diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 97a06702f..8732a9fb1 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -175,10 +175,6 @@
                 "{{ template_dir }}/scripts/Installers/Windows2016/Update-DockerImages.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "inline": ["choco install vcredist140 -y"]
-        },
         {
             "type": "powershell",
             "valid_exit_codes": [
diff --git a/images/win/scripts/ImageHelpers/ChocoHelpers.ps1 b/images/win/scripts/ImageHelpers/ChocoHelpers.ps1
index f81ad0a1f..ee1f39128 100644
--- a/images/win/scripts/ImageHelpers/ChocoHelpers.ps1
+++ b/images/win/scripts/ImageHelpers/ChocoHelpers.ps1
@@ -1,33 +1,32 @@
-function Install-Choco {
+function Choco-Install {
     [CmdletBinding()]
     param(
         [Parameter(Mandatory)]
-        [string]$install,
-        [int]$retries = 5
+        [string] $PackageName,
+        [string[]] $ArgumentList,
+        [int] $RetryCount = 5
     )
 
-    begin { }
     process {
-        $condition = $false
-        $count = 0
-        do {
-            Write-Output "running: powershell choco install $install -y"
-            powershell choco install $install -y
+        $count = 1
+        while($true)
+        {
+            Write-Host "Running [#$count]: choco install $packageName -y $argumentList"
+            choco install $packageName -y @argumentList
 
-            $installed = powershell choco list -lo $install --all
-            $match = (($installed -match "^$install.*").Length -ne 0)
-            if ($match) {
-                Write-Output "package installed: $install"
-                $condition = $true
+            $pkg = choco list --localonly $packageName --exact --all --limitoutput
+            if ($pkg) {
+                Write-Host "Package installed: $pkg"
+                break
             }
             else {
                 $count++
-                if ($count -eq $retries) {
-                    Write-Error "Could not install $install after $count attempts"
+                if ($count -ge $retryCount) {
+                    Write-Host "Could not install $packageName after $count attempts"
                     exit 1
                 }
+                Start-Sleep -Seconds 30
             }
-        } while ($condition -eq $false)
+        }
     }
-    end { }
 }
\ No newline at end of file
diff --git a/images/win/scripts/ImageHelpers/ImageHelpers.psm1 b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
index 9e750b8db..b34539265 100644
--- a/images/win/scripts/ImageHelpers/ImageHelpers.psm1
+++ b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
@@ -27,5 +27,5 @@ Export-ModuleMember -Function @(
     'Get-WinVersion'
     'Test-IsWin19'
     'Test-IsWin16'
-    'Install-Choco'
+    'Choco-Install'
 )
diff --git a/images/win/scripts/Installers/Install-7zip.ps1 b/images/win/scripts/Installers/Install-7zip.ps1
index 4e86ad3c6..419c81782 100644
--- a/images/win/scripts/Installers/Install-7zip.ps1
+++ b/images/win/scripts/Installers/Install-7zip.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install 7zip
 ################################################################################
 
-choco install 7zip.install -y
+Choco-Install -PackageName 7zip.install
diff --git a/images/win/scripts/Installers/Install-AWS.ps1 b/images/win/scripts/Installers/Install-AWS.ps1
index 124f32d20..b5ad9a6d2 100644
--- a/images/win/scripts/Installers/Install-AWS.ps1
+++ b/images/win/scripts/Installers/Install-AWS.ps1
@@ -3,7 +3,7 @@
 ##  Desc:  Install awscli
 ################################################################################
 
-choco install awscli -y
+Choco-Install -PackageName awscli
 
 $env:PATH =$env:PATH + ";$Env:Programfiles\Amazon\AWSCLIV2"
 
diff --git a/images/win/scripts/Installers/Install-AliyunCli.ps1 b/images/win/scripts/Installers/Install-AliyunCli.ps1
index 95b462b61..b46eb8a60 100644
--- a/images/win/scripts/Installers/Install-AliyunCli.ps1
+++ b/images/win/scripts/Installers/Install-AliyunCli.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install Alibaba Cloud CLI
 ################################################################################
 
-choco install aliyun-cli -y
\ No newline at end of file
+Choco-Install -PackageName aliyun-cli
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-AzureCli.ps1 b/images/win/scripts/Installers/Install-AzureCli.ps1
index ca96558a5..4b5d7dae1 100644
--- a/images/win/scripts/Installers/Install-AzureCli.ps1
+++ b/images/win/scripts/Installers/Install-AzureCli.ps1
@@ -3,7 +3,7 @@
 ##  Desc:  Install Azure CLI
 ################################################################################
 
-Install-Choco "azure-cli"
+Choco-Install -PackageName azure-cli
 
 $AzureCliExtensionPath = Join-Path $Env:CommonProgramFiles 'AzureCliExtensionDirectory'
 New-Item -ItemType "directory" -Path $AzureCliExtensionPath
diff --git a/images/win/scripts/Installers/Install-Bazel.ps1 b/images/win/scripts/Installers/Install-Bazel.ps1
index fb14a856b..fabbecd01 100644
--- a/images/win/scripts/Installers/Install-Bazel.ps1
+++ b/images/win/scripts/Installers/Install-Bazel.ps1
@@ -3,6 +3,6 @@
 ##  Desc:  Install Bazel and Bazelisk (A user-friendly launcher for Bazel)
 ################################################################################
 
-choco install bazel -y
+Choco-Install -PackageName bazel
 
 npm install -g @bazel/bazelisk
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-Cmake.ps1 b/images/win/scripts/Installers/Install-Cmake.ps1
index b0ba514ee..37183d5e6 100644
--- a/images/win/scripts/Installers/Install-Cmake.ps1
+++ b/images/win/scripts/Installers/Install-Cmake.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install Cmake
 ################################################################################
 
-choco install cmake.install -y --installargs 'ADD_CMAKE_TO_PATH=""System""'
+Choco-Install -PackageName cmake.install -ArgumentList "--installargs",'ADD_CMAKE_TO_PATH=""System""'
diff --git a/images/win/scripts/Installers/Install-Docker.ps1 b/images/win/scripts/Installers/Install-Docker.ps1
index ec4f0d895..35e988ada 100644
--- a/images/win/scripts/Installers/Install-Docker.ps1
+++ b/images/win/scripts/Installers/Install-Docker.ps1
@@ -13,8 +13,8 @@ Write-Host "Install-Package Docker"
 Install-Package -Name docker -ProviderName DockerMsftProvider -Force
 Start-Service docker
 
-choco install docker-compose -y
+Write-Host "Install-Package Docker-Compose"
+Choco-Install -PackageName docker-compose
 
-# Install helm
 Write-Host "Install Helm"
-choco install kubernetes-helm
\ No newline at end of file
+Choco-Install -PackageName kubernetes-helm
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-Edge.ps1 b/images/win/scripts/Installers/Install-Edge.ps1
index b84f0fc14..430e8bbb9 100644
--- a/images/win/scripts/Installers/Install-Edge.ps1
+++ b/images/win/scripts/Installers/Install-Edge.ps1
@@ -3,7 +3,7 @@
 ##  Desc:  Install latest stable version of Microsoft Edge browser
 ################################################################################
 
-choco install microsoft-edge -y
+Choco-Install -PackageName microsoft-edge
 
 # Install Microsoft Edge Web Driver
 Write-Host "Install Edge WebDriver"
diff --git a/images/win/scripts/Installers/Install-Git.ps1 b/images/win/scripts/Installers/Install-Git.ps1
index 0466fcd1c..5270675af 100644
--- a/images/win/scripts/Installers/Install-Git.ps1
+++ b/images/win/scripts/Installers/Install-Git.ps1
@@ -32,7 +32,7 @@ Install-Exe -Url $downloadUrl `
                 "/o:BashTerminalOption=ConHost", `
                 "/COMPONENTS=gitlfs")
 
-choco install hub
+Choco-Install -PackageName hub
 
 # Disable GCM machine-wide
 [Environment]::SetEnvironmentVariable("GCM_INTERACTIVE", "Never", [System.EnvironmentVariableTarget]::Machine)
diff --git a/images/win/scripts/Installers/Install-GitVersion.ps1 b/images/win/scripts/Installers/Install-GitVersion.ps1
index b97358e0c..1e27e49f9 100644
--- a/images/win/scripts/Installers/Install-GitVersion.ps1
+++ b/images/win/scripts/Installers/Install-GitVersion.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install GitVersion
 ################################################################################
 
-choco install gitversion.portable -y
+Choco-Install -PackageName gitversion.portable
diff --git a/images/win/scripts/Installers/Install-InnoSetup.ps1 b/images/win/scripts/Installers/Install-InnoSetup.ps1
index 8020120d1..17f26962e 100644
--- a/images/win/scripts/Installers/Install-InnoSetup.ps1
+++ b/images/win/scripts/Installers/Install-InnoSetup.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install Inno Setup
 ################################################################################
 
-choco install innosetup -y
+Choco-Install -PackageName innosetup
diff --git a/images/win/scripts/Installers/Install-JavaTools.ps1 b/images/win/scripts/Installers/Install-JavaTools.ps1
index 68c0209fd..e88fc7453 100644
--- a/images/win/scripts/Installers/Install-JavaTools.ps1
+++ b/images/win/scripts/Installers/Install-JavaTools.ps1
@@ -61,9 +61,9 @@ setx JAVA_HOME_11_X64 $latestJava11Install /M
 
 # Install Java tools
 # Force chocolatey to ignore dependencies on Ant and Maven or else they will download the Oracle JDK
-choco install ant -y -i
-choco install maven -y -i --version=3.6.3
-choco install gradle -y
+Choco-Install -PackageName ant -ArgumentList "-i"
+Choco-Install -PackageName maven -ArgumentList "-i", "--version=3.6.3"
+Choco-Install -PackageName gradle
 
 # Move maven variables to Machine. They may not be in the environment for this script so we need to read them from the registry.
 $userSid = (Get-WmiObject win32_useraccount -Filter "name = '$env:USERNAME' AND domain = '$env:USERDOMAIN'").SID
diff --git a/images/win/scripts/Installers/Install-Jq.ps1 b/images/win/scripts/Installers/Install-Jq.ps1
index 1ccb42da8..5a383d797 100644
--- a/images/win/scripts/Installers/Install-Jq.ps1
+++ b/images/win/scripts/Installers/Install-Jq.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install jq
 ################################################################################
 
-choco install jq -y
+Choco-Install -PackageName jq
diff --git a/images/win/scripts/Installers/Install-Julia.ps1 b/images/win/scripts/Installers/Install-Julia.ps1
index f1f421168..6677b5d1d 100644
--- a/images/win/scripts/Installers/Install-Julia.ps1
+++ b/images/win/scripts/Installers/Install-Julia.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install Julia
 ################################################################################
 
-choco install julia -y --ia "/DIR=C:\Julia"
+Choco-Install -PackageName julia -ArgumentList "--ia","/DIR=C:\Julia"
diff --git a/images/win/scripts/Installers/Install-KubernetesCli.ps1 b/images/win/scripts/Installers/Install-KubernetesCli.ps1
index 8c7350c0f..c6ad04bc7 100644
--- a/images/win/scripts/Installers/Install-KubernetesCli.ps1
+++ b/images/win/scripts/Installers/Install-KubernetesCli.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install KubernetesCli
 ################################################################################
 
-choco install kubernetes-cli -y
+Choco-Install -PackageName kubernetes-cli
diff --git a/images/win/scripts/Installers/Install-Mercurial.ps1 b/images/win/scripts/Installers/Install-Mercurial.ps1
index 65a5cdefa..da820d1b3 100644
--- a/images/win/scripts/Installers/Install-Mercurial.ps1
+++ b/images/win/scripts/Installers/Install-Mercurial.ps1
@@ -3,7 +3,7 @@
 ##  Desc:  Install Mercurial
 ################################################################################
 
-choco install hg -y --version 5.0.0
+Choco-Install -PackageName hg -ArgumentList "--version", "5.0.0"
 
 $hgPath = "${env:ProgramFiles}\Mercurial\"
 Add-MachinePathItem $hgPath
diff --git a/images/win/scripts/Installers/Install-MinGW.ps1 b/images/win/scripts/Installers/Install-MinGW.ps1
index c2aa0f52c..ac585b9d8 100644
--- a/images/win/scripts/Installers/Install-MinGW.ps1
+++ b/images/win/scripts/Installers/Install-MinGW.ps1
@@ -5,7 +5,7 @@
 
 Import-Module -Name ImageHelpers -Force
 
-Install-Choco "mingw"
+Choco-Install -PackageName mingw
 
 # Make a copy of mingw32-make.exe to make.exe, which is a more discoverable name
 # and so the same command line can be used on Windows as on macOS and Linux
diff --git a/images/win/scripts/Installers/Install-NSIS.ps1 b/images/win/scripts/Installers/Install-NSIS.ps1
index c8c5e370e..71ceb70d7 100644
--- a/images/win/scripts/Installers/Install-NSIS.ps1
+++ b/images/win/scripts/Installers/Install-NSIS.ps1
@@ -3,7 +3,7 @@
 ##  Desc:  Install NSIS
 ################################################################################
 
-choco install nsis -y
+Choco-Install -PackageName nsis
 
 $NsisPath = "${env:ProgramFiles(x86)}\NSIS\"
 Add-MachinePathItem $NsisPath
diff --git a/images/win/scripts/Installers/Install-NodeLts.ps1 b/images/win/scripts/Installers/Install-NodeLts.ps1
index e1ec5f0fb..c1ee0579a 100644
--- a/images/win/scripts/Installers/Install-NodeLts.ps1
+++ b/images/win/scripts/Installers/Install-NodeLts.ps1
@@ -12,7 +12,7 @@ $CachePath = 'C:\npm\cache'
 New-Item -Path $PrefixPath -Force -ItemType Directory
 New-Item -Path $CachePath -Force -ItemType Directory
 
-choco install nodejs-lts -y --force
+Choco-Install -PackageName nodejs-lts -ArgumentList "--force"
 
 Add-MachinePathItem $PrefixPath
 $env:Path = Get-MachinePath
diff --git a/images/win/scripts/Installers/Install-OpenSSL.ps1 b/images/win/scripts/Installers/Install-OpenSSL.ps1
index 5ff783398..4f43ad435 100644
--- a/images/win/scripts/Installers/Install-OpenSSL.ps1
+++ b/images/win/scripts/Installers/Install-OpenSSL.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install OpenSSL
 ################################################################################
 
-choco install openssl.light -y
+Choco-Install -PackageName openssl.light
diff --git a/images/win/scripts/Installers/Install-PHP.ps1 b/images/win/scripts/Installers/Install-PHP.ps1
index 72db2ee27..f4fc4f1d1 100644
--- a/images/win/scripts/Installers/Install-PHP.ps1
+++ b/images/win/scripts/Installers/Install-PHP.ps1
@@ -8,10 +8,10 @@ Import-Module -Name ImageHelpers
 
 # Install latest PHP in chocolatey
 $installDir = "c:\tools\php"
-choco install php -y --force --params "/InstallDir:$installDir"
+Choco-Install -PackageName php -ArgumentList "--force", "--params", "/InstallDir:$installDir"
 
 # Install latest Composer in chocolatey
-choco install composer --ia "/DEV=$installDir /PHP=$installDir"
+Choco-Install -PackageName composer -ArgumentList "--ia", "/DEV=$installDir /PHP=$installDir"
 
 # update path to extensions and enable curl and mbstring extensions, and enable php openssl extensions.
 ((Get-Content -path $installDir\php.ini -Raw) -replace ';extension=curl','extension=curl' -replace ';extension=mbstring','extension=mbstring' -replace ';extension_dir = "ext"','extension_dir = "ext"' -replace 'extension=";php_openssl.dll"','extension_dir = "php_openssl.dll"') | Set-Content -Path $installDir\php.ini
diff --git a/images/win/scripts/Installers/Install-Packer.ps1 b/images/win/scripts/Installers/Install-Packer.ps1
index 4374175d1..6d74fbf77 100644
--- a/images/win/scripts/Installers/Install-Packer.ps1
+++ b/images/win/scripts/Installers/Install-Packer.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install Packer
 ################################################################################
 
-choco install packer -y
+Choco-Install -PackageName packer
diff --git a/images/win/scripts/Installers/Install-Perl.ps1 b/images/win/scripts/Installers/Install-Perl.ps1
index 59b1e11a0..350e6c676 100644
--- a/images/win/scripts/Installers/Install-Perl.ps1
+++ b/images/win/scripts/Installers/Install-Perl.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install Perl
 ################################################################################
 
-choco install strawberryperl -y
+Choco-Install -PackageName strawberryperl
diff --git a/images/win/scripts/Installers/Install-Sbt.ps1 b/images/win/scripts/Installers/Install-Sbt.ps1
index b96ed5ac8..bc0e95a20 100644
--- a/images/win/scripts/Installers/Install-Sbt.ps1
+++ b/images/win/scripts/Installers/Install-Sbt.ps1
@@ -8,7 +8,7 @@ Import-Module -Name ImageHelpers
 
 # Install the latest version of sbt.
 # See https://chocolatey.org/packages/sbt
-choco install sbt -y
+Choco-Install -PackageName sbt
 
 $env:SBT_HOME="${env:ProgramFiles(x86)}\sbt"
 
diff --git a/images/win/scripts/Installers/Install-Svn.ps1 b/images/win/scripts/Installers/Install-Svn.ps1
index 45dd52319..315c4ef8a 100644
--- a/images/win/scripts/Installers/Install-Svn.ps1
+++ b/images/win/scripts/Installers/Install-Svn.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install Subversion
 ################################################################################
 
-choco install svn -y
+Choco-Install -PackageName svn
diff --git a/images/win/scripts/Installers/Install-VSWhere.ps1 b/images/win/scripts/Installers/Install-VSWhere.ps1
index d60986540..5c623c936 100644
--- a/images/win/scripts/Installers/Install-VSWhere.ps1
+++ b/images/win/scripts/Installers/Install-VSWhere.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install latest stable version of VSWhere
 ################################################################################
 
-choco install vswhere -y
+Choco-Install -PackageName vswhere
diff --git a/images/win/scripts/Installers/Install-Wix.ps1 b/images/win/scripts/Installers/Install-Wix.ps1
index 076be86c9..25469dab8 100644
--- a/images/win/scripts/Installers/Install-Wix.ps1
+++ b/images/win/scripts/Installers/Install-Wix.ps1
@@ -3,9 +3,9 @@
 ##  Desc:  Install WIX.
 ################################################################################
 
-Import-Module -Name ImageHelpers -Force;
+Import-Module -Name ImageHelpers -Force
 
-choco install wixtoolset -y --force
+Choco-Install -PackageName wixtoolset -ArgumentList "--force"
 
 if(Test-IsWin19)
 {
diff --git a/images/win/scripts/Installers/Install-Zstd.ps1 b/images/win/scripts/Installers/Install-Zstd.ps1
index 098334ebe..2251143bc 100644
--- a/images/win/scripts/Installers/Install-Zstd.ps1
+++ b/images/win/scripts/Installers/Install-Zstd.ps1
@@ -3,4 +3,4 @@
 ##  Desc:  Install zstd
 ################################################################################
 
-choco install zstandard -y
+Choco-Install -PackageName zstandard
diff --git a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
index 6f7dd13e8..d8fa7a059 100644
--- a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
@@ -111,7 +111,10 @@ choco feature enable -n allowGlobalConfirmation
 Remove-Item -Path $env:ChocolateyInstall\bin\cpack.exe -Force
 
 # Install webpi
-choco install webpicmd -y
+Choco-Install -PackageName webpicmd
+
+# Install vcredist140
+Choco-Install -PackageName vcredist140
 
 
 # Expand disk size of OS drive
diff --git a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
index 4f05935c9..92e153d73 100644
--- a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
@@ -109,7 +109,7 @@ choco feature enable -n allowGlobalConfirmation
 Remove-Item -Path $env:ChocolateyInstall\bin\cpack.exe -Force
 
 # Install webpi
-choco install webpicmd -y
+Choco-Install -PackageName webpicmd
 
 # Expand disk size of OS drive