Creating certificates and keys for OpenVPN server with EasyRSA on MacOS

This guide covers how to create certificates and keys for OpenVPN server and clients using the EasyRSA tool on MacOS.

The instructions are very similar for most flavours of linux such as Ubuntu once the correct packages are installed (e.g. on Ubuntu: apt-get install openvpn easy-rsa).

If privacy and security are of the utmost concern, generate all certificates and keys on a “clean” machine and verify the signatures of each download.

Step 1: Resolve MacOS Dependencies

This guide assumes that you’re running MacOS Sierra or later.

XCode and Command Line Tools

Ensure that you have installed the XCode Command Line Tools.

To check, the command xcode-select -p outputs a file path beginning with /Applications/ if they are already installed.

If Command Line Tools is not installed, open the Terminal app and enter xcode-select --install to trigger the installation app.

Another way to trigger the installation app is to attempt to use a command line developer tool such as the GNU C compiler gcc (e.g. gcc --version). If the tools are not installed, you will be greeted by a graphical MacOS installation prompt instead of the expected Terminal output from gcc. You don’t necessarily need the full XCode so you can click the “install” button for just the command line tools.

Work your way through the installer and follow Apple’s steps until you can start working with the necessary commands. The CLI commands will become available to you after you agree to all of Apple’s terms and conditions.

If you experience troubles with the next step, assuming that it is the result of some future change by Apple, it may be beneficial to install the full XCode in addition to the CLI tools. It’s available for free on the App Store, but take note that it’s a hefty multi-gigabyte download.


EasyRSA requires a late-version of the open-source openssl library.

Apple bundles its own crypto libraries in MacOS but these are generally out of date. At the time of writing, the openssl command bundled with MacOS is not likely compatible with EasyRSA and will produce errors if you try to use it (note: the binary is at /usr/bin/openssl).

A newer EasyRSA-compatible version of OpenSSL is easy to install with the brew package manager ( Installing via brew will not clobber or harm the Apple version that’s already on your system. If you need to install brew, go to the project’s website and follow the simple instructions on the landing page.

Assuming you have brew installed, open a Terminal and run the command:

brew install openssl

Brew will download and install openssl to its default package install directory of /usr/local/Cellar.

The package will be installed in “keg only” mode: brew will not create a symlink for its openssl in /usr/local/bin or anywhere else in your $PATH. You will not have a conflicting openssl command, and Apple’s binary will remain intact.

To get EasyRSA to use the openssl binary installed by the brew package, you will need to know its path. Run brew’s package info command and examine the output:

brew info openssl

In my example, I could see that openssl resolved to /usr/local/Cellar/openssl/1.0.2n. In your case, this may be a different path due to a more recent version being available in the future. Next, inspect this folder to locate the binary and determine the full path to it. In my example case, the full path to the binary was:


Note down the correct path to the openssl binary for your case. When configuring EasyRSA in the next step, you will need to specify this path in an EASYRSA_OPENSSL variable.

Step 2: Download EasyRSA

Go to and download the latest .tgz version for your Mac.

Save the file to a folder that you wish to work from (your certificates and keys will be generated here) and unpack it using the Archive utility (double click on it in Finder).

Note that the easy-rsa tools were written with traditional linux/unix-type environments in mind and therefore assume that all paths to the scripts have no spaces in them.

Going forward I will assume the path of your unpacked EasyRSA folder is: ~/vpn/easyrsa. The ‘~’ character is a shortcut to your home folder that works in Terminal, i.e. on a Mac its a placeholder for /Users/your_username and on a typical linux environment /home/username.

Step 3: Configure EasyRSA

Assuming that the path of your unpacked EasyRSA folder is: ~/vpn/easyrsa, open Terminal and navigate to the unpacked folder:

cd ~/vpn/easyrsa

Copy the vars.example “starter” configuration file to vars:

cp vars.example vars

Now customize the initial “starter” configuration file’s settings in vars to reflect your own.

Open it in a text editor and look for the following lines. Uncomment them (i.e. delete the preceding # character) and fill them in with your appropriate values. Specify something for each field below:

#set_var EASYRSA_REQ_PROVINCE  "California"
#set_var EASYRSA_REQ_CITY  "San Francisco"
#set_var EASYRSA_REQ_ORG   "Copyleft Certificate Co"
#set_var EASYRSA_REQ_OU        "My Organizational Unit"

Look for the following field and uncomment it:

#set_var EASYRSA_KEY_SIZE        2048

We’ll be using a 2048-bit key (the current default) for this example so the value will not be changed.

A larger key size is more secure but will result in longer connection + wait times over the VPN. At the time of writing in late 2017, its generally believed that a 2048-bit key is sufficient for most usage scenarios. A 4096-bit key is believed to provide additional privacy vs. more powerful state-sponsored actors.

EasyRSA by default uses the openssl binary found in the $PATH. Find the following line, uncomment it, and update the value with the path to the brew-installed openssl binary from Step 1. For example, in my case, the following line:

#set_var EASYRSA_OPENSSL   "openssl"


set_var EASYRSA_OPENSSL "/usr/local/Cellar/openssl/1.0.2n/bin/openssl"

Step 4: Generate Certificate Authority (CA)

Navigate into your easyrsa/ folder. For example:

cd ~/vpn/easyrsa

Initialize the PKI (public key infrastructure) with the easyrsa script. This will create a pki/ subfolder:

./easyrsa init-pki

Create the CA (certificate authority):

./easyrsa build-ca nopass

You will be prompted to input a Common Name. Input the name server and hit ENTER.

The generated CA certificate can now be found at pki/ca.crt.

Step 5: Generate Server Certificate + Key + DH Parameters

Assuming you’re still inside your easyrsa/ folder from the previous step, generate your server certificate and key:

./easyrsa build-server-full server nopass

The generated server certificate can now be found at: pki/issued/server.crt

The generated server key can now be found at: pki/private/server.key

Now generate the Diffie-Hellman (DH) parameters for key exchange. This process can take several minutes depending on your system:

./easyrsa gen-dh

The generated DH parameters can be found at: pki/dh.pem.

You now have all of the files necessary to configure an OpenVPN server.

Step 6: Generate client credentials

You should generate a unique set of credentials for each and every client that will connect to your VPN. You can repeat this step for any client that you need to create credentials for.

All clients in your setup should have a unique name. Change exampleclient in the following to something descriptive that you will recognize and be able to associate with the user/client:

./easyrsa build-client-full exampleclient nopass

The generated client certificate: pki/issued/exampleclient.crt

The generated client key can be found at: pki/private/exampleclient.key

When distributing credentials to a client, they will need at least these 3 files:

  • A client certificate (e.g. pki/issued/exampleclient.crt)
  • The corresponding client key (e.g. pki/private/exampleclient.key)
  • A copy of the CA certificate (pki/ca.crt)

These client credentials can be loaded into a VPN app like Tunnelblick or Viscosity along with client configuration information that corresponds to your VPN server’s specific settings.

Understanding client config files

Client configuration information is usually provided in the form of an additional file: a plaintext config file with the .ovpn extension. Both Tunnelblick and Viscosity recognize the .ovpn extension and file format.

Later versions of openvpn support specifying all of the client configuration information, client certificate, client key, and CA certificate as demarcated blocks within the config file itself, so that clients only need to be provided with a single .ovpn file.

Security reminder

It is good to practice to try and keep all .ovpn, certificate, and key files as safe as possible with exposure to as few eyes/hands/hard-disks/clouds/etc as possible. Distribute them as securely as you can to your clients/users.

Next steps

Now you need a working openvpn server and a client that wishes to connect to your VPN!

I hope this guide was helpful to you. For all the server tutorials out there, as far as I know this is one of the few comprehensive guides out there for creating all required certificates and keys on MacOS.

Router as OpenVPN server

If your openvpn server is your router, you can now login to it’s admin control panel and input the server-related certificate + key + DH parameters that you created above.

Before you activate the VPN server, ensure that your router’s firmware is up-to-date and that you have set a long and reasonably secure password for the admin user.

Running your own server

If you are planning to setup your own openvpn server, there are numerous other resources available online to guide you through the server installation and configuration process for a variety of different operating systems.

You will find that you need all the keys and certificates that you created by following this guide.

These resources will generally include guidance for crafting .ovpn client configuration files to include specific settings that correspond to your server’s particular setup, so that clients can successfully connect.

Send emails from MacOS Terminal or scripts using Rackspace’s SMTP server

This guide will help configure MacOS so it can send emails from the command-line (Terminal) and shell scripts via an SMTP server. This is useful for enabling scripts, scheduled jobs, etc. to send email notifications.

The example in this post work for Rackspace’s SMTP server. The guide is adaptable to other SMTP servers and email providers, while acknowledging that you may need to adjust certain details. Email providers can vary in how they require users to authenticate and interface with their SMTP servers.

There are lot of examples online for using gmail’s SMTP servers, but since I couldn’t find any complete examples for Rackspace, I decided to write this post!

Configuring postfix on MacOS

MacOS/OSX comes bundled with the postfix mail server. We will configure that to use Rackspace’s SMTP server to send mail.


To use Rackspace’s SMTP, its a given that you must be a Rackspace customer. Create an email address that you wish to be the “sender” of any notifications. Note this email account’s credentials as you’ll need to include them in your postfix configuration.

I recommend that you use a dedicated email address for sending automated notifications (e.g. no-reply@.., notify@.., etc), rather than an email address with an inbox that is important to your business. Within Rackspace’s control panel, you have the option to configure an auto-responder for your automated notification address so that anyone that replies to a notification or sends anything else to it will receive a canned reply in response.

Step1: Edit main postfix configuration file

Make a copy of your original postfix conf file:

sudo cp /etc/postfix/ /etc/postfix/

Open postfix’s config file for editing:

sudo nano /etc/postfix/

In an untouched postfix configuration on MacOS, the following 3x separate lines have the following values:

  • mydomain_fallback = localhost
  • mail_owner = _postfix
  • setgid_group = _postdrop.

If you have previously edited your postfix settings, you may wish to search for each item and reset these back to their default values (first confirm that you aren’t about to break anything!).

Add the following to the very end of the open postfix config file:

relayhost =
smtp_sasl_mechanism_filter = AUTH LOGIN
smtp_sasl_security_options =

These setting are specific to Rackspace’s requirements. If you are using another SMTP server, you will need to specify different values.

Save and exit the editor.

Step 2: create the sasl_passwd file for postfix to use

Create the /etc/postfix/sasl_passwd file referenced in with the following line of text, substituting the and password placeholders with your own:

Next, use the postmap tool to create a lookup table from the sasl_passwd file:

sudo postmap /etc/postfix/sasl_passwd

This will create the file sasl_passwd.db

Step 3: Restart postfix

sudo postfix reload

You might see some warnings, but they should be benign. We don’t need a full mail system, just the ability to send smtp emails. Move on to the next step to test your configuration!

Step 4: Send a test email

The following command sends a test email to Give it a shot by substituting your email address:

echo "testing testing test email" | mail -s test

Note this command does not produce any output when it runs successfully.

Next, check for the test email in your inbox (if its not there, be sure to also check the spam folder). You may want to add your notification email address to your recipient inbox’s address book to ensure better deliverability.

Troubleshooting tips

If you need to troubleshoot, it can be helpful to check the mail queue:

sudo mailq 

You can clear all queued emails with the following command:

sudo postsuper -d ALL

On OSX, postfix logged to the /var/log/mail.log file. On MacOS, this log file doesn’t exist.

For troubleshooting with MacOS, you can view the log in real-time with the command:

sudo log stream --predicate  '(process == "smtpd") || (process == "smtp")' --info

You could have this running in one Terminal tab, and then try to send a test email in another tab, to see what messages you receive.


Thanks to this article from <> which has instructions for using gmail, as well as some commenters on various forums that provided tips to adapt SMTP settings for Rackspace. Rackspace’s documentation was also helpful in realizing a working configuration.

Stripping leading and trailing slashes from paths in Ansible

This post covers how to use ansible’s regex_replace filter to strip leading and/or trailing slashes from file paths and URL fragments.

The final example demonstrates how to generate a valid filename from a file or URL path by removing leading and trailing slashes, and replacing any remaining slashes with underscores. This could be useful for a variety of applications from backup scripts to web scraping.

Stripping slashes

Regexes and jinja2 expressions in ansible can be a pain in the ass, especially when it comes to escaping the right thing.

The key to the following examples is a double-escape of the forward slash character. They have been tested on ansible v.

Remove leading slashes

{{ variable_name | regex_replace('^\\/', '') }}

Remove trailing slashes

{{ variable_name | regex_replace('\\/$', '') }}

Stripping both leading and trailing slashes

This example makes use of the | (OR) to combine the previous two examples into one regex:

{{ variable_name | regex_replace('^\\/|\\/$', '') 

Here’s a quick debug task that demonstrates the above in action:

- debug:
    msg: "Look Ma! No leading or trailing slashes! -- {{ item | regex_replace('^\\/|\\/$', '') }}"
    - "/home/and/lots/of/folders/trailing_and_leading/"
    - "no_leading/but/there/is/trailing/"
    - "/leading/but/no_trailing"
    - "no_leading/and/no_trailing"

Creating a valid filename from a path

To create a valid filename from a path, we need to remove leading and trailing slashes, then replace any remaining slashes with underscores. This sort of thing can be useful for naming backup files, data obtained from URL scraping, etc.

This is accomplished by adding a second regex_replace to the previous example that replaces all slashes with underscores, e.g. regex_replace('\\/', '_').

The combined regex that creates a valid filename from given a path:

{{ variable_name | regex_replace('^\\/|\\/$', '') | regex_replace('\\/', '_') }}

If variable_name held a value like “/var/www” or “/var/www/” it would result in: “var_www”.

In case you want to replace the slashes in the path with a character other than an underscore, you can adjust the examples to use any valid filename character instead of a slash (e.g. the ‘^’ character).

Working around a regex_replace bug in the shell module

In my working version of ansible (2.3.x) the regex_replace filter is ignored (!) when it is applied to variables in a tasks using the shell module. The value of unfiltered variables are substituted into the shell command fine, and using any other filter works fine too.

Workaround: employ the set_fact module to build a new fact (variable) based on the original variable, applying the regex_replace filter here as required. Reference the new fact in the shell module to take advantage of the pre-filtered values.

In the following example, assume that the hypothetical {{ list_of_paths }} variable contains a list of strings containing file/dir/URL paths. The set_fact module builds the new {{ paths }} fact such that it contains a “pi” item corresponding to every item in the original list. Each of these items has a “stripped” property containing the filtered value and a “path” property containing the original unfiltered value.

- name: workaround example
    paths: "{{ paths|default([]) + [{'pi': {'path': item, 'stripped': item|regex_replace('^\\/|\\/$', '')|regex_replace('\\/', '_')}}] }}"
      with_items: "{{ list_of_paths }}"

When looping over {{ paths }} in a shell task (e.g. via with_items), the filtered slash-free values for items can be referenced via {{ item.stripped }}. The original unfiltered path can be referenced via {{ item.path }}.

Install and secure phpmyadmin: require access via an SSH tunnel

Phpmyadmin is a popular database administration and query tool for MySQL and MariaDB. This guide covers how to install it, plus add an additional layer of security that only permits access via an encrypted ssh tunnel (also known as ssh port forwarding). This guide covers Debian and Ubuntu systems running apache2.

This particular approach is easy to automate and improves on other examples that I’ve come across online. Its the only tutorial that I know of that does things The Debian Way, in this case meaning that phpmyadmin’s customized configuration is applied without editing any of its packaged-managed conf files. This ensures that future package updates do not risk overwriting your security-minded configuration.

Why extra security measures are recommended for phpmyadmin

Phpmyadmin is a popular choice for attackers because it is widely deployed, easy to find, easy to attack, and it provides convenient access to potentially highly sensitive and/or valuable data.

A default package install of phpmyadmin on a public-facing web server is wide open to the Internet. It is often easily found with the default directory pattern “/phpmyadmin”.

A quick look at almost any website’s logs will reveal an endless barrage of attempts to locate phpmyadmin, probing a wide range of likely URL patterns and alternate names. In cases where phpmyadmin is discovered, its practically certain the logs will subsequently reveal attackers attempting to brute force and/or exploit their way in.

Another significant concern with phpmyadmin is that it does not come with ssl configured out-of-the-box. Login credentials and any data that’s accessed can be picked up by anyone that cares to listen in anywhere between your computer and the database server. This is especially a concern for anyone who accesses phpmyadmin via an untrusted network, such as public wifi.

Part 1: install phpmyadmin

First, make sure that you have mysql or mariadb installed and configured, and have taken basic steps to secure the setup. The mysql_secure_installation command is bundled with the mysql + mariadb packages and helps cover the basics.

Install the phpmyadmin package:

sudo apt-get update
sudo apt-get install phpmyadmin

The configuration script will prompt with a number of questions. When asked if you would like to automatically configure phpmyadmin for your web server, choose ‘apache2’.

Once the process is complete, you should be able to access phpmyadmin in a web browser by appending “/phpmyadmin” to your server’s URL, e.g.:

Part 2: Secure phpmyadmin

The following assumes that both apache2 and phpmyadmin were installed via the package manager.

Step 1: create a new conf file

Open your favourite editor and create a file called phpmyadmin-secure.conf in /etc/apache2/conf-available, e.g.:

sudo nano /etc/apache2/conf-available/phpmyadmin-secure.conf

For apache2.4, add the following content:

# ensure that phpmyadmin can only be accessed via localhost 
# remote users must use an ssh tunnel for access
<Directory /usr/share/phpmyadmin>
    Require local

You can double check your apache version with the command: apache2 -v.

For the older apache 2.2.x you need to use an older syntax inside the <Directory> block. If you do not need IPv6 support, delete the last directive in the following block (the entire line containing ::1):

<Directory /usr/share/phpmyadmin>
    Order Deny,Allow
    Deny from all
    Allow from
    Allow from ::1

These directives tell apache that anything in the package install location /usr/share/phpmyadmin should only be accessible by localhost ( Every other IP address, i.e. anything else on the internet, should be forbidden.

Save and exit (control+x in nano).

Step 2: Enable the conf file

Use a2enconf to enable the conf file:

cd /etc/apache2/conf-available
sudo a2enconf phpmyadmin-secure.conf

This command will create a symlink in apache’s conf-enabled/ directory that points to the conf file in the conf-available/ directory.

Note that the a2disconf command also exists and is invoked in a similar manner to a2enconf. It performs the reverse operation and disables the conf file by removing it from conf-enabled/ after it performs some checks.

Step 3: Reload apache and test

Apache must be reloaded or restarted for the updated configuration to take effect:

sudo service apache2 reload

After reloading/restarting apache, try to access phpmyadmin at its URL, e.g.:

You should see an error 403 / forbidden.

Tip: when making changes to apache’s conf files, you can check that the syntax is valid prior to reloading/restarting the server with the command apachectl configtest. Its a good idea to test your configuration before applying it because Apache will refuse to start if it has an invalid config, taking your site(s) offline until you can start it with a valid one.

Tip: if you want to hide the fact that phpmyadmin is even installed on your server at all, you can use apache’s mod_rewrite and/or RedirectMatch directives to produce a 404 ‘not found’ instead of a 403 response code.

Part 3: Access phpmyadmin via an ssh tunnel (ssh port forwarding)

To access your phpmyadmin install, connect to your server with ssh, using its tunnel options.

On your local machine, pick an arbitrary unused port and open a terminal (or an ssh client such as puTTy if your machine is a Windows PC). I use 5050 in the example below, but you can replace this with any available port number. Connect to the remote server via ssh:

ssh -L 5050:localhost:80

The -L option is key to establishing the tunnel. It tells ssh to forward any connections made to your local machine’s port 5050 to the remote host’s port 80 for as long as the ssh session is active.

Any web server (apache in our case) listening on port 80 will perceive that connections via the tunnel are coming from localhost and not from over a network / the internet.

Once you have a successful connection the server, visit the following URL in your browser to confirm you can access phpmyadmin:


All traffic between you and the remote host (including credentials and data) will be encrypted via ssh for as long as your session remains open.

All done!

You can now use phpmyadmin with the knowledge that this powerful and useful but also risky tool is not nearly as exposed to the open internet as it would be with a default install, and that you have taken a small but significant step in the endless battle to protect your credentials and data.

Troubleshooting tips

  • If you can’t access phpmyadmin, one possible gotcha to consider is if your website or app has mod_rewrite redirection rules in place (e.g. to force users to use https, to redirect certain url patterns, etc). These rules may be interfering when you try to access phpmyadmin via the tunnel. If you need to carve out an exception for localhost, but not other hosts, you could add a Rewrite Condition such as: RewriteCond %{HTTP_HOST} !^localhost to exempt it from your other rewrite conditions.

Using rbenv to support multiple versions of ruby on MacOS

This guide covers using the brew package manager to install rbenv on MacOS to enable you to install multiple versions of ruby and switch between them.

Apple bundles ruby with its operating system but the version is generally outdated and often unsuitable for developers working on their latest project. Later versions of Mac OSX through to MacOS Sierra include Ruby 2.0. Earlier OSX variants, specifically the “cats” (Mountain Lion, Lion, Snow Leopard), ship with Ruby 1.8.7. The current stable version at the time of this post is 2.4.x.

rvm is another tool that, similar to rbenv, can be used to switch between multiple versions of ruby. Overall, rbenv has a lighter touch on the MacOS system, and so is the preferred choice for this guide.


  • brew


Install rbenv and ruby-build with brew:

brew install rbenv ruby-build

Add rbenv to your bash profile so that it loads every time you open the Terminal app:

echo 'if which rbenv > /dev/null; then eval "$(rbenv init -)"; fi' >> ~/.bash_profile
source ~/.bash_profile

Thanks to: for the snippet.

Next, close and re-open your Terminal app to ensure that rbenv is initialized from your updated bash profile.

Now you can install any ruby version that you like. The following example installs v2.4.0.

rbenv install 2.4.0

rbenv gives you options when choosing which version of ruby you’d like to use:

rbenv shell 2.4.0 temporarily changes the ruby version in your current shell and forces its use over other versions that might be specified by a .ruby-version file in your current working directory. This command works by setting the RBENV_VERSION environment variable in your session. To remove it, run unset RBENV_VERSION.

rbenv local 2.4.0 creates a .ruby-version file in your current directory such that any time ruby is invoked from that directory (or a subtree), rbenv will select the version of ruby that you specified. This is useful for project folders, and you can check the .ruby-version file into your project’s revision control.

rbenv global 2.4.0 changes your default ruby to the specified version in all cases where a version is not specified (e.g. due to a .ruby-version file or if the RBENV_VERSION environment variable is set). Your current Terminal session and any other sessions will be affected.

You can confirm the ruby version in play with the command:

ruby -v

If you don’t see your desired ruby version number in the command’s output (e.g. 2.4.0) and find an older one instead (e.g. 2.0.0 the MacOS default), be sure to close the Terminal and start fresh with a completely terminal window/session, and take note if your working folder has a .ruby-version file set and what the value of the RBENV_VERSION environment variable is (echo $RBENV_VERSION).

Once you are working in a newer ruby environment, you may need to check the gems and other libraries in a project that was started with an earlier version, to ensure they are compatible or need an update.

Using s3cmd to access S3 buckets from EC2 instances with IAM Role authentication

s3cmd is an open-source command line tool for uploading, retrieving and managing data in Amazon S3 and other providers that implement the S3 protocol (e.g. Google Cloud Storage, DreamHost DreamObjects, etc). It is popular tool with a variety of applications, including backup scripts.

This post covers using s3cmd within an EC2 instance, with authentication to S3 managed via IAM Roles (IAM = Identity and Access Management).

If your project doesn’t have dependencies on scripts and/or pre-existing code that require s3cmd, and you don’t mind locking your project deeper into AWS’ ecosystem, a good alternative is Amazon’s own AWS CLI.

Configuring an IAM Role

When an EC2 instance is launched with an associated IAM role, access keys and secret keys do not need to be stored in config files on the instance itself.

After such an instance is launched, AWS-aware services and scripts on the it can access AWS resources subject to the permissions defined in the IAM role’s associated IAM role policy. Authentication is seamlessly handled via the AWS SDK.

s3cmd versions 1.5.0-alpha2 and above support IAM roles and authentication via the AWS SDK.

IAM roles

Log in to your AWS account and access the AWS IAM Dashboard (also referred to as the IAM Management Console) to manage role-based permissions.

Create an IAM role for your instances if you haven’t already.

IAM role policy

In the IAM Management Console, ensure that your IAM role has an attached policy that provides access to any S3 resource(s) that you want your instance(s) to access via s3cmd. It’s advisable to ensure that role policies are restricted to the minimum amount of scope possible.

Within the IAM Management Console:

  • Choose Roles and select the role that your EC2 instances belong to (or will belong to)
  • Review your existing policies to confirm what your instances can currently access
  • If necessary, use the Create Role Policy button to add a policy with the Policy Generator

For example, suppose you had a an s3 bucket called example-log-bucket and you wanted to configure your EC2 instances to send access logs to it.

Following the order of the Policy Generator’s input fields, you’d create: an Allow policy for the Amazon S3 service regarding the actions s3:ListBucket, s3:PutObject, and s3:PutObjectAcl, and apply them to the ARN arn:aws:s3:::example-log-bucket.

To learn more about how to specify ARNs that identify your various AWS services, see the Amazon docs:

Note that you can use wildcards in ARNs when defining a Role Policy.

Installing and configuring s3cmd on the EC2 instance(s)

s3cmd versions 1.5.0-alpha2 and above support IAM roles.

In earlier versions, an access key and secret key had to be specified in a .s3cfg file in the home directory of the user running the s3cmd command, or in environment variables.

Option A: Install s3cmd with the Ubuntu/Debian apt package manager

If you’re running Ubuntu 16.04 or later (test box at the time of writing) the package version is sufficiently up-to-date (>1.5.0). Install s3cmd with apt-get:

sudo apt-get install s3cmd

Option B: Install s3cmd with the python pip package manager

Pip is an alternative to Debian/Ubuntu apt-get, especially if you are using a different distro or like to use python/pip.

sudo pip install s3cmd

Check the version number with s3cmd --version. If you discover that its <1.5.0, you can specify a particular version for pip to install as follows, substituting in your desired version number (e.g. 1.5.0-alpha3) in place of VERSION_NUMBER below:

pip install s3cmd==VERSION_NUMBER

Configure s3cmd on the EC2 instance(s)

Once an EC2 instance is launched with a suitable IAM Role and associated IAM Role Policy, its easy to get started with s3cmd. The following example is set in the context of the currently logged in user.

Open/create the file ~/.s3cfg using a text editor:

nano ~/.s3cfg

Populate the file with the following content. Rather than filling in hardcoded credentials, leave each of the fields blank (use the example as is; do not specify any values):

access_key =
secret_key = 
security_token =

Save the file and exit the editor.

Later versions of s3cmd that support IAM Roles will auto-magically detect the appropriate authentication values.

s3cmd will now be able to interact with any AWS resource(s) that it is permitted to access, subject to s3cmd’s capabilities and the IAM Role’s active Role Policies.

Use s3cmd

s3cmd has over 60 command line options. Check out the documentation:

How to install Ansible on MacOS using pip

Ansible is a powerful devops/automation tool that helps you control fleets of servers and their applications with ease.

This post covers installing ansible on MacOS using the installation method recommended by the project: pip, the python package manager. There are a few other ways to install ansible on MacOS, including with the brew package manager.

This post assumes that you are interested in installing ansible only for the current user only. If you require a system-wide/multi-user installation, skip to Step 8 to learn more about the MacOS System Integrity Protection (SIP) feature before proceeding.

Installing Ansible with pip

You may be able to skip steps 1, 2, and/or 3 if you already have XCode, XCode Command Line Tools, and/or pip installed on your system.

Step 1: install XCode

Most developers already have XCode installed. If you’re not sure, you can look for it in the Applications folder on your Mac.

XCode is available for free on the App Store. It can be helpful to run XCode at least once after installing it to help it complete its installation process, and get you to agree to any license terms.

The following steps will fail if you have not agreed to Xcode’s license terms.

Step 2: install XCode command line tools

The XCode command line tools include compilers and other tools necessary to proceed. In the MacOS Terminal app, run the command:

xcode-select --install

If this is a fresh install, you will be prompted to agree to Apple’s terms for the command line tools. After you consent, they will download and install.

If you already have the command-line tools installed. The script will let you know and exit.

Once the XCode command line tools are installed, you can use development tools like the gcc compiler. For example, you should be able to run the following command and successfully receive gcc’s version information as output:

gcc --version

If everything looks good and the above command does not throw an error, proceed to the next step.

Step 3: install pip

Pip is the python package manager. It is conceptually similar to other well-known package management tools such as npm (node/javascript) or apt (debian/ubuntu linux distributions).

MacOS comes pre-installed with python, but not pip. To install it, input the following into the Terminal app:

sudo easy_install pip

There is no harm to running this command in cases where pip is already installed.

Step 4: install ansible

To install ansible system-wide, run the following command:

sudo pip install ansible

If you prefer a local install within your user account, you can remove the ‘sudo’ and add the --user flag to the above.

After the installation process has completed, you can verify the install was a success by executing a basic command like: ansible --version. It should run without error.

Step 5: create /etc/ansible

Ansible looks for default configuration files in /etc/ansible. This directory is unlikely to exist on your machine. The following command will create this folder if it doesn’t already exist:

sudo mkdir -p /etc/ansible

Step 6: install optional/helpful packages

It can be helpful to install the python passlib library because MacOS doesn’t use the same types of password hashes as linux does, and you are likely going to want to manage linux machines with ansible. Passlib provides a common and consistent hash generator across operating systems.

To install passlib globally on your Mac:

sudo pip install passlib

If you installed ansible locally, you can use the command pip install --user passlib instead.

Step 7: test out your installation

Per above, if the install was successful, you can now use the ansible command from the Terminal:

ansible --version

A “hello world” of sorts for ansible is pinging yourself:

ansible localhost -m ping

You can also try running an arbitrary command on yourself (such as uname -a or whereis bash):

ansible localhost -a 'uname -a'

To get ansible to detect facts about your machine, try the following. Note the filter argument: it restricts what is returned so you don’t get BLASTED with facts.

By default ansible gathers almost everything there is to know about its target machines and populates them into variables that you can then use in your tasks, roles, and plays. As you learn ansible, you’ll discover this is incredibly useful. Ansible users can customize this behaviour and optionally turn it off to realize performance gains when it isn’t required. For now though, you’re just getting started:

ansible localhost -m setup -a 'filter=ansible_distribution'

Step 8: upgrade ansible

It can be a good idea to upgrade ansible right off the bat to ensure that everything is current, and to understand how the MacOS System Integrity Protection (SIP) feature impacts your installation:

sudo pip install ansible --upgrade 

If this command partially runs and then produces an error, it is because of the SIP feature, originally introduced in OSX El Capitan. You can work around that by adding the --user python parameter to the above command. With this argument, upgrades will be installed for the current user only vs. system-wide, and the upgrade will succeed. The revised command:

sudo pip install ansible --upgrade --user python

Understanding MacOS’ System Integrity Protection (SIP) Feature

SIP was introduced in OSX El Capitan and prevents certain system files, such as those associated with MacOS-bundled python, from being clobbered by anyone — including root.

To avoid SIP-related issues on a system-wide install, you may want to consider using a different python than the one bundled with MacOS. Using a python virtualenv is one option. Another option for multi-user systems is to install user-specific copies of python + pip + ansible within each appropriate user account (e.g. via brew package manager for MacOS).

A more thorough discussion of issues regarding the use of pip on MacOS systems with SIP can be found here:

Step 9: get started!

Congratulations! You have installed ansible on MacOS!

If you’re new to ansible, check out the documentation at to get started!