diff --git a/auditbeat/Jenkinsfile.yml b/auditbeat/Jenkinsfile.yml
index c68b5689f48..53c2707f4e0 100644
--- a/auditbeat/Jenkinsfile.yml
+++ b/auditbeat/Jenkinsfile.yml
@@ -47,6 +47,7 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+            #- "windows-2008-r2" https://github.com/elastic/beats/issues/19799
     windows-2016:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
diff --git a/filebeat/Jenkinsfile.yml b/filebeat/Jenkinsfile.yml
index d2e1d866526..e31dee8ccc9 100644
--- a/filebeat/Jenkinsfile.yml
+++ b/filebeat/Jenkinsfile.yml
@@ -46,6 +46,7 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+            #- "windows-2008-r2"  https://github.com/elastic/beats/issues/19795
     windows-2016:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
diff --git a/heartbeat/Jenkinsfile.yml b/heartbeat/Jenkinsfile.yml
index 032ec411892..8c891804a3c 100644
--- a/heartbeat/Jenkinsfile.yml
+++ b/heartbeat/Jenkinsfile.yml
@@ -78,4 +78,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
-
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test heartbeat for windows-2008"
+            labels:
+                - "windows-2008"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tag
diff --git a/metricbeat/Jenkinsfile.yml b/metricbeat/Jenkinsfile.yml
index e6c4ffcef0e..5b56c6d6338 100644
--- a/metricbeat/Jenkinsfile.yml
+++ b/metricbeat/Jenkinsfile.yml
@@ -40,6 +40,7 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+            #- "windows-2008-r2"  https://github.com/elastic/beats/issues/19800
     windows-2016:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
diff --git a/packetbeat/Jenkinsfile.yml b/packetbeat/Jenkinsfile.yml
index ef373bb5f15..417b0278f13 100644
--- a/packetbeat/Jenkinsfile.yml
+++ b/packetbeat/Jenkinsfile.yml
@@ -78,3 +78,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test packetbeat for windows-2008"
+            labels:
+                - "windows-2008"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags
diff --git a/winlogbeat/Jenkinsfile.yml b/winlogbeat/Jenkinsfile.yml
index 3b9c71bf0c3..45834e5f2b2 100644
--- a/winlogbeat/Jenkinsfile.yml
+++ b/winlogbeat/Jenkinsfile.yml
@@ -19,6 +19,7 @@ stages:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
             - "windows-2019"
+            #- "windows-2008-r2"  https://github.com/elastic/beats/issues/19798
     windows-2016:
         mage: "mage build unitTest"
         platforms:             ## override default labels in this specific stage.
diff --git a/x-pack/auditbeat/Jenkinsfile.yml b/x-pack/auditbeat/Jenkinsfile.yml
index f4e55ea6372..6c14dc249ad 100644
--- a/x-pack/auditbeat/Jenkinsfile.yml
+++ b/x-pack/auditbeat/Jenkinsfile.yml
@@ -79,3 +79,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test auditbeat for windows-2008"
+            labels:
+                - "windows-2008"
+            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 d324e3381af..1348b17b825 100644
--- a/x-pack/elastic-agent/Jenkinsfile.yml
+++ b/x-pack/elastic-agent/Jenkinsfile.yml
@@ -78,3 +78,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/elastic-agent for windows-2008"
+            labels:
+                - "windows-2008"
+            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 d28520b7c32..cd42a01cbcb 100644
--- a/x-pack/filebeat/Jenkinsfile.yml
+++ b/x-pack/filebeat/Jenkinsfile.yml
@@ -79,3 +79,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/filebeat for windows-2008"
+            labels:
+                - "windows-2008"
+            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 117d92e3179..c63ed28cdf2 100644
--- a/x-pack/functionbeat/Jenkinsfile.yml
+++ b/x-pack/functionbeat/Jenkinsfile.yml
@@ -76,3 +76,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/functionbeat for windows-2008"
+            labels:
+                - "windows-2008"
+            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 8506eb12e69..ed5d12dd7c7 100644
--- a/x-pack/metricbeat/Jenkinsfile.yml
+++ b/x-pack/metricbeat/Jenkinsfile.yml
@@ -68,3 +68,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/metricbeat for windows-2008"
+            labels:
+                - "windows-2008"
+            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 a3c11636dc6..00a7c1c6333 100644
--- a/x-pack/packetbeat/Jenkinsfile.yml
+++ b/x-pack/packetbeat/Jenkinsfile.yml
@@ -51,3 +51,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/winlogbeat for windows-2008"
+            labels:
+                - "windows-2008"
+            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 45dfcad9d45..0bb02dfbdef 100644
--- a/x-pack/winlogbeat/Jenkinsfile.yml
+++ b/x-pack/winlogbeat/Jenkinsfile.yml
@@ -51,3 +51,14 @@ stages:
                 - "windows-10"
             branches: true     ## for all the branches
             tags: true         ## for all the tags
+    windows-2008:
+        mage: "mage build unitTest"
+        platforms:             ## override default labels in this specific stage.
+            - "windows-2008-r2"
+        when:                  ## Override the top-level when.
+            comments:
+                - "/test x-pack/winlogbeat for windows-2008"
+            labels:
+                - "windows-2008"
+            branches: true     ## for all the branches
+            tags: true         ## for all the tags