diff --git a/auditbeat/Jenkinsfile.yml b/auditbeat/Jenkinsfile.yml
index 84bef6a6ceb..6f5374224d4 100644
--- a/auditbeat/Jenkinsfile.yml
+++ b/auditbeat/Jenkinsfile.yml
@@ -34,3 +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/filebeat/Jenkinsfile.yml b/filebeat/Jenkinsfile.yml
index d0f36b24536..6b5a23b7fb2 100644
--- a/filebeat/Jenkinsfile.yml
+++ b/filebeat/Jenkinsfile.yml
@@ -33,3 +33,4 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+            #- "windows-2016"  https://github.com/elastic/beats/issues/19641
diff --git a/heartbeat/Jenkinsfile.yml b/heartbeat/Jenkinsfile.yml
index 71369fd5814..c465138791b 100644
--- a/heartbeat/Jenkinsfile.yml
+++ b/heartbeat/Jenkinsfile.yml
@@ -32,3 +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 09f1a49b9e2..9860919d006 100644
--- a/metricbeat/Jenkinsfile.yml
+++ b/metricbeat/Jenkinsfile.yml
@@ -40,3 +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 580826bf2fa..f755f322477 100644
--- a/packetbeat/Jenkinsfile.yml
+++ b/packetbeat/Jenkinsfile.yml
@@ -32,3 +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 74eb55586d0..82ce7912d3b 100644
--- a/winlogbeat/Jenkinsfile.yml
+++ b/winlogbeat/Jenkinsfile.yml
@@ -19,3 +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 3bb96fbbc64..969aa0a8e08 100644
--- a/x-pack/auditbeat/Jenkinsfile.yml
+++ b/x-pack/auditbeat/Jenkinsfile.yml
@@ -33,3 +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 f5074df5965..04a6b227721 100644
--- a/x-pack/elastic-agent/Jenkinsfile.yml
+++ b/x-pack/elastic-agent/Jenkinsfile.yml
@@ -32,3 +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 437f4c074db..b2db448f532 100644
--- a/x-pack/filebeat/Jenkinsfile.yml
+++ b/x-pack/filebeat/Jenkinsfile.yml
@@ -33,3 +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 20a8527eae3..a8d42ce5fb9 100644
--- a/x-pack/functionbeat/Jenkinsfile.yml
+++ b/x-pack/functionbeat/Jenkinsfile.yml
@@ -32,3 +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 00fa2c1265e..d02dc5e16aa 100644
--- a/x-pack/metricbeat/Jenkinsfile.yml
+++ b/x-pack/metricbeat/Jenkinsfile.yml
@@ -35,3 +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 41257081e1f..fd30546f70a 100644
--- a/x-pack/packetbeat/Jenkinsfile.yml
+++ b/x-pack/packetbeat/Jenkinsfile.yml
@@ -18,3 +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 396d1f03a7c..788d4a35369 100644
--- a/x-pack/winlogbeat/Jenkinsfile.yml
+++ b/x-pack/winlogbeat/Jenkinsfile.yml
@@ -18,3 +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