as case insensitive

This means that:

  • Foo@Example.Org and are the same
  • and are different

The main reason is that there are email systems expecting case sensitivity in the part before the @ sign.

I think excluding those users from being able to use GitLab is a bad idea.

See especially the comments at the Stack Overflow answer to Are email addresses case sensitive?

Relevant RFC 5321: Simple Mail Transfer Protocol sections:

Important comments:

I work at a large company and there is another person with the same first and last name. I discovered today that his local-part differs from mine only in capitalization. This has been working properly, so I was surprised to see “no widely used mail systems distinguish different addresses based on case”. We use MS Exchange which I would call “widely used”. – Matthew James Briggs Nov 24 ’15 at 20:14

RFC 5321 2.4. General Syntax Principles and Transaction Model – SMTP implementations MUST take care to preserve the case of mailbox local-parts. In particular, for some hosts, the user “smith” is different from the user “Smith”. Mailbox domains follow normal DNS rules and are hence not case sensitive. – Adam111p Apr 27 ’16 at 10:02

Most important parts of the answer:

From RFC 5321, section-2.3.11:

The standard mailbox naming convention is defined to be “local-part@domaiN“; contemporary usage permits a much broader set of applications than simple “user names”. Consequently, and due to a long history of problems when intermediate hosts have attempted to optimize transport by modifying them, the local-part MUST be interpreted and assigned semantics only by the host specified in the domain part of the address.

So yes, the part before the “@” could be case-sensitive, since it is entirely under the control of the host system. In practice though, no widely used mail systems distinguish different addresses based on case.

The part after the @ sign however is the domain and according to RFC 1035, section 3.1,

“Name servers and resolvers must compare [domains] in a case-insensitive manner”


Posted in Communications Development, Development, Internet protocol suite, SMTP, Software Development | Leave a Comment »

TLS tests for your mail server

Posted by jpluimers on 2017/11/09

Need to do some more research on this to ensure I didn’t goof up:


Posted in *nix, *nix-tools, Communications Development, Development, Internet protocol suite, postfix, Power User, Security, sendmail, SMTP | Leave a Comment »

NOC Zone and NOC Apps – A Service and Free Mobile App for Website Monitoring

Posted by jpluimers on 2015/10/16

Interesting: this works through an on-line service that monitors up to 2 servers for free (including protocols like HTTP, SMTP and PING).

You can get reports at either through:

I’m using this to monitor my boxes at home.

A demo video is below.


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Posted in *nix, Communications Development, Development, HTTP, Internet protocol suite, Power User, SMTP, TCP | Leave a Comment »

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