diff --git a/build-jenkins-agent-windows.pkr.hcl b/build-jenkins-agent-windows.pkr.hcl
index 96aeb3b91..4b97584cc 100644
--- a/build-jenkins-agent-windows.pkr.hcl
+++ b/build-jenkins-agent-windows.pkr.hcl
@@ -95,8 +95,20 @@ build {
     inline = [
       "$ErrorActionPreference = 'Stop'",
       "goss --version",
-      "goss --use-alpha=1 --gossfile C:/goss-windows.yaml --loglevel DEBUG validate --retry-timeout 300s",
-      "goss --use-alpha=1 --gossfile C:/goss-common.yaml --loglevel DEBUG validate --retry-timeout 300s",
+      "goss --use-alpha=1 --gossfile C:/goss-windows.yaml --loglevel DEBUG validate --retry-timeout 60s",
+    ]
+  }
+
+  provisioner "powershell" {
+    environment_vars  = local.provisioning_env_vars
+    inline = [
+      "goss --use-alpha=1 --gossfile C:/goss-common.yaml --loglevel DEBUG validate --retry-timeout 60s",
+    ]
+  }
+
+  provisioner "powershell" {
+    environment_vars  = local.provisioning_env_vars
+    inline = [
       "Remove-Item -Force C:/goss-windows.yaml",
       "Remove-Item -Force C:/goss-common.yaml",
       "Remove-Item -Force C:/visualstudio.vsconfig",
diff --git a/goss/goss-windows.yaml b/goss/goss-windows.yaml
index ac7d50871..ae32fd823 100644
--- a/goss/goss-windows.yaml
+++ b/goss/goss-windows.yaml
@@ -55,12 +55,11 @@ command:
     stdout:
       - 2.4.1
   visualstudio:
-    exec: C:\Program Files (x86)\Microsoft Visual Studio\2019\Community\MSBuild\Current\Bin\MSBuild.exe -nologo -version
+    exec: ("C:\\Program Files (x86)\\Microsoft Visual Studio\\2019\\Community\\MSBuild\\Current\\Bin\\MSBuild.exe" "/nologo" "/version")
     exit-status: 0
     stdout:
       - /16\.\d+\.\d+\.\d+/
-    skip: |
-      {{ not (eq .Env.AGENT_OS_VERSION "2019") }}
+    skip: {{ not (eq .Env.AGENT_OS_VERSION "2019") }}
 file:
   C:\Program Files\Chromium\Application\:
     contains: []
diff --git a/updatecli/updatecli.d/jdk11.yml b/updatecli/updatecli.d/jdk11.yml
index a893cd479..f53bf7f0c 100644
--- a/updatecli/updatecli.d/jdk11.yml
+++ b/updatecli/updatecli.d/jdk11.yml
@@ -50,6 +50,7 @@ targets:
     name: Update the JDK11 version in the goss test
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - goss/goss-linux.yaml
         - goss/goss-windows.yaml
diff --git a/updatecli/updatecli.d/jdk17.yml b/updatecli/updatecli.d/jdk17.yml
index 2a9665464..6e206f8dc 100644
--- a/updatecli/updatecli.d/jdk17.yml
+++ b/updatecli/updatecli.d/jdk17.yml
@@ -50,6 +50,7 @@ targets:
     name: Update the JDK17 version in the goss test
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - goss/goss-linux.yaml
         - goss/goss-windows.yaml
diff --git a/updatecli/updatecli.d/jdk21.yml b/updatecli/updatecli.d/jdk21.yml
index 975818ff9..28752996d 100644
--- a/updatecli/updatecli.d/jdk21.yml
+++ b/updatecli/updatecli.d/jdk21.yml
@@ -48,6 +48,7 @@ targets:
     name: Update the JDK21 version in the goss test
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - goss/goss-linux.yaml
         - goss/goss-windows.yaml
diff --git a/updatecli/updatecli.d/jdk8.yml b/updatecli/updatecli.d/jdk8.yml
index 77a5eb69f..0fc886b37 100644
--- a/updatecli/updatecli.d/jdk8.yml
+++ b/updatecli/updatecli.d/jdk8.yml
@@ -54,6 +54,7 @@ targets:
           captureindex: 1
       - addprefix: '1.8.0_'
     spec:
+      engine: "yamlpath"
       files:
         - goss/goss-linux.yaml
         - goss/goss-windows.yaml
diff --git a/updatecli/updatecli.d/nodejs-windows.yml b/updatecli/updatecli.d/nodejs-windows.yml
index 10e204af3..213a1583c 100644
--- a/updatecli/updatecli.d/nodejs-windows.yml
+++ b/updatecli/updatecli.d/nodejs-windows.yml
@@ -54,6 +54,7 @@ targets:
     sourceid: lastReleaseVersion
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - goss/goss-windows.yaml
       key: $.command.nodejs.stdout[0]
diff --git a/updatecli/updatecli.d/pwsh.yml b/updatecli/updatecli.d/pwsh.yml
index 92f3b0549..c9e8d9e14 100644
--- a/updatecli/updatecli.d/pwsh.yml
+++ b/updatecli/updatecli.d/pwsh.yml
@@ -47,12 +47,13 @@ targets:
     kind: yaml
     spec:
       file: "provisioning/tools-versions.yml"
-      key: "windows_pwsh_version"
+      key: $.windows_pwsh_version
     scmid: default
   updatePwshVersionInGoss:
     name: Update the `Pwsh` version in the goss test
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - "goss/goss-windows.yaml"
       key: $.command.pwsh.stdout[0]
diff --git a/updatecli/updatecli.d/python3.yml b/updatecli/updatecli.d/python3.yml
index f4b852e23..18a3e5e2c 100644
--- a/updatecli/updatecli.d/python3.yml
+++ b/updatecli/updatecli.d/python3.yml
@@ -43,6 +43,7 @@ targets:
     name: Update the `python3` version in the goss test
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - "goss/goss-windows.yaml" #fixed only on windows
       key: $.command.python3.stdout[0]
diff --git a/updatecli/updatecli.d/ruby.yml b/updatecli/updatecli.d/ruby.yml
index d6bbd2ae5..b529c4963 100644
--- a/updatecli/updatecli.d/ruby.yml
+++ b/updatecli/updatecli.d/ruby.yml
@@ -20,7 +20,7 @@ sources:
     name: "Get the latest Ruby version"
     spec:
       image: "ruby"
-      tagFilter: >-
+      tagfilter: >-
         \d\.\d\.\d$
       versionfilter:
         kind: regex
@@ -58,6 +58,7 @@ targets:
     sourceid: rubyDockerImageLatestVersion
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - goss/goss-windows.yaml
       key: $.command.ruby.stdout[0]
diff --git a/updatecli/updatecli.d/vagrant.yml b/updatecli/updatecli.d/vagrant.yml
index 0509fa6e2..157e46181 100644
--- a/updatecli/updatecli.d/vagrant.yml
+++ b/updatecli/updatecli.d/vagrant.yml
@@ -49,6 +49,7 @@ targets:
     name: "Update the `vagrant` version in the goss test"
     kind: yaml
     spec:
+      engine: "yamlpath"
       files:
         - goss/goss-windows.yaml # windows only as the linux arm64 vagrant version is not pinned
       key: $.command.vagrant.stdout[0]