diff --git a/images/win/scripts/ImageHelpers/ImageHelpers.psm1 b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
index 1f52d22e..3f10d70b 100644
--- a/images/win/scripts/ImageHelpers/ImageHelpers.psm1
+++ b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
@@ -16,10 +16,8 @@ Export-ModuleMember -Function @(
     'Set-SystemVariable'
     'Install-Binary'
     'Install-VisualStudio'
-    'Get-ToolcachePackages'
     'Get-ToolsetContent'
     'Get-ToolsetToolFullPath'
-    'Get-ToolsByName'
     'Stop-SvcWithErrHandling'
     'Set-SvcWithErrHandling'
     'Start-DownloadWithRetry'
diff --git a/images/win/scripts/ImageHelpers/InstallHelpers.ps1 b/images/win/scripts/ImageHelpers/InstallHelpers.ps1
index aed13b99..a28273c2 100644
--- a/images/win/scripts/ImageHelpers/InstallHelpers.ps1
+++ b/images/win/scripts/ImageHelpers/InstallHelpers.ps1
@@ -286,12 +286,6 @@ function Get-VSExtensionVersion
     return $packageVersion
 }
 
-function Get-ToolcachePackages
-{
-    $toolcachePath = Join-Path $env:ROOT_FOLDER "toolcache.json"
-    Get-Content -Raw $toolcachePath | ConvertFrom-Json
-}
-
 function Get-ToolsetContent
 {
     $toolsetJson = Get-Content -Path $env:TOOLSET_JSON_PATH -Raw
@@ -350,24 +344,6 @@ function Get-ToolsetToolFullPath
     return Join-Path $foundVersion $Arch
 }
 
-function Get-ToolsByName
-{
-    Param
-    (
-        [Parameter(Mandatory = $True)]
-        [string]$SoftwareName
-    )
-
-    (Get-ToolcachePackages).PSObject.Properties | Where-Object { $_.Name -match $SoftwareName } | ForEach-Object {
-        $packageNameParts = $_.Name.Split("-")
-        [PSCustomObject] @{
-            ToolName = $packageNameParts[1]
-            Versions = $_.Value
-            Architecture = $packageNameParts[3,4] -join "-"
-        }
-    }
-}
-
 function Get-WinVersion
 {
     (Get-CimInstance -ClassName Win32_OperatingSystem).Caption
diff --git a/images/win/scripts/Installers/Download-ToolCache.ps1 b/images/win/scripts/Installers/Download-ToolCache.ps1
deleted file mode 100644
index 8656fb6a..00000000
--- a/images/win/scripts/Installers/Download-ToolCache.ps1
+++ /dev/null
@@ -1,92 +0,0 @@
-################################################################################
-##  File:  Download-ToolCache.ps1
-##  Team:  CI-Build
-##  Desc:  Download tool cache
-################################################################################
-
-Function Install-NpmPackage {
-    [CmdletBinding()]
-    param(
-        [Parameter(Mandatory=$true)]
-        [System.String] $PackageName,
-        [Parameter(Mandatory=$true)]
-        [System.Uri] $FeedPrefix
-    )
-
-    Push-Location -Path $env:TEMP
-
-    $FeedUri = $FeedPrefix.AbsoluteUri
-
-    Write-Host "Installing npm $PackageName from ${FeedUri}"
-    npm install $PackageName --registry "${FeedUri}"
-
-    if($LASTEXITCODE) {
-        Write-Host "$PackageName installation failure;  Error: ${LASTEXITCODE}"
-
-        exit 1
-    }
-
-    Pop-Location
-}
-
-Function NPMFeed-AuthSetup {
-    param(
-        [Parameter(Mandatory=$true)]
-        [System.String] $AccessToken,
-        [Parameter(Mandatory=$true)]
-        [System.Uri] $FeedPrefix
-    )
-
-    $FeedHost = $FeedPrefix.Host
-
-    Write-Host "Configure auth for github package registry"
-    $npmrcContent = "//${FeedHost}/:_authToken=${AccessToken}"
-    $npmrcContent | Out-File -FilePath "$($env:TEMP)/.npmrc" -Encoding utf8
-}
-
-Function Set-DefaultRubyVersion {
-    param(
-        [Parameter(Mandatory=$true)]
-        [System.Version] $Version,
-        [System.String] $Arch = "x64"
-    )
-    $rubyPath = $Env:AGENT_TOOLSDIRECTORY + "/Ruby/${Version}*/${Arch}/bin"
-    $rubyDir = Get-Item -Path $rubyPath
-
-    Write-Host "Use Ruby ${Version} as a system Ruby"
-    Add-MachinePathItem -PathItem $rubyDir.FullName
-
-    $env:Path = Get-MachinePath
-
-    # Update ruby gem to latest version
-    Invoke-Expression "gem update --system"
-}
-
-$FeedPrefix = "https://npm.pkg.github.com"
-$AccessToken = $env:GITHUB_FEED_TOKEN
-
-# HostedToolCache Path
-$Dest = "C:/"
-$Path = "hostedtoolcache/windows"
-$ToolsDirectory = $Dest + $Path
-
-# Define AGENT_TOOLSDIRECTORY environment variable
-$env:AGENT_TOOLSDIRECTORY = $ToolsDirectory
-setx AGENT_TOOLSDIRECTORY $ToolsDirectory /M
-
-# Install HostedToolCache tools via NPM
-$ToolVersionsFileContent = Get-Content -Path "$env:ROOT_FOLDER/toolcache.json" -Raw
-$ToolVersions = ConvertFrom-Json -InputObject $ToolVersionsFileContent
-
-NPMFeed-AuthSetup -AccessToken $AccessToken -FeedPrefix $FeedPrefix
-
-$ToolVersions.PSObject.Properties | ForEach-Object {
-    $PackageName = $_.Name
-    $PackageVersions = $_.Value
-    $NpmPackages = $PackageVersions | ForEach-Object { "$PackageName@$_" }
-    foreach($NpmPackage in $NpmPackages) {
-        Install-NpmPackage -PackageName $NpmPackage -FeedPrefix $FeedPrefix
-    }
-}
-
-Set-DefaultRubyVersion -Version "2.5"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-Ruby.ps1 b/images/win/scripts/Installers/Install-Ruby.ps1
new file mode 100644
index 00000000..e2b1763f
--- /dev/null
+++ b/images/win/scripts/Installers/Install-Ruby.ps1
@@ -0,0 +1,141 @@
+################################################################################
+##  File:  Install-Ruby.ps1
+##  Desc:  Install rubyinstaller2
+################################################################################
+
+function Get-RubyVersions
+{
+    param (
+        [System.String] $Arch = "x64",
+        [System.String] $Extension = "7z"
+    )
+
+    $uri = "https://api.github.com/repos/oneclick/rubyinstaller2/releases"
+    try
+    {
+        $versionLists = @{}
+        $assets = (Invoke-RestMethod -Uri $uri).Where{ -not $_.prerelease }.assets
+        $7zArchives = $assets.Where{ $_.name.EndsWith("$Arch.$Extension") }
+        $majorMinorGroups = $7zArchives | Group-Object { $_.name.Replace("rubyinstaller-", "").Substring(0, 3) }
+        foreach($majorMinorGroup in $majorMinorGroups)
+        {
+            $group = $majorMinorGroup.Group
+            $sortVersions = $group | Sort-Object {[Version]$_.name.Replace("rubyinstaller-", "").Replace("-$Arch.$Extension","").Replace("-",".")}
+            $latestVersion = $sortVersions | Select-Object -Last 1
+            $versionLists[$majorMinorGroup.Name] = $latestVersion.browser_download_url
+
+        }
+        return $versionLists
+    }
+    catch
+    {
+        Write-Host "Enable to send request to the '$uri'. Error: '$_'"
+        exit 1
+    }
+}
+
+# Most of this logic is from
+# https://github.com/MSP-Greg/actions-ruby/blob/master/lib/main.js
+function Install-Ruby
+{
+    param(
+        [String]$PackagePath,
+        [String]$Architecture = "x64"
+    )
+
+    # Expand archive with binaries
+    $packageName = [IO.Path]::GetFileNameWithoutExtension((Split-Path -Path $PackagePath -Leaf))
+    $tempFolder = Join-Path -Path $env:TEMP -ChildPath $packageName
+    Extract-7Zip -Path $PackagePath -DestinationPath $env:TEMP
+
+    # Get Ruby version from binaries
+    $rubyVersion = & "$tempFolder\bin\ruby.exe" -e "print RUBY_VERSION"
+
+    if ($rubyVersion)
+    {
+        Write-Host "Installing Ruby $rubyVersion"
+        $rubyToolcachePath = Join-Path -Path $env:AGENT_TOOLSDIRECTORY -ChildPath "Ruby"
+        $rubyVersionPath = Join-Path -Path $rubyToolcachePath -ChildPath $rubyVersion
+        $rubyArchPath = Join-Path -Path $rubyVersionPath -ChildPath $Architecture
+
+        if (-not (Test-Path $rubyToolcachePath))
+        {
+            Write-Host "Create Ruby toolcache folder"
+            New-Item -ItemType Directory -Path $rubyToolcachePath | Out-Null
+        }
+
+        Write-Host "Creating Ruby '${rubyVersion}' folder in '${rubyVersionPath}'"
+        New-Item -ItemType Directory -Path $rubyVersionPath -Force | Out-Null
+
+        Write-Host "Moving Ruby '${rubyVersion}' files to '${rubyArchPath}'"
+        Move-Item -Path $tempFolder -Destination $rubyArchPath | Out-Null
+
+        Write-Host "Installing Bundler"
+        cmd.exe /c "$rubyArchPath\bin\gem.cmd install bundler -v ""~> 2"" --no-document"
+
+        if ($LASTEXITCODE -ne 0)
+        {
+            Throw "Error happened during Ruby installation"
+            exit 1
+        }
+
+        Write-Host "Creating complete file"
+        New-Item -ItemType File -Path $rubyVersionPath -Name "$Architecture.complete" | Out-Null
+    }
+    else
+    {
+        Write-Host "Ruby application is not found. Failed to expand '$PackagePath' archive"
+        exit 1
+    }
+}
+
+function Set-DefaultRubyVersion
+{
+    param(
+        [Parameter(Mandatory=$true)]
+        [System.Version] $Version,
+        [System.String] $Arch = "x64"
+    )
+
+    $rubyPath = Join-Path $env:AGENT_TOOLSDIRECTORY "/Ruby/${Version}*/${Arch}/bin"
+    $rubyDir = (Get-Item -Path $rubyPath).FullName
+
+    Write-Host "Use Ruby ${Version} as a system Ruby"
+    Add-MachinePathItem -PathItem $rubyDir | Out-Null
+    $env:Path = Get-MachinePath
+
+    # Update ruby gem to latest version
+    Invoke-Expression "gem update --system --no-document"
+}
+
+# Define AGENT_TOOLSDIRECTORY environment variable
+$toolsDirectory = "C:/hostedtoolcache/windows"
+$env:AGENT_TOOLSDIRECTORY = $toolsDirectory
+setx AGENT_TOOLSDIRECTORY $toolsDirectory /M
+
+# Install Ruby
+$rubyTools = (Get-ToolsetContent).toolcache | Where-Object { $_.name -eq "Ruby" }
+$rubyToolVersions = $rubyTools.versions
+
+# Get Ruby versions from the repo
+$rubyLatestMajorVersions = Get-RubyVersions
+
+Write-Host "Starting installation Ruby..."
+foreach($rubyVersion in $rubyToolVersions)
+{
+    Write-Host "Starting Ruby $rubyVersion installation"
+    # Get url for the latest major Ruby version
+    $url = $rubyLatestMajorVersions[$rubyVersion]
+    if ($url)
+    {
+        $tempRubyPackagePath = Start-DownloadWithRetry -Url $url
+        Install-Ruby -PackagePath $tempRubyPackagePath
+    }
+    else
+    {
+        Write-Host "Url not found for the '$rubyVersion' version"
+        exit 1
+    }
+}
+
+Set-DefaultRubyVersion -Version $rubyTools.default -Arch $rubyTools.arch
\ No newline at end of file
diff --git a/images/win/scripts/Tests/Toolset.Tests.ps1 b/images/win/scripts/Tests/Toolset.Tests.ps1
index 0116ab22..70acfc16 100644
--- a/images/win/scripts/Tests/Toolset.Tests.ps1
+++ b/images/win/scripts/Tests/Toolset.Tests.ps1
@@ -62,12 +62,6 @@ function Test-DefaultVersion {
 }
 
 $tools = Get-ToolsetContent | Select-Object -ExpandProperty toolcache
-# convert old tool-cache to toolset format on-flight to re-use code
-(Get-ToolcachePackages).PSObject.Properties | ForEach-Object {
-    $packageNameParts = $_.Name.Split("-")
-    $tools += @{ name = $packageNameParts[1]; arch = $packageNameParts[3]; versions = $_.Value; default = "." }
-}
-
 foreach ($tool in $tools) {
     Describe "$($tool.name) [$($tool.arch)]" {
         $toolExecs = Get-ToolExecutables -Name $tool.name
diff --git a/images/win/toolsets/toolcache-2016.json b/images/win/toolsets/toolcache-2016.json
deleted file mode 100644
index b3f9c3c0..00000000
--- a/images/win/toolsets/toolcache-2016.json
+++ /dev/null
@@ -1,5 +0,0 @@
-{
-    "@actions/toolcache-ruby-windows-x64": [
-        "2.4", "2.5", "2.6", "2.7"
-    ]
-}
\ No newline at end of file
diff --git a/images/win/toolsets/toolcache-2019.json b/images/win/toolsets/toolcache-2019.json
deleted file mode 100644
index b3f9c3c0..00000000
--- a/images/win/toolsets/toolcache-2019.json
+++ /dev/null
@@ -1,5 +0,0 @@
-{
-    "@actions/toolcache-ruby-windows-x64": [
-        "2.4", "2.5", "2.6", "2.7"
-    ]
-}
\ No newline at end of file
diff --git a/images/win/toolsets/toolset-2016.json b/images/win/toolsets/toolset-2016.json
index f5d30694..7e730911 100644
--- a/images/win/toolsets/toolset-2016.json
+++ b/images/win/toolsets/toolset-2016.json
@@ -1,5 +1,17 @@
 {
     "toolcache": [
+        {
+            "name": "Ruby",
+            "arch": "x64",
+            "platform" : "win32",
+            "versions": [
+                "2.4",
+                "2.5",
+                "2.6",
+                "2.7"
+            ],
+            "default": "2.5"
+        },
         {
             "name": "Python",
             "url" : "https://raw.githubusercontent.com/actions/python-versions/main/versions-manifest.json",
diff --git a/images/win/toolsets/toolset-2019.json b/images/win/toolsets/toolset-2019.json
index ebb7aa82..4b1c5328 100644
--- a/images/win/toolsets/toolset-2019.json
+++ b/images/win/toolsets/toolset-2019.json
@@ -1,5 +1,17 @@
 {
     "toolcache": [
+        {
+            "name": "Ruby",
+            "arch": "x64",
+            "platform" : "win32",
+            "versions": [
+                "2.4",
+                "2.5",
+                "2.6",
+                "2.7"
+            ],
+            "default": "2.5"
+        },
         {
             "name": "Python",
             "url" : "https://raw.githubusercontent.com/actions/python-versions/main/versions-manifest.json",
diff --git a/images/win/windows2016.json b/images/win/windows2016.json
index 120e7ac9..ed3bf71d 100644
--- a/images/win/windows2016.json
+++ b/images/win/windows2016.json
@@ -26,13 +26,11 @@
         "capture_name_prefix": "packer",
         "image_version": "dev",
         "image_os": "win16",
-        "github_feed_token": "{{env `GITHUB_FEED_TOKEN`}}",
         "announcements": "{{env `ANNOUNCEMENTS`}}"
     },
     "sensitive-variables": [
         "install_password",
-        "client_secret",
-        "github_feed_token"
+        "client_secret"
     ],
     "builders": [
         {
@@ -92,11 +90,6 @@
             "source": "{{ template_dir }}/scripts/Tests",
             "destination": "{{user `image_folder`}}"
         },
-        {
-            "type": "file",
-            "source": "{{template_dir}}/toolsets/toolcache-2016.json",
-            "destination": "{{user `root_folder`}}/toolcache.json"
-        },
         {
             "type": "file",
             "source": "{{template_dir}}/toolsets/toolset-2016.json",
@@ -226,12 +219,11 @@
         {
             "type": "powershell",
             "environment_vars": [
-                "GITHUB_FEED_TOKEN={{ user `github_feed_token` }}",
                 "TOOLSET_JSON_PATH={{user `toolset_json_path`}}",
                 "ROOT_FOLDER={{user `root_folder`}}"
             ],
             "scripts": [
-                "{{ template_dir }}/scripts/Installers/Download-ToolCache.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-Ruby.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-PyPy.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-Toolset.ps1",
                 "{{ template_dir }}/scripts/Installers/Configure-Toolset.ps1",
diff --git a/images/win/windows2019.json b/images/win/windows2019.json
index a27bf27d..756391ed 100644
--- a/images/win/windows2019.json
+++ b/images/win/windows2019.json
@@ -26,13 +26,11 @@
         "capture_name_prefix": "packer",
         "image_version": "dev",
         "image_os": "win19",
-        "github_feed_token": "{{env `GITHUB_FEED_TOKEN`}}",
         "announcements": "{{env `ANNOUNCEMENTS`}}"
     },
     "sensitive-variables": [
         "install_password",
-        "client_secret",
-        "github_feed_token"
+        "client_secret"
     ],
     "builders": [
         {
@@ -92,11 +90,6 @@
             "source": "{{ template_dir }}/scripts/Tests",
             "destination": "{{user `image_folder`}}"
         },
-        {
-            "type": "file",
-            "source": "{{template_dir}}/toolsets/toolcache-2019.json",
-            "destination": "{{user `root_folder`}}/toolcache.json"
-        },
         {
             "type": "file",
             "source": "{{template_dir}}/toolsets/toolset-2019.json",
@@ -225,11 +218,10 @@
         {
             "type": "powershell",
             "environment_vars": [
-                "GITHUB_FEED_TOKEN={{ user `github_feed_token` }}",
                 "ROOT_FOLDER={{user `root_folder`}}"
             ],
             "scripts": [
-                "{{ template_dir }}/scripts/Installers/Download-ToolCache.ps1"
+                "{{ template_dir }}/scripts/Installers/Install-Ruby.ps1"
             ]
         },
         {