diff --git a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
index e22d9da8d..7998f1cb7 100644
--- a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
@@ -92,6 +92,7 @@ else {
 }
 
 # Run the installer
+[Net.ServicePointManager]::SecurityProtocol = [Net.ServicePointManager]::SecurityProtocol -bor "Tls12"
 Invoke-Expression ((new-object net.webclient).DownloadString('https://chocolatey.org/install.ps1'))
 
 # Turn off confirmation
diff --git a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
index 09567e71a..9930e6a6d 100644
--- a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
@@ -92,6 +92,7 @@ else {
 }
 
 # Run the installer
+[Net.ServicePointManager]::SecurityProtocol = [Net.ServicePointManager]::SecurityProtocol -bor "Tls12"
 Invoke-Expression ((new-object net.webclient).DownloadString('https://chocolatey.org/install.ps1'))
 
 # Turn off confirmation