Joe Beaudry Systems Engineer An Engineer who loves learning new things, developing for the cloud, and helping to streamline processes.

Unleashing the Kraken

Octopus Deploy Demonstration


  • Git Client to pull down Repository
  • Vagrant to spin up Boxes
    • I am currently using Vagrant/VirtualBox (If you have hyper-v installed you may have to disable that to have Vagrant/Virtualbox work)
    • Clone this Repo to follow along
  • Chocolatey


The Purpose for this demonstration is to show people the simplicity of using Octopus for daily deploy tasks. In this demonstration octopus will be used to deploy a powershell module from the Powershell Gallery, deploying a basic website, and configuring IIS Settings.


Spin up VMs

To get started use git to clone down this repository on your local machine. On your local machine open a powershell Session navigate into the cloned repository and then run the command below. (This step requires you have vagrant installed)

Vagrant up

Generate Package for deployment

The Vagrant up will spin up the 2 Virtual Machines for the purpose of our demo.

While the 2 VMs spin up, we will start to work on generating our Nuget file to be used by our Octopus Server to Deploy to our WebServer.

Open up another powershell session on your local machine while vagrant runs and navigate to the working directory of the repository. From there we will navigate to the Blue_skies directory to generate our nuget package. (Step Requires you to have Chocolatey to install nuget or have nuget.exe installed)

cd blue_skies

choco install nuget.commandline -confirm

Now that we have nuget installed we can start working on generating our nuget package. Nuget packages are generated via nuspec files in which I have already provided one. They are effectively zip files with useful versioning and metadata.

nuget pack .\blue_skies.nuspec

you should now have a nupkg file that we can use push to our octopus server once that has come up.

Configure Web Server

At this point Octopus is most likely still installing SQL, but our web server should be up. Now we should make sure the webserver has IIS Setup on it so that we can deploy code to it.

Open up your virtual box instance for “Web” and log in to the vm

U: administrator - p: vagrant

Once logged in there will be a command prompt, just type powershell to kick off a powershell session and run the code below.

import-module servermanager
add-windowsfeature Web-Server, Web-WebServer, Web-Security,Web-Filtering

We Should be able to hit the Test Site on IIS on our Local Machine

We are also going to install the octopus tentacle now. Go back on to your webserver vm, and go to your powershell session and run the command below.

* if it fails just run again

choco install octopusdeploy.tentacle -confirm

Getting Octopus Going

Logging in

At this point we should be able to access our octopus server on our local machine using Octopus.

U: Admin - p: Vagrant!

Generating API Key

Once we have logged in we will generate ourselves an API key for publishing our nupkg.

This can be done by clicking your user in the top right, and then clicking on the API Key tab. you will then click new API key and it will prompt you for a purpose. Be sure to document your API Key for after.

Creating Environment

Now we will create our “Environment” to place our Web Server in. This can be done by clicking environment in the top header on our octopus dashboard. Once there you will click on the Green Add Environment button in the right. Here you will name it, and I would recommend checking Use Guided Failure mode by default.

*Guided failure allows for you to kick off a job where it left off if it failed on a step. 

Adding a Machine

On our newly created environment we will click on Add a deployment target.

  • There we will select Listening tentacle
  • This will provide us with a server thumbprint that we will use on our Tentacle so be sure to document that

Once we have gathered our machine thumbprint on Octopus we will run this code below on our WebServer VM

Make sure to Apply your thumbprint below!

May have to re-enter powershell after installing tentacle and webserver

cd "C:\Program Files\Octopus Deploy\Tentacle"
Start-Process ".\Tentacle.exe" -ArgumentList "create-instance --instance `"Tentacle`" --config `"C:\Octopus\Tentacle.config`" --console" -wait -nonewwindow
Start-Process ".\Tentacle.exe" -ArgumentList "new-certificate --instance `"Tentacle`" --if-blank --console" -wait -nonewwindow
Start-Process ".\Tentacle.exe" -ArgumentList "configure --instance `"Tentacle`" --reset-trust --console" -wait -nonewwindow
Start-Process ".\Tentacle.exe" -ArgumentList "configure --instance `"Tentacle`" --home `"C:\Octopus`" --app `"C:\Octopus\Applications`" --port `"10933`" --console" -wait -nonewwindow
Start-Process ".\Tentacle.exe" -ArgumentList "configure --instance `"Tentacle`" --trust `"YourThumbPrintHere`" --console" -wait -nonewwindow
Set-NetFirewallProfile -Profile Domain,Public,Private -Enabled False
Start-Process ".\Tentacle.exe" -ArgumentList "service --instance `"Tentacle`" --install --start --console" -wait -nonewwindow

Back on Octopus

We will - Configure hostname to be ‘’ - Leave Port and Proxy default

Creating our First Project

Creating our first project is quite easy. Navigate to projects at the top and click to all proects. You will then see an Add project button in the top right where you can click to generate a new project.

Before we get deep into creating our project we need to publish our Nuget Package we generated at the beginning.

We will need the API Key we Generated previously.

On YOUR machine navigate to your Blue Skies Directory if you arent already there and run.

Nuget push blue_skies.1.0.0.nupkg -ApiKey "yourApiKey" -Source http://localhost:8080/nuget/packages

Now Let’s validate it uploaded.

On the Top Right of your dashboard on Octopus Click on Library, and you should see “Blue_Skies” under available packages.

Now That we have a package to deploy let’s add a step to our Demo Project!

On your dashboard click on the Demo Deploy we created, then click on process on the left hand side and then on the middle of the screen click on add step. We will then click on Deploy a package. We will then name the step. Define the Target to run on Web-Server

Once that is set we will search for our package. Type the package name in the packageID field. For this demo we will not have any Configuration Variables or XML Transforms so we can uncheck those.

However we do want to create an IIS WebSite and AppPool. So at the bottom we will click on configure features and then click on IIS Web Site and Application Pool

Once you select that the page will reload with IIS Configuration Settings.

Since we did not delete the default site we are just going to re-configure that. So fill in the Website name with Default Web Site

Same for the Application Pool so name the Application Pool DefaultAppPool

Make sure to enable Anonymous Authentication and disable Windows Authentication

Then scroll to the bottom and save.

Let’s Run it!

Once the project has been created click on Create Release.

Click on Save.

And then Deploy to Demo, where you can then click on Deploy release again. You will then be brough to a deploy page where you can see the packages get Deployed.

Check on your Site and you should now be on the Blue Skies test site

Bonus Section

Deploying Powershell Modules from Powershell Gallery

So we have our site deployed, but now we want some pester tests, how would we handle getting pester on this node if it isnt already installed?

On the top left click on Library and navigate to external feeds.

In the top right we will then Add Feed

We will name it, and then paste in to our URL field, there should be no username or password

You will then click Save and test and we can use Pester for the test package name.

Now that we can access the powershell Gallery let’s create a new project for deploying pester

We will click on Projects > All Projects > Add a project.

The process will be similar. We will Add A step to deploy a package except this time instead of Selecting IIS Web Site and Application Pool we will configure the process for Custom Installation Directory

First we Will need to change our Package Feed to Powershell Gallery, and then we can use our package ID of Pester.

We will still use the Web-Server target for our Job.

 In this Example we are going to want to install to the whole system. 


For our install to location we will use C:\Windows\System32\WindowsPowerShell\v1.0\Modules

Before we run the release we are going to take a look at Channels and lock our pester to a prior version.

Example Say we have a public package and want to make sure we arent accidentally deploying the latest. So We will want to set a maximum version. To do this click on channels on the left, we dont have any other channels at this time, so we will click on the default which is being used. We will then click on Add Version Rule, apply it to our Deploy Pester Step. We will then set a maximum version by following these Rules for our use case (,3.4.0]

From here let’s create our release and Deploy it out! When you go to create your release notice it’s set to “Latest” using 3.4.0 not 3.4.3 (At time of writing this) This is a great way to make sure new not vetted versions are deployed.


Lastly we want to make sure we arent excessively deploying things and over loading the Hard drive, so under library and lifecycles let’s click on our default lifecycle and setup some retention policies. This will make sure we don’t hold onto too many release or packages are held on the server.

Select your lifecycle Click on change on the default retention policy and set as you see fit.

Using Credentials in your Profile

Do you find logging into azure powershell as annoying as I do?

Recently I have been getting annoyed with the constant need to log in to an Azure Subscription on my powershell sessions, so I decided to solve this but tweaking my profile with a module that allows me to grab from the Windows Credential Manager.

I took a minute and thought about how to make the shell a bit smarter and figure out a way for my session to already be logged in to AzureRM when I open it.

This will require:

  • (Currently the latest as of writing this)
  • And an active azure subscription

Install and Use Better Credentials

Install Module

If you have git installed

cd C:\Users\%youruser%\Documents\WindowsPowerShell\Modules
git clone

If no git

Download the module from the git repo and extract it to


If you are on powershell version 5

Install-Module BetterCredentials

Using Module

Now you need to create the credential in your credential manager.

#Use this line to store your credentials to a variable to pass to the command to add to the windows credential manager
$Creds = Get-Credential 
#Used to store the credentials 
BetterCredentials\Get-Credential -Credential $Creds -Store

Once Stored, you are now able to run

$AzureCreds = BetterCredentials\Get-Credential -username "yourUsername"

And this will allow you to easily/quickly pull your credentials from the Windows Credential Manager

Bringing it together

Now that you have the initial pieces in place you can modify your profile to configure the auto login. this can be found here - C:\Users\%yourUser%\Documents\WindowsPowerShell\Microsoft.PowerShell_profile.ps1

Import-Module BetterCredentials
$AzureCreds = BetterCredentials\Get-Credential -username "yourUsername"
Login-AzureRmAccount -SubscriptionName "your desired default subscription" -Credential $AzureCreds


This is just my simple usecase for this, but this use of BetterCredentials and its ability to store and grab from the Credential manager can offer you some other solutions:

  • Other Modules requiring Credentials you want Stored
  • Light automation where you don’t want to pass in plaintext passwords
  • Scheduled tasks

Hopefully this helps you out and you come up with some other things to share.

Testing the Waters

Who Am I?

Hi, I am a systems engineer at a “Sales Enablement Company” called Brainshark. Currently my role focuses on Infrastructure and building automation tooling with Powershell and Azure Resource Manager Templates

On ocassion I will dabble with javascript, C#, or python, and docker. I really just enjoy working on helping others figure out what they can do to better their workflows and allow for their jobs to be made easier and more repeatable in an automated fashion.

I started my journey into operations and infrastructure around the age of 14 when I decided I wanted to manage, maintain, and configure various video game servers for myself and friends. When I built my first server and was able to log in and play I realized I was doing something cool!

Currently, I have been spending a lot of time automating the cloud and building out things a little more complex than game servers. I am excited to share some of the cool projects I am working on and hopefully help others find better ways of doing things or even just seeing your opinions and ideas based on what I share!