diff --git a/shippable.yml b/shippable.yml
index df16be224a..75ba5e8578 100644
--- a/shippable.yml
+++ b/shippable.yml
@@ -24,24 +24,28 @@ matrix:
     - env: T=windows/2012/1
     - env: T=windows/2012-R2/1
     - env: T=windows/2016/1
+    - env: T=windows/2019/1
 
     - env: T=windows/2008/2
     - env: T=windows/2008-R2/2
     - env: T=windows/2012/2
     - env: T=windows/2012-R2/2
     - env: T=windows/2016/2
+    - env: T=windows/2019/2
 
     - env: T=windows/2008/3
     - env: T=windows/2008-R2/3
     - env: T=windows/2012/3
     - env: T=windows/2012-R2/3
     - env: T=windows/2016/3
+    - env: T=windows/2019/3
 
     - env: T=windows/2008/4
     - env: T=windows/2008-R2/4
     - env: T=windows/2012/4
     - env: T=windows/2012-R2/4
     - env: T=windows/2016/4
+    - env: T=windows/2019/4
 
     - env: T=network
 
diff --git a/test/runner/completion/windows.txt b/test/runner/completion/windows.txt
index 6924be4e13..a4f3bf589b 100644
--- a/test/runner/completion/windows.txt
+++ b/test/runner/completion/windows.txt
@@ -3,3 +3,4 @@
 2012
 2012-R2
 2016
+2019
\ No newline at end of file