diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 5b97df88b..ad4ddce59 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -134,7 +134,7 @@ jobs:
             echo 'ridk is unavailable'
           }
         } elseif ($plat.Contains('mswin')) {
-          &"$env:VCPKG_INSTALLATION_ROOT\vcpkg" list
+          Get-ChildItem "$env:VCPKG_INSTALLATION_ROOT\installed\vcpkg\info"
         }
     - name: RbConfig::CONFIG
       run: ruby -rrbconfig -rpp -e 'pp RbConfig::CONFIG'
diff --git a/common.js b/common.js
index 43acc26c7..d45784634 100644
--- a/common.js
+++ b/common.js
@@ -12,7 +12,7 @@ const linuxOSInfo = require('linux-os-info')
 
 export const windows = (os.platform() === 'win32')
 // Extract to SSD on Windows, see https://github.com/ruby/setup-ruby/pull/14
-export const drive = (windows ? (process.env['GITHUB_WORKSPACE'] || 'C')[0] : undefined)
+export const drive = (windows ? (process.env['RUNNER_TEMP'] || 'C')[0] : undefined)
 
 export const inputs = {
   selfHosted: undefined
@@ -334,7 +334,7 @@ function engineToToolCacheName(engine) {
   }[engine]
 }
 
-export function getToolCacheRubyPrefix(platform, engine, version) {
+export function getToolCacheRubyPrefix(_platform, engine, version) {
   const toolCache = getToolCachePath()
   return path.join(toolCache, engineToToolCacheName(engine), version, os.arch())
 }
@@ -356,15 +356,7 @@ 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|vcruntime\d{3})-ruby\d{3}\.dll$/)))
-}
-
 export function setupPath(newPathEntries) {
-  let msys2Type = null
   const envPath = windows ? 'Path' : 'PATH'
   const originalPath = process.env[envPath].split(path.delimiter)
   let cleanPath = originalPath.filter(entry => !/\bruby\b/i.test(entry))
@@ -382,29 +374,13 @@ export function setupPath(newPathEntries) {
     core.exportVariable(envPath, cleanPath.join(path.delimiter))
   }
 
-  // Then add new path entries using core.addPath()
-  let newPath
-  const windowsToolchain = core.getInput('windows-toolchain')
-  if (windows && windowsToolchain !== 'none') {
-    // main Ruby dll determines whether mingw or ucrt build
-    msys2Type = os.arch() === 'arm64'
-      ? 'clangarm64'
-      : 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\\${msys2Type}\\bin`, 'C:\\msys64\\usr\\bin']
-    newPath = [...newPathEntries, ...msys2]
-  } else {
-    newPath = newPathEntries
-  }
   console.log(`Entries added to ${envPath} to use selected Ruby:`)
-  for (const entry of newPath) {
+  for (const entry of newPathEntries) {
     console.log(`  ${entry}`)
   }
   core.endGroup()
 
-  core.addPath(newPath.join(path.delimiter))
-  return msys2Type
+  core.addPath(newPathEntries.join(path.delimiter))
 }
 
 export async function setupJavaHome(rubyPrefix) {
diff --git a/dist/index.js b/dist/index.js
index d42d55d26..803a6e557 100644
--- a/dist/index.js
+++ b/dist/index.js
@@ -332,7 +332,7 @@ const linuxOSInfo = __nccwpck_require__(8487)
 
 const windows = (os.platform() === 'win32')
 // Extract to SSD on Windows, see https://github.com/ruby/setup-ruby/pull/14
-const drive = (windows ? (process.env['GITHUB_WORKSPACE'] || 'C')[0] : undefined)
+const drive = (windows ? (process.env['RUNNER_TEMP'] || 'C')[0] : undefined)
 
 const inputs = {
   selfHosted: undefined
@@ -654,7 +654,7 @@ function engineToToolCacheName(engine) {
   }[engine]
 }
 
-function getToolCacheRubyPrefix(platform, engine, version) {
+function getToolCacheRubyPrefix(_platform, engine, version) {
   const toolCache = getToolCachePath()
   return path.join(toolCache, engineToToolCacheName(engine), version, os.arch())
 }
@@ -676,15 +676,7 @@ 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|vcruntime\d{3})-ruby\d{3}\.dll$/)))
-}
-
 function setupPath(newPathEntries) {
-  let msys2Type = null
   const envPath = windows ? 'Path' : 'PATH'
   const originalPath = process.env[envPath].split(path.delimiter)
   let cleanPath = originalPath.filter(entry => !/\bruby\b/i.test(entry))
@@ -702,29 +694,13 @@ function setupPath(newPathEntries) {
     core.exportVariable(envPath, cleanPath.join(path.delimiter))
   }
 
-  // Then add new path entries using core.addPath()
-  let newPath
-  const windowsToolchain = core.getInput('windows-toolchain')
-  if (windows && windowsToolchain !== 'none') {
-    // main Ruby dll determines whether mingw or ucrt build
-    msys2Type = os.arch() === 'arm64'
-      ? 'clangarm64'
-      : 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\\${msys2Type}\\bin`, 'C:\\msys64\\usr\\bin']
-    newPath = [...newPathEntries, ...msys2]
-  } else {
-    newPath = newPathEntries
-  }
   console.log(`Entries added to ${envPath} to use selected Ruby:`)
-  for (const entry of newPath) {
+  for (const entry of newPathEntries) {
     console.log(`  ${entry}`)
   }
   core.endGroup()
 
-  core.addPath(newPath.join(path.delimiter))
-  return msys2Type
+  core.addPath(newPathEntries.join(path.delimiter))
 }
 
 async function setupJavaHome(rubyPrefix) {
@@ -74085,8 +74061,15 @@ async function install(platform, engine, version) {
     rubyPrefix = path.join(os.homedir(), '.rubies', `${engine}-${version}`)
   }
 
+  const paths = [path.join(rubyPrefix, 'bin')]
+
+  // JRuby can use compiled extension code via ffi, so make sure gcc exists.
+  if (platform.startsWith('windows') && engine === 'jruby') {
+    paths.push(...await (__nccwpck_require__(3216).installJRubyTools)())
+  }
+
   // Set the PATH now, so the MSYS2 'tar' is in Path on Windows
-  common.setupPath([path.join(rubyPrefix, 'bin')])
+  common.setupPath(paths)
 
   if (!inToolCache) {
     await io.mkdirP(rubyPrefix)
@@ -74258,48 +74241,23 @@ __nccwpck_require__.r(__webpack_exports__);
 /* harmony export */ __nccwpck_require__.d(__webpack_exports__, {
 /* harmony export */   "getAvailableVersions": () => (/* binding */ getAvailableVersions),
 /* harmony export */   "install": () => (/* binding */ install),
-/* harmony export */   "installJRubyTools": () => (/* binding */ installJRubyTools),
-/* harmony export */   "addVCVARSEnv": () => (/* binding */ addVCVARSEnv)
+/* harmony export */   "installJRubyTools": () => (/* binding */ installJRubyTools)
 /* harmony export */ });
 // 7z arguments
 //   -aoa overwrite existing, -bd disable progress indicator
 
-// OpenSSL version detection is needed in installGCCTools and installJRubyTools
-
 const fs = __nccwpck_require__(7147)
 const os = __nccwpck_require__(2037)
 const path = __nccwpck_require__(1017)
 const cp = __nccwpck_require__(2081)
 const core = __nccwpck_require__(2186)
 const exec = __nccwpck_require__(1514)
-const io = __nccwpck_require__(7436)
 const tc = __nccwpck_require__(7784)
 const common = __nccwpck_require__(4717)
 const rubyInstallerVersions = __nccwpck_require__(6459)
+const toolchainVersions = __nccwpck_require__(3344)
 
-const drive = common.drive
-
-const msys2GCCReleaseURI  = 'https://github.com/ruby/setup-msys2-gcc/releases/download'
-
-const msys2BasePath = process.env['GHCUP_MSYS2'] || 'C:\\msys64'
-const vcPkgBasePath = process.env['VCPKG_INSTALLATION_ROOT']
-
-// needed for Ruby 2.0-2.3, cert file used by Git for Windows
-const certFile = [
-  'C:\\Program Files\\Git\\mingw64\\etc\\ssl\\cert.pem',
-  'C:\\Program Files\\Git\\mingw64\\ssl\\cert.pem',
-  'C:\\Program Files\\Git\\clangarm64\\etc\\ssl\\cert.pem',
-  'C:\\Program Files\\Git\\clangarm64\\ssl\\cert.pem'
-].find(file => fs.existsSync(file))
-if (certFile === undefined) {
-  throw new Error("Cannot find Git's cert file")
-}
-
-// location & path for old RubyInstaller DevKit (MSYS1), used with Ruby 2.0-2.3
-const msys1 = `${drive}:\\DevKit64`
-const msysPathEntries = [`${msys1}\\mingw\\x86_64-w64-mingw32\\bin`, `${msys1}\\mingw\\bin`, `${msys1}\\bin`]
-
-function getAvailableVersions(platform, engine) {
+function getAvailableVersions(_platform, engine) {
   if (engine === 'ruby') {
     return Object.keys(rubyInstallerVersions).filter(version => os.arch() in rubyInstallerVersions[version])
   } else {
@@ -74310,14 +74268,10 @@ function getAvailableVersions(platform, engine) {
 async function install(platform, engine, version) {
   const url = rubyInstallerVersions[version][os.arch()]
 
-  // The windows-2016 and windows-2019 images have MSYS2 build tools (C:/msys64/usr)
-  // and MinGW build tools installed.  The windows-2022 image has neither.
-  const hasMSYS2PreInstalled = ['windows-2019', 'windows-2016'].includes(platform)
-
   if (!url.endsWith('.7z')) {
     throw new Error(`URL should end in .7z: ${url}`)
   }
-  const base = url.slice(url.lastIndexOf('/') + 1, url.length - '.7z'.length)
+  const base = path.posix.basename(url, '.7z')
 
   let rubyPrefix, inToolCache
   if (common.shouldUseToolCache(engine, version)) {
@@ -74328,230 +74282,202 @@ async function install(platform, engine, version) {
       rubyPrefix = common.getToolCacheRubyPrefix(platform, engine, version)
     }
   } else {
-    rubyPrefix = `${drive}:\\${base}`
+    rubyPrefix = `${common.drive}:\\${base}`
   }
 
   if (!inToolCache) {
     await downloadAndExtract(engine, version, url, base, rubyPrefix);
   }
 
+  const paths = [`${rubyPrefix}\\bin`]
   const windowsToolchain = core.getInput('windows-toolchain')
   if (windowsToolchain === 'none') {
-    common.setupPath([`${rubyPrefix}\\bin`])
+    common.setupPath(paths)
     return rubyPrefix
   }
 
-  let toolchainPaths = (version === 'mswin') ? await setupMSWin() : await setupMingw(version)
-  const msys2Type = common.setupPath([`${rubyPrefix}\\bin`, ...toolchainPaths])
-
-  // install msys2 tools for all Ruby versions, only install mingw or ucrt for Rubies >= 2.4
+  const toolchainUrl = toolchainVersions[version][os.arch()]
 
-  if (!hasMSYS2PreInstalled) {
-    await installMSYS2Tools()
-  }
-
-  // windows 2016 and 2019 need ucrt64 installed, 2022 and future images need
-  // ucrt64 or mingw64 installed, depending on Ruby version
-  if ((msys2Type === 'ucrt64') || (common.floatVersion(version) >= 2.4)) {
-    await installGCCTools(msys2Type, version)
-  }
+  // Examples:
+  // - DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe
+  // - msys2-clangarm64.7z
+  // - vcpkg-x64-windows.7z
+  const toolchainName = path.posix.basename(toolchainUrl).split('-')[0].toLowerCase()
 
-  if (version === 'mswin') {
-    await installVCPkg()
-  }
+  if (toolchainName === 'msys2') {
+    paths.push(...await installMSYS2(toolchainUrl, rubyPrefix))
+  } else {
+    if (toolchainName === 'vcpkg') {
+      paths.push(...await installVCPKG(toolchainUrl))
+    } else if (toolchainName === 'devkit') {
+      paths.push(...await installMSYS1(toolchainUrl))
+    } else {
+      throw new Error(`Unknown toolchain type: ${toolchainUrl}`)
+    }
 
-  const ridk = `${rubyPrefix}\\bin\\ridk.cmd`
-  if (fs.existsSync(ridk)) {
-    await common.measure('Adding ridk env variables', async () => addRidkEnv(ridk))
+    // Install msys2 for other rubies to provide better command line tools
+    paths.push(...await installMSYS2(toolchainVersions['head'][os.arch()]))
   }
 
+  common.setupPath(paths)
   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, version) {
-  // 2022-Dec ruby/msys2-gcc-pkgs now uses a suffix to delineate different archive versions.
-  // At present, the only use is to indicate the included OpenSSL version.
-  // With no suffix, archives include OpenSSL 1.1.1, with a '-3.0' suffix, they include
-  // OpenSSL 3.0.x.  Note that the mswin archive uses OpenSSL 3.
-  // As of Jan-2023, OpenSSL 3 is used in Ruby 3.2 & all head versions.  MSYS2 updated
-  // to OpenSSL 3 on 14-Jan-2023.
-  let suffix = ''
-  if (common.isHeadVersion(version) || common.floatVersion(version) >= 3.2) {
-    suffix = '-3.0'
-  }
-  const downloadPath = await common.measure(`Downloading ${type}${suffix} build tools`, async () => {
-    let url = `${msys2GCCReleaseURI}/msys2-gcc-pkgs/${type}${suffix}.7z`
+async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
+  const downloadPath = await common.measure('Downloading Ruby', async () => {
     console.log(url)
     return await tc.downloadTool(url)
   })
 
-  await common.measure(`Extracting  ${type}${suffix} build tools`, async () =>
-    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${msys2BasePath}`], { silent: true }))
-}
-
-// Actions windows-2022 image does not contain any MSYS2 build tools.  Install tools for it.
-// A subset of the MSYS2 base-devel group
-async function installMSYS2Tools() {
-  const downloadPath = await common.measure(`Downloading msys2 build tools`, async () => {
-    const suffix = os.arch() === 'arm64' ? '-arm64' : ''
+  const extractPath = process.env.RUNNER_TEMP
+  await common.measure('Extracting  Ruby', async () =>
+    // -xr extract but exclude share\doc files
+    exec.exec('7z', ['x', downloadPath, '-bd', `-xr!${base}\\share\\doc`, `-o${extractPath}`], { silent: true }))
 
-    let url = `${msys2GCCReleaseURI}/msys2-gcc-pkgs/msys2${suffix}.7z`
-    console.log(url)
-    return await tc.downloadTool(url)
-  })
+  const parentDir = path.dirname(rubyPrefix)
+  if (!fs.existsSync(parentDir)) {
+    fs.mkdirSync(parentDir, { recursive: true })
+  }
 
-  // need to remove all directories, since they may indicate old packages are installed,
-  // otherwise, error of "error: duplicated database entry"
-  fs.rmSync(`${msys2BasePath}\\var\\lib\\pacman\\local`, { recursive: true, force: true })
+  const extractedPath = path.join(extractPath, base)
+  if (extractedPath[0] === rubyPrefix[0]) {
+    fs.renameSync(extractedPath, rubyPrefix)
+  } else {
+    fs.symlinkSync(extractedPath, rubyPrefix, 'junction')
+  }
 
-  await common.measure(`Extracting  msys2 build tools`, async () =>
-    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${msys2BasePath}`], { silent: true }))
+  if (common.shouldUseToolCache(engine, version)) {
+    common.createToolCacheCompleteFile(rubyPrefix)
+  }
 }
 
-// Windows JRuby can install gems that require compile tools, only needed for
-// windows-2022 and later images
 async function installJRubyTools() {
-  await installMSYS2Tools()
-  await installGCCTools(os.arch() === 'arm64' ? 'clangarm64' : 'mingw64', '3.4')
-}
-
-// Install vcpkg files needed to build mswin Ruby
-async function installVCPkg() {
-  const downloadPath = await common.measure(`Downloading mswin vcpkg packages`, async () => {
-    let url = `${msys2GCCReleaseURI}/msys2-gcc-pkgs/mswin.7z`
-    console.log(url)
-    return await tc.downloadTool(url)
-  })
-
-  await common.measure(`Extracting  mswin vcpkg packages`, async () =>
-    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${vcPkgBasePath}`], { silent: true }))
+  return await installMSYS2(toolchainVersions['head'][os.arch()])
 }
 
-async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
-  const parentDir = path.dirname(rubyPrefix)
-
-  const downloadPath = await common.measure('Downloading Ruby', async () => {
+async function installMSYS2(url, rubyPrefix = process.env.RUNNER_TEMP) {
+  const downloadPath = await common.measure('Downloading msys2 build tools', async () => {
     console.log(url)
     return await tc.downloadTool(url)
   })
 
-  await common.measure('Extracting  Ruby', async () =>
-    // -xr extract but exclude share\doc files
-    exec.exec('7z', ['x', downloadPath, '-bd', `-xr!${base}\\share\\doc`, `-o${parentDir}`], { silent: true }))
+  const extractPath = path.join(process.env.RUNNER_TEMP, 'msys64')
+  await common.measure('Extracting  msys2 build tools', async () =>
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${extractPath}`], { silent: true }))
 
-  if (base !== path.basename(rubyPrefix)) {
-    await io.mv(path.join(parentDir, base), rubyPrefix)
+  // https://github.com/oneclick/rubyinstaller2/blob/HEAD/lib/ruby_installer/build/msys2_installation.rb
+  //
+  // ri2 searches for msys64 in the following order:
+  // - ENV["MSYS2_PATH"]
+  // - File.join(RbConfig::TOPDIR, "msys64")
+  // - File.join(File.dirname(RbConfig::TOPDIR), "msys64")
+  // - "C:\msys64"
+  // - ...
+  //
+  // The first option ENV["MSYS2_PATH"] is only supported in ruby >=3.0.7.
+  // Therefore we use the second option to avoid conflict with existing "C:\msys64"
+  const msys2Path = path.join(rubyPrefix, 'msys64')
+  if (extractPath !== msys2Path) {
+    fs.symlinkSync(extractPath, msys2Path, 'junction')
   }
 
-  if (common.shouldUseToolCache(engine, version)) {
-    common.createToolCacheCompleteFile(rubyPrefix)
+  const ridk = `${rubyPrefix}\\bin\\ridk.cmd`
+  if (fs.existsSync(ridk)) {
+    await common.measure('Setting up ridk environment', async () => exportCommandEnv(`set MAKE=make && "${ridk}" enable`))
   }
-}
 
-async function setupMingw(version) {
-  core.exportVariable('MAKE', 'make.exe')
-
-  // rename these to avoid confusion when Ruby is using OpenSSL 1.0.2.
-  // most current extconf files look for 1.1.x dll files first, which is the version of the renamed files
-  if (common.floatVersion(version) <= 2.4) {
-    renameSystem32Dlls()
-  }
+  // Examples:
+  // - msys2-clangarm64.7z
+  // - msys2-ucrt64-gcc@14.7z
+  // - msys2-mingw64-gcc@14-openssl@1.1.7z
+  const msys2Type = path.posix.basename(url).split(/[-.]/)[1]
+  return [`${msys2Path}\\${msys2Type}\\bin`, `${msys2Path}\\usr\\bin`]
+}
 
-  if (common.floatVersion(version) <= 2.3) {
-    core.exportVariable('SSL_CERT_FILE', certFile)
-    await common.measure('Installing MSYS1', async () => installMSYS1(version))
-    return msysPathEntries
-  } else {
-    return []
+async function installMSYS1(url) {
+  const certFile = [
+    'C:\\Program Files\\Git\\mingw64\\etc\\ssl\\cert.pem',
+    'C:\\Program Files\\Git\\mingw64\\ssl\\cert.pem',
+  ].find(file => fs.existsSync(file))
+  if (certFile === undefined) {
+    throw new Error("Cannot find Git's cert file")
   }
-}
 
-// Ruby 2.0-2.3
-async function installMSYS1(version) {
-  const url = 'https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe'
-  const downloadPath = await tc.downloadTool(url)
-  await exec.exec('7z', ['x', downloadPath, `-o${msys1}`], { silent: true })
+  const downloadPath = await common.measure('Downloading msys1 build tools', async () => {
+    console.log(url)
+    return await tc.downloadTool(url)
+  })
 
-  // below are set in the old devkit.rb file ?
-  core.exportVariable('RI_DEVKIT', msys1)
-  core.exportVariable('CC' , 'gcc')
-  core.exportVariable('CXX', 'g++')
-  core.exportVariable('CPP', 'cpp')
-  core.info(`Installed RubyInstaller DevKit for Ruby ${version}`)
-}
+  const msys1Path = `${common.drive}:\\DevKit64`
+  await common.measure('Extracting  msys1 build tools', async () =>
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${msys1Path}`], { silent: true }))
+
+  await common.measure('Setting up DevKit environment', async () => {
+    // ssl dlls cause issues with msys1 Rubies
+    const sys32 = 'C:\\Windows\\System32\\'
+    const badFiles = [`${sys32}libcrypto-1_1-x64.dll`, `${sys32}libssl-1_1-x64.dll`]
+    const existing = badFiles.filter((dll) => fs.existsSync(dll))
+    if (existing.length > 0) {
+      core.warning(`Renaming ${existing.join(' and ')} to avoid dll resolution conflicts on Ruby < 2.4`)
+      existing.forEach(dll => fs.renameSync(dll, `${dll}_`))
+    }
+
+    exportEnv({
+      CC: 'gcc',
+      CPP: 'cpp',
+      CXX: 'g++',
+      MAKE: 'make',
+      RI_DEVKIT: msys1Path,
+      SSL_CERT_FILE: certFile
+    })
+  })
 
-async function setupMSWin() {
-  core.exportVariable('MAKE', 'nmake.exe')
-  return await common.measure('Setting up MSVC environment', async () => addVCVARSEnv())
+  return [`${msys1Path}\\mingw\\x86_64-w64-mingw32\\bin`, `${msys1Path}\\mingw\\bin`, `${msys1Path}\\bin`]
 }
 
 /* Sets MSVC environment for use in Actions
  *   allows steps to run without running vcvars*.bat, also for PowerShell
- *   adds a convenience VCVARS environment variable
  *   this assumes a single Visual Studio version being available in the Windows images */
-function addVCVARSEnv() {
-  let cmd = 'vswhere -latest -property installationPath'
-  let vcVars = `${cp.execSync(cmd).toString().trim()}\\VC\\Auxiliary\\Build\\vcvars64.bat`
-
-  if (!fs.existsSync(vcVars)) {
-    throw new Error(`Missing vcVars file: ${vcVars}`)
-  }
-  core.exportVariable('VCVARS', vcVars)
+async function installVCPKG(url) {
+  const downloadPath = await common.measure('Downloading mswin vcpkg packages', async () => {
+    console.log(url)
+    return await tc.downloadTool(url)
+  })
 
-  cmd = `cmd.exe /c ""${vcVars}" && set"`
+  const extractPath = process.env.VCPKG_INSTALLATION_ROOT
+  await common.measure('Extracting  mswin vcpkg packages', async () =>
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${extractPath}`], { silent: true }))
 
-  let newEnv = new Map()
-  let newSet = cp.execSync(cmd).toString().trim().split(/\r?\n/)
-  newSet = newSet.filter(line => /\S=\S/.test(line))
-  newSet.forEach(s => {
-    let [k,v] = common.partition(s, '=')
-    newEnv.set(k,v)
-  })
+  return await common.measure('Setting up MSVC environment', async () => {
+    const cmd = 'vswhere -latest -property installationPath'
+    const vcVarsBat = os.arch() === 'arm64' ? 'vcvarsarm64.bat' : 'vcvars64.bat'
+    const vcVars = `${cp.execSync(cmd).toString().trim()}\\VC\\Auxiliary\\Build\\${vcVarsBat}`
 
-  let newPathEntries = undefined
-  for (let [k, v] of newEnv) {
-    if (process.env[k] !== v) {
-      if (/^Path$/i.test(k)) {
-        const newPathStr = v.replace(`${path.delimiter}${process.env['Path']}`, '')
-        newPathEntries = newPathStr.split(path.delimiter)
-      } else {
-        core.exportVariable(k, v)
-      }
+    if (!fs.existsSync(vcVars)) {
+      throw new Error(`Missing vcVars file: ${vcVars}`)
     }
-  }
-  return newPathEntries
-}
 
-// ssl files cause issues with non RI2 Rubies (<2.4) and ruby/ruby's CI from build folder due to dll resolution
-function renameSystem32Dlls() {
-  const sys32 = 'C:\\Windows\\System32\\'
-  const badFiles = [`${sys32}libcrypto-1_1-x64.dll`, `${sys32}libssl-1_1-x64.dll`]
-  const existing = badFiles.filter((dll) => fs.existsSync(dll))
-  if (existing.length > 0) {
-    console.log(`Renaming ${existing.join(' and ')} to avoid dll resolution conflicts on Ruby <= 2.4`)
-    existing.forEach(dll => fs.renameSync(dll, `${dll}_`))
-  }
+    return exportCommandEnv(`set MAKE=nmake && "${vcVars}"`)
+  })
 }
 
-// Sets MSYS2 ENV variables set from running `ridk enable`
-function addRidkEnv(ridk) {
-  let newEnv = new Map()
-  let cmd = `cmd.exe /c "${ridk} enable && set"`
-  let newSet = cp.execSync(cmd).toString().trim().split(/\r?\n/)
-  newSet = newSet.filter(line => /^\S+=\S+/.test(line))
-  newSet.forEach(s => {
-    let [k, v] = common.partition(s, '=')
-    newEnv.set(k, v)
-  })
+// Run a cmd command, export its environment, and return new paths
+function exportCommandEnv(command) {
+  const cmd = `cmd.exe /s /c "${command} >NUL && "${process.execPath}" -e console.log(JSON.stringify(process.env))"`
+  const env = JSON.parse(cp.execSync(cmd).toString())
 
-  for (let [k, v] of newEnv) {
+  const paths = env.Path.replace(`${path.delimiter}${process.env.Path}`, '').split(path.delimiter)
+  delete env.Path
+
+  exportEnv(env)
+  return paths
+}
+
+function exportEnv(env) {
+  for (const [k, v] of Object.entries(env)) {
     if (process.env[k] !== v) {
-      if (!/^Path$/i.test(k)) {
-        console.log(`${k}=${v}`)
-        core.exportVariable(k, v)
-      }
+      console.log(`${k}=${v}`)
+      core.exportVariable(k, v)
     }
   }
 }
@@ -74767,6 +74693,14 @@ module.exports = JSON.parse('{"ruby":["1.9.3-p551","2.0.0-p648","2.1.9","2.2.10"
 
 /***/ }),
 
+/***/ 3344:
+/***/ ((module) => {
+
+"use strict";
+module.exports = JSON.parse('{"2.0.0":{"x64":"https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"},"2.1.9":{"x64":"https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"},"2.2.6":{"x64":"https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"},"2.3.0":{"x64":"https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"},"2.3.1":{"x64":"https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"},"2.3.3":{"x64":"https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"},"2.4.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.2":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.4":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.9":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.4.10":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.0":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.8":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.5.9":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.0":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.2":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.4":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.8":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.9":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.6.10":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.0":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.2":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.4":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"2.7.8":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.0":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.2":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.4":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.0.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.0":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.2":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.4":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.1.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"},"3.2.0":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.2":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.4":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.2.8":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.0":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.1":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.2":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.3":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.4":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.5":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.6":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.3.8":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.4.1":{"arm64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64-mingw-w64@r688.7z","x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.4.2":{"arm64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64-mingw-w64@r688.7z","x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"3.4.3":{"arm64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64-mingw-w64@r688.7z","x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"},"head":{"arm64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64.7z","x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64.7z"},"mingw":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64.7z"},"mswin":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"},"ucrt":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64.7z"}}');
+
+/***/ }),
+
 /***/ 6459:
 /***/ ((module) => {
 
@@ -74922,13 +74856,6 @@ async function setupRuby(options = {}) {
   createGemRC(engine, version)
   envPreInstall()
 
-  // JRuby can use compiled extension code, so make sure gcc exists.
-  // As of Jan-2022, JRuby compiles against msvcrt.
-  if (platform.startsWith('windows') && engine === 'jruby' &&
-    !fs.existsSync('C:\\msys64\\mingw64\\bin\\gcc.exe')) {
-    await (__nccwpck_require__(3216).installJRubyTools)()
-  }
-
   const rubyPrefix = await installer.install(platform, engine, version)
 
   await common.measure('Print Ruby version', async () =>
diff --git a/generate-windows-versions.rb b/generate-windows-versions.rb
index 80ad57065..6fb1fd26d 100644
--- a/generate-windows-versions.rb
+++ b/generate-windows-versions.rb
@@ -1,11 +1,11 @@
-require 'net/http'
+require 'open-uri'
 require 'yaml'
 require 'json'
 
 min_requirements = ['~> 2.0.0', '~> 2.1.9', '>= 2.2.6'].map { |req| Gem::Requirement.new(req) }
 
 url = 'https://raw.githubusercontent.com/oneclick/rubyinstaller.org-website/master/_data/downloads.yaml'
-entries = YAML.load(Net::HTTP.get(URI(url)), symbolize_names: true)
+entries = YAML.load(URI.open(url, &:read), symbolize_names: true)
 
 versions = entries.select { |entry|
   entry[:filetype] == 'rubyinstaller7z' and
@@ -31,18 +31,63 @@
   min_requirements.any? { |req| req.satisfied_by?(Gem::Version.new(version)) }
 }.to_h
 
+latest_version = Gem::Version.new(versions.keys.last)
+head_version = Gem::Version.new("#{latest_version.bump}.0dev")
+
 versions['head'] = {
-  'arm64': 'https://github.com/oneclick/rubyinstaller2/releases/download/rubyinstaller-head/rubyinstaller-head-arm.7z',
-  'x64': 'https://github.com/oneclick/rubyinstaller2/releases/download/rubyinstaller-head/rubyinstaller-head-x64.7z'
+  'arm64' => 'https://github.com/oneclick/rubyinstaller2/releases/download/rubyinstaller-head/rubyinstaller-head-arm.7z',
+  'x64' => 'https://github.com/oneclick/rubyinstaller2/releases/download/rubyinstaller-head/rubyinstaller-head-x64.7z'
 }
 versions['mingw'] = {
-  'x64': 'https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-mingw.7z'
+  'x64' => 'https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-mingw.7z'
 }
 versions['mswin'] = {
-  'x64': 'https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-mswin.7z'
+  'x64' => 'https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-mswin.7z'
 }
 versions['ucrt'] = {
-  'x64': 'https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-ucrt.7z'
+  'x64' => 'https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-ucrt.7z'
 }
 
 File.binwrite 'windows-versions.json', "#{JSON.pretty_generate(versions)}\n"
+
+base_url = 'https://github.com/ruby/setup-msys2-gcc/releases/latest/download/windows-toolchain.json'
+windows_toolchain = JSON.parse(URI.open(base_url, &:read), symbolize_names: true)
+
+versions.each do |raw_version, archs|
+  version = Gem::Version.correct?(raw_version) ? Gem::Version.new(raw_version) : head_version
+
+  archs.each_key do |raw_arch|
+    arch = raw_arch == 'arm64' ? 'aarch64' : raw_arch
+
+    platform =
+      case raw_version
+      when 'head', 'ucrt'
+        "#{arch}-mingw-ucrt"
+      when 'mingw'
+        "#{arch}-mingw32"
+      when 'mswin'
+        "#{arch}-mswin64"
+      else
+        if version >= Gem::Version.new('3.1.0.dev')
+          "#{arch}-mingw-ucrt"
+        else
+          "#{arch}-mingw32"
+        end
+      end
+
+    toolchain =
+      windows_toolchain.select do |pkg|
+        pkg[:platform] == platform && pkg[:required_ruby_version].any? do |requirement|
+          Gem::Requirement.new(requirement).satisfied_by?(version)
+        end
+      end
+
+    unless toolchain.one?
+      raise "#{toolchain.empty? ? 'no' : 'multiple'} toolchains found for #{raw_version} #{raw_arch}: #{toolchain}"
+    end
+
+    archs[raw_arch] = URI.join(base_url, toolchain.first[:href])
+  end
+end
+
+File.binwrite 'windows-toolchain-versions.json', "#{JSON.pretty_generate(versions)}\n"
diff --git a/index.js b/index.js
index 1bba0a4be..62e46feb9 100644
--- a/index.js
+++ b/index.js
@@ -70,13 +70,6 @@ export async function setupRuby(options = {}) {
   createGemRC(engine, version)
   envPreInstall()
 
-  // JRuby can use compiled extension code, so make sure gcc exists.
-  // As of Jan-2022, JRuby compiles against msvcrt.
-  if (platform.startsWith('windows') && engine === 'jruby' &&
-    !fs.existsSync('C:\\msys64\\mingw64\\bin\\gcc.exe')) {
-    await require('./windows').installJRubyTools()
-  }
-
   const rubyPrefix = await installer.install(platform, engine, version)
 
   await common.measure('Print Ruby version', async () =>
diff --git a/ruby-builder.js b/ruby-builder.js
index 8244fec49..93a690960 100644
--- a/ruby-builder.js
+++ b/ruby-builder.js
@@ -46,8 +46,15 @@ export async function install(platform, engine, version) {
     rubyPrefix = path.join(os.homedir(), '.rubies', `${engine}-${version}`)
   }
 
+  const paths = [path.join(rubyPrefix, 'bin')]
+
+  // JRuby can use compiled extension code via ffi, so make sure gcc exists.
+  if (platform.startsWith('windows') && engine === 'jruby') {
+    paths.push(...await require('./windows').installJRubyTools())
+  }
+
   // Set the PATH now, so the MSYS2 'tar' is in Path on Windows
-  common.setupPath([path.join(rubyPrefix, 'bin')])
+  common.setupPath(paths)
 
   if (!inToolCache) {
     await io.mkdirP(rubyPrefix)
diff --git a/windows-toolchain-versions.json b/windows-toolchain-versions.json
new file mode 100644
index 000000000..6910dcd3c
--- /dev/null
+++ b/windows-toolchain-versions.json
@@ -0,0 +1,258 @@
+{
+  "2.0.0": {
+    "x64": "https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"
+  },
+  "2.1.9": {
+    "x64": "https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"
+  },
+  "2.2.6": {
+    "x64": "https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"
+  },
+  "2.3.0": {
+    "x64": "https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"
+  },
+  "2.3.1": {
+    "x64": "https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"
+  },
+  "2.3.3": {
+    "x64": "https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe"
+  },
+  "2.4.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.2": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.4": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.9": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.4.10": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.0": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.8": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.5.9": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.0": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.2": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.4": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.8": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.9": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.6.10": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.0": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.2": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.4": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "2.7.8": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.0": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.2": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.4": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.0.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.0": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.2": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.4": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.1.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14-openssl@1.1.7z"
+  },
+  "3.2.0": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.2": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.4": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.2.8": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.0": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.1": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.2": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.3": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.4": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.5": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.6": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.3.8": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.4.1": {
+    "arm64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64-mingw-w64@r688.7z",
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.4.2": {
+    "arm64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64-mingw-w64@r688.7z",
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "3.4.3": {
+    "arm64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64-mingw-w64@r688.7z",
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64-mingw-w64@r688-gcc@14.7z"
+  },
+  "head": {
+    "arm64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-clangarm64.7z",
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64.7z"
+  },
+  "mingw": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-mingw64.7z"
+  },
+  "mswin": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"
+  },
+  "ucrt": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/msys2-ucrt64.7z"
+  }
+}
diff --git a/windows.js b/windows.js
index c3b6c2304..f998f6797 100644
--- a/windows.js
+++ b/windows.js
@@ -1,42 +1,18 @@
 // 7z arguments
 //   -aoa overwrite existing, -bd disable progress indicator
 
-// OpenSSL version detection is needed in installGCCTools and installJRubyTools
-
 const fs = require('fs')
 const os = require('os')
 const path = require('path')
 const cp = require('child_process')
 const core = require('@actions/core')
 const exec = require('@actions/exec')
-const io = require('@actions/io')
 const tc = require('@actions/tool-cache')
 const common = require('./common')
 const rubyInstallerVersions = require('./windows-versions.json')
+const toolchainVersions = require('./windows-toolchain-versions.json')
 
-const drive = common.drive
-
-const msys2GCCReleaseURI  = 'https://github.com/ruby/setup-msys2-gcc/releases/download'
-
-const msys2BasePath = process.env['GHCUP_MSYS2'] || 'C:\\msys64'
-const vcPkgBasePath = process.env['VCPKG_INSTALLATION_ROOT']
-
-// needed for Ruby 2.0-2.3, cert file used by Git for Windows
-const certFile = [
-  'C:\\Program Files\\Git\\mingw64\\etc\\ssl\\cert.pem',
-  'C:\\Program Files\\Git\\mingw64\\ssl\\cert.pem',
-  'C:\\Program Files\\Git\\clangarm64\\etc\\ssl\\cert.pem',
-  'C:\\Program Files\\Git\\clangarm64\\ssl\\cert.pem'
-].find(file => fs.existsSync(file))
-if (certFile === undefined) {
-  throw new Error("Cannot find Git's cert file")
-}
-
-// location & path for old RubyInstaller DevKit (MSYS1), used with Ruby 2.0-2.3
-const msys1 = `${drive}:\\DevKit64`
-const msysPathEntries = [`${msys1}\\mingw\\x86_64-w64-mingw32\\bin`, `${msys1}\\mingw\\bin`, `${msys1}\\bin`]
-
-export function getAvailableVersions(platform, engine) {
+export function getAvailableVersions(_platform, engine) {
   if (engine === 'ruby') {
     return Object.keys(rubyInstallerVersions).filter(version => os.arch() in rubyInstallerVersions[version])
   } else {
@@ -47,14 +23,10 @@ export function getAvailableVersions(platform, engine) {
 export async function install(platform, engine, version) {
   const url = rubyInstallerVersions[version][os.arch()]
 
-  // The windows-2016 and windows-2019 images have MSYS2 build tools (C:/msys64/usr)
-  // and MinGW build tools installed.  The windows-2022 image has neither.
-  const hasMSYS2PreInstalled = ['windows-2019', 'windows-2016'].includes(platform)
-
   if (!url.endsWith('.7z')) {
     throw new Error(`URL should end in .7z: ${url}`)
   }
-  const base = url.slice(url.lastIndexOf('/') + 1, url.length - '.7z'.length)
+  const base = path.posix.basename(url, '.7z')
 
   let rubyPrefix, inToolCache
   if (common.shouldUseToolCache(engine, version)) {
@@ -65,230 +37,202 @@ export async function install(platform, engine, version) {
       rubyPrefix = common.getToolCacheRubyPrefix(platform, engine, version)
     }
   } else {
-    rubyPrefix = `${drive}:\\${base}`
+    rubyPrefix = `${common.drive}:\\${base}`
   }
 
   if (!inToolCache) {
     await downloadAndExtract(engine, version, url, base, rubyPrefix);
   }
 
+  const paths = [`${rubyPrefix}\\bin`]
   const windowsToolchain = core.getInput('windows-toolchain')
   if (windowsToolchain === 'none') {
-    common.setupPath([`${rubyPrefix}\\bin`])
+    common.setupPath(paths)
     return rubyPrefix
   }
 
-  let toolchainPaths = (version === 'mswin') ? await setupMSWin() : await setupMingw(version)
-  const msys2Type = common.setupPath([`${rubyPrefix}\\bin`, ...toolchainPaths])
-
-  // install msys2 tools for all Ruby versions, only install mingw or ucrt for Rubies >= 2.4
-
-  if (!hasMSYS2PreInstalled) {
-    await installMSYS2Tools()
-  }
+  const toolchainUrl = toolchainVersions[version][os.arch()]
 
-  // windows 2016 and 2019 need ucrt64 installed, 2022 and future images need
-  // ucrt64 or mingw64 installed, depending on Ruby version
-  if ((msys2Type === 'ucrt64') || (common.floatVersion(version) >= 2.4)) {
-    await installGCCTools(msys2Type, version)
-  }
+  // Examples:
+  // - DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe
+  // - msys2-clangarm64.7z
+  // - vcpkg-x64-windows.7z
+  const toolchainName = path.posix.basename(toolchainUrl).split('-')[0].toLowerCase()
 
-  if (version === 'mswin') {
-    await installVCPkg()
-  }
+  if (toolchainName === 'msys2') {
+    paths.push(...await installMSYS2(toolchainUrl, rubyPrefix))
+  } else {
+    if (toolchainName === 'vcpkg') {
+      paths.push(...await installVCPKG(toolchainUrl))
+    } else if (toolchainName === 'devkit') {
+      paths.push(...await installMSYS1(toolchainUrl))
+    } else {
+      throw new Error(`Unknown toolchain type: ${toolchainUrl}`)
+    }
 
-  const ridk = `${rubyPrefix}\\bin\\ridk.cmd`
-  if (fs.existsSync(ridk)) {
-    await common.measure('Adding ridk env variables', async () => addRidkEnv(ridk))
+    // Install msys2 for other rubies to provide better command line tools
+    paths.push(...await installMSYS2(toolchainVersions['head'][os.arch()]))
   }
 
+  common.setupPath(paths)
   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, version) {
-  // 2022-Dec ruby/msys2-gcc-pkgs now uses a suffix to delineate different archive versions.
-  // At present, the only use is to indicate the included OpenSSL version.
-  // With no suffix, archives include OpenSSL 1.1.1, with a '-3.0' suffix, they include
-  // OpenSSL 3.0.x.  Note that the mswin archive uses OpenSSL 3.
-  // As of Jan-2023, OpenSSL 3 is used in Ruby 3.2 & all head versions.  MSYS2 updated
-  // to OpenSSL 3 on 14-Jan-2023.
-  let suffix = ''
-  if (common.isHeadVersion(version) || common.floatVersion(version) >= 3.2) {
-    suffix = '-3.0'
-  }
-  const downloadPath = await common.measure(`Downloading ${type}${suffix} build tools`, async () => {
-    let url = `${msys2GCCReleaseURI}/msys2-gcc-pkgs/${type}${suffix}.7z`
+async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
+  const downloadPath = await common.measure('Downloading Ruby', async () => {
     console.log(url)
     return await tc.downloadTool(url)
   })
 
-  await common.measure(`Extracting  ${type}${suffix} build tools`, async () =>
-    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${msys2BasePath}`], { silent: true }))
-}
-
-// Actions windows-2022 image does not contain any MSYS2 build tools.  Install tools for it.
-// A subset of the MSYS2 base-devel group
-async function installMSYS2Tools() {
-  const downloadPath = await common.measure(`Downloading msys2 build tools`, async () => {
-    const suffix = os.arch() === 'arm64' ? '-arm64' : ''
+  const extractPath = process.env.RUNNER_TEMP
+  await common.measure('Extracting  Ruby', async () =>
+    // -xr extract but exclude share\doc files
+    exec.exec('7z', ['x', downloadPath, '-bd', `-xr!${base}\\share\\doc`, `-o${extractPath}`], { silent: true }))
 
-    let url = `${msys2GCCReleaseURI}/msys2-gcc-pkgs/msys2${suffix}.7z`
-    console.log(url)
-    return await tc.downloadTool(url)
-  })
+  const parentDir = path.dirname(rubyPrefix)
+  if (!fs.existsSync(parentDir)) {
+    fs.mkdirSync(parentDir, { recursive: true })
+  }
 
-  // need to remove all directories, since they may indicate old packages are installed,
-  // otherwise, error of "error: duplicated database entry"
-  fs.rmSync(`${msys2BasePath}\\var\\lib\\pacman\\local`, { recursive: true, force: true })
+  const extractedPath = path.join(extractPath, base)
+  if (extractedPath[0] === rubyPrefix[0]) {
+    fs.renameSync(extractedPath, rubyPrefix)
+  } else {
+    fs.symlinkSync(extractedPath, rubyPrefix, 'junction')
+  }
 
-  await common.measure(`Extracting  msys2 build tools`, async () =>
-    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${msys2BasePath}`], { silent: true }))
+  if (common.shouldUseToolCache(engine, version)) {
+    common.createToolCacheCompleteFile(rubyPrefix)
+  }
 }
 
-// Windows JRuby can install gems that require compile tools, only needed for
-// windows-2022 and later images
 export async function installJRubyTools() {
-  await installMSYS2Tools()
-  await installGCCTools(os.arch() === 'arm64' ? 'clangarm64' : 'mingw64', '3.4')
+  return await installMSYS2(toolchainVersions['head'][os.arch()])
 }
 
-// Install vcpkg files needed to build mswin Ruby
-async function installVCPkg() {
-  const downloadPath = await common.measure(`Downloading mswin vcpkg packages`, async () => {
-    let url = `${msys2GCCReleaseURI}/msys2-gcc-pkgs/mswin.7z`
+async function installMSYS2(url, rubyPrefix = process.env.RUNNER_TEMP) {
+  const downloadPath = await common.measure('Downloading msys2 build tools', async () => {
     console.log(url)
     return await tc.downloadTool(url)
   })
 
-  await common.measure(`Extracting  mswin vcpkg packages`, async () =>
-    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${vcPkgBasePath}`], { silent: true }))
-}
-
-async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
-  const parentDir = path.dirname(rubyPrefix)
-
-  const downloadPath = await common.measure('Downloading Ruby', async () => {
-    console.log(url)
-    return await tc.downloadTool(url)
-  })
-
-  await common.measure('Extracting  Ruby', async () =>
-    // -xr extract but exclude share\doc files
-    exec.exec('7z', ['x', downloadPath, '-bd', `-xr!${base}\\share\\doc`, `-o${parentDir}`], { silent: true }))
-
-  if (base !== path.basename(rubyPrefix)) {
-    await io.mv(path.join(parentDir, base), rubyPrefix)
+  const extractPath = path.join(process.env.RUNNER_TEMP, 'msys64')
+  await common.measure('Extracting  msys2 build tools', async () =>
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${extractPath}`], { silent: true }))
+
+  // https://github.com/oneclick/rubyinstaller2/blob/HEAD/lib/ruby_installer/build/msys2_installation.rb
+  //
+  // ri2 searches for msys64 in the following order:
+  // - ENV["MSYS2_PATH"]
+  // - File.join(RbConfig::TOPDIR, "msys64")
+  // - File.join(File.dirname(RbConfig::TOPDIR), "msys64")
+  // - "C:\msys64"
+  // - ...
+  //
+  // The first option ENV["MSYS2_PATH"] is only supported in ruby >=3.0.7.
+  // Therefore we use the second option to avoid conflict with existing "C:\msys64"
+  const msys2Path = path.join(rubyPrefix, 'msys64')
+  if (extractPath !== msys2Path) {
+    fs.symlinkSync(extractPath, msys2Path, 'junction')
   }
 
-  if (common.shouldUseToolCache(engine, version)) {
-    common.createToolCacheCompleteFile(rubyPrefix)
+  const ridk = `${rubyPrefix}\\bin\\ridk.cmd`
+  if (fs.existsSync(ridk)) {
+    await common.measure('Setting up ridk environment', async () => exportCommandEnv(`set MAKE=make && "${ridk}" enable`))
   }
-}
 
-async function setupMingw(version) {
-  core.exportVariable('MAKE', 'make.exe')
+  // Examples:
+  // - msys2-clangarm64.7z
+  // - msys2-ucrt64-gcc@14.7z
+  // - msys2-mingw64-gcc@14-openssl@1.1.7z
+  const msys2Type = path.posix.basename(url).split(/[-.]/)[1]
+  return [`${msys2Path}\\${msys2Type}\\bin`, `${msys2Path}\\usr\\bin`]
+}
 
-  // rename these to avoid confusion when Ruby is using OpenSSL 1.0.2.
-  // most current extconf files look for 1.1.x dll files first, which is the version of the renamed files
-  if (common.floatVersion(version) <= 2.4) {
-    renameSystem32Dlls()
+async function installMSYS1(url) {
+  const certFile = [
+    'C:\\Program Files\\Git\\mingw64\\etc\\ssl\\cert.pem',
+    'C:\\Program Files\\Git\\mingw64\\ssl\\cert.pem',
+  ].find(file => fs.existsSync(file))
+  if (certFile === undefined) {
+    throw new Error("Cannot find Git's cert file")
   }
 
-  if (common.floatVersion(version) <= 2.3) {
-    core.exportVariable('SSL_CERT_FILE', certFile)
-    await common.measure('Installing MSYS1', async () => installMSYS1(version))
-    return msysPathEntries
-  } else {
-    return []
-  }
-}
+  const downloadPath = await common.measure('Downloading msys1 build tools', async () => {
+    console.log(url)
+    return await tc.downloadTool(url)
+  })
 
-// Ruby 2.0-2.3
-async function installMSYS1(version) {
-  const url = 'https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe'
-  const downloadPath = await tc.downloadTool(url)
-  await exec.exec('7z', ['x', downloadPath, `-o${msys1}`], { silent: true })
-
-  // below are set in the old devkit.rb file ?
-  core.exportVariable('RI_DEVKIT', msys1)
-  core.exportVariable('CC' , 'gcc')
-  core.exportVariable('CXX', 'g++')
-  core.exportVariable('CPP', 'cpp')
-  core.info(`Installed RubyInstaller DevKit for Ruby ${version}`)
-}
+  const msys1Path = `${common.drive}:\\DevKit64`
+  await common.measure('Extracting  msys1 build tools', async () =>
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${msys1Path}`], { silent: true }))
+
+  await common.measure('Setting up DevKit environment', async () => {
+    // ssl dlls cause issues with msys1 Rubies
+    const sys32 = 'C:\\Windows\\System32\\'
+    const badFiles = [`${sys32}libcrypto-1_1-x64.dll`, `${sys32}libssl-1_1-x64.dll`]
+    const existing = badFiles.filter((dll) => fs.existsSync(dll))
+    if (existing.length > 0) {
+      core.warning(`Renaming ${existing.join(' and ')} to avoid dll resolution conflicts on Ruby < 2.4`)
+      existing.forEach(dll => fs.renameSync(dll, `${dll}_`))
+    }
 
-async function setupMSWin() {
-  core.exportVariable('MAKE', 'nmake.exe')
-  return await common.measure('Setting up MSVC environment', async () => addVCVARSEnv())
+    exportEnv({
+      CC: 'gcc',
+      CPP: 'cpp',
+      CXX: 'g++',
+      MAKE: 'make',
+      RI_DEVKIT: msys1Path,
+      SSL_CERT_FILE: certFile
+    })
+  })
+
+  return [`${msys1Path}\\mingw\\x86_64-w64-mingw32\\bin`, `${msys1Path}\\mingw\\bin`, `${msys1Path}\\bin`]
 }
 
 /* Sets MSVC environment for use in Actions
  *   allows steps to run without running vcvars*.bat, also for PowerShell
- *   adds a convenience VCVARS environment variable
  *   this assumes a single Visual Studio version being available in the Windows images */
-export function addVCVARSEnv() {
-  let cmd = 'vswhere -latest -property installationPath'
-  let vcVars = `${cp.execSync(cmd).toString().trim()}\\VC\\Auxiliary\\Build\\vcvars64.bat`
-
-  if (!fs.existsSync(vcVars)) {
-    throw new Error(`Missing vcVars file: ${vcVars}`)
-  }
-  core.exportVariable('VCVARS', vcVars)
+async function installVCPKG(url) {
+  const downloadPath = await common.measure('Downloading mswin vcpkg packages', async () => {
+    console.log(url)
+    return await tc.downloadTool(url)
+  })
 
-  cmd = `cmd.exe /c ""${vcVars}" && set"`
+  const extractPath = process.env.VCPKG_INSTALLATION_ROOT
+  await common.measure('Extracting  mswin vcpkg packages', async () =>
+    exec.exec('7z', ['x', downloadPath, '-aoa', '-bd', `-o${extractPath}`], { silent: true }))
 
-  let newEnv = new Map()
-  let newSet = cp.execSync(cmd).toString().trim().split(/\r?\n/)
-  newSet = newSet.filter(line => /\S=\S/.test(line))
-  newSet.forEach(s => {
-    let [k,v] = common.partition(s, '=')
-    newEnv.set(k,v)
-  })
+  return await common.measure('Setting up MSVC environment', async () => {
+    const cmd = 'vswhere -latest -property installationPath'
+    const vcVarsBat = os.arch() === 'arm64' ? 'vcvarsarm64.bat' : 'vcvars64.bat'
+    const vcVars = `${cp.execSync(cmd).toString().trim()}\\VC\\Auxiliary\\Build\\${vcVarsBat}`
 
-  let newPathEntries = undefined
-  for (let [k, v] of newEnv) {
-    if (process.env[k] !== v) {
-      if (/^Path$/i.test(k)) {
-        const newPathStr = v.replace(`${path.delimiter}${process.env['Path']}`, '')
-        newPathEntries = newPathStr.split(path.delimiter)
-      } else {
-        core.exportVariable(k, v)
-      }
+    if (!fs.existsSync(vcVars)) {
+      throw new Error(`Missing vcVars file: ${vcVars}`)
     }
-  }
-  return newPathEntries
-}
 
-// ssl files cause issues with non RI2 Rubies (<2.4) and ruby/ruby's CI from build folder due to dll resolution
-function renameSystem32Dlls() {
-  const sys32 = 'C:\\Windows\\System32\\'
-  const badFiles = [`${sys32}libcrypto-1_1-x64.dll`, `${sys32}libssl-1_1-x64.dll`]
-  const existing = badFiles.filter((dll) => fs.existsSync(dll))
-  if (existing.length > 0) {
-    console.log(`Renaming ${existing.join(' and ')} to avoid dll resolution conflicts on Ruby <= 2.4`)
-    existing.forEach(dll => fs.renameSync(dll, `${dll}_`))
-  }
+    return exportCommandEnv(`set MAKE=nmake && "${vcVars}"`)
+  })
 }
 
-// Sets MSYS2 ENV variables set from running `ridk enable`
-function addRidkEnv(ridk) {
-  let newEnv = new Map()
-  let cmd = `cmd.exe /c "${ridk} enable && set"`
-  let newSet = cp.execSync(cmd).toString().trim().split(/\r?\n/)
-  newSet = newSet.filter(line => /^\S+=\S+/.test(line))
-  newSet.forEach(s => {
-    let [k, v] = common.partition(s, '=')
-    newEnv.set(k, v)
-  })
+// Run a cmd command, export its environment, and return new paths
+function exportCommandEnv(command) {
+  const cmd = `cmd.exe /s /c "${command} >NUL && "${process.execPath}" -e console.log(JSON.stringify(process.env))"`
+  const env = JSON.parse(cp.execSync(cmd).toString())
+
+  const paths = env.Path.replace(`${path.delimiter}${process.env.Path}`, '').split(path.delimiter)
+  delete env.Path
+
+  exportEnv(env)
+  return paths
+}
 
-  for (let [k, v] of newEnv) {
+function exportEnv(env) {
+  for (const [k, v] of Object.entries(env)) {
     if (process.env[k] !== v) {
-      if (!/^Path$/i.test(k)) {
-        console.log(`${k}=${v}`)
-        core.exportVariable(k, v)
-      }
+      console.log(`${k}=${v}`)
+      core.exportVariable(k, v)
     }
   }
 }