diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 05333241a..c78b05ee9 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -509,6 +509,12 @@
                 "{{ template_dir }}/scripts/Installers/Install-AWS-SAM.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-AWS-CLI-SM.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -707,6 +713,12 @@
                 "{{ template_dir }}/scripts/Installers/Validate-AWS-SAM.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-AWS-CLI-SM.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index cf10a9033..6e9107805 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -476,6 +476,12 @@
                 "{{ template_dir }}/scripts/Installers/Install-AWS-SAM.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-AWS-CLI-SM.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -692,6 +698,12 @@
                 "{{ template_dir }}/scripts/Installers/Validate-AWS-SAM.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-AWS-CLI-SM.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
diff --git a/images/win/scripts/Installers/Install-AWS-CLI-SM.ps1 b/images/win/scripts/Installers/Install-AWS-CLI-SM.ps1
new file mode 100644
index 000000000..df5e4dff6
--- /dev/null
+++ b/images/win/scripts/Installers/Install-AWS-CLI-SM.ps1
@@ -0,0 +1,9 @@
+################################################################################
+##  File:  Install-AWS-CLI-SM.ps1
+##  Desc:  Install AWS CLI Session Manager
+################################################################################
+
+$sessionManagerName = "SessionManagerPluginSetup.exe"
+$sessionManagerUrl = "https://s3.amazonaws.com/session-manager-downloads/plugin/latest/windows/$sessionManagerName"
+Install-Binary -Url $sessionManagerUrl -Name $sessionManagerName -ArgumentList ("/silent", "/install")
+Add-MachinePathItem -PathItem "C:\Program Files\Amazon\SessionManagerPlugin\bin"
diff --git a/images/win/scripts/Installers/Validate-AWS-CLI-SM.ps1 b/images/win/scripts/Installers/Validate-AWS-CLI-SM.ps1
new file mode 100644
index 000000000..b6d9df4c5
--- /dev/null
+++ b/images/win/scripts/Installers/Validate-AWS-CLI-SM.ps1
@@ -0,0 +1,14 @@
+################################################################################
+##  File:  Validate-AWS-CLI-SM.ps1
+##  Desc:  Validate aws cli session manager
+################################################################################
+
+$sessionMessage = session-manager-plugin
+
+if ($sessionMessage -Match "*plugin was installed successfully*") {
+    Write-Host "$sessionMessage"
+    exit 0
+} else {
+    Write-Host "$sessionMessage"
+    exit 1
+}
\ No newline at end of file