diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 4e3824fb..58f19862 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -79,7 +79,7 @@ jobs:
           git commit -s -m "chore: self mutation"
           git push origin HEAD:$PULL_REQUEST_REF
   rosetta-compat:
-    runs-on: ubuntu-latest
+    runs-on: ${{ matrix.os }}
     permissions: {}
     env:
       CI: "true"
@@ -101,11 +101,14 @@ jobs:
       - name: compile+test
         run: |-
           npx projen compile
-          npx projen test
+          npx projen test --runInBand
       - name: Check Rosetta version
         run: test $(npx jsii-rosetta --version) = "${{ matrix.rosetta }}"
     strategy:
       matrix:
+        include:
+          - rosetta: 5.4.0
+            os: windows-latest
         rosetta:
           - 1.85.0
           - 5.0.14
@@ -113,3 +116,5 @@ jobs:
           - 5.2.0
           - 5.3.0
           - 5.4.0
+        os:
+          - ubuntu-latest
diff --git a/.projenrc.ts b/.projenrc.ts
index bf78d740..9dd3f361 100644
--- a/.projenrc.ts
+++ b/.projenrc.ts
@@ -47,6 +47,11 @@ const project = new CdklabsTypeScriptProject({
   jestOptions: {
     jestConfig: {
       setupFilesAfterEnv: ['<rootDir>/test/setup-jest.ts'],
+      testMatch: [
+        // On Windows the standard tests paths are not matched
+        // Use this simplified version instead that works good enough in this repo
+        '<rootDir>/test/**/*.test.ts',
+      ],
     },
   },
   tsconfig: {
diff --git a/package.json b/package.json
index ecf09ac2..fc63d553 100644
--- a/package.json
+++ b/package.json
@@ -78,6 +78,7 @@
       "<rootDir>/test/setup-jest.ts"
     ],
     "testMatch": [
+      "<rootDir>/test/**/*.test.ts",
       "<rootDir>/src/**/__tests__/**/*.ts?(x)",
       "<rootDir>/(test|src)/**/*(*.)@(spec|test).ts?(x)"
     ],
diff --git a/projenrc/rosetta.ts b/projenrc/rosetta.ts
index 4d0c8c0c..229c3d74 100644
--- a/projenrc/rosetta.ts
+++ b/projenrc/rosetta.ts
@@ -25,11 +25,14 @@ export class RosettaPeerDependency extends Component {
     super(project);
 
     const constraint = this.calculateVersionConstraint(options.supportedVersions);
+    const minVersions = this.calculateMinimalVersions(options.supportedVersions);
+    const latestVersion = this.calculateLatestVersion(options.supportedVersions);
+
     project.addDevDeps(constraint);
     project.addPeerDeps(constraint);
 
     project.github?.tryFindWorkflow('build')?.addJob('rosetta-compat', {
-      runsOn: ['ubuntu-latest'],
+      runsOn: ['${{ matrix.os }}'],
       permissions: {},
       env: {
         CI: 'true',
@@ -38,8 +41,13 @@ export class RosettaPeerDependency extends Component {
       strategy: {
         matrix: {
           domain: {
-            rosetta: this.calculateMinimalVersions(options.supportedVersions),
+            rosetta: minVersions,
+            os: ['ubuntu-latest'],
           },
+          include: [{
+            rosetta: latestVersion,
+            os: 'windows-latest',
+          }],
         },
       },
       steps: [{
@@ -68,7 +76,7 @@ export class RosettaPeerDependency extends Component {
       },
       {
         name: 'compile+test',
-        run: ['npx projen compile', 'npx projen test'].join('\n'),
+        run: ['npx projen compile', 'npx projen test --runInBand'].join('\n'),
       },
       {
         name: 'Check Rosetta version',
@@ -95,4 +103,9 @@ export class RosettaPeerDependency extends Component {
 
     return discoveredVersions;
   }
+
+  private calculateLatestVersion(versions: RosettaPeerDependencyOptions['supportedVersions']): string {
+    const discoveredVersions = this.calculateMinimalVersions(versions);
+    return discoveredVersions.sort().pop() ?? 'latest';
+  }
 }
diff --git a/src/cli.ts b/src/cli.ts
index 5ecac7c4..eba98920 100644
--- a/src/cli.ts
+++ b/src/cli.ts
@@ -59,7 +59,7 @@ export async function main() {
     .option('readme', { alias: 'r', type: 'boolean', required: false, desc: 'Include the user defined README.md in the documentation.' })
     .option('submodule', { alias: 's', type: 'string', required: false, desc: 'Generate docs for a specific submodule (or "root")' })
     .option('split-by-submodule', { type: 'boolean', required: false, desc: 'Generate a separate file for each submodule' })
-    .example('$0', 'Generate documentation for the current module as a single file (auto-resolves node depedencies)')
+    .example('$0', 'Generate documentation for the current module as a single file (auto-resolves node dependencies)')
     .argv;
 
   const submodule = args.submodule === 'root' ? undefined : args.submodule;
diff --git a/src/docgen/view/_npm.ts b/src/docgen/view/_npm.ts
index c0201a11..f81ce153 100644
--- a/src/docgen/view/_npm.ts
+++ b/src/docgen/view/_npm.ts
@@ -38,7 +38,7 @@ export class Npm {
       // code execution as part of the install command using npm hooks. (e.g postInstall)
       '--ignore-scripts',
       // save time by not running audit
-      '--no-autit',
+      '--no-audit',
       // ensures npm does not insert anything in $PATH
       '--no-bin-links',
       // don't write or update a package-lock.json file
@@ -132,17 +132,20 @@ export class Npm {
       return this.#npmCommand;
     }
 
+    // Get the platform specific npm command
+    const npm = npmPlatformAwareCommand();
+
     try {
       // If the npm in $PATH is >= v7, we can use that directly. The
       // `npm version --json` command returns a JSON object containing the
       // versions of several components (npm, node, v8, etc...). We are only
       // interested in the `npm` key here.
       const { exitCode, stdout } = await this.runCommand(
-        'npm', ['version', '--json'],
+        npm, ['version', '--json'],
         chunksToObject,
       );
       if (exitCode === 0 && major((stdout as any).npm) >= 7) {
-        return this.#npmCommand = 'npm';
+        return this.#npmCommand = npm;
       }
     } catch (e) {
       this.logger('Could not determine version of npm in $PATH:', e);
@@ -152,7 +155,7 @@ export class Npm {
     // the full type system.
     this.logger('The npm in $PATH is not >= v7. Installing npm@8 locally...');
     const result = await this.runCommand(
-      'npm',
+      npm,
       ['install', 'npm@8', '--no-package-lock', '--no-save', '--json'],
       chunksToObject,
       {
@@ -162,7 +165,7 @@ export class Npm {
     );
     assertSuccess(result);
 
-    this.#npmCommand = join(this.workingDirectory, 'node_modules', '.bin', 'npm');
+    this.#npmCommand = join(this.workingDirectory, 'node_modules', '.bin', npm);
     this.logger(`Done installing npm@8 at ${this.#npmCommand}`);
     return this.#npmCommand;
   }
@@ -188,7 +191,10 @@ export class Npm {
     options?: SpawnOptionsWithoutStdio,
   ): Promise<CommandResult<T>> {
     return new Promise<CommandResult<T>>((ok, ko) => {
-      const child = spawn(command, args, { ...options, stdio: ['inherit', 'pipe', 'pipe'] });
+      // On Windows, spawning a program ending in .cmd or .bat needs to run in a shell
+      // https://nodejs.org/en/blog/vulnerability/april-2024-security-releases-2
+      const shell = onWindows() && (command.endsWith('.cmd') || command.endsWith('.bat'));
+      const child = spawn(command, args, { shell, ...options, stdio: ['inherit', 'pipe', 'pipe'] });
       const stdout = new Array<Buffer>();
       child.stdout.on('data', (chunk) => {
         stdout.push(Buffer.from(chunk));
@@ -310,7 +316,7 @@ function chunksToObject(chunks: readonly Buffer[], encoding: BufferEncoding = 'u
     // observed these log lines always start with 'npm', so we filter those out.
     // for example: "npm notice New patch version of npm available! 8.1.0 -> 8.1.3"
     // for example: "npm ERR! must provide string spec"
-    const onlyJson = raw.split(os.EOL)
+    const onlyJson = raw.split(/[\r\n]+/) // split on any newlines, because npm returns inconsistent newline characters on Windows
       .filter(l => !l.startsWith('npm'))
       // Suppress debugger messages, if present...
       .filter(l => l !== 'Debugger attached.')
@@ -330,3 +336,22 @@ type ResponseObject =
   | { readonly error: { readonly code: string; readonly summary: string; readonly detail: string } }
   // The successful objects are treated as opaque blobs here
   | { readonly error: undefined; readonly [key: string]: unknown };
+
+/**
+ * Helper to detect if we are running on Windows.
+ */
+function onWindows() {
+  return process.platform === 'win32';
+}
+
+/**
+ * Get the npm binary path depending on the platform.
+ * @returns "npm.cmd" on Windows, otherwise "npm"
+ */
+function npmPlatformAwareCommand() {
+  if (onWindows()) {
+    return 'npm.cmd';
+  }
+
+  return 'npm';
+}
diff --git a/src/docgen/view/documentation.ts b/src/docgen/view/documentation.ts
index 5942b2cc..c915c61a 100644
--- a/src/docgen/view/documentation.ts
+++ b/src/docgen/view/documentation.ts
@@ -407,7 +407,14 @@ export class Documentation {
       });
 
       const ts = new reflect.TypeSystem();
-      for (let dotJsii of await glob.promise(`${this.assembliesDir}/**/${SPEC_FILE_NAME}`)) {
+
+      // assembliesDir might include backslashes on Windows.
+      // The glob pattern must only used forward slashes, so we pass the assembliesDir as CWD which does not have this restriction
+      const assemblies = await glob.promise(`**/${SPEC_FILE_NAME}`, {
+        cwd: path.normalize(this.assembliesDir),
+        absolute: true,
+      });
+      for (let dotJsii of assemblies) {
         // we only transliterate the top level assembly and not the entire type-system.
         // note that the only reason to translate dependant assemblies is to show code examples
         // for expanded python arguments - which we don't to right now anyway.
diff --git a/test/docgen/view/documentation.test.ts b/test/docgen/view/documentation.test.ts
index fb6104fd..00d0e961 100644
--- a/test/docgen/view/documentation.test.ts
+++ b/test/docgen/view/documentation.test.ts
@@ -76,7 +76,7 @@ test('package installation does not run lifecycle hooks, includes optional depen
   }
 });
 
-// This test is only revent when running on non-macOS platforms.
+// This test is only relevant when running on non-macOS platforms.
 (process.platform === 'darwin' ? test.skip : test)('package installation uses --force when EBADPLATFORM is encountered', async () => {
   // The package has a hard dependency on fsevents, which only supports macOS platforms.
   const docs = await Documentation.forPackage(