Rory Primrose

Learn from my mistakes, you don't have time to make them yourself

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Simple Octopus Tentacle Installation

I’ve been rebuilding my Octopus Deploy infrastructure to make use of the new VM, network and security support in Azure. Having to install an Octopus Tentacle on each target machine is obviously cumbersome and PowerShell is a really good answer.

The Octopus Deploy documentation already contains the bulk of the work for the script. I did find however that the netsh called failed because PowerShell didn’t like it being quoted.

In order to streamline this process as much as possible, I want the script to also download the latest tentacle MSI, install it and then clean up.

Drop this script into a ps1 and run it on the target server and all should be good.

$serverThumbprint = "[YOUR-SERVER-THUMBPRINT]"
$serverUri = "[YOUR-SERVER-URI]"
$tentacleInstallApiKey = "[YOUR-TENTACLE-INSTALL-APIKEY]"
$environment = "[YOUR-TARGET-ENVIRONMENT]"

function Tentacle-Configure([string]$arguments)
    Write-Output "Configuring Tentacle with $arguments"

    $pinfo = New-Object System.Diagnostics.ProcessStartInfo
    $pinfo.FileName = "C:\Program Files\Octopus Deploy\Tentacle\Tentacle.exe"
    $pinfo.RedirectStandardError = $true
    $pinfo.RedirectStandardOutput = $true
    $pinfo.CreateNoWindow = $true; 
    $pinfo.UseShellExecute = $false;
    $pinfo.UseShellExecute = $false
    $pinfo.Arguments = $arguments
    $p = New-Object System.Diagnostics.Process
    $p.StartInfo = $pinfo
    $p.Start() | Out-Null
    $stdout = $p.StandardOutput.ReadToEnd()
    $stderr = $p.StandardError.ReadToEnd()
    Write-Host $stdout
    Write-Host $stderr
    if ($p.ExitCode -ne 0) {
        Write-Host "Exit code: " + $p.ExitCode
        throw "Configuration failed"

function Get-ExternalIP {
    return (Invoke-WebRequest

Write-Output "Beginning Tentacle installation"

Write-Output "Downloading Octopus Tentacle MSI..."
$downloader = new-object System.Net.WebClient
$downloader.DownloadFile("", "Tentacle.msi")

Write-Output "Installing Tentacle"
$msiExitCode = (Start-Process -FilePath "msiexec.exe" -ArgumentList "/i Tentacle.msi /quiet" -Wait -Passthru).ExitCode
if ($msiExitCode -ne 0) {
    Write-Output "Tentacle MSI installer returned exit code $msiExitCode"
    throw "Installation aborted"

$ipAddress = Get-ExternalIP
Write-Output "Detected IP address as $ipAddress"

Write-Output "Configuring Tentacle"
Tentacle-Configure "create-instance --instance `"Tentacle`" --config `"C:\Octopus\Tentacle.config`" --console"
Tentacle-Configure "new-certificate --instance `"Tentacle`" --if-blank --console"
Tentacle-Configure "configure --instance `"Tentacle`" --reset-trust --console"
Tentacle-Configure "configure --instance `"Tentacle`" --home `"C:\Octopus`" --app `"C:\Octopus\Applications`" --port `"10933`" --console"
Tentacle-Configure "configure --instance `"Tentacle`" --trust `"$serverThumbprint`" --console"
netsh advfirewall firewall add rule "name=Octopus Deploy Tentacle" dir=in action=allow protocol=TCP localport=10933
Tentacle-Configure "register-with --instance `"Tentacle`" --server `"$serverUri`" --apiKey=`"$tentacleInstallApiKey`" --publicHostName `"$ipAddress`" --role `"$role`" --environment `"$environment`" --comms-style TentaclePassive --console"
Tentacle-Configure "service --instance `"Tentacle`" --install --start --console"

Write-Output "Installation Tentacle"

Remove-Item "Tentacle.msi"
Remove-Item $PSCommandPath
Written on September 30, 2015