diff --git a/auditbeat/Jenkinsfile.yml b/auditbeat/Jenkinsfile.yml
index 0b4f618db048..6f5374224d4b 100644
--- a/auditbeat/Jenkinsfile.yml
+++ b/auditbeat/Jenkinsfile.yml
@@ -34,4 +34,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test auditbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/heartbeat/Jenkinsfile.yml b/heartbeat/Jenkinsfile.yml
index 962e459d42de..c465138791b3 100644
--- a/heartbeat/Jenkinsfile.yml
+++ b/heartbeat/Jenkinsfile.yml
@@ -32,4 +32,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test heartbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/metricbeat/Jenkinsfile.yml b/metricbeat/Jenkinsfile.yml
index 0559316a45a7..9860919d0068 100644
--- a/metricbeat/Jenkinsfile.yml
+++ b/metricbeat/Jenkinsfile.yml
@@ -40,4 +40,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test metricbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/packetbeat/Jenkinsfile.yml b/packetbeat/Jenkinsfile.yml
index b58690e70748..f755f3224777 100644
--- a/packetbeat/Jenkinsfile.yml
+++ b/packetbeat/Jenkinsfile.yml
@@ -32,4 +32,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test packetbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/winlogbeat/Jenkinsfile.yml b/winlogbeat/Jenkinsfile.yml
index 8c08baae5b52..82ce7912d3b8 100644
--- a/winlogbeat/Jenkinsfile.yml
+++ b/winlogbeat/Jenkinsfile.yml
@@ -19,4 +19,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test winlogbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/x-pack/auditbeat/Jenkinsfile.yml b/x-pack/auditbeat/Jenkinsfile.yml
index ec2b37cf7498..42c1a5d8cb47 100644
--- a/x-pack/auditbeat/Jenkinsfile.yml
+++ b/x-pack/auditbeat/Jenkinsfile.yml
@@ -33,4 +33,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test auditbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/x-pack/elastic-agent/Jenkinsfile.yml b/x-pack/elastic-agent/Jenkinsfile.yml
index 38742dd54905..04a6b2277212 100644
--- a/x-pack/elastic-agent/Jenkinsfile.yml
+++ b/x-pack/elastic-agent/Jenkinsfile.yml
@@ -32,4 +32,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/elastic-agent for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/x-pack/filebeat/Jenkinsfile.yml b/x-pack/filebeat/Jenkinsfile.yml
index b883e179837c..b2db448f532a 100644
--- a/x-pack/filebeat/Jenkinsfile.yml
+++ b/x-pack/filebeat/Jenkinsfile.yml
@@ -33,4 +33,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/filebeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/x-pack/functionbeat/Jenkinsfile.yml b/x-pack/functionbeat/Jenkinsfile.yml
index 3abd11682000..a8d42ce5fb9d 100644
--- a/x-pack/functionbeat/Jenkinsfile.yml
+++ b/x-pack/functionbeat/Jenkinsfile.yml
@@ -32,4 +32,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/functionbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/x-pack/metricbeat/Jenkinsfile.yml b/x-pack/metricbeat/Jenkinsfile.yml
index 0dde57a3a434..d02dc5e16aae 100644
--- a/x-pack/metricbeat/Jenkinsfile.yml
+++ b/x-pack/metricbeat/Jenkinsfile.yml
@@ -35,4 +35,14 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/metricbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/x-pack/packetbeat/Jenkinsfile.yml b/x-pack/packetbeat/Jenkinsfile.yml
index 7f0a9a2f7016..ab7456b98b22 100644
--- a/x-pack/packetbeat/Jenkinsfile.yml
+++ b/x-pack/packetbeat/Jenkinsfile.yml
@@ -18,4 +18,14 @@ stages:
         withModule: true
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/winlogbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/x-pack/winlogbeat/Jenkinsfile.yml b/x-pack/winlogbeat/Jenkinsfile.yml
index 8975e947d083..788d4a353696 100644
--- a/x-pack/winlogbeat/Jenkinsfile.yml
+++ b/x-pack/winlogbeat/Jenkinsfile.yml
@@ -18,4 +18,14 @@ stages:
         withModule: true
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+    windows-2016:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
             - "windows-2016"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/winlogbeat for windows-2016"
+            labels:
+                - "windows-2016"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags