diff --git a/.github/docker/Dockerfile.win b/.github/docker/Dockerfile.win
new file mode 100644
index 0000000..2f0409c
--- /dev/null
+++ b/.github/docker/Dockerfile.win
@@ -0,0 +1,23 @@
+#escape=`
+FROM mcr.microsoft.com/windows/servercore:ltsc2016
+
+# Set the Node.js version you want to install
+ENV NODE_VERSION 16.20.1
+
+# Download and install Node.js
+RUN powershell -Command `
+    $ErrorActionPreference = 'Stop'; `
+    Invoke-WebRequest -Uri https://nodejs.org/dist/v$env:NODE_VERSION/node-v$env:NODE_VERSION-win-x64.zip -OutFile node.zip; `
+    Expand-Archive -Path node.zip -DestinationPath C:\; `
+    Rename-Item -Path C:\node-v$env:NODE_VERSION-win-x64 -NewName C:\nodejs; `
+    Remove-Item -Force node.zip
+
+# Add Node.js to PATH
+ENV PATH="C:\nodejs;C:\nodejs\node_modules\npm\bin;${PATH}"
+
+WORKDIR "C:\mongodb-client-encryption"
+COPY . .
+
+RUN node "C:\mongodb-client-encryption\.github\scripts\libmongocrypt.mjs"
+
+CMD ["ping", "-i", "20", "localhost"]
diff --git a/.github/scripts/build_linux.mjs b/.github/scripts/buildx.mjs
similarity index 80%
rename from .github/scripts/build_linux.mjs
rename to .github/scripts/buildx.mjs
index 45562d8..fb5f342 100644
--- a/.github/scripts/build_linux.mjs
+++ b/.github/scripts/buildx.mjs
@@ -13,7 +13,7 @@ function resolveRoot(...paths) {
 
 /** `xtrace` style command runner, uses spawn so that stdio is inherited */
 async function run(command, args = [], options = {}) {
-    const commandDetails = `+ ${command} ${args.join(' ')}${options.cwd ? ` (in: ${options.cwd})` : ''}`
+  const commandDetails = `+ ${command} ${args.join(' ')}${options.cwd ? ` (in: ${options.cwd})` : ''}`;
   console.error(commandDetails);
   const proc = child_process.spawn(command, args, {
     stdio: 'inherit',
@@ -37,16 +37,23 @@ async function main() {
     await run('docker', ['buildx', 'create', '--name', 'builder', '--bootstrap', '--use']);
   }
 
+  const platform =
+    process.platform === 'win32' ? 'windows/amd64' : 'linux/s390x,linux/arm64,linux/amd64';
+  const dockerFile =
+    process.platform === 'win32'
+      ? resolveRoot('./.github/docker/Dockerfile.win')
+      : resolveRoot('./.github/docker/Dockerfile.glibc');
+
   await run('docker', [
     'buildx',
     'build',
     // '--progress=plain', // By default buildx detects tty and does some fancy collapsing, set progress=plain for debugging
     '--platform',
-    'linux/s390x,linux/arm64,linux/amd64',
+    platform,
     '--output',
     'type=local,dest=./prebuilds,platform-split=false',
     '-f',
-    resolveRoot('./.github/docker/Dockerfile.glibc'),
+    dockerFile,
     resolveRoot('.')
   ]);
 
diff --git a/.github/scripts/libmongocrypt.mjs b/.github/scripts/libmongocrypt.mjs
index fb0ccd1..a5f6a54 100644
--- a/.github/scripts/libmongocrypt.mjs
+++ b/.github/scripts/libmongocrypt.mjs
@@ -174,7 +174,10 @@ export async function downloadLibMongoCrypt(nodeDepsRoot, { ref }) {
 
   const unzipArgs = ['-xzv', '-C', `_libmongocrypt-${ref}`, `${prebuild}/nocrypto`];
   console.error(`+ tar ${unzipArgs.join(' ')}`);
-  const unzip = child_process.spawn('tar', unzipArgs, { stdio: ['pipe', 'inherit'], cwd: resolveRoot('.') });
+  const unzip = child_process.spawn('tar', unzipArgs, {
+    stdio: ['pipe', 'inherit'],
+    cwd: resolveRoot('.')
+  });
 
   const [response] = await events.once(https.get(downloadURL), 'response');
 
@@ -230,7 +233,15 @@ async function main() {
   await run('npm', ['install', '--ignore-scripts']);
   // The prebuild command will make both a .node file in `./build` (local and CI testing will run on current code)
   // it will also produce `./prebuild/xx.tgz`. prebuild has GH upload functionality.
+  if (process.platform === 'win32') {
+    await fs.writeFile(resolveRoot('.npmrc'), 'msvs_version=2017\n', 'utf8');
+  }
+
   await run('npm', ['run', 'prebuild']);
+
+  if (process.platform === 'win32') {
+    await fs.rm(resolveRoot('.npmrc'), { force: true });
+  }
 }
 
 await main();
diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 17cce5a..8635870 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -8,46 +8,74 @@ on:
 name: build
 
 jobs:
-  builds:
+  macos_builds:
     outputs:
       artifact_id: ${{ steps.upload.outputs.artifact-id }}
     strategy:
       matrix:
-        os: [ubuntu-latest, windows-2019, macos-11, macos-latest]
+        os: [macos-11, macos-latest]
     runs-on: ${{ matrix.os }}
     steps:
       - uses: actions/checkout@v4
 
-      - if: ${{ runner.os == 'Linux' }}
-        name: Set up QEMU
+      - name: Build ${{ matrix.os }} Prebuild
+        run: node .github/scripts/libmongocrypt.mjs
+        shell: bash
+
+      - id: upload
+        name: Upload prebuild
+        uses: actions/upload-artifact@v4
+        with:
+          name: build-${{ matrix.os }}
+          path: prebuilds/
+          if-no-files-found: 'error'
+          retention-days: 1
+
+  linux_builds:
+    outputs:
+      artifact_id: ${{ steps.upload.outputs.artifact-id }}
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: Set up QEMU
         uses: docker/setup-qemu-action@v3
 
-      - if: ${{ runner.os == 'Linux' }}
-        name: Set up Docker Buildx
+      - name: Set up Docker Buildx
         uses: docker/setup-buildx-action@v3
 
-      - if: ${{ runner.os == 'Linux' }}
-        name: Build ${{ runner.os }} Prebuild
-        run: node .github/scripts/build_linux.mjs
+      - name: Run Buildx
+        run: node .github/scripts/buildx.mjs
 
-      - if: ${{ runner.os != 'Linux' }}
-        name: Setup nodejs
-        uses: actions/setup-node@v4
+      - id: upload
+        name: Upload prebuild
+        uses: actions/upload-artifact@v4
         with:
-          node-version: 'lts/*'
-          cache: 'npm'
-          registry-url: 'https://registry.npmjs.org'
+          name: build-linux
+          path: prebuilds/
+          if-no-files-found: 'error'
+          retention-days: 1
 
-      - if: ${{ runner.os != 'Linux' }}
-        name: Build ${{ runner.os }} Prebuild
-        run: node .github/scripts/libmongocrypt.mjs
-        shell: bash
+  windows_builds:
+    runs-on: windows-latest
+    outputs:
+      artifact_id: ${{ steps.upload.outputs.artifact-id }}
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: Build Docker image
+        run: |
+          docker build -f .github/docker/Dockerfile.win --tag m:latest .
+          docker run -d --name m m:latest
+          docker cp m:C:\\mongodb-client-encryption\\prebuilds prebuilds
+          docker stop m
+          docker rm m:latest
 
       - id: upload
         name: Upload prebuild
         uses: actions/upload-artifact@v4
         with:
-          name: build-${{ matrix.os }}
+          name: build-windows
           path: prebuilds/
           if-no-files-found: 'error'
           retention-days: 1