diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index fcb0ed4c..8e3bcfbf 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -323,6 +323,12 @@
                 "{{ template_dir }}/scripts/Installers/Download-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-OpenSSL.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -547,12 +553,6 @@
                 "{{ template_dir }}/scripts/Installers/Install-GitVersion.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Install-OpenSSL.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
@@ -620,6 +620,12 @@
                 "{{ template_dir }}/scripts/Installers/Validate-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-OpenSSL.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -820,12 +826,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-GitVersion.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-OpenSSL.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index 8f82a6eb..400be83f 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -298,6 +298,12 @@
                 "{{ template_dir }}/scripts/Installers/Download-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-OpenSSL.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -528,12 +534,6 @@
                 "{{ template_dir }}/scripts/Installers/Install-GitVersion.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Install-OpenSSL.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
@@ -607,6 +607,12 @@
                 "{{ template_dir }}/scripts/Installers/Validate-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-OpenSSL.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -801,12 +807,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-GitVersion.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-OpenSSL.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[