diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index 51f30c263022..cdff56e1a133 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -217,6 +217,11 @@ stages:
             BITS: 64
             NPY_USE_BLAS_ILP64: '1'
             OPENBLAS_SUFFIX: '64_'
+          PyPy36-32bit:
+            PYTHON_VERSION: 'PyPy3.6'
+            PYTHON_ARCH: 'x32'
+            TEST_MODE: fast
+            BITS: 32
     steps:
     - template: azure-steps-windows.yml
   - job: Linux_PyPy3
diff --git a/azure-steps-windows.yml b/azure-steps-windows.yml
index 4c4e1d177e89..28762f5d9528 100644
--- a/azure-steps-windows.yml
+++ b/azure-steps-windows.yml
@@ -4,10 +4,31 @@ steps:
     versionSpec: $(PYTHON_VERSION)
     addToPath: true
     architecture: $(PYTHON_ARCH)
-- script: python -m pip install --upgrade pip
+  condition: not(contains(variables['PYTHON_VERSION'], 'PyPy'))
+- powershell: |
+    $url = "http://buildbot.pypy.org/nightly/py3.6/pypy-c-jit-latest-win32.zip"
+    $output = "pypy.zip"
+    $wc = New-Object System.Net.WebClient
+    $wc.DownloadFile($url, $output)
+    echo "downloaded $url to $output"
+    mkdir pypy3
+    Expand-Archive $output -DestinationPath pypy3
+    move pypy3/pypy-c-*/* pypy3
+    cp pypy3/pypy3.exe pypy3/python.exe
+    $pypypath = Join-Path (Get-Item .).FullName pypy3
+    $env:Path = $pypypath + ";" + $env:Path
+    setx PATH $env:Path
+    python -mensurepip
+    echo "##vso[task.prependpath]$pypypath"
+  condition: contains(variables['PYTHON_VERSION'], 'PyPy')
+  displayName: "Install PyPy pre-release"
+
+- script: python -m pip install --upgrade pip wheel
   displayName: 'Install tools'
+
 - script: python -m pip install -r test_requirements.txt
   displayName: 'Install dependencies; some are optional to avoid test skips'
+
 - powershell: |
     $ErrorActionPreference = "Stop"
     # Download and get the path to "openblas.a". We cannot copy it
@@ -16,7 +37,7 @@ steps:
     # since OPENBLAS will be picked up by the openblas discovery
     $target = $(python tools/openblas_support.py)
     mkdir openblas
-    echo Copying $target to openblas/openblas$env:OPENBLAS_SUFFIX.a
+    echo "Copying $target to openblas/openblas$env:OPENBLAS_SUFFIX.a"
     cp $target openblas/openblas$env:OPENBLAS_SUFFIX.a
     If ( Test-Path env:NPY_USE_BLAS_ILP64 ){
         echo "##vso[task.setvariable variable=OPENBLAS64_]$pwd\openblas"
@@ -27,35 +48,40 @@ steps:
 
 - powershell: |
     choco install -y mingw --forcex86 --force --version=7.3.0
+    refreshenv
   displayName: 'Install 32-bit mingw for 32-bit builds'
   condition: eq(variables['BITS'], 32)
 # NOTE: for Windows builds it seems much more tractable to use runtests.py
 # vs. manual setup.py and then runtests.py for testing only
+
 - powershell: |
     If ($(BITS) -eq 32) {
         $env:CFLAGS = "-m32"
         $env:LDFLAGS = "-m32"
         $env:PATH = "C:\\ProgramData\\chocolatey\\lib\\mingw\\tools\\install\\mingw$(BITS)\\bin;" + $env:PATH
-        refreshenv
     }
     python -c "from tools import openblas_support; openblas_support.make_init('numpy')"
-    pip wheel -v -v -v --no-build-isolation --no-use-pep517 --wheel-dir=dist .
+    python -m pip wheel -v -v -v --no-build-isolation --no-use-pep517 --wheel-dir=dist .
 
     ls dist -r | Foreach-Object {
-        pip install $_.FullName
+        python -m pip install $_.FullName
     }
   displayName: 'Build NumPy'
+
 - bash: |
     pushd . && cd .. && target=$(python -c "import numpy, os; print(os.path.abspath(os.path.join(os.path.dirname(numpy.__file__), '.libs')))") && popd
-    pip download -d destination --only-binary :all: --no-deps numpy==1.14
+    python -m pip download -d destination --only-binary :all: --no-deps numpy==1.14
     cd destination && unzip numpy*.whl && cp numpy/.libs/*.dll $target
     ls $target
   displayName: 'Add extraneous & older DLL to numpy/.libs to probe DLL handling robustness'
   condition: eq(variables['PYTHON_VERSION'], '3.6')
 - script: pushd . && cd .. && python -c "from ctypes import windll; windll.kernel32.SetDefaultDllDirectories(0x00000800); import numpy" && popd
   displayName: 'For gh-12667; Windows DLL resolution'
+  condition: eq(variables['PYTHON_VERSION'], '3.6')
+
 - script: python runtests.py -n --show-build-log --mode=$(TEST_MODE) -- -rsx --junitxml=junit/test-results.xml
   displayName: 'Run NumPy Test Suite'
+
 - task: PublishTestResults@2
   condition: succeededOrFailed()
   inputs: