diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index c5ec41c36..e680c23d3 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -53,6 +53,10 @@ jobs:
         env: [{ STATIC_DEPS: true }, { STATIC_DEPS: false }]
 
         include:
+          - os: windows-2016
+            python-version: 2.7
+            env: { STATIC_DEPS: true }  # always static
+
           - os: ubuntu-latest
             python-version: "3.9"
             env: {STATIC_DEPS: true, WITH_REFNANNY: true}
@@ -109,6 +113,8 @@ jobs:
 
           # Windows sub-jobs
           # ==============
+          - os: windows-2019
+            python-version: 2.7  # needs older image
           - os: windows-2019
             env: { STATIC_DEPS: false }  # always static