diff --git a/shippable.yml b/shippable.yml
index 1426589808..ad3c253e8a 100644
--- a/shippable.yml
+++ b/shippable.yml
@@ -48,6 +48,13 @@ matrix:
     - env: T=windows/2016/4
     - env: T=windows/2019/4
 
+    - env: T=windows/2008/5
+    - env: T=windows/2008-R2/5
+    - env: T=windows/2012/5
+    - env: T=windows/2012-R2/5
+    - env: T=windows/2016/5
+    - env: T=windows/2019/5
+
     - env: T=network
 
     - env: T=osx/10.11/1
diff --git a/test/integration/targets/win_chocolatey/aliases b/test/integration/targets/win_chocolatey/aliases
index 215e0b0692..4f4664b685 100644
--- a/test/integration/targets/win_chocolatey/aliases
+++ b/test/integration/targets/win_chocolatey/aliases
@@ -1 +1 @@
-shippable/windows/group4
+shippable/windows/group5
diff --git a/test/integration/targets/win_copy/aliases b/test/integration/targets/win_copy/aliases
index 3cf5b97e80..4f4664b685 100644
--- a/test/integration/targets/win_copy/aliases
+++ b/test/integration/targets/win_copy/aliases
@@ -1 +1 @@
-shippable/windows/group3
+shippable/windows/group5
diff --git a/test/integration/targets/win_get_url/aliases b/test/integration/targets/win_get_url/aliases
index 4cd27b3cb2..4f4664b685 100644
--- a/test/integration/targets/win_get_url/aliases
+++ b/test/integration/targets/win_get_url/aliases
@@ -1 +1 @@
-shippable/windows/group1
+shippable/windows/group5
diff --git a/test/integration/targets/win_iis_webbinding/aliases b/test/integration/targets/win_iis_webbinding/aliases
index 3cf5b97e80..4f4664b685 100644
--- a/test/integration/targets/win_iis_webbinding/aliases
+++ b/test/integration/targets/win_iis_webbinding/aliases
@@ -1 +1 @@
-shippable/windows/group3
+shippable/windows/group5
diff --git a/test/integration/targets/win_mapped_drive/aliases b/test/integration/targets/win_mapped_drive/aliases
index 4cd27b3cb2..4f4664b685 100644
--- a/test/integration/targets/win_mapped_drive/aliases
+++ b/test/integration/targets/win_mapped_drive/aliases
@@ -1 +1 @@
-shippable/windows/group1
+shippable/windows/group5
diff --git a/test/integration/targets/win_regedit/aliases b/test/integration/targets/win_regedit/aliases
index 423ce39108..4f4664b685 100644
--- a/test/integration/targets/win_regedit/aliases
+++ b/test/integration/targets/win_regedit/aliases
@@ -1 +1 @@
-shippable/windows/group2
+shippable/windows/group5
diff --git a/test/integration/targets/win_scheduled_task/aliases b/test/integration/targets/win_scheduled_task/aliases
index 423ce39108..4f4664b685 100644
--- a/test/integration/targets/win_scheduled_task/aliases
+++ b/test/integration/targets/win_scheduled_task/aliases
@@ -1 +1 @@
-shippable/windows/group2
+shippable/windows/group5