diff --git a/.appveyor.yml b/.appveyor.yml
index fde3a6aa..6ee159e9 100644
--- a/.appveyor.yml
+++ b/.appveyor.yml
@@ -1,6 +1,9 @@
 # NOTE: this file is auto-generated via ci/bootstrap.py (ci/templates/.appveyor.yml).
 version: '{branch}-{build}'
 build: off
+image:
+  - Visual Studio 2015
+  - Visual Studio 2019
 environment:
   matrix:
     - TOXENV: check
@@ -8,8 +11,26 @@ environment:
     - TOXENV: 'py35-pytest46-xdist127-coverage55'
     - TOXENV: 'py36-pytest46-xdist127-coverage55,py36-pytest46-xdist133-coverage55,py36-pytest54-xdist133-coverage55,py36-pytest62-xdist202-coverage55'
     - TOXENV: 'py37-pytest46-xdist127-coverage55,py37-pytest46-xdist133-coverage55,py37-pytest54-xdist133-coverage55,py37-pytest62-xdist202-coverage55'
+    - TOXENV: 'py38-pytest46-xdist133-coverage55,py38-pytest54-xdist133-coverage55,py38-pytest62-xdist202-coverage55'
+    - TOXENV: 'py39-pytest62-xdist202-coverage55'
     - TOXENV: 'pypy-pytest46-xdist127-coverage55'
-
+    - TOXENV: 'pypy3-pytest46-xdist127-coverage55,pypy3-pytest46-xdist133-coverage55,pypy3-pytest54-xdist133-coverage55,pypy3-pytest62-xdist202-coverage55'
+matrix:
+  exclude:
+    - image: Visual Studio 2015
+      TOXENV: 'py27-pytest46-xdist127-coverage55'
+    - image: Visual Studio 2019
+      TOXENV: 'py36-pytest46-xdist127-coverage55,py36-pytest46-xdist133-coverage55,py36-pytest54-xdist133-coverage55,py36-pytest62-xdist202-coverage55'
+    - image: Visual Studio 2019
+      TOXENV: 'py37-pytest46-xdist127-coverage55,py37-pytest46-xdist133-coverage55,py37-pytest54-xdist133-coverage55,py37-pytest62-xdist202-coverage55'
+    - image: Visual Studio 2019
+      TOXENV: 'py38-pytest46-xdist133-coverage55,py38-pytest54-xdist133-coverage55,py38-pytest62-xdist202-coverage55'
+    - image: Visual Studio 2019
+      TOXENV: 'py39-pytest62-xdist202-coverage55'
+    - image: Visual Studio 2019
+      TOXENV: 'pypy-pytest46-xdist127-coverage55'
+    - image: Visual Studio 2019
+      TOXENV: 'pypy3-pytest46-xdist127-coverage55,pypy3-pytest46-xdist133-coverage55,pypy3-pytest54-xdist133-coverage55,pypy3-pytest62-xdist202-coverage55'
 init:
   - ps: echo $env:TOXENV
   - ps: ls C:\Python*
diff --git a/ci/templates/.appveyor.yml b/ci/templates/.appveyor.yml
index 92630e15..01ca3493 100644
--- a/ci/templates/.appveyor.yml
+++ b/ci/templates/.appveyor.yml
@@ -1,5 +1,8 @@
 version: '{branch}-{build}'
 build: off
+image:
+  - Visual Studio 2015
+  - Visual Studio 2019
 environment:
   matrix:
     - TOXENV: check
@@ -7,8 +10,26 @@ environment:
     - TOXENV: '{{ py35_environments|join(",") }}'
     - TOXENV: '{{ py36_environments|join(",") }}'
     - TOXENV: '{{ py37_environments|join(",") }}'
+    - TOXENV: '{{ py38_environments|join(",") }}'
+    - TOXENV: '{{ py39_environments|join(",") }}'
     - TOXENV: '{{ pypy_environments|join(",") }}'
-
+    - TOXENV: '{{ pypy3_environments|join(",") }}'
+matrix:
+  exclude:
+    - image: Visual Studio 2015
+      TOXENV: '{{ py27_environments|join(",") }}'
+    - image: Visual Studio 2019
+      TOXENV: '{{ py36_environments|join(",") }}'
+    - image: Visual Studio 2019
+      TOXENV: '{{ py37_environments|join(",") }}'
+    - image: Visual Studio 2019
+      TOXENV: '{{ py38_environments|join(",") }}'
+    - image: Visual Studio 2019
+      TOXENV: '{{ py39_environments|join(",") }}'
+    - image: Visual Studio 2019
+      TOXENV: '{{ pypy_environments|join(",") }}'
+    - image: Visual Studio 2019
+      TOXENV: '{{ pypy3_environments|join(",") }}'
 init:
   - ps: echo $env:TOXENV
   - ps: ls C:\Python*