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DevOpsGroup Blog Upgrading to Octopus Deploy 2.0

Upgrading to Octopus Deploy 2.0

On 20th December 2013, Paul Stovell and the Octopus Team released Octopus Deploy 2.0. We’ve had a chance to play with the product for sometime, and it’s a great next version.

Here’s 5 great reasons to upgrade;

  1. Configurable Dashboards
  2. Sensitive variables
  3. Polling Tentacles (Pull or Push)
  4. IIS website and application pool configuration
  5. Rolling deployments

So let’s take a look at how the upgrade process works.

Step 1 – Backup your existing database

Things to check before you upgrade;

  1. Your administrator username and password (especially, if you are not using Active Directory)
  2. Before attempting to migrate, make sure that you don’t have any projects, environments, or machines with duplicated names (this is no longer allowed in Octopus 2.0, and the migration wizard will report an error if it finds duplicates).
  3. IIS Configuration. Are you using ARR or rewrite rules of any kind.
  4. SMTP Server Settings (these are not kept in upgrade)

The first step is to ensure that you have a  recent database backup that you can restore in case anything goes wrong.

Confirm the location of your backup file. You’ll need this file at a later stage in the upgrade process (and if anything goes wrong)

Step 2 – Install Octopus 2.0

Download the latest installer MSI from the Octopus Website at

Next follow the installer instructions and the Octopus Manager process. This process is really straight forward, and if you’ve installed Octopus before you’ll be familiar with most of the process. There’s a great video here on how to install


Step 3 – Import Previous Octopus Database

Once you’ve installed Octopus 2.0, you’ll most likely want to import your old v1.6 database with all your existing configuration. To do this, select the “import from Octopus 1.6” option and choose the database back-up from the process you followed in step 1 and follow the instructions.

Step 4 – Post Upgrade Steps (server)

When you have completed the installation it’s essential to task a copy of the master key for backups. Instructions on how to backup the key can be found here:

Once you have the server installed there’s a couple of items you’ll need to configure again.

SMTP Server Settings are not kept, so these will need to be re-entered.

Step 5 – Upgrading Tentacles

If you are upgrading from version 1.6 – Octopus 2.0 server can no longer communicate with Tentacle 1.6. So in addition to upgrading Octopus, you’ll also need to upgrade any Tentacles manually. There are two ways to achieve this;

  1. Download and Install the new Octopus Deploy Tentacle MSI on each target server
  2. Use  a PowerShell script to download the latest Tentacle MSI, install it, import the X.509 certificate used for Tentacle 1.6, and configure it in listening mode. The powershell script is as follows;
function Upgrade-Tentacle {    Write-Output "Beginning Tentacle installation"   Write-Output "Downloading Octopus Tentacle MSI..."   $downloader = new-object System.Net.WebClient   $downloader.DownloadFile("", "Tentacle.msi")      Write-Output "Installing MSI"   $msiExitCode = (Start-Process -FilePath "msiexec.exe" -ArgumentList "/i Tentacle.msi /quiet" -Wait -Passthru).ExitCode   Write-Output "Tentacle MSI installer returned exit code $msiExitCode"   if ($msiExitCode -ne 0) {     throw "Installation aborted"   }      Write-Output "Configuring and registering Tentacle"       cd "${env:ProgramFiles(x86)}Octopus Tentacle 2.0Agent"   Write-Output "Stopping the 1.0 Tentacle"      & .tentacle.exe create-instance --instance "Tentacle" --config "${env:SystemDrive}OctopusTentacleTentacle.config" --console   & .tentacle.exe configure --instance "Tentacle" --home "${env:SystemDrive}Octopus" --console   & .tentacle.exe configure --instance "Tentacle" --app "${env:SystemDrive}OctopusApplications" --console   & .tentacle.exe configure --instance "Tentacle" --port "10933" --console   & .tentacle.exe import-certificate --instance "Tentacle" --from-registry  --console   Write-Output "Stopping the 1.0 Tentacle"   Stop-Service "Tentacle"   Write-Output "Starting the 2.0 Tentacle"   & .tentacle.exe service --instance "Tentacle" --install --start --console      Write-Output "Tentacle commands complete" }    Upgrade-Tentacle

Step 6 – Upgrade TeamCity Integration

The JetBrains TeamCity Plugin has also been released and requires an upgrade. To do this

  1. Download the plugin from the Octopus Website
  2. Shutdown the TeamCity server.
  3. Copy the zip archive ( with the plugin into the <TeamCity Data Directory>/plugins directory.
  4. Start the TeamCity server: the plugin files will be unpacked and processed automatically. The plugin will be available in the Plugins List in the Administration area.

Please Note: The API Key’s for the users will have changed and will need to be re-entered into the Octopus Deploy Runner Configuration within the Build Step


We think that overall the Octopus Team have done a great job making the upgrade process easy. There’s still a few little issues to iron out, but overall the process is robust and simple. It’s a shame that automatic upgrade of the tentacles couldn’t have been supported as this may cause pain for customers with a large server install base, but Powershell automation makes for a great workaround.

As we learn more about Octopus 2.0, we’ll continue to let you know what we find. Good Luck with Upgrading — it’s definitely worth it!

DevOpsGuys use Octopus Deploy to deliver automated deployment solutions – ensuring frequent, low-risk software releases into multiple environments. Our engineers have deployed thousands of software releases using Octopus Deploy and we can help you do the same.

Contact us today – we’d be more than happy to help.

3 thoughts on “Upgrading to Octopus Deploy 2.0

  1. loved finding this article, however having come late to the upgrade party and having spent best part of 4 days trying to make the upgrade from 1.6 to 2.0 work I gave up and threw the whole thing out and started from scratch with a clean install… this upgrade process is too complex, too difficult to be reliable and in the end its just not worth doing.. (IMNHO)

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