Moving to TLSv1.2 or newer: Nginx, Apache, Postfix, Dovecot

Moving on from “should we do it?” (with the answer to most real-world scenarios being “yes, and as a bonus it can help block a lot of spambots“), here’s how to restrict several Internet services — Nginx, Apache, Postfix, and Dovecot — to TLSv1.2 or newer.

As usual, these are not complete guides for any of those servers; I’m assuming you already have them working fine (including TLS encryption), and just want to disable any TLS protocols lower than v1.2. (If you need to add TLS to a non-TLS server, see instructions for Nginx, Apache, Postfix, and Dovecot.)

Nginx:

In each virtual host’s server section — or, even better, if you’re using Let’s Encrypt, in /etc/letsencrypt/options-ssl-nginx.conf or its equivalent –, add the following (or replace any existing ssl_protocols entry):

ssl_protocols TLSv1.2 TLSv1.3;

Restart Nginx, and test it on SSL Labs. You should get something like this1:

TLS v1.2 and v1.3 only

(Note: if you’re using a very old version of Nginx, it may not accept the “TLSv1.3” parameter and refuse to start; in such a case, remove it — or, better yet, upgrade your system. ūüôā )

Apache:

Similarly to Nginx, you can add one of the following to each Virtual Host, or to the global HTTPS configuration (typically in /etc/httpd/conf.d/ssl.conf), or, if using Let’s Encrypt, to /etc/letsencrypt/options-ssl-apache.conf :

SSLProtocol            +TLSv1.2 +TLSv1.3

or:

SSLProtocol             all -SSLv2 -SSLv3 -TLSv1 -TLSv1.1

Right now, they’ll do the same thing: allow TLSv1.2 and v1.3 only. Personally, I like the¬†second version (which disables older protocols) better, for two reasons: 1) it’ll work even with some ancient Apache version that doesn’t recognize “TLSv1.3”, and 2) when future TLS versions are added, they’ll be enabled, making it more future-proof.

Again, you can test the new configuration on SSL Labs.

Postfix:

Add the following to /etc/postfix/main.cf (replacing any equivalent entries, if they exist).

smtp_tls_mandatory_protocols=!SSLv2, !SSLv3, !TLSv1, !TLSv1.1
smtpd_tls_mandatory_protocols=!SSLv2, !SSLv3, !TLSv1, !TLSv1.1
smtp_tls_protocols=!SSLv2, !SSLv3, !TLSv1, !TLSv1.1
smtpd_tls_protocols=!SSLv2, !SSLv3, !TLSv1, !TLSv1.1

After restarting Postfix, you can test its available protocols with Immuniweb’s SSL Security Test (specify something like yourhostname:25, or yourhostname:465 if not using STARTTLS).

Dovecot:

Add the following (or replace it if it exists) to your SSL configuration (typically /etc/dovecot/conf.d/10-ssl.conf):

ssl_min_protocol = TLSv1.2

Restart Dovecot, and test it on Immuniweb’s test (use something like yourhostname:143 , or yourhostname:993 if not using STARTTLS).

Moving to TLSv1.2 or newer: is now the time?

TLSv1.0, used not only for HTTPS but also for secure SMTP, IMAP, etc., has been around for a while — 1999, in fact –, and, while not “hopelessly broken” like SSL 2 and 3 are, there have been many successful attacks/exploits against it in the past two decades, and while most implementations (in terms of both servers¬†and clients) have been patched to work around those, there may always be another one just around the corner. Also, TLSv1.0 came from a time where it was desirable to support as many different ciphers as possible, which means that, by default, some ciphers later found to be insecure may still be enabled.

Therefore, the end of TLSv1.0 has been talked about for a while, and, indeed, the main browser vendors — Google, Mozilla, Apple, and Microsoft — have announced that they’ll deprecate TLSv1.0 (and 1.1, which is little more than a revision of 1.0) by early 2020.

Now, until a few days ago I still had TLSv1.0 enabled on my servers (including Nginx, Postfix and Dovecot); my belief was that¬†some encryption was always better than¬†no encryption, and besides we were mostly talking about¬†public websites, that didn’t ask for user credentials or anything. Furthermore, any modern browsers/email clients default to secure protocols (TLSv1.2 or better), so there would never be, “in real life”, a situation where important/sensitive data (say, me logging on to my own mail server, or to one of my WordPresses was being transmitted in an insecure way.

On the other hand… doesn’t the above mean that, “in real life”, nobody will really be using TLSv1.0 “legitimately”? Doesn’t it mean that setting up TLSv1.2 as a minimum will have no adverse consequences?

So I investigated it a little:

  • in terms of browsers/clients, requiring TLSv1.2 or above means: 1) no Internet Explorer before version 11; 2) no Safari before 6.x; 3) no default Android browser before Android 4.4.x (but those users can still use Chrome or other non-default browsers). (You can check this out on SSL Labs). I don’t have a way to check email clients that old, but you can assume that anything released after the browsers just mentioned will be OK;
  • in terms of my own¬†server logs (mostly Nginx, but also Postfix, in terms of opportunistic encryption), apparently, only spambots and such are using TLSv1.0; any “legitimate” email servers use TLSv1.2 or 1.3. The same thing with my websites — any TLSv1.0 entries in my logs are always from some bot (and not one for a “well-known” search engine), not actual visitors. 1

In short: you can probably move to requiring TLSv1.2 or above¬†now (and, indeed, I’ve done so since a few days ago), unless you’re in some very peculiar situation — maybe your site needs to be accessed by users of a company whose IT policy includes not using software newer than 20 years old? Or you have a CEO who’s always refused to upgrade his beloved Symbian phone, but who’d flip out if he couldn’t access your company’s webmail with it? ūüôā Otherwise, my advice is: go TLSv1.2 and don’t look back.

However, and since this post is already quite long, I’ll leave the specific instructions for disabling TLS before 1.2 in Nginx, Apache, Postfix, and Dovecot for the next one

How to configure TLS encryption in Dovecot

DovecotAs with most other internet services, Dovecot can be configured to use TLS encryption — and, unlike some others (such as web servers or SMTP servers), there’s little reason not to¬†enforce it.

Notes:

  • Like other recent TLS tutorials on this blog, this is, of course, not a full Dovecot guide — that would be far too complex for a blog post. Instead, it’s just focused on enabling/configuring TLS encryption. I’ll be assuming you already have Dovecot configured, and are able to access mailboxes on your server using an email client.
  • I’ll be focusing on IMAP only, not POP3 or anything else.
  • The server will be configured to require¬†encryption, for both privacy and security reasons. I don’t know of any modern email client that doesn’t allow encrypted connections (and even then, you might work around it by configuring an encrypted tunnel, but that falls out of this post’s scope).

1. Getting a certificate

While I believe most modern email clients will support ECDSA certificates, such clients are not a known quantity like, say, web browsers are, so I suggest that you create an RSA certificate, unless you already have one whose Common Name (CN) matches your¬†server’s public name (e.g. mail.domain.com). Dovecot versions 2.2.31 and newer support configuring¬†alternative certificates so that you could support both kinds at the same time, but there’s probably little gain in doing that, since most clients will likely default to RSA anyway (and, unless you’re using Let’s Encrypt, certificates are not free).

So, put your certificate and private key in /etc/dovecot/. Let’s assume the certificate is called myserver-full.crt¬†1, and the private key is myserver.key. You should protect the private key from any users on your server, so do, for instance,

chown root:dovecot /etc/dovecot/myserver.key
chmod 640 /etc/dovecot/myserver.key

2. Configuring Dovecot for TLS

I’m assuming your Dovecot installation has a basic configuration file in /etc/dovecot/dovecot.conf, but the real “meat” of the configuration is in included files in /etc/dovecot/conf.d/. Your system may be slightly different, but I’m sure you can adapt. ūüôā Also, the numbers at the beginning of the file names may differ in your system.

This one isn’t really related to TLS, but it’s a good idea: edit /etc/dovecot/conf.d/20-imap.conf, and look for a line like this:

mail_plugins = $mail_plugins

and add to it (separated by a space):

imap_zlib

After all, there’s no reason not to use compression here, and bandwidth (especially on mobile) is still precious.

Now, edit /etc/dovecot/conf.d/10-ssl.conf, and add 2:

ssl = required
ssl_cert = </etc/dovecot/myserver-full.crt
ssl_key = </etc/dovecot/myserver.key
ssl_cipher_list = ECDHE-RSA-CHACHA20-POLY1305:ALL:!LOW:!SSLv2:!EXP:!aNULL
ssl_protocols = !SSLv2 !SSLv3
ssl_prefer_server_ciphers = yes

(The ssl_cipher_list line, besides setting secure defaults, sets the ChaCha20 protocol as the first one to be tried, since it’s considered one of the fastest and most secure. Note that it’ll require Dovecot linked to LibreSSL or OpenSSL 1.1.x to use that cipher, though Dovecot won’t complain if it doesn’t have access to it; it’ll just use the normal, secure defaults.)

If you don’t change anything else from the default configuration, the server will be listening on port 143 (IMAP) and port 993 (IMAPS). “But,” you ask, “isn’t standard IMAP unencrypted? I thought you were enforcing encryption…” Yes, but the standard IMAP port can be “upgraded” to TLS by entering the STARTTLS command, and email clients not only support that, but typically default to it (if not, just make sure you enable it). The server will refuse to authenticate any users on port 143 before they’ve “STARTTLSed”.

If you wanted to use only IMAP+STARTTLS, or only IMAPS, just edit /etc/dovecot/conf.d/10-master.conf,¬† look for the “service” configuration, and disable the one you don’t want. But I see no problem with keeping both enabled.

Thoughts? Questions?

(To do the same to SMTP / Postfix, please see How to configure TLS encryption in Postfix.)

Ubuntu/Debian: Installing Nginx/Postfix/Dovecot using OpenSSL 1.1.x

OpenSSLSo, let’s say you have a Ubuntu or Debian server, using one or more of Nginx, Postfix, and Dovecot, and you’d like to have them link to OpenSSL 1.1.x instead of the default OpenSSL (as of Ubuntu 17.04, it’s version 1.0.2g). (Reasons may include wanting to use modern ciphers such as ChaCha20, or trying out support for the most recent TLS 1.3 draft. Also, if you want to try out LibreSSL instead of OpenSSL 1.1, please check out the previous post.)

So, here’s a relatively simple way, that¬†doesn’t change the system’s default OpenSSL (believe me, that wouldn’t be a good idea, unless you recompiled¬†everything):

Install dependencies:

apt-get install build-essential
apt-get build-dep openssl nginx dovecot postfix

Install OpenSSL 1.1.x:

  • download the latest 1.1.x source from www.openssl.org
  • compile and install it with:
./config --prefix=/usr/local/openssl11 --openssldir=/usr/local/openssl11 && make && make install

Install Nginx:

rm -rf /usr/local/src/nginx-openssl11
mkdir /usr/local/src/nginx-openssl11
cd /usr/local/src/nginx-openssl11
apt-get source nginx # ignore the permissions error at the end
  • edit nginx-<version>/debian/rules: ¬†add

–with-openssl=/usr/local/src/openssl-

to the beginning of the common_configure_flags option (note that that’s the source directory you used to compile OpenSSL 1.1.x, not where you installed it to);

debuild -uc -us -b
  • install the required packages in the parent directory with “dpkg -i ” (do dpkg -l | grep nginx to see which you have installed; typically you’ll want to install the newly¬†created versions of those);
apt-mark hold nginx* # to prevent nginx from being updated from Ubuntu / Debian updates

Done! You can now play around with the Mozilla TLS Guide to add support for modern ciphers to your Nginx’s configuration, and use SSLLabs’s SSL Server Test tool to check if they are correctly enabled.

Install Postfix:

It’s just like Nginx (replacing “nginx” with “postfix” in every command / directory name, of course), except that the changes to debian/rules are these:

  • find -DHAS_SSL, add¬†-I/usr/include/openssl11/include/openssl¬†in front of it;
  • find AUXLIBS += , add¬†-L/usr/local/openssl11/lib in front of it
  • find the line with dh_shlibdeps -a, add¬†–dpkg-shlibdeps-params=–ignore-missing-info to it
  • don’t forget the apt-mark hold postfix* at the end.

Install Dovecot:

Again, use the Nginx instructions, using “dovecot” instead of “nginx” everywhere, except that the changes to debian/rules should be:

  • after the line:
export DEB_BUILD_MAINT_OPTIONS=hardening=+all

add:

export SSL_CFLAGS=-I/usr/local/openssl11/include
export SSL_LIBS=-L/usr/local/openssl11/lib -lssl -lcrypto
  • after the section:
override_dh_makeshlibs:
# Do not add an ldconfig trigger; none of the dovecot shared libraries
# are public.
        dh_makeshlibs -n

add:

override_dh_shlibdeps:
        dh_shlibdeps --dpkg-shlibdeps-params=--ignore-missing-info

NOTE: the indentation in the second line needs to be a¬†tab, don’t use spaces.

Again, remember to apt-mark hold dovecot* after installation.

How to check if your new installations of Postfix and/or Dovecot are using OpenSSL 1.1.x instead of the default OpenSSL 1.0.x? You could use ldd to check what SSL / TLS libraries your binaries and/or libraries link to, but the best way is probably to use a tool such as sslscan, which you can use to check what ciphers your SMTP, IMAP, etc. support (including with STARTTLS). If you see ChaCha20 in there, everything is fine. ūüôā

If you ever want to go back to “normal” versions of these servers, just do apt-mark unhold nginx* (for instance).

Ubuntu/Debian: Installing Nginx/Postfix/Dovecot using LibreSSL

LibreSSLSo, let’s say you have a Ubuntu or Debian server, using one or more of Nginx, Postfix, and Dovecot, and you’d like to have them link to LibreSSL instead of the default OpenSSL. (I won’t go much into the possible reasons for it; maybe you’re bothered because modern distros are still sticking with OpenSSL 1.0.x, which is ancient and doesn’t support modern ciphers such as ChaCha20, or you trust the OpenBSD developers more than you trust the OpenSSL ones, or — and there’s nothing wrong with that — you want to do it just for fun. You could also use OpenSSL 1.1.x — check out this (very similar) post.)

So, here’s a relatively simple way, that¬†doesn’t change the system’s default OpenSSL (believe me, that wouldn’t be a good idea, unless you recompiled¬†everything):

Install dependencies:

apt-get install build-essential
apt-get build-dep openssl nginx dovecot postfix

Install LibreSSL:

  • download the latest portable source from www.libressl.org
  • compile and install it with:
./configure --prefix=/usr/local/libressl --with-openssldir=/usr/local/libressl && make && make install

Install Nginx:

rm -rf /usr/local/src/nginx-libressl
mkdir /usr/local/src/nginx-libressl
cd /usr/local/src/nginx-libressl
apt-get source nginx # ignore the permissions error at the end
  • edit the file¬†nginx-<vers√£o>/debian/rules: ¬†add
-I/usr/local/libressl/include

to the line beginning with “debian_cflags:=“, and:

-L/usr/local/libressl/lib

to the line that begins with “debian_ldflags:“. After that, enter the nginx-<version>¬†directory and compile the packages with the command:

debuild -uc -us -b
  • install the required packages in the parent directory with “dpkg -i <package names>” (do “dpkg -l | grep nginx” to see which you have installed; typically you’ll want to install the newly¬†created versions of those);
apt-mark hold nginx* # to prevent nginx from being updated from Ubuntu / Debian updates

Done! You can now play around with the Mozilla TLS Guide to add support for modern ciphers to your Nginx’s configuration, and use SSL Labs’s SSL Server Test tool to check if they are correctly enabled.

Install Postfix:

It’s just like Nginx (replacing “nginx” with “postfix” in every command / directory name, of course), except that the changes to debian/rules are these:

  • find -DHAS_SSL, add¬†-I/usr/include/libressl/include/openssl¬†in front of it;
  • find AUXLIBS += , add¬†-L/usr/local/libressl/lib in front of it
  • find the line with dh_shlibdeps -a, add¬†–dpkg-shlibdeps-params=–ignore-missing-info to it
  • don’t forget the apt-mark hold postfix* at the end.

Install Dovecot:

Again, use the Nginx instructions, using “dovecot” instead of “nginx” everywhere, except that the changes to debian/rules should be:

  • after the line:
export DEB_BUILD_MAINT_OPTIONS=hardening=+all

add:

export SSL_CFLAGS=-I/usr/local/libressl/include
export SSL_LIBS=-L/usr/local/libressl/lib -lssl -lcrypto
  • after the section:
override_dh_makeshlibs:
# Do not add an ldconfig trigger; none of the dovecot shared libraries
# are public.
        dh_makeshlibs -n

add:

override_dh_shlibdeps:
        dh_shlibdeps --dpkg-shlibdeps-params=--ignore-missing-info

NOTE: the indentation in the second line needs to be a¬†tab, don’t use spaces.

Again, remember to apt-mark hold dovecot* after installation.

How to check if your new installations of Postfix and/or Dovecot are using LibreSSL instead of the default OpenSSL? You could use ldd to check what SSL / TLS libraries your binaries and/or libraries link to, but the best way is probably to use a tool such as sslscan, which you can use to check what ciphers your SMTP, IMAP, etc. support (including with STARTTLS). If you see ChaCha20 in there, everything is fine. ūüôā

If you ever want to go back to “normal” versions of these servers, just do apt-mark unhold nginx* (for instance).

I’ve also added /usr/local/libressl/bin to the beginning of my PATH environment variable, so that the LibreSSL binaries are used by default (e.g. to generate keys, CSRs, etc.), although this isn’t necessary for Nginx, etc. to work.