How to Install the Outline Knowledge Base & Wiki on Ubuntu (The Easy Way)

Outline is a beautiful, fast and flexible team knowledge base and wiki software used to organize your internal documentation, operations manuals, handbooks and more.

While Outline has a hosted solution, it is open-source software. This means you can install and manage it on your own server. The Outline team has some documentation for installing it on your own, but it’s somewhat complicated (even for an experienced developer like myself).

After trying and failing many times, I decided to help you avoid the hassle by writing an easy, step-by-step tutorial to get the Outline team knowledge base and wiki running on your own server. And do it successfully – the first time!

Vision of Results

By carefully following each step of this tutorial on how to install the Outline team knowledge base and wiki on Ubuntu, you will experience the following results:

• A publicly accessible, SSL-secured URL where you can access your new Outline self hosted install. You can see the example install I built using the exact same process documented in this tutorial: https://outline.thomasgriffin.com
• A daily cron that checks for and automatically renews your SSL certificate
• A monthly cron that automatically checks for and applies any new official Outline releases.
• Peace of mind knowing you eliminated the headache of having to figure this out yourself. 💯

Prerequisites

You’ll need the following things to complete this tutorial successfully:

1. A Digital Ocean account. While there are other hosting platforms you could use, I’ve chosen Digital Ocean because of the ease of setting up the server scaffolding necessary to support Outline. I cannot guarantee this tutorial will work on any other server platform as I have not tried it there.
2. The ability to modify DNS records to add a subdomain for public access to your Outline instance. I recommend Cloudflare, as I will be using it for demonstration in this tutorial.
3. An Amazon Web Services (AWS) account. You need this to setup and configure both IAM and S3 to host all of your Outline assets.
4. A Google Workspace (formerly GSuite) account. Outline offers many different types of authentication (such as Slack or Microsoft), but I’ve chosen Google because I have a Google Workspace account readily available to use for testing.

Based on my own experience of running through this tutorial multiple times to validate its results, this will take you approximately 45-60 minutes to complete. If you need to register for any of the above services, it may take you a little longer.

Additionally, this setup will typically cost you ~$6/month (excluding Google Workspace or other authentication provider fees), but if you sign up for Digital Ocean using my link, you’ll get your first 2 months free. I believe that to be reasonable given the value that Outline can provide to your team and its productivity.

Table of Contents

Since this tutorial is lengthy and technical, I’ve created a helpful table of contents to reference in case you need to jump around.

• Setting up the Server on Digital Ocean
  • Provisioning a Non-Root User
• Installing and Configuring Server Prerequisites
  • Installing Core Components
  • Installing Docker
  • Installing Docker Compose
  • Securing Docker
• Configuring Subdomain DNS Records, Nginx and Let’s Encrypt
  • DNS Records
  • Nginx
  • Let’s Encrypt
• Setting Up AWS IAM and S3
  • Creating the S3 Bucket
  • Creating the IAM User and Policy
• Creating a Google Workspace Oauth App
  • Creating the Cloud Project
  • Adding Authentication APIs
  • Configuring the Oauth Consent Flow
  • Generating Oauth Credentials
• Creating and Running the Outline Docker Image
• Configuring the Nginx Server Block
• Viewing and Authenticating Into Your Outline Self Hosted Install
• Configuring SMTP
• Configuring Automatic Updates for Your Outline Self Hosted Install
  • Daily Scheduled Jobs
  • Monthly Updates
• Helpful Commands, Tips and Tricks
  • Removing Old Database Volumes
  • Completely Wiping Docker
• Wrapping Up

Let’s get started installing the Outline team knowledge base and wiki on Ubuntu!

Setting Up the Server on Digital Ocean

Outline requires a Unix based operating system to work, and since Ubuntu is popular, I’ll use that as our operating system.

Head over to your Digital Ocean account and create a new droplet. Select Ubuntu 22.04 LTS x64 as your image, then select the option you prefer most for your server. I like the $6/month 1GB Intel SSD option, as performing SSH commands with it is notably faster than the base $5/month option.

Next, select the data center of your choice and your desired authentication method (SSH keys are the preferred option, but if that doesn’t work for you, they support root passwords).

Choose the rest of your configuration options (I recommend enabling backups), customize your droplet hostname, add any tags and then create your new droplet.

Once your droplet has been provisioned, SSH into the server using your favorite terminal client (replacing yourip with the IP given to you by Digital Ocean):

ssh -A [email protected]

Once logged in, let’s go ahead and get everything updated on the droplet. Select “Y” or hit Return to update/upgrade anything that it recommends during the process.

sudo apt update && sudo apt upgrade

Since upgrading is likely to require some services to restart, go ahead and reboot the server now.

sudo reboot

Rebooting will log you out of your terminal session. Wait a couple of minutes, then log back in again (replacing yourip with the IP given to you by Digital Ocean):

ssh -A [email protected]

Provisioning a Non-Root User

Next, you need to follow the guide for Initial Server Setup with Ubuntu 22.04 on Digital Ocean. In this guide, you’ll establish a more secure environment for your server, including creating a non-root user and setting up some helpful firewalls to lock down access to your server.

Please follow all the steps listed in the article! The rest of the tutorial assumes you have.

Once you’ve finished following the steps there, make sure to SSH back into your server using the new user you just created.

You are now ready to continue with installing the server prerequisites for Outline.

Installing and Configuring Server Prerequisites

Installing Core Components

Let’s install some general utilities that your server needs to get Outline up and running successfully.

First, make sure you are logged in as the non-root user you just created.

Then, run the following command in your terminal:

sudo apt update && sudo apt install apt-transport-https ca-certificates curl software-properties-common nano curl wget zip unzip gnupg

Type “Y” and hit Return to accept any prompts during installation.

Installing Docker

Outline runs inside of a Docker container, so you’ll need to install and configure Docker on your new server to get Outline up and running. You’ll add a new source for Docker to pull the latest stable release and verify its installation on your server.

Run the following commands, one after the other:

sudo apt update

curl -fsSL https://download.docker.com/linux/ubuntu/gpg | sudo gpg --dearmor -o /usr/share/keyrings/docker-archive-keyring.gpg

echo "deb [arch=$(dpkg --print-architecture) signed-by=/usr/share/keyrings/docker-archive-keyring.gpg] https://download.docker.com/linux/ubuntu $(lsb_release -cs) stable" | sudo tee /etc/apt/sources.list.d/docker.list > /dev/null

sudo apt update && apt-cache policy docker-ce && sudo apt install docker-ce

Type “Y” and hit Return to accept any prompts during installation. At this point, Docker should be installed successfully on your server. To verify, run this command:

sudo systemctl status docker

You should see something output like this:

If you entered the command above, to exit the Docker menu, type :q

Now, remember the non-root user you created earlier? If not, please follow the guide for Initial Server Setup with Ubuntu 22.04 on Digital Ocean.

You’ll want to add this user to the docker group so that you don’t have to prefix docker commands with sudo each time. Run the following command, replacing ${USER} with the username you chose earlier.

sudo usermod -aG docker ${USER} && su - ${USER}

Now when you run the groups command, you should now see your user added to the docker group.

Installing Docker Compose

In order to builder the Docker image necessary to run the open source Outline knowledge base and team wiki on your server, you need to install and configure Docker Compose.

Run the following command:

sudo apt update && sudo apt install docker-ce-cli containerd.io docker-compose-plugin docker-compose

Type “Y” and hit Return to accept any prompts during installation.

You should be able to run the following command and see the version output below:

docker compose version

Excellent! Docker is ready to be used with Docker Compose, and you now have the necessary tools installed to compose and deploy your custom Outline docker-compose.yml file.

Securing Docker

Docker and UFW do not play along well together. Docker overwrites much of the iptables functionality used by UFW. This means that by default, Docker exposes all of your server ports to the world. Yikes!

This is not good, so you need to secure Docker and limit port exposure on your machine. There is an excellent Github repository that explains this in more detail if you are interested in learning more.

To secure Docker and allow UFW to work as expected, run the following command:

sudo nano /etc/ufw/after.rules

When prompted, add the following code to the very end of the file (after the final COMMIT text):

# BEGIN UFW AND DOCKER
*filter
:ufw-user-forward - [0:0]
:ufw-docker-logging-deny - [0:0]
:DOCKER-USER - [0:0]
-A DOCKER-USER -j ufw-user-forward

-A DOCKER-USER -j RETURN -s 10.0.0.0/8
-A DOCKER-USER -j RETURN -s 172.16.0.0/12
-A DOCKER-USER -j RETURN -s 192.168.0.0/16

-A DOCKER-USER -p udp -m udp --sport 53 --dport 1024:65535 -j RETURN

-A DOCKER-USER -j ufw-docker-logging-deny -p tcp -m tcp --tcp-flags FIN,SYN,RST,ACK SYN -d 192.168.0.0/16
-A DOCKER-USER -j ufw-docker-logging-deny -p tcp -m tcp --tcp-flags FIN,SYN,RST,ACK SYN -d 10.0.0.0/8
-A DOCKER-USER -j ufw-docker-logging-deny -p tcp -m tcp --tcp-flags FIN,SYN,RST,ACK SYN -d 172.16.0.0/12
-A DOCKER-USER -j ufw-docker-logging-deny -p udp -m udp --dport 0:32767 -d 192.168.0.0/16
-A DOCKER-USER -j ufw-docker-logging-deny -p udp -m udp --dport 0:32767 -d 10.0.0.0/8
-A DOCKER-USER -j ufw-docker-logging-deny -p udp -m udp --dport 0:32767 -d 172.16.0.0/12

-A DOCKER-USER -j RETURN

-A ufw-docker-logging-deny -m limit --limit 3/min --limit-burst 10 -j LOG --log-prefix "[UFW DOCKER BLOCK] "
-A ufw-docker-logging-deny -j DROP

COMMIT
# END UFW AND DOCKER

Hit Crtl + X, Y then Return to save the file. Next, reload the UFW application by running this command:

sudo systemctl restart ufw

Finally, you need to reboot your machine for all the upgrades and changes to take full effect. Run the following command to reboot your machine:

sudo reboot

At this point, the SSH connection to your machine will close. Wait about 60 seconds or so, then log back in, replacing ${USER} with the non-root user you created earlier along with the IP address for your server:

ssh -A ${USER}@yourip

Before moving on with Docker, you need to configure a few other services and systems first. You’ll do that now and return to Docker later in the tutorial.

Configuring Subdomain DNS Records, Nginx and Let’s Encrypt

DNS Records

As I mentioned earlier, I’m using Cloudflare to manage my DNS records. You’ll need to grab the IP address of your new Digital Ocean droplet and create a new A record that points to a subdomain of your choosing.

Add your new A record and update your DNS records. I’ve chosen my subdomain to be outline, so you can see my Outline self hosted install at https://outline.thomasgriffin.com. If you’re using Cloudflare, turn off their proxy setting for now. You can turn it back on once you finish the tutorial.

Now that you’ve configured subdomain access, you need to add a web server and SSL certificate to handle public requests.

For this tutorial, you’ll use Nginx as a reverse proxy to access Outline in your Docker container, and you’ll use Let’s Encrypt to handle SSL certificate generation and management.

Nginx

Ubuntu ships with an older version of Nginx by default, so you’ll want to grab the latest release to use.

Run the following commands in order in your terminal:

curl https://nginx.org/keys/nginx_signing.key | gpg --dearmor \
	| sudo tee /usr/share/keyrings/nginx-archive-keyring.gpg >/dev/null

echo "deb [signed-by=/usr/share/keyrings/nginx-archive-keyring.gpg arch=amd64] \
http://nginx.org/packages/ubuntu `lsb_release -cs` nginx" \
    | sudo tee /etc/apt/sources.list.d/nginx.list

sudo apt update && sudo apt install nginx

Nginx is now installed on your server. Let’s go ahead and allow web traffic on the server. Run the following command in your terminal:

sudo ufw allow 80 && sudo ufw allow 443

That’s all you need to do for now. You’ll return to Nginx to receive and properly handle incoming traffic later in the tutorial.

Let’s Encrypt

Let’s Encrypt is a server utility to manage SSL certificates. You’ll use this to generate and maintain the SSL certificate for your Outline install.

Run the following commands in order to get Let’s Encrypt installed on your server:

sudo apt install snapd && sudo snap install core && sudo snap refresh core

sudo snap install --classic certbot

Let’s link the certbot command to the /usr/bin directory so you can run the certbot command without the snap prefix:

sudo ln -s /snap/bin/certbot /usr/bin/certbot

Now you are ready to generate your SSL certificate for the subdomain chosen. Mine subdomain is outline, e.g. outline.thomasgriffin.com. Run the command below, replacing ${DOMAIN} with whatever subdomain/domain combination you have chosen for your Outline self hosted install.

sudo certbot certonly --standalone --agree-tos --no-eff-email --staple-ocsp --preferred-challenges http -m [email protected]${DOMAIN} -d ${DOMAIN} --pre-hook="systemctl stop nginx" --post-hook="systemctl start nginx"

You should now have your new SSL certificate stored at /etc/letsencrypt/live.

Because you created the SSL certificate using the Certbot Snap tool, Certbot automatically creates a timer to renew the certificate for you. Nice!

Setting Up AWS IAM and S3

Outline can accepts various types of file attachments for its documents. Because of this, you need a file storage solution to host and deliver those attachments.

Let’s setup a special IAM user and S3 bucket dedicated to your Outline install. As you create these items, jot down the associated zones, keys, secrets and names. You’ll use them later when configuring your docker-compose.yml file.

If you don’t have an AWS account yet, go ahead and create one now.

For this tutorial, I’m using the following names for the Username and Bucket Name:

• Username: Outline
• Bucket Name: tg-outline-assets

Because S3 bucket names are unique, you’ll need to create your own custom bucket name. I’ll note the areas where you need to add that in the following steps.

Creating the S3 Bucket

Let’s create your S3 bucket to hold Outline attachments and assets.

As I mentioned earlier, I will be using the bucket name tg-outline-assets. You must change this to your own unique bucket name.

Navigate to S3 in the AWS Console and click on “Create bucket” to get started.

Enter the bucket name (for this tutorial, it is tg-outline-assets) and select the desired region. You will need to jot down your bucket region, as you’ll use this later when setting up your docker-compose.yml file.

In the Object Ownership section, select the ACLs enabled option, leaving the Bucket owner preferred option toggled on.

In the Block Public Access section, toggle off the Block all public access setting and check the box to acknowledge the warnings. This is necessary to allow certain images to be uploaded and viewed in your Outline install.

For the remainder of the bucket settings, leave them as they have been defaulted. Scroll down to the bottom and click “Create bucket” to create your new S3 bucket.

On the main S3 bucket screen, find your new bucket and click on it. Then, click on the Permissions tab.

Scroll to the bottom of the Permissions tab and click to edit Cross-origin resource sharing (CORS).

Add the following policy configuration in the editor and save, replacing ${DOMAIN} with the domain you have chosen for your Outline install. In this example, I am using https://outline.thomasgriffin.com (include the https:// protocol).

[
    {
        "AllowedHeaders": [
            "*"
        ],
        "AllowedMethods": [
            "PUT",
            "POST",
            "DELETE"
        ],
        "AllowedOrigins": [
            "${DOMAIN}"
        ],
        "ExposeHeaders": []
    },
    {
        "AllowedHeaders": [],
        "AllowedMethods": [
            "GET"
        ],
        "AllowedOrigins": [
            "*"
        ],
        "ExposeHeaders": []
    }
]

Creating the IAM User and Policy

Search for “IAM” and get started by clicking “Add Users”.

Set the username as Outline and select “Access key – Programmatic access” as the credential type.

On the next screen, select “Attach existing policies directly”, then click on the “Create policy” button to create a custom access policy for this user.

On the next screen, select the “JSON” tab and paste the following policy code in the editor, replacing ${BUCKET} with the name of your S3 bucket you just created:

{
    "Version": "2012-10-17",
    "Statement": [
        {
            "Sid": "VisualEditor",
            "Effect": "Allow",
            "Action": [
                "s3:GetObjectAcl",
                "s3:DeleteObject",
                "s3:PutObject",
                "s3:GetObject",
                "s3:PutObjectAcl"
            ],
            "Resource": "arn:aws:s3:::${BUCKET}/*"
        }
    ]
}

Proceed to adding any tags you would like, then continue to the next screen to give the policy a name and optional description. I’ve chosen to name the policy OutlineS3. After review, click “Create policy” to create the new access policy.

Now that the new custom policy has been created, you need to attach it to your new IAM user. Click back over to your other IAM tab and hit the Refresh icon just above the policy results table. Type “Outline” in the search bar and then select your new custom policy.

Proceed to the next screen, adding any desired tags. Then review the modifications and click “Create user” to create the new Outline IAM user.

Once you have created the new user, I suggest you download the access credentials for safe keeping or note them somewhere, as you’ll use them when configuring your docker-compose.yml file later in the tutorial.

Creating a Google Workspace Oauth App

Next, you need to enable authentication into Outline. While many authentication methods exist, I’ve chosen Google because I have a Google Workspace account readily available with my domain.

If using Google doesn’t work for you, you are free to try other authentication methods listed in their documentation. I cannot guarantee they will work, as I have only tested and verified the process with Google.

Creating the Cloud Project

Head over to the Google Developers Console and, if necessary, switch to the appropriate Google Workspace user account.

Select the project caret dropdown in the header menu and click on “New Project” to get started.

Give the project a name (I’ve called it Outline Auth), select the locations and click “Create” to create the new project.

Adding Authentication APIs

Make sure that your new project is selected in the header menu (the same place where you clicked the dropdown caret to get started), and then click on the “Enable APIs and Services” button to add the necessary authentication APIs to your project.

In the search bar, type “google+” and then select the Google+ API option. Once selected, click “Enable” to enable the API for your project.

Configuring the Oauth Consent Flow

Next, you need to configure the Oauth consent flow for authentication requests.

Click on the “Oauth consent screen” link in the lefthand sidebar. Select the “Internal” option and then click “Create”.

Give the app a name (I’ve named mine Outline Auth) and fill out the User support email. Under Authorized domains, add your top level domain.

For this tutorial, since my Outline instance is found at https://outline.thomasgriffin.com, I’ll add thomasgriffin.com as an authorized domain.

Finish by adding in a developer contact email address and click “Save and Continue”.

On the Scopes screen, click on “Add or Remove Scopes” and select the first, second and third options in the list. Then scroll to the bottom of the flyout window and click “Update”.

Scroll to the bottom of the screen and click “Save and Continue”.

Generating Oauth Credentials

Finally, you need to generate Oauth credentials for the Google Cloud project you’ve created.

Click on the “Credentials” link in the lefthand sidebar. Click on the “Create Credentials” button and then select “Oauth client ID” for the credential type.

Once the next screen, select “Web application” as the application type and give it a name. For this tutorial, I have named mine Outline Oauth Client.

Under “Authorized JavaScript origins”, enter your subdomain URL. For this tutorial, mine is https://outline.thomasgriffin.com.

Under Authorized redirect URIs, enter the following URL, replacing ${DOMAIN} with your subdomain/domain name:

https://${DOMAIN}/auth/google.callback

Click “Create” to create your new project credentials. Copy the client ID and secret and jot them down in a safe place, as you’ll use them when you configure your docker-compose.yml file in the next step.

Creating and Running the Outline Docker Image

You are now ready to generate your custom docker-compose.yml file that defines the services necessary to run Outline on your droplet.

First, you’ll need to create a new directory on the server as your Outline project “home”. Remember the non-root user you created from the Digital Ocean tutorial at the beginning of this article? You’ll use that user’s home directory to store your files. Run the command below, replacing ${USER} with the name of the user you created earlier.

mkdir -p /home/${USER}/docker && mkdir -p /home/${USER}/docker/logs && cd /home/${USER}/docker && touch docker.env && touch docker-compose.yml

Before you boot Docker, you’ll need to add some necessary environment variables to your new docker.env file. I’m not using all of the available variables for this tutorial, so if you want to know more, click here to see all of the available environment variables.

Here are the variables you will be using in your docker.env file:

## Required Variables
SECRET_KEY=
UTILS_SECRET=
FORCE_HTTPS=
ENABLE_UPDATES=
WEB_CONCURRENCY=

## Postgres Variables
POSTGRES_USER=
POSTGRES_PASSWORD=
POSTGRES_DB=
DATABASE_URL=
PGSSLMODE=

## Redis Variables
REDIS_URL=

## Domain Variables
URL=
PORT=

## Rate Limiting Variables
RATE_LIMITER_ENABLED=
RATE_LIMITER_DURATION_WINDOW=
RATE_LIMITER_REQUESTS=

## AWS Variables
AWS_REGION=
AWS_S3_FORCE_PATH_STYLE=
AWS_S3_UPLOAD_BUCKET_NAME=
AWS_S3_UPLOAD_BUCKET_URL=
AWS_S3_UPLOAD_MAX_SIZE=
AWS_ACCESS_KEY_ID=
AWS_SECRET_ACCESS_KEY=

## Google Login Authentication Variables
GOOGLE_CLIENT_ID=
GOOGLE_CLIENT_SECRET=

A few points of information on the variables listed above:

• We’ll generate 3 unique keys for the ${SECRET_KEY}, ${UTILS_SECRET} and ${POSTGRES_PASSWORD} variables.
• Since we will be terminating SSL, we can set the ${FORCE_HTTPS} variable to false.
• For the ${URL} variable, replace it with the HTTPS URL for your Outline install, e.g. https://outline.thomasgriffin.com
• Grab the access keys, client IDs and other keys that you generated when walking through the AWS and Google Workspace parts of the tutorial. You’ll need to enter them in your docker.env file.
• Wherever else you see ${VARIABLE} in the docker.env file, make sure to replace it with the appropriate value.

To generate the unique keys, run the following command three times. After each time, copy the output and replace ${SECRET_KEY}, ${UTILS_SECRET} and ${POSTGRES_PASSWORD} variables respectively in the docker.env file contents below.

openssl rand -hex 32

To edit the file in the terminal, run the following command:

nano docker.env

Here’s the code that goes in docker.env. Don’t forget to run the commands and replace the appropriate variables!

## Required Variables
SECRET_KEY=${SECRET_KEY}
UTILS_SECRET=${UTILS_SECRET}
FORCE_HTTPS=false
ENABLE_UPDATES=true
WEB_CONCURRENCY=2

## Postgres Variables
POSTGRES_USER=outline_user
POSTGRES_PASSWORD=${POSTGRES_PASSWORD}
POSTGRES_DB=outline
DATABASE_URL=postgres://outline_user:${POSTGRES_PASSWORD}@postgres:5432/outline
PGSSLMODE=disable

## Redis Variables
REDIS_URL=redis://redis:6379

## Domain Variables
URL=${URL}
PORT=3000

## Rate Limiting Variables
RATE_LIMITER_ENABLED=true
RATE_LIMITER_DURATION_WINDOW=60
RATE_LIMITER_REQUESTS=600

## AWS Variables
AWS_REGION=${AWS_BUCKET_REGION}
AWS_S3_FORCE_PATH_STYLE=false
AWS_S3_UPLOAD_BUCKET_NAME=${AWS_BUCKET_NAME}
AWS_S3_UPLOAD_BUCKET_URL=https://${AWS_BUCKET_NAME}.s3.${AWS_BUCKET_REGION}.amazonaws.com
AWS_S3_UPLOAD_MAX_SIZE=26214400
AWS_ACCESS_KEY_ID=${AWS_ACCESS_KEY}
AWS_SECRET_ACCESS_KEY=${AWS_SECRET_KEY}

## Google Login Authentication Variables
GOOGLE_CLIENT_ID=${GOOGLE_CLIENT_ID}
GOOGLE_CLIENT_SECRET=${GOOGLE_CLIENT_SECRET}

Next, you’ll modify the docker-compose.yml file to define the images you need to run Outline:

nano docker-compose.yml

Add the following code in the command prompt:

version: "3"
services:

  outline:
    image: outlinewiki/outline:latest
    restart: always
    env_file: docker.env
    command: sh -c "yarn db:migrate --env=production-ssl-disabled && yarn start --env=production-ssl-disabled"
    ports:
      - "3000:3000"
    depends_on:
      - postgres
      - redis

  redis:
    image: redis:7
    restart: always
    env_file: docker.env
    expose:
      - "6379"
    volumes:
      - ./redis.conf:/redis.conf
    command: ["redis-server", "/redis.conf"]

  postgres:
    image: postgres:14
    restart: always
    env_file: docker.env
    expose:
      - "5432"
    volumes:
      - database-data:/var/lib/postgresql/data

volumes:
  database-data:

Finally, save the file (Ctrl + X, Y and then Return). Now you are ready to get Outline up and running with Docker!

Run the following command to boot your new Outline Docker container:

docker-compose up -d

You should see some information output to your terminal. It will look something like this:

If you happen to see an error, a common one is because docker-compose does not like tabs. You’ll want to convert tabs to spaces in the docker-compose.yml file.

You can validate that things are working in the container by running this command:

docker ps

Additionally, it’s helpful to check the Docker logs to ensure no errors have been encountered. You can check those logs by running the following command:

docker-compose logs

If you see any errors in the logs, take a break from the tutorial to get them resolved.

If you have any issues resolving them, you can leave a comment on this article, reach out to me via my contact form or ping me on Twitter. I’m happy to help!

Now you are ready to configure the Nginx server block so that your new Outline knowledge base and team wiki install is accessible to the public.

Configuring the Nginx Server Block

This is the final step to accessing your new Outline knowledge base and team wiki install. You need to be able to receive and handle incoming web traffic from your new subdomain, e.g. https://outline.thomasgriffin.com.

Because Outline is running in Docker, Nginx needs to act as a reverse proxy for web traffic. You’ll configure those details now.

First, you need to improve your SSL security exchanges by creating a Diffie-Helman exchange key. Run the following command in your terminal:

sudo openssl dhparam -out /etc/ssl/certs/dhparam.pem 2048

Next, run the following command to create a new configuration file for your Outline application:

sudo nano /etc/nginx/conf.d/outline.conf

Inside of the editing screen, copy and paste the code below, replacing the following variables:

• Replace ${DOMAIN} with the domain you have selected, e.g. outline.thomasgriffin.com
• Replace ${USER} with the non-root user you created when you followed the initial setup tutorial for Ubuntu on Digital Ocean, e.g. thomas

server {
	listen 80;
	listen [::]:80;

	server_name ${DOMAIN};

	return 301 https://$host$request_uri;
}

server {
	listen 443 ssl http2;
	listen [::]:443 ssl http2;

	server_name ${DOMAIN};

	access_log off;
	error_log /home/${USER}/docker/logs/error.log;

	ssl_protocols TLSv1.2 TLSv1.3;
	ssl_ciphers ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES256-SHA:ECDHE-ECDSA-DES-CBC3-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128-SHA256:AES256-SHA256:AES128-SHA:AES256-SHA:DES-CBC3-SHA:!DSS;
	ssl_prefer_server_ciphers on;
	ssl_session_timeout 24h;
	ssl_stapling on;
	ssl_stapling_verify on;
	ssl_certificate /etc/letsencrypt/live/${DOMAIN}/fullchain.pem;
	ssl_certificate_key /etc/letsencrypt/live/${DOMAIN}/privkey.pem;
	ssl_trusted_certificate /etc/letsencrypt/live/${DOMAIN}/chain.pem;
	ssl_dhparam /etc/ssl/certs/dhparam.pem;
	ssl_session_cache shared:OutlineSSL:10m;
	ssl_session_tickets off;

	location / {
		proxy_pass http://127.0.0.1:3000;
		
		proxy_set_header Upgrade $http_upgrade;
		proxy_set_header Connection "Upgrade";
		proxy_set_header Host $host;
		
		proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
		proxy_set_header Host $host;
		proxy_set_header Host $http_host;
		proxy_set_header X-Real-IP $remote_addr;
		proxy_set_header X-Scheme $scheme;
		proxy_set_header X-Forwarded-Proto $scheme;
		proxy_redirect off;
	}
}

Once done editing, hit Ctrl + X, then Y and Return to save the file.

You can further optimize your Nginx server blocks later. These are some basic configuration settings designed to get you up and running in a secure way.

To verify everything looks good, run the following command:

sudo nginx -t

If you received any errors, review them and edit your outline.conf file to fix the errors, and then re-run the command above to validate the fixes.

Once everything looks good, run the following command to reload Nginx and apply the configuration changes:

sudo systemctl restart nginx

Viewing and Authenticating Into Your Outline Self Hosted Install

You should be able to visit your url, e.g. https://outline.thomasgriffin.com, and see a screen that looks like this:

Click on the button to log in with Google, and then log in using the email address domain associated with the custom Oauth client you created earlier.

Congratulations! Enjoy your new Outline self hosted install! 🎉

From here, I’ll be sharing some additional configurations, such as setting up SMTP so email works from your server as well as configuring Outline to automatically check for and apply updates once per month.

I’ve spent countless hours both figuring out how to get Outline installed for myself as well as writing, testing and validating this tutorial. If it has been helpful to you, please share it with others using the social buttons associated with this tutorial.

Thanks in advance for your vote of support when you do!

Let’s continue with the tutorial.

Configuring SMTP

If you want to invite teammates to your Outline self hosted install, you need to configure SMTP support. Otherwise, your emails will never leave the server.

You’ll need a transactional email service for this. I recommend SendLayer. It’s one of my company’s products, and it’s got a free plan for your first 500 emails.

Sign up for a free plan. Once done, add a domain for sending email. I recommend using a separate subdomain for transactional emails. For example, mine is outlinemail.thomasgriffin.com.

After you add your domain, you’ll be asked to add some new DNS records to finish the setup process. Just like you did in the steps above to add your subdomain for your Outline install, you’ll do the same type of work here.

Here’s an example of the records you’ll be asked to configure:

Once you have configured and verified your DNS records, head over to the SMTP Credentials tab. You’ll need to grab the credentials to add to your docker.env file.

Once you have those SMTP credentials in hand, return to your docker.env file (located at /home/${USER}/docker) and add the following at the bottom, replacing the SMTP variables with the credentials from SendLayer. The ${FROM_EMAIL} variable should be from the subdomain you’ve setup for SMTP, and the ${REPLY_EMAIL} variable can be whatever you would like it to be.

## SMTP Variables
SMTP_HOST=smtp.sendlayer.net
SMTP_PORT=587
SMTP_USERNAME=${SMTP_USERNAME}
SMTP_PASSWORD=${SMTP_PASSWORD}
SMTP_FROM_EMAIL=${FROM_EMAIL}
SMTP_REPLY_EMAIL=${REPLY_EMAIL}
SMTP_SECURE=false

Once you’ve saved the file, you’ll need to apply the changes to your Docker containers. Run the following command in your terminal:

docker-compose down --remove-orphans && docker-compose up -d

You may notice a brief 502 Bad Gateway error from Nginx after you reload Docker. It usually resolves in under 30 seconds.

You can now invite your teammates to collaborate on your new Outline install.. and they’ll actually receive your email invitations!

Configuring Automatic Updates for Your Outline Self Hosted Install

If you’re anything like me, once you set something up, you find it a hassle to revisit and maintain it with rudimentary updates.

Fortunately, you can easily automate this task using the system cron. Let’s create two jobs: one that triggers daily Outline scheduled jobs, and one that automatically checks for updates once per month (and if an update for Outline found, it’s automatically installed, applied and restarted).

Daily Scheduled Jobs

Run this command in your terminal to create the new daily cron job to trigger Outline scheduled jobs:

sudo nano /etc/cron.daily/outline-daily

Add the following code when prompted, replacing the ${DOMAIN} variable with the domain you’ve chosen for your Outline install (e.g. outline.thomasgriffin.com) and ${UTILS_SECRET} with the UTILS_SECRET variable from your docker.env file:

#!/bin/sh
curl https://${DOMAIN}/api/cron.daily?token=${UTILS_SECRET}

Save the file (Ctrl + X, Y and then Return). Then, make it executable by running the following command:

sudo chmod +x /etc/cron.daily/outline-daily

The cron will now run once per daily and trigger any jobs that Outline has scheduled.

Monthly Updates

Run this command in your terminal to create the new monthly cron job to update Outline:

sudo nano /etc/cron.monthly/outline-update

Add the following code when prompted, replacing the ${USER} variable with the non-root user you created at the beginning of this tutorial:

#!/bin/sh
cd /home/${USER}/docker
docker-compose down --remove-orphans
docker pull outlinewiki/outline
docker pull redis:7
docker pull postgres:14
docker-compose run --rm outline yarn db:migrate --env=production-ssl-disabled
docker-compose up -d

Save the file (Ctrl + X, Y and then Return).

Next, you need to make sure the monthly cron is executable. Run this command in your terminal:

sudo chmod +x /etc/cron.monthly/outline-update

The cron will now run once per month and automatically update Outline to the latest released version. It will also run any new database migrations that might be part of the Outline update.

Once again, congratulations! You’ve installed the Outline team knowledge base and wiki on Ubuntu successfully!

If you have found this helpful, please let the world know. I spent lots of time getting this to work and writing this tutorial for you. You can quickly share it using the social buttons on this article.

Also, I’d love to know if you’ve gotten it setup successfully or if you need some help. Drop a comment below, reach out on my contact form or ping me on Twitter.

Helpful Commands, Tips and Tricks

When working with complex setups like this, it’s helpful to have a list of commands/tips/tricks to make the management and debugging aspect easier.

Below, you will find some helpful things I’ve used during the process of getting Outline running on my own site.

Removing Old Database Volumes

If for some reason Postgres does not behave when you initially run Docker, you may end up with a bad volume of data.

Because of how Docker works, subsequent shut downs and start ups will skip steps for provisioning databases and users. If you find that you are missing a database or user role in the logs (docker-compose logs), you can run the following two commands to remove old database volumes so they can be fully rebuilt:

docker volume ls
docker volume rm <volume_name>

Note that when you do this, you’ll lose all of your data. This is mostly helpful when initially setting up your Outline install.

Typically the postgres volume will be obvious, having postgres somewhere in its name. Remove it, then you can bring the docker containers down (docker-compose down) and back up again (docker-compose up -d).

Completely Wiping Docker

It’s not hard, but it was hard to find the right commands to do it easily.

To remove all containers and volumes, run this command:

docker rm -vf $(docker ps -aq)

To remove all the images, run this command:

docker rmi -f $(docker images -aq)

Then you are free to run docker-compose up -d again, and it will do so in a completely fresh way.

Wrapping Up

Thank you for your time. I hope you are experiencing the Vision of Results as I described them earlier.

If you have found this helpful, please share it with others. I spent numerous hours getting this to work and documenting it for you. You can quickly share it using the social buttons on this article.

Additionally, I’d love to know if you’ve gotten it setup successfully or if you need some help. Drop a comment below, reach out on my contact form or ping me on Twitter.

And if you are interested in more of my writing, here’s a few great places to start:

• Reflections on Greatness (And How to Become Great) Everybody wants to be great at something. But what does it actually take to be great? The answer might surprise, and I share an interesting graph to explain why.
• How to Communicate Effectively (In Any Situation) Effective communication is a critical skill that everyone needs to develop. In this article, I define the requirements, provide commentary and share helpful examples on how you can be more effective in your communication.
• Welcome to Leadership Flourish as a leader with battle-tested leadership principles, insights and tactics.

Have a great day!
Thomas

Thomas Griffin

Hello! I'm Thomas, and I’m the co-founder of OptinMonster, a partner at Awesome Motive, and a leader of leaders. My software powers organizational success for more than 20 million websites across the globe, and my content is read by thousands each month.

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