diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index ba6197d26..ccfdf0cc0 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -612,7 +612,8 @@
         {
             "type": "powershell",
             "environment_vars": [
-                "ROOT_FOLDER={{user `root_folder`}}"
+                "ROOT_FOLDER={{user `root_folder`}}",
+                "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
             ],
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-Boost.ps1"
@@ -782,15 +783,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-Go.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "environment_vars": [
-                "ROOT_FOLDER={{user `root_folder`}}"
-            ],
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-Boost.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index 3b5ba9d79..77935fd76 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -573,7 +573,8 @@
         {
             "type": "powershell",
             "environment_vars": [
-                "ROOT_FOLDER={{user `root_folder`}}"
+                "ROOT_FOLDER={{user `root_folder`}}",
+                "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
             ],
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-Boost.ps1"
@@ -767,15 +768,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-Go.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "environment_vars": [
-                "ROOT_FOLDER={{user `root_folder`}}"
-            ],
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-Boost.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
diff --git a/images/win/scripts/Installers/Install-Boost.ps1 b/images/win/scripts/Installers/Install-Boost.ps1
index d46a150c8..a11013fe3 100644
--- a/images/win/scripts/Installers/Install-Boost.ps1
+++ b/images/win/scripts/Installers/Install-Boost.ps1
@@ -8,11 +8,11 @@ Import-Module -Name ImageHelpers
 
 $SoftwareName = "Boost"
 $BoostDirectory = Join-Path -Path $env:AGENT_TOOLSDIRECTORY -ChildPath $SoftwareName
-$BoostVersions = (Get-ToolsByName -SoftwareName $SoftwareName).Versions | Foreach-Object {"{0}.0" -f $_}
+$BoostVersions = (Get-ToolsetContent | Select-Object -ExpandProperty toolcache | Where-Object { $_.Name -eq "Boost"}).Versions
 
 foreach($BoostVersion in $BoostVersions)
 {
-    $BoostInstallationDir = Join-Path -Path $BoostDirectory -ChildPath $BoostVersion
+    $BoostInstallationDir = Join-Path -Path $BoostDirectory -ChildPath "$BoostVersion\X86_64"
 
     $EnvBoostPath = "BOOST_ROOT_{0}" -f ($BoostVersion.Replace('.', '_'))
     setx $EnvBoostPath $BoostInstallationDir /M | Out-Null
diff --git a/images/win/scripts/Installers/Install-Toolset.ps1 b/images/win/scripts/Installers/Install-Toolset.ps1
index bc2aa59d2..197c52684 100644
--- a/images/win/scripts/Installers/Install-Toolset.ps1
+++ b/images/win/scripts/Installers/Install-Toolset.ps1
@@ -15,7 +15,13 @@ Function Install-Asset {
     $assetArchivePath = Start-DownloadWithRetry -Url $ReleaseAsset.download_url -Name $ReleaseAsset.filename
 
     Write-Host "Extract $($ReleaseAsset.filename) content..."
-    7z.exe x $assetArchivePath -o"$assetFolderPath" -y | Out-Null
+    if ($assetArchivePath.EndsWith(".tar.gz")) {
+        $assetTarPath = $assetArchivePath.TrimEnd(".tar.gz")
+        Extract-7Zip -Path $assetArchivePath -DestinationPath $assetTarPath
+        Extract-7Zip -Path $assetTarPath -DestinationPath $assetFolderPath
+    } else {
+        Extract-7Zip -Path $assetArchivePath -DestinationPath $assetFolderPath
+    }
 
     Write-Host "Invoke installation script..."
     Push-Location -Path $assetFolderPath
@@ -48,7 +54,7 @@ $ErrorActionPreference = "Stop"
 Import-Module -Name ImageHelpers -Force
 
 # Get toolcache content from toolset
-$ToolsToInstall = @("Python", "Node")
+$ToolsToInstall = @("Python", "Node", "Boost")
 $tools = Get-ToolsetContent | Select-Object -ExpandProperty toolcache | Where {$ToolsToInstall -contains $_.Name}
 
 foreach ($tool in $tools) {
@@ -60,7 +66,7 @@ foreach ($tool in $tools) {
         $asset = $assets | Where-Object version -like $toolVersion `
                          | Sort-Object -Property {[version]$_.version} -Descending `
                          | Select-Object -ExpandProperty files `
-                         | Where-Object { ($_.platform -eq $tool.platform) -and ($_.arch -eq $tool.arch) } `
+                         | Where-Object { ($_.platform -eq $tool.platform) -and ($_.arch -eq $tool.arch) -and ($_.toolset -eq $tool.toolset) } `
                          | Select-Object -First 1
 
         Write-Host "Installing $($tool.name) $toolVersion $($tool.arch)..."
diff --git a/images/win/scripts/Installers/Validate-Boost.ps1 b/images/win/scripts/Installers/Validate-Boost.ps1
deleted file mode 100644
index 83bf3d083..000000000
--- a/images/win/scripts/Installers/Validate-Boost.ps1
+++ /dev/null
@@ -1,39 +0,0 @@
-################################################################################
-##  File:  Validate-Boost.ps1
-##  Desc:  Validate Boost
-################################################################################
-
-Import-Module -Name ImageHelpers
-
-function Validate-BoostVersion
-{
-    Param
-    (
-        [String]$BoostRootPath,
-        [String]$BoostRelease
-    )
-
-    $ReleasePath = Join-Path -Path $BoostRootPath -ChildPath $BoostRelease
-
-    if (Test-Path "$ReleasePath\b2.exe")
-    {
-        Write-Host "Boost.Build $BoostRelease is successfully installed"
-        return
-    }
-
-    Write-Host "$BoostRelease not found"
-    exit 1
-}
-
-$SoftwareName = 'Boost'
-$BoostRootDirectory = Join-Path -Path $env:AGENT_TOOLSDIRECTORY -ChildPath $SoftwareName
-$BoostTools = Get-ToolsByName -SoftwareName $SoftwareName
-
-foreach ($BoostTool in $BoostTools)
-{
-    $BoostVersionsToInstall = $BoostTool.Versions | Foreach-Object {"{0}.0" -f $_}
-    foreach($BoostVersion in $BoostVersionsToInstall)
-    {
-        Validate-BoostVersion -BoostRootPath $BoostRootDirectory -BoostRelease $BoostVersion
-    }
-}
diff --git a/images/win/scripts/Installers/Validate-Toolset.ps1 b/images/win/scripts/Installers/Validate-Toolset.ps1
index c54600531..ad0ce41b1 100644
--- a/images/win/scripts/Installers/Validate-Toolset.ps1
+++ b/images/win/scripts/Installers/Validate-Toolset.ps1
@@ -67,8 +67,8 @@ foreach($tool in $tools) {
 
     foreach ($version in $tool.versions) {
         # Add wildcard if missing
-        if (-not $version.Contains('*')) {
-            $version += '.*'
+        if ($version.Split(".").Length -lt 3) {
+            $version += ".*"
         }
 
         # Check if version folder exists
@@ -90,8 +90,10 @@ foreach($tool in $tools) {
             exit 1
         }
 
-        Write-Host "Run validation test for $($tool.name)($($tool.arch)) $($foundVersion.name) executables..."
-        Run-ExecutableTests -Executables $toolExecs -ToolPath $foundVersionArchPath
+        if ($toolExecs) {
+            Write-Host "Run validation test for $($tool.name)($($tool.arch)) $($foundVersion.name) executables..."
+            Run-ExecutableTests -Executables $toolExecs -ToolPath $foundVersionArchPath
+        }
     }
 
     if (-not ([string]::IsNullOrEmpty($tool.default))) {
diff --git a/images/win/toolcache-2016.json b/images/win/toolcache-2016.json
index 449be64fa..b3f9c3c02 100644
--- a/images/win/toolcache-2016.json
+++ b/images/win/toolcache-2016.json
@@ -1,8 +1,5 @@
 {
     "@actions/toolcache-ruby-windows-x64": [
         "2.4", "2.5", "2.6", "2.7"
-    ],
-    "@actions/toolcache-boost-windows-msvc-14.1-x32-x64": [
-        "1.69", "1.72"
     ]
 }
\ No newline at end of file
diff --git a/images/win/toolcache-2019.json b/images/win/toolcache-2019.json
index 354f518f6..b3f9c3c02 100644
--- a/images/win/toolcache-2019.json
+++ b/images/win/toolcache-2019.json
@@ -1,11 +1,5 @@
 {
     "@actions/toolcache-ruby-windows-x64": [
         "2.4", "2.5", "2.6", "2.7"
-    ],
-    "@actions/toolcache-boost-windows-msvc-14.1-x32-x64": [
-        "1.69"
-    ],
-    "@actions/toolcache-boost-windows-msvc-14.2-x32-x64": [
-        "1.72"
     ]
 }
\ No newline at end of file
diff --git a/images/win/toolset-2016.json b/images/win/toolset-2016.json
index 9eb2be40a..edc8dde25 100644
--- a/images/win/toolset-2016.json
+++ b/images/win/toolset-2016.json
@@ -47,6 +47,17 @@
                 "12.*",
                 "14.*"
             ]
+        },
+        {
+            "name": "Boost",
+            "url" : "https://raw.githubusercontent.com/actions/boost-versions/master/versions-manifest.json",
+            "arch": "x86_64",
+            "platform" : "win32",
+            "toolset": "msvc14.1",
+            "versions": [
+                "1.69.0",
+                "1.72.0"
+            ]
         }
     ]
 }
\ No newline at end of file
diff --git a/images/win/toolset-2019.json b/images/win/toolset-2019.json
index 9eb2be40a..ff5fef6ba 100644
--- a/images/win/toolset-2019.json
+++ b/images/win/toolset-2019.json
@@ -47,6 +47,26 @@
                 "12.*",
                 "14.*"
             ]
+        },
+        {
+            "name": "Boost",
+            "url" : "https://raw.githubusercontent.com/akv-platform/boost-hostedtoolcache/master/versions-manifest.json",
+            "arch": "x86_64",
+            "platform" : "win32",
+            "toolset": "msvc14.1",
+            "versions": [
+                "1.69.0"
+            ]
+        },
+        {
+            "name": "Boost",
+            "url" : "https://raw.githubusercontent.com/actions/boost-versions/master/versions-manifest.json",
+            "arch": "x86_64",
+            "platform" : "win32",
+            "toolset": "msvc14.2",
+            "versions": [
+                "1.72.0"
+            ]
         }
     ]
 }
\ No newline at end of file