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I have been running a production server with Ubuntu 18 installed. Recently, I found that my web application was not allowed on some of the firewalls installed at the customer location.

I found that my server is communicating at TLSv1.0, TLSv1.1, TLSv1.2 protocols, I assume that the firewall setting is allowing communication with the server on TLSv1.3 protocol only.

As Ubuntu 18 is shipped with OpenSSL version 1.1.0, and to make server support TLS v1.3 I have to upgrade OpenSSL to version 1.1.1 which is the latest one.

As this is a production server running nginx server, I don't want to directly try anything on the server. 

root@energy-prod:~# nginx -v
nginx version: nginx/1.14.0 (Ubuntu)

What is the best way to upgrade OpenSSL to v1.1.1 without disturbing any other settings of the server?

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  • 2
    FYI: »OpenSSL 1.1.1 SRU into Bionic« lists.ubuntu.com/archives/ubuntu-devel/2018-December/… In the meantime talk to the respective contact who is in charge of the firewall configuration, ask for requirements/recommendations/waivers. I doubt that you are the only one running 18.04 and having this problem nor do I think that not supporting TLS 1.3 at this point in time is the issue as it's still quite new and contrary to your statement I read that it still causes issues with some middleboxes, but you won't find out if you don't ask.
    – LiveWireBT
    Dec 19, 2018 at 4:33
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    Upgrading will not be possible until that SRU goes through. There's just too much stuff that depends on OpenSSL to do the upgrade yourself, because it could break everything.
    – Thomas Ward ♦
    Jan 24, 2019 at 19:42
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    finally bugs.launchpad.net/ubuntu/+source/openssl/+bug/1797386 is in Progress now
    – Tino
    Feb 28, 2019 at 12:59

1 Answer 1

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NOTE: As of ~August 2019, openSSL 1.1.1 should be available for installation via normal package upgrades/installations for 18.04. Or, you can download the .deb package directly from here.

According to the OpenSSL website:

The latest stable version is the 1.1.1 series. This is also our Long Term Support (LTS) version, supported until 11th September 2023.

Since this is not in the current Ubuntu repositories, you will need to download, compile, and install the latest OpenSSL version manually.

Below are the instructions to follow:

  1. Open a terminal (Ctrl+Alt+t).
  2. Fetch the tarball: wget https://www.openssl.org/source/openssl-1.1.1g.tar.gz
  3. Unpack the tarball with tar -zxf openssl-1.1.1g.tar.gz && cd openssl-1.1.1g
  4. Issue the command ./config.
  5. Issue the command make (You may need to run sudo apt install make gcc before running this command successfully).
  6. Run make test to check for possible errors.
  7. Backup current openssl binary: sudo mv /usr/bin/openssl ~/tmp
  8. Issue the command sudo make install.
  9. Create symbolic link from newly install binary to the default location: 
    sudo ln -s /usr/local/bin/openssl /usr/bin/openssl
  10. Run the command sudo ldconfig to update symlinks and rebuild the library cache.

Assuming that there were no errors in executing steps 4 through 10, you should have successfully installed the new version of OpenSSL.

Again, from the terminal issue the command:

openssl version

Your output should be as follows:

OpenSSL 1.1.1g  21 Apr 2020
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    Regarding "As of ~June 2019, openSSL 1.1.1 should be available for installation via normal package upgrades/installations": Just not note that this does not appear to be the case on Ubuntu 18.04 (at least on the two machines I tried on)...
    – logidelic
    Jul 26, 2019 at 13:13
  • @logidelic Interesting. Thanks for pointing that out. I'll make a note of that. My main systems are 19.04 and I have a couple of derivatives(Mint) based off of bionic(18.04) that have already received backports. Apparently, launchpad.net/ubuntu/+source/openssl/1.1.1-1ubuntu2.1~18.04.4 it may still only be 'proposed'', or available as source in 18.04. I'm not really sure of the status.
    – Kevin Bowen
    Jul 26, 2019 at 14:34
  • Worked on Debian Jessie as well. Used 1.1.1c as this is the same version in Buster.
    – Rudolf Vavruch
    Sep 25, 2019 at 8:41
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    I don't have enough points to post an answer. Here's what I did on ubuntu 18.04: 1. sudo apt-get upgrade openssl 2. export LD_LIBRARY_PATH="/usr/local/lib". After this, things worked. In fact, the export may be all that I needed to do.
    – thebiggestlebowski
    Feb 14, 2020 at 19:48
  • @Marmayogi There is one problem with this: If someone is using PHP, then fopen might stop working for https URLs with the following error: error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed. This is because OPENSSDIR is set to /usr/local/ssl. To fix it, I went to /usr/local/ssl deleted the empty certs folder and create a link to the Ubuntu default folder for certificates '/etc/ssl/certs', with this command: ln -s /etc/ssl/certs /usr/local/ssl/
    – Valentin
    May 11, 2020 at 20:49

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