This is a tutorial on how to secure the latest version of Redmine (3.4.4) at the time of writing on Ubuntu Server 16.04, running Apache 2 and Phusion Passenger using Let’s Encrypt.


Let’s Encrypt is a free and automated certificate authority, created by the Electronic Frontier Foundation (EFF) to assist web developers and the technology community in securing their websites and creating a more secure Internet in general by providing an easy way to add free TLS certificates to their servers.

Step 1: Install the Let’s Encrypt Certbot Utility

NB: Unless specified, run all the following commands on the bash prompt of your VPS/Dedicated Server.

Add the Certbot PPA

Certbot is a suite of command line tools created by Let’s Encrypt. We will start by installing it from their Ubuntu repository.

sudo add-apt-repository ppa:certbot/certbot

Update the APT repository.

sudo apt-get update

Install the Let’s Encrypt Apache Utility:

sudo apt-get install python-certbot-apache

Run the Certbot tool for Apache

Substitute the values in square brackets with your own domain e.g. and your email e.g.

sudo certbot --apache -d [your domain],www.[your domain] --agree-tos -m [your email] -n --redirect --must-staple --rsa-key-size 4096 --hsts --uir --staple-ocsp

Your Redmine site should now be secured with TLS. Notice the green padlock symbol on the left of the URL.

Redmine Secured

You should also have an A+ rating on the SSLLabs Test:[your domain][your domain]

SSL Labs Test

Here’s the responsive view on an iPhone:

Redmine Responsive View

Step 2: Auto-renew the installed Let’s Encrypt certificates

Create a new cronjob as a sudo user:

sudo crontab -e

Choose nano as the crontab editor:

no crontab for root - using an empty one

Select an editor.  To change later, run 'select-editor'.
  1. /bin/ed
  2. /bin/nano        <---- easiest
  3. /usr/bin/vim.basic
  4. /usr/bin/vim.tiny

Choose 1-4 [2]: 2

Add the following content to the crontab:

15 3 * * * certbot renew --quiet

Save the new cronjob by pressing control + o on your keyboard, then exit nano by pressing control + x. Your new cronjob for automatically renewing certificates should now be installed.