diff --git a/common.js b/common.js
index d505d0a..feb7e15 100644
--- a/common.js
+++ b/common.js
@@ -155,7 +155,15 @@ export function win2nix(path) {
   return path.replace(/\\/g, '/').replace(/ /g, '\\ ')
 }
 
+// JRuby is installed after setupPath is called, so folder doesn't exist
+function rubyIsUCRT(path) {
+  return !!(fs.existsSync(path) &&
+    fs.readdirSync(path, { withFileTypes: true }).find(dirent =>
+      dirent.isFile() && dirent.name.match(/^x64-ucrt-ruby\d{3}\.dll$/)))
+}
+
 export function setupPath(newPathEntries) {
+  let win_build_sys = null
   const envPath = windows ? 'Path' : 'PATH'
   const originalPath = process.env[envPath].split(path.delimiter)
   let cleanPath = originalPath.filter(entry => !/\bruby\b/i.test(entry))
@@ -176,8 +184,11 @@ export function setupPath(newPathEntries) {
   // Then add new path entries using core.addPath()
   let newPath
   if (windows) {
+    // main Ruby dll determines whether mingw or ucrt build
+    win_build_sys = rubyIsUCRT(newPathEntries[0]) ? 'ucrt64' : 'mingw64'
+
     // add MSYS2 in path for all Rubies on Windows, as it provides a better bash shell and a native toolchain
-    const msys2 = ['C:\\msys64\\mingw64\\bin', 'C:\\msys64\\usr\\bin']
+    const msys2 = [`C:\\msys64\\${win_build_sys}\\bin`, 'C:\\msys64\\usr\\bin']
     newPath = [...newPathEntries, ...msys2]
   } else {
     newPath = newPathEntries
@@ -189,4 +200,5 @@ export function setupPath(newPathEntries) {
   core.endGroup()
 
   core.addPath(newPath.join(path.delimiter))
+  return win_build_sys
 }
diff --git a/windows.js b/windows.js
index b987dc4..3b7d6b6 100644
--- a/windows.js
+++ b/windows.js
@@ -50,15 +50,53 @@ export async function install(platform, engine, version) {
 
   let toolchainPaths = (version === 'mswin') ? await setupMSWin() : await setupMingw(version)
 
-  common.setupPath([`${rubyPrefix}\\bin`, ...toolchainPaths])
-
   if (!inToolCache) {
     await downloadAndExtract(engine, version, url, base, rubyPrefix);
   }
 
+  const winMSYS2Type = common.setupPath([`${rubyPrefix}\\bin`, ...toolchainPaths])
+
+  const virtualEnv = common.getVirtualEnvironmentName()
+
+  if (( winMSYS2Type === 'ucrt64') || !['windows-2019', 'windows-2016'].includes(virtualEnv)) {
+    await installGCCTools(winMSYS2Type)
+
+    if (!['windows-2019', 'windows-2016'].includes(virtualEnv)) {
+      await installMSY2Tools()
+    }
+  }
+
   return rubyPrefix
 }
 
+// Actions windows-2022 image does not contain any mingw or ucrt build tools.  Install tools for it,
+// and also install ucrt tools on earlier versions, which have msys2 and mingw tools preinstalled.
+async function installGCCTools(type) {
+  const downloadPath = await common.measure(`Download ${type} build tools`, async () => {
+    let url = `https://github.com/MSP-Greg/setup-msys2-gcc/releases/download/msys2-gcc-pkgs/${type}.7z`
+    console.log(url)
+    return await tc.downloadTool(url)
+  })
+
+  await common.measure(`Extracting ${type} build tools`, async () =>
+    // -aoa overwrite existing, -bd disable progress indicator
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', '-oC:\\msys64'], { silent: true }))
+}
+
+// Actions windows-2022 image does not contain any MSYS2 build tools.  Install tools for it.
+// A subset of the MSYS2 base-devel group
+async function installMSY2Tools() {
+  const downloadPath = await common.measure(`Download msys2 build tools`, async () => {
+    let url = `https://github.com/MSP-Greg/setup-msys2-gcc/releases/download/msys2-gcc-pkgs/msys2.7z`
+    console.log(url)
+    return await tc.downloadTool(url)
+  })
+
+  await common.measure(`Extracting msys2 build tools`, async () =>
+    // -aoa overwrite existing, -bd disable progress indicator
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', '-oC:\\msys64'], { silent: true }))
+}
+
 async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
   const parentDir = path.dirname(rubyPrefix)
 
@@ -68,7 +106,7 @@ async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
   })
 
   await common.measure('Extracting Ruby', async () =>
-    exec.exec('7z', ['x', downloadPath, `-xr!${base}\\share\\doc`, `-o${parentDir}`], { silent: true }))
+    exec.exec('7z', ['x', downloadPath, '-bd', `-xr!${base}\\share\\doc`, `-o${parentDir}`], { silent: true }))
 
   if (base !== path.basename(rubyPrefix)) {
     await io.mv(path.join(parentDir, base), rubyPrefix)