Personal notes on hardening an new ubuntu 24.04 LTS postfix setup for incoming smtp TLS traffic.

Create a Diffie–Hellman key exchange

openssl dhparam -out /etc/postfix/dh2048.pem 2048

for offering a new random DH group.

SMTPD - Incoming Traffic

# SMTPD - Incoming Traffic

postscreen_dnsbl_action = drop
postscreen_dnsbl_sites =
        bl.spamcop.net,
        zen.spamhaus.org

smtpd_banner = <put your banner here>

smtpd_helo_required = yes
smtpd_starttls_timeout = 30s

smtpd_tls_CApath = /etc/ssl/certs
smtpd_tls_cert_file = /root/.acme.sh/<your_domain>/fullchain.cer
smtpd_tls_key_file = /root/.acme.sh/<your_domain>/<your_domain>.key

smtpd_tls_dh1024_param_file = ${config_directory}/dh2048.pem
smtpd_tls_ciphers = HIGH

# Wick ciphers
smtpd_tls_exclude_ciphers =
        3DES,
        AES128-GCM-SHA256,
        AES128-SHA,
        AES128-SHA256,
        AES256-GCM-SHA384,
        AES256-SHA,
        AES256-SHA256,
        CAMELLIA128-SHA,
        CAMELLIA256-SHA,
        DES-CBC3-SHA,
        DHE-RSA-DES-CBC3-SHA,
        aNULL,
        eNULL,
        CBC

smtpd_tls_loglevel = 1
smtpd_tls_mandatory_ciphers = HIGH
smtpd_tls_protocols = !SSLv2, !SSLv3, !TLSv1, !TLSv1.1
smtpd_tls_security_level = may
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtpd_use_tls = yes
tls_preempt_cipherlist = yes

unknown_local_recipient_reject_code = 550

Local Testing

testssl -t smtp <your_domain>.:25

Online Testing

https://cryptcheck.fr/smtp/

result

LibreOps & LibreDNS

LibreOps announced a new public service: LibreDNS, a new DoH/DoT (DNS over Https/DNS over TLS) free public service for people that want to bypass DNS restrictions and/or want to use TLS in their DNS queries. Firefox has already collaborated with Cloudflare for this case but I believe we can do better than using a centralized public service of a profit-company.

Personal Notes

So here are my personal notes for using LibreDNS in firefox

Firefox

Open Preferences/Options

Enable DoH

TRR mode 2

Now the tricky part.

TRR mode is 2 when you enable DoH. What does this mean?

2 is when firefox is trying to use DoH but if it fails (or timeout) then firefox will go back to ask your operating system’s DNS.

DoH is a URL, so the first time firefox needs to resolve doh.libredns.gr and it will ask your operating system for that.

host file

There is way to exclude doh.libredns.gr from DoH , and use your /etc/hosts file instead your local DNS and enable TRR mode to 3, which means you will ONLY use DoH service for DNS queries.

# grep doh.libredns.gr /etc/hosts
116.202.176.26 doh.libredns.gr

TRR mode 3

and in

about:config

DNS Leak

Try DNS Leak Test to verify that your local ISP is NOT your firefox DNS

https://dnsleaktest.com/

Thunderbird

Thunderbird also supports DoH and here are my settings

PS: Do not forget, this is NOT a global change, just your firefox will ask libredns for any dns query.

Prologue

I should have written this post like a decade ago, but laziness got the better of me.

I use TLS with IMAP and SMTP mail server. That means I encrypt the connection by protocol against the mail server and not by port (ssl Vs tls). Although I do not accept any authentication before STARTTLS command is being provided (that means no cleartext passwords in authentication), I was leaving the PLAIN TEXT authentication mechanism in the configuration. That’s not an actual problem unless you are already on the server and you are trying to connect on localhost but I can do better.

LDAP

I use OpenLDAP as my backend authentication database. Before all, the ldap attribute password must be changed from cleartext to CRAM-MD5

Typing the doveadm command from dovecot with the password method:

# doveadm pw

Enter new password:    test
Retype new password:   test
{CRAM-MD5}e02d374fde0dc75a17a557039a3a5338c7743304777dccd376f332bee68d2cf6

will return the CRAM-MD5 hash of our password (test)

Then we need to edit our DN (distinguished name) with ldapvi:

From:

uid=USERNAME,ou=People,dc=example,dc=org
userPassword: test

To:

uid=USERNAME,ou=People,dc=example,dc=org
userPassword: {CRAM-MD5}e02d374fde0dc75a17a557039a3a5338c7743304777dccd376f332bee68d2cf6

Dovecot

Dovecot is not only the imap server but also the “Simple Authentication and Security Layer” aka SASL service. That means that imap & smtp are speaking with dovecot for authentication and dovecot uses ldap as the backend. To change AUTH=PLAIN to cram-md5 we need to do the below change:

file: 10-auth.conf

From:

auth_mechanisms = plain

To:

auth_mechanisms = cram-md5

Before restarting dovecot, we need to make one more change. This step took me a couple hours to figure it out! On our dovecot-ldap.conf.ext configuration file, we need to tell dovecot NOT to bind to ldap for authentication but let dovecot to handle the authentication process itself:

From:

# Enable Authentication Binds
# auth_bind = yes

To:

# Enable Authentication Binds
auth_bind = no

To guarantee that the entire connection is protected by TLS encryption, change in 10-ssl.conf the below setting:

From:

ssl = yes

To:

ssl = required

SSL/TLS is always required, even if non-plaintext authentication mechanisms are used. Any attempt to authenticate before SSL/TLS is enabled will cause an authentication failure.

After that, restart your dovecot instance.

Testing

# telnet example.org imap

Trying 172.12.13.14 ...
Connected to example.org.
Escape character is '^]'.
* OK [CAPABILITY IMAP4rev1 LITERAL+ SASL-IR LOGIN-REFERRALS ID ENABLE IDLE STARTTLS AUTH=CRAM-MD5] Dovecot ready.

1 LOGIN USERNAME@example.org test

1 NO [ALERT] Unsupported authentication mechanism.
^]
telnet> clo

That meas no cleartext authentication is permitted

MUA

Now the hard part, the mail clients:

RainLoop

My default webmail client since v1.10.1.123 supports CRAM-MD5
To verify that, open your application.ini file under your data folder and search for something like that:

    imap_use_auth_plain = On
    imap_use_auth_cram_md5 = On
    smtp_use_auth_plain = On
    smtp_use_auth_cram_md5 = On

as a bonus, rainloop supports STARTTLS and authentication for imap & smtp, even when talking to 127.0.0.1

Thunderbird

K9