diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 7821f2723..1e0586467 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -117,7 +117,7 @@ jobs:
       shell: bash
       run: which -a bundle
       # https://github.com/ruby/setup-ruby/issues/658
-      if: "matrix.ruby != 'mingw' && matrix.ruby != 'mswin' && matrix.ruby != 'ucrt'"
+      if: "matrix.ruby != 'mingw' && !startsWith(matrix.ruby, 'mswin') && matrix.ruby != 'ucrt'"
     - name: which rake
       run: which -a rake
       if: runner.os != 'Windows'
diff --git a/README.md b/README.md
index 1c8c319df..d7180f449 100644
--- a/README.md
+++ b/README.md
@@ -15,7 +15,8 @@ This action currently supports these versions of MRI, JRuby and TruffleRuby:
 
 | Interpreter | Versions |
 | ----------- | -------- |
-| `ruby` | 1.9.3, 2.0.0, 2.1.9, 2.2, all versions from 2.3.0 until 4.1.0-preview1, head, debug, mingw, mswin, ucrt |
+| `ruby` | 1.9.3, 2.0.0, 2.1.9, 2.2, all versions from 2.3.0 until 4.1.0-preview1, head, debug, mingw, ucrt |
+| `mswin` | 3.4.11 - 4.0.9, head (Windows only) |
 | `jruby` | 9.1.17.0 - 10.1.3.0, head |
 | `truffleruby` | 19.3.0 - 40.0.0, head |
 | `truffleruby+graalvm` | 21.2.0 - 40.0.0, head |
@@ -29,7 +30,10 @@ Native extensions are automatically compiled with AddressSanitizer when using `r
 `ruby-asan` and `asan-release` are currently only available on `ubuntu-24.04` and `ubuntu-26.04`.
 
 Regarding Windows ruby master builds, `mingw` is a MSYS2/MinGW build, `head` & `ucrt` are MSYS2/UCRT64
-builds, and `mswin` is a MSVC/VS 2022 build.
+builds.
+
+`mswin` is CRuby built with MSVC, available on Windows only. `mswin-4.0` resolves to the latest 4.0.x release, and `mswin` and `mswin-head` to the latest master build.
+The list of available versions is in [windows-mswin-versions.json](windows-mswin-versions.json).
 
 Preview and RC versions of Ruby might be available too on Ubuntu and macOS (not on Windows).
 However, it is recommended to test against `ruby-head` rather than previews,
@@ -62,7 +66,8 @@ only has builds of CRuby 3.2 and newer, as older CRuby versions do not compile o
 
 The prebuilt releases are generated by [ruby-builder](https://github.com/ruby/ruby-builder)
 and on Windows by [RubyInstaller2](https://github.com/oneclick/rubyinstaller2).
-The `mingw`, `ucrt` and `mswin` builds are generated by [ruby-loco](https://github.com/MSP-Greg/ruby-loco).
+The `mingw` and `ucrt` builds are generated by [ruby-loco](https://github.com/MSP-Greg/ruby-loco).
+The `mswin` builds are published at [cache.ruby-lang.org](https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/) and maintained by [hsbt](https://github.com/hsbt).
 `ruby-head` is generated by [ruby-dev-builder](https://github.com/ruby/ruby-dev-builder),
 `jruby-head` is generated by [jruby-dev-builder](https://github.com/ruby/jruby-dev-builder),
 `truffleruby-head` and `truffleruby+graalvm-head` are generated by [truffleruby-dev-builder](https://github.com/ruby/truffleruby-dev-builder).
diff --git a/common.js b/common.js
index 79ad6266f..2634299fe 100644
--- a/common.js
+++ b/common.js
@@ -70,7 +70,12 @@ export async function time(name, block) {
 
 export function isHeadVersion(rubyVersion) {
   // asan-release counts as "head" because the version cannot be selected -- you can only get whatever's latest
-  return ['head', 'debug',  'mingw', 'mswin', 'ucrt', 'asan', 'asan-release'].includes(rubyVersion)
+  return ['head', 'debug',  'mingw', 'ucrt', 'asan', 'asan-release'].includes(rubyVersion)
+}
+
+// mswin is CRuby built with MSVC, so it follows the same version-dependent defaults
+export function isCRuby(engine) {
+  return engine === 'ruby' || engine === 'mswin'
 }
 
 export function isStableVersion(engine, rubyVersion) {
@@ -86,7 +91,7 @@ export function hasBundlerDefaultGem(engine, rubyVersion) {
 }
 
 export function isBundler1Default(engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return floatVersion(rubyVersion) >= 2.6 && floatVersion(rubyVersion) < 2.7
   } else if (engine.startsWith('truffleruby')) {
     return floatVersion(rubyVersion) < 21.0
@@ -98,7 +103,7 @@ export function isBundler1Default(engine, rubyVersion) {
 }
 
 export function isBundler2PlusDefault(engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return floatVersion(rubyVersion) >= 2.7
   } else if (engine.startsWith('truffleruby')) {
     return floatVersion(rubyVersion) >= 21.0
@@ -110,7 +115,7 @@ export function isBundler2PlusDefault(engine, rubyVersion) {
 }
 
 export function isBundler2dot2PlusDefault(engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return floatVersion(rubyVersion) >= 3.0
   } else if (engine.startsWith('truffleruby')) {
     return floatVersion(rubyVersion) >= 22.0
@@ -130,7 +135,7 @@ export function isBundler4PlusDefault(engine, rubyVersion) {
 
 export function targetRubyVersion(engine, rubyVersion) {
   const version = floatVersion(rubyVersion)
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return version
   } else if (engine === 'jruby') {
     if (version === 9.1) {
@@ -446,6 +451,7 @@ export function isExactCacheKeyMatch(key, cacheKey) {
 }
 
 export async function download(url) {
-  const auth = inputs.token ? `token ${inputs.token}` : undefined
+  // The token is for github.com, so it must not reach other hosts such as cache.ruby-lang.org
+  const auth = inputs.token && new URL(url).hostname === 'github.com' ? `token ${inputs.token}` : undefined
   return await tc.downloadTool(url, undefined, auth)
 }
diff --git a/dist/index.js b/dist/index.js
index 7585bd54f..00ce226d6 100644
--- a/dist/index.js
+++ b/dist/index.js
@@ -316,6 +316,7 @@ __nccwpck_require__.r(__webpack_exports__);
 /* harmony export */   isBundler2PlusDefault: () => (/* binding */ isBundler2PlusDefault),
 /* harmony export */   isBundler2dot2PlusDefault: () => (/* binding */ isBundler2dot2PlusDefault),
 /* harmony export */   isBundler4PlusDefault: () => (/* binding */ isBundler4PlusDefault),
+/* harmony export */   isCRuby: () => (/* binding */ isCRuby),
 /* harmony export */   isExactCacheKeyMatch: () => (/* binding */ isExactCacheKeyMatch),
 /* harmony export */   isHeadVersion: () => (/* binding */ isHeadVersion),
 /* harmony export */   isSelfHostedRunner: () => (/* binding */ isSelfHostedRunner),
@@ -405,7 +406,12 @@ async function time(name, block) {
 
 function isHeadVersion(rubyVersion) {
   // asan-release counts as "head" because the version cannot be selected -- you can only get whatever's latest
-  return ['head', 'debug',  'mingw', 'mswin', 'ucrt', 'asan', 'asan-release'].includes(rubyVersion)
+  return ['head', 'debug',  'mingw', 'ucrt', 'asan', 'asan-release'].includes(rubyVersion)
+}
+
+// mswin is CRuby built with MSVC, so it follows the same version-dependent defaults
+function isCRuby(engine) {
+  return engine === 'ruby' || engine === 'mswin'
 }
 
 function isStableVersion(engine, rubyVersion) {
@@ -421,7 +427,7 @@ function hasBundlerDefaultGem(engine, rubyVersion) {
 }
 
 function isBundler1Default(engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return floatVersion(rubyVersion) >= 2.6 && floatVersion(rubyVersion) < 2.7
   } else if (engine.startsWith('truffleruby')) {
     return floatVersion(rubyVersion) < 21.0
@@ -433,7 +439,7 @@ function isBundler1Default(engine, rubyVersion) {
 }
 
 function isBundler2PlusDefault(engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return floatVersion(rubyVersion) >= 2.7
   } else if (engine.startsWith('truffleruby')) {
     return floatVersion(rubyVersion) >= 21.0
@@ -445,7 +451,7 @@ function isBundler2PlusDefault(engine, rubyVersion) {
 }
 
 function isBundler2dot2PlusDefault(engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return floatVersion(rubyVersion) >= 3.0
   } else if (engine.startsWith('truffleruby')) {
     return floatVersion(rubyVersion) >= 22.0
@@ -465,7 +471,7 @@ function isBundler4PlusDefault(engine, rubyVersion) {
 
 function targetRubyVersion(engine, rubyVersion) {
   const version = floatVersion(rubyVersion)
-  if (engine === 'ruby') {
+  if (isCRuby(engine)) {
     return version
   } else if (engine === 'jruby') {
     if (version === 9.1) {
@@ -781,7 +787,8 @@ function isExactCacheKeyMatch(key, cacheKey) {
 }
 
 async function download(url) {
-  const auth = inputs.token ? `token ${inputs.token}` : undefined
+  // The token is for github.com, so it must not reach other hosts such as cache.ruby-lang.org
+  const auth = inputs.token && new URL(url).hostname === 'github.com' ? `token ${inputs.token}` : undefined
   return await tc.downloadTool(url, undefined, auth)
 }
 
@@ -46052,7 +46059,7 @@ async function compareGemVersion(a, b, rubyPrefix) {
 // rubygems-update.  See https://github.com/ruby/setup-ruby/pull/551 and
 // https://github.com/rubygems/rubygems/issues/7329
 async function rubygemsLatest(gem, platform, engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (common.isCRuby(engine)) {
     const floatVersion = common.floatVersion(rubyVersion)
     if (common.isHeadVersion(rubyVersion)) {
       console.log('Ruby master builds use included RubyGems')
@@ -46103,22 +46110,29 @@ const exec = __nccwpck_require__(95236)
 const common = __nccwpck_require__(97211)
 const rubyInstallerVersions = __nccwpck_require__(18287)
 const toolchainVersions = __nccwpck_require__(24977)
+const mswinVersions = __nccwpck_require__(22158)
+const mswinToolchainVersions = __nccwpck_require__(82768)
 
 function getAvailableVersions(_platform, engine) {
-  if (engine === 'ruby') {
-    return Object.keys(rubyInstallerVersions).filter(version => os.arch() in rubyInstallerVersions[version])
+  const versions = engine === 'mswin' ? mswinVersions : rubyInstallerVersions
+  if (versions) {
+    return Object.keys(versions).filter(version => os.arch() in versions[version])
   } else {
     return undefined
   }
 }
 
 async function install(platform, engine, version) {
-  const url = rubyInstallerVersions[version][os.arch()]
+  let url = (engine === 'mswin' ? mswinVersions : rubyInstallerVersions)[version][os.arch()]
+  if (engine === 'mswin' && version === 'head') {
+    url = await getLatestMswinHeadURL(url)
+  }
 
-  if (!url.endsWith('.7z')) {
-    throw new Error(`URL should end in .7z: ${url}`)
+  const ext = path.posix.extname(url)
+  if (ext !== '.7z' && ext !== '.zip') {
+    throw new Error(`URL should end in .7z or .zip: ${url}`)
   }
-  const base = path.posix.basename(url, '.7z')
+  const base = path.posix.basename(url, ext)
 
   let rubyPrefix, inToolCache
   if (common.shouldUseToolCache(engine, version)) {
@@ -46136,6 +46150,10 @@ async function install(platform, engine, version) {
     await downloadAndExtract(engine, version, url, base, rubyPrefix);
   }
 
+  if (engine === 'mswin') {
+    exportEnv({ SSL_CERT_FILE: findGitCertFile() })
+  }
+
   const paths = [`${rubyPrefix}\\bin`]
   const windowsToolchain = core.getInput('windows-toolchain')
   if (windowsToolchain === 'none') {
@@ -46143,7 +46161,7 @@ async function install(platform, engine, version) {
     return rubyPrefix
   }
 
-  const toolchainUrl = toolchainVersions[version][os.arch()]
+  const toolchainUrl = (engine === 'mswin' ? mswinToolchainVersions : toolchainVersions)[version][os.arch()]
 
   // Examples:
   // - DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe
@@ -46170,6 +46188,33 @@ async function install(platform, engine, version) {
   return rubyPrefix
 }
 
+// mswin master builds are published daily under dated names, so pick the latest one from the index
+async function getLatestMswinHeadURL(indexURL) {
+  // Retry like tc.downloadTool does for the archive, so a transient failure of the index does not fail the job
+  let response
+  for (let attempt = 1; attempt <= 3; attempt++) {
+    try {
+      response = await fetch(indexURL, { signal: AbortSignal.timeout(30000) })
+      if (response.ok) break
+    } catch (error) {
+      if (attempt === 3) throw error
+    }
+    if (attempt < 3) await new Promise(resolve => setTimeout(resolve, 5000))
+  }
+  if (!response.ok) {
+    throw new Error(`Failed to fetch ${indexURL}: ${response.status} ${response.statusText}`)
+  }
+
+  const platform = `${os.arch()}-mswin64_140`
+  const builds = (await response.json()).builds.filter(build => build.channel === 'dev' && build.platform === platform)
+  if (builds.length === 0) {
+    throw new Error(`No mswin head build for ${platform} in ${indexURL}`)
+  }
+
+  // The index is sorted by name, and the date in the name can differ from the date it was published
+  return builds.reduce((latest, build) => build.published_at > latest.published_at ? build : latest).url
+}
+
 async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
   const downloadPath = await common.measure('Downloading Ruby', async () => {
     console.log(url)
@@ -46241,15 +46286,22 @@ async function installMSYS2(url, rubyPrefix = process.env.RUNNER_TEMP) {
   return [`${msys2Path}\\${msys2Type}\\bin`, `${msys2Path}\\usr\\bin`]
 }
 
-async function installMSYS1(url) {
+// DevKit and mswin Rubies have no usable CA certificates on runners, so they use the bundle of Git for Windows
+function findGitCertFile() {
   const certFile = [
     'C:\\Program Files\\Git\\ucrt64\\etc\\ssl\\cert.pem',
     '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',
   ].find(file => fs.existsSync(file))
   if (certFile === undefined) {
     throw new Error("Cannot find Git's cert file")
   }
+  return certFile
+}
+
+async function installMSYS1(url) {
+  const certFile = findGitCertFile()
 
   const downloadPath = await common.measure('Downloading msys1 build tools', async () => {
     console.log(url)
@@ -88071,11 +88123,27 @@ module.exports = /*#__PURE__*/JSON.parse('{"ruby":["1.9.3-p551","2.0.0-p648","2.
 
 /***/ }),
 
+/***/ 82768:
+/***/ ((module) => {
+
+"use strict";
+module.exports = /*#__PURE__*/JSON.parse('{"3.4.11":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"},"3.4.12":{"arm64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-arm64-windows.7z","x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"},"4.0.7":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"},"4.0.8":{"x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"},"4.0.9":{"arm64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-arm64-windows.7z","x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"},"head":{"arm64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-arm64-windows.7z","x64":"https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"}}');
+
+/***/ }),
+
+/***/ 22158:
+/***/ ((module) => {
+
+"use strict";
+module.exports = /*#__PURE__*/JSON.parse('{"3.4.11":{"x64":"https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-3.4.11-x64-mswin64_140.zip"},"3.4.12":{"arm64":"https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-3.4.12-arm64-mswin64_140.zip","x64":"https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-3.4.12-x64-mswin64_140.zip"},"4.0.7":{"x64":"https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.7-x64-mswin64_140.zip"},"4.0.8":{"x64":"https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.8-x64-mswin64_140.zip"},"4.0.9":{"arm64":"https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.9-arm64-mswin64_140.zip","x64":"https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.9-x64-mswin64_140.zip"},"head":{"arm64":"https://cache.ruby-lang.org/pub/ruby/binaries/index.json","x64":"https://cache.ruby-lang.org/pub/ruby/binaries/index.json"}}');
+
+/***/ }),
+
 /***/ 24977:
 /***/ ((module) => {
 
 "use strict";
-module.exports = 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+module.exports = 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
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@@ -88083,7 +88151,7 @@ module.exports = /*#__PURE__*/JSON.parse('{"2.0.0":{"x64":"https://github.com/on
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 "use strict";
-module.exports = 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+module.exports = 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
 /***/ })
 
@@ -88218,7 +88286,7 @@ async function setupRuby(options = {}) {
   const [engine, parsedVersion] = parseRubyEngineAndVersion(inputs['ruby-version'])
 
   let installer
-  if (platform.startsWith('windows-') && engine === 'ruby' && !common.isSelfHostedRunner()) {
+  if (platform.startsWith('windows-') && common.isCRuby(engine) && !common.isSelfHostedRunner()) {
     installer = __nccwpck_require__(26373)
   } else {
     installer = __nccwpck_require__(64572)
@@ -88304,6 +88372,9 @@ function parseRubyEngineAndVersion(rubyVersion) {
   if (/^(\d+)/.test(rubyVersion) || common.isHeadVersion(rubyVersion)) { // X.Y.Z => ruby-X.Y.Z
     engine = 'ruby'
     version = rubyVersion
+  } else if (rubyVersion === 'mswin') { // mswin has always been the master build
+    engine = 'mswin'
+    version = 'head'
   } else if (!rubyVersion.includes('-')) { // myruby -> myruby-stableVersion
     engine = rubyVersion
     version = '' // Let the logic in validateRubyEngineAndVersion() find the version
diff --git a/generate-test-matrix.rb b/generate-test-matrix.rb
index e9e792cc1..20cd5fcdb 100644
--- a/generate-test-matrix.rb
+++ b/generate-test-matrix.rb
@@ -45,6 +45,7 @@ def unique_versions(versions, segment_count, *symbolic)
 # Versions
 ruby_builder_versions = JSON.load(File.read('ruby-builder-versions.json'))
 windows_versions = JSON.load(File.read('windows-versions.json'))
+windows_mswin_versions = JSON.load(File.read('windows-mswin-versions.json'))
 
 # ruby: each minor release + head
 ruby_versions = unique_versions(ruby_builder_versions['ruby'], 2, 'head')
@@ -59,8 +60,12 @@ def unique_versions(versions, segment_count, *symbolic)
 truffleruby_versions = %w[truffleruby truffleruby-head truffleruby+graalvm truffleruby+graalvm-head]
 matrix += (macos_arm64_runners + ubuntu_runners).product(truffleruby_versions)
 
+# mswin: each minor release + head
+windows_ruby_mswin_versions = unique_versions(windows_mswin_versions.keys, 2, 'head')
+matrix += windows_runners.product(windows_ruby_mswin_versions.map { |version| "mswin-#{version}"})
+
 # ruby-loco: head
-ruby_loco_versions = %w[mingw mswin ucrt]
+ruby_loco_versions = %w[mingw ucrt]
 matrix += windows_x64_runners.product(ruby_loco_versions)
 
 # asan: latest release + head
diff --git a/generate-windows-versions.rb b/generate-windows-versions.rb
index a7c21c3fe..6105994bd 100644
--- a/generate-windows-versions.rb
+++ b/generate-windows-versions.rb
@@ -12,6 +12,11 @@
   %r{\A#{Regexp.escape 'https://github.com/MSP-Greg/ruby-loco/releases/download'}/\w[\w.-]*/\w[\w.-]*\z}
 ].freeze
 
+MSWIN_VERSIONS_URLS_REGEXPS = [
+  %r{\A#{Regexp.escape 'https://cache.ruby-lang.org/pub/ruby/binaries/mswin64'}/\w[\w.-]*\.zip\z},
+  %r{\A#{Regexp.escape 'https://cache.ruby-lang.org/pub/ruby/binaries/index.json'}\z}
+].freeze
+
 WINDOWS_TOOLCHAIN_VERSIONS_URLS_REGEXPS = [
   %r{\A#{Regexp.escape 'https://github.com/oneclick/rubyinstaller/releases/download/devkit-4.7.2/DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe'}\z},
   %r{\A#{Regexp.escape 'https://github.com/ruby/setup-msys2-gcc/releases/download'}/\w[\w.-]*/\w[\w@.-]*\z},
@@ -66,9 +71,6 @@ def validate(versions, allowed_urls_regexps)
 versions['mingw'] = {
   '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'
-}
 versions['ucrt'] = {
   'x64' => 'https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-ucrt.7z'
 }
@@ -79,6 +81,20 @@ def validate(versions, allowed_urls_regexps)
 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)
 
+find_toolchain = -> platform, version {
+  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 #{platform} #{version}: #{toolchain}"
+  end
+
+  toolchain.first
+}
+
 versions.each do |raw_version, archs|
   version = Gem::Version.correct?(raw_version) ? Gem::Version.new(raw_version) : head_version
 
@@ -91,8 +107,6 @@ def validate(versions, allowed_urls_regexps)
         "#{arch}-mingw-ucrt"
       when 'mingw'
         "#{arch}-mingw32"
-      when 'mswin'
-        "#{arch}-mswin64"
       else
         if version >= Gem::Version.new('3.1.0.dev')
           "#{arch}-mingw-ucrt"
@@ -101,20 +115,50 @@ def validate(versions, allowed_urls_regexps)
         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
+    toolchain = find_toolchain.(platform, version)
 
-    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]).to_s
+    archs[raw_arch] = URI.join(base_url, toolchain[:href]).to_s
   end
 end
 
 validate(versions, WINDOWS_TOOLCHAIN_VERSIONS_URLS_REGEXPS)
 File.binwrite 'windows-toolchain-versions.json', "#{JSON.pretty_generate(versions)}\n"
+
+mswin_index_url = 'https://cache.ruby-lang.org/pub/ruby/binaries/index.json'
+mswin_builds = JSON.parse(URI.open(mswin_index_url, &:read), symbolize_names: true)[:builds].select { |build|
+  build[:platform].end_with?('-mswin64_140')
+}
+mswin_arch = -> build { build[:platform].delete_suffix('-mswin64_140') }
+
+release_builds = mswin_builds.select { |build|
+  build[:channel] == 'release' && Gem::Version.new(build[:version]) >= Gem::Version.new('3.4')
+}
+dev_builds = mswin_builds.select { |build| build[:channel] == 'dev' }
+
+mswin_versions = release_builds.group_by { |build|
+  build[:version]
+}.sort_by { |version, _|
+  Gem::Version.new(version)
+}.to_h { |version, builds|
+  [version, builds.sort_by(&mswin_arch).to_h { |build| [mswin_arch.(build), build[:url]] }]
+}
+
+# The latest master build is picked from the index at runtime, see getLatestMswinHeadURL in windows.js
+mswin_versions['head'] = dev_builds.map(&mswin_arch).uniq.sort.to_h { |arch| [arch, mswin_index_url] }
+
+mswin_toolchain_versions = mswin_versions.to_h do |raw_version, archs|
+  version = raw_version == 'head' ? head_version : Gem::Version.new(raw_version)
+
+  toolchains = archs.map do |arch, _|
+    toolchain = find_toolchain.("#{arch}-mswin64", version)
+
+    [arch, URI.join(base_url, toolchain[:href]).to_s]
+  end
+  [raw_version, toolchains.to_h]
+end
+
+validate(mswin_versions, MSWIN_VERSIONS_URLS_REGEXPS)
+File.binwrite 'windows-mswin-versions.json', "#{JSON.pretty_generate(mswin_versions)}\n"
+
+validate(mswin_toolchain_versions, WINDOWS_TOOLCHAIN_VERSIONS_URLS_REGEXPS)
+File.binwrite 'windows-mswin-toolchain-versions.json', "#{JSON.pretty_generate(mswin_toolchain_versions)}\n"
diff --git a/index.js b/index.js
index 5d08a5863..3897877e3 100644
--- a/index.js
+++ b/index.js
@@ -54,7 +54,7 @@ export async function setupRuby(options = {}) {
   const [engine, parsedVersion] = parseRubyEngineAndVersion(inputs['ruby-version'])
 
   let installer
-  if (platform.startsWith('windows-') && engine === 'ruby' && !common.isSelfHostedRunner()) {
+  if (platform.startsWith('windows-') && common.isCRuby(engine) && !common.isSelfHostedRunner()) {
     installer = require('./windows')
   } else {
     installer = require('./ruby-builder')
@@ -140,6 +140,9 @@ function parseRubyEngineAndVersion(rubyVersion) {
   if (/^(\d+)/.test(rubyVersion) || common.isHeadVersion(rubyVersion)) { // X.Y.Z => ruby-X.Y.Z
     engine = 'ruby'
     version = rubyVersion
+  } else if (rubyVersion === 'mswin') { // mswin has always been the master build
+    engine = 'mswin'
+    version = 'head'
   } else if (!rubyVersion.includes('-')) { // myruby -> myruby-stableVersion
     engine = rubyVersion
     version = '' // Let the logic in validateRubyEngineAndVersion() find the version
diff --git a/rubygems.js b/rubygems.js
index 7d65c54e1..83b560653 100644
--- a/rubygems.js
+++ b/rubygems.js
@@ -36,7 +36,7 @@ async function compareGemVersion(a, b, rubyPrefix) {
 // rubygems-update.  See https://github.com/ruby/setup-ruby/pull/551 and
 // https://github.com/rubygems/rubygems/issues/7329
 async function rubygemsLatest(gem, platform, engine, rubyVersion) {
-  if (engine === 'ruby') {
+  if (common.isCRuby(engine)) {
     const floatVersion = common.floatVersion(rubyVersion)
     if (common.isHeadVersion(rubyVersion)) {
       console.log('Ruby master builds use included RubyGems')
diff --git a/windows-mswin-toolchain-versions.json b/windows-mswin-toolchain-versions.json
new file mode 100644
index 000000000..00b303caa
--- /dev/null
+++ b/windows-mswin-toolchain-versions.json
@@ -0,0 +1,23 @@
+{
+  "3.4.11": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"
+  },
+  "3.4.12": {
+    "arm64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-arm64-windows.7z",
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"
+  },
+  "4.0.7": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"
+  },
+  "4.0.8": {
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"
+  },
+  "4.0.9": {
+    "arm64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-arm64-windows.7z",
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"
+  },
+  "head": {
+    "arm64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-arm64-windows.7z",
+    "x64": "https://github.com/ruby/setup-msys2-gcc/releases/latest/download/vcpkg-x64-windows.7z"
+  }
+}
diff --git a/windows-mswin-versions.json b/windows-mswin-versions.json
new file mode 100644
index 000000000..832963ba7
--- /dev/null
+++ b/windows-mswin-versions.json
@@ -0,0 +1,23 @@
+{
+  "3.4.11": {
+    "x64": "https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-3.4.11-x64-mswin64_140.zip"
+  },
+  "3.4.12": {
+    "arm64": "https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-3.4.12-arm64-mswin64_140.zip",
+    "x64": "https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-3.4.12-x64-mswin64_140.zip"
+  },
+  "4.0.7": {
+    "x64": "https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.7-x64-mswin64_140.zip"
+  },
+  "4.0.8": {
+    "x64": "https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.8-x64-mswin64_140.zip"
+  },
+  "4.0.9": {
+    "arm64": "https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.9-arm64-mswin64_140.zip",
+    "x64": "https://cache.ruby-lang.org/pub/ruby/binaries/mswin64/ruby-4.0.9-x64-mswin64_140.zip"
+  },
+  "head": {
+    "arm64": "https://cache.ruby-lang.org/pub/ruby/binaries/index.json",
+    "x64": "https://cache.ruby-lang.org/pub/ruby/binaries/index.json"
+  }
+}
diff --git a/windows-toolchain-versions.json b/windows-toolchain-versions.json
index 39a21bc2d..803ddf4e1 100644
--- a/windows-toolchain-versions.json
+++ b/windows-toolchain-versions.json
@@ -345,9 +345,6 @@
   "mingw": {
     "x64": "https://github.com/ruby/setup-msys2-gcc/releases/download/v20261024.010459/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-versions.json b/windows-versions.json
index afc2d36e7..ecae7c959 100644
--- a/windows-versions.json
+++ b/windows-versions.json
@@ -345,9 +345,6 @@
   "mingw": {
     "x64": "https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-mingw.7z"
   },
-  "mswin": {
-    "x64": "https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-mswin.7z"
-  },
   "ucrt": {
     "x64": "https://github.com/MSP-Greg/ruby-loco/releases/download/ruby-master/ruby-ucrt.7z"
   }
diff --git a/windows.js b/windows.js
index 9bc195952..3a1f27a9e 100644
--- a/windows.js
+++ b/windows.js
@@ -10,22 +10,29 @@ const exec = require('@actions/exec')
 const common = require('./common')
 const rubyInstallerVersions = require('./windows-versions.json')
 const toolchainVersions = require('./windows-toolchain-versions.json')
+const mswinVersions = require('./windows-mswin-versions.json')
+const mswinToolchainVersions = require('./windows-mswin-toolchain-versions.json')
 
 export function getAvailableVersions(_platform, engine) {
-  if (engine === 'ruby') {
-    return Object.keys(rubyInstallerVersions).filter(version => os.arch() in rubyInstallerVersions[version])
+  const versions = engine === 'mswin' ? mswinVersions : rubyInstallerVersions
+  if (versions) {
+    return Object.keys(versions).filter(version => os.arch() in versions[version])
   } else {
     return undefined
   }
 }
 
 export async function install(platform, engine, version) {
-  const url = rubyInstallerVersions[version][os.arch()]
+  let url = (engine === 'mswin' ? mswinVersions : rubyInstallerVersions)[version][os.arch()]
+  if (engine === 'mswin' && version === 'head') {
+    url = await getLatestMswinHeadURL(url)
+  }
 
-  if (!url.endsWith('.7z')) {
-    throw new Error(`URL should end in .7z: ${url}`)
+  const ext = path.posix.extname(url)
+  if (ext !== '.7z' && ext !== '.zip') {
+    throw new Error(`URL should end in .7z or .zip: ${url}`)
   }
-  const base = path.posix.basename(url, '.7z')
+  const base = path.posix.basename(url, ext)
 
   let rubyPrefix, inToolCache
   if (common.shouldUseToolCache(engine, version)) {
@@ -43,6 +50,10 @@ export async function install(platform, engine, version) {
     await downloadAndExtract(engine, version, url, base, rubyPrefix);
   }
 
+  if (engine === 'mswin') {
+    exportEnv({ SSL_CERT_FILE: findGitCertFile() })
+  }
+
   const paths = [`${rubyPrefix}\\bin`]
   const windowsToolchain = core.getInput('windows-toolchain')
   if (windowsToolchain === 'none') {
@@ -50,7 +61,7 @@ export async function install(platform, engine, version) {
     return rubyPrefix
   }
 
-  const toolchainUrl = toolchainVersions[version][os.arch()]
+  const toolchainUrl = (engine === 'mswin' ? mswinToolchainVersions : toolchainVersions)[version][os.arch()]
 
   // Examples:
   // - DevKit-mingw64-64-4.7.2-20130224-1432-sfx.exe
@@ -77,6 +88,33 @@ export async function install(platform, engine, version) {
   return rubyPrefix
 }
 
+// mswin master builds are published daily under dated names, so pick the latest one from the index
+async function getLatestMswinHeadURL(indexURL) {
+  // Retry like tc.downloadTool does for the archive, so a transient failure of the index does not fail the job
+  let response
+  for (let attempt = 1; attempt <= 3; attempt++) {
+    try {
+      response = await fetch(indexURL, { signal: AbortSignal.timeout(30000) })
+      if (response.ok) break
+    } catch (error) {
+      if (attempt === 3) throw error
+    }
+    if (attempt < 3) await new Promise(resolve => setTimeout(resolve, 5000))
+  }
+  if (!response.ok) {
+    throw new Error(`Failed to fetch ${indexURL}: ${response.status} ${response.statusText}`)
+  }
+
+  const platform = `${os.arch()}-mswin64_140`
+  const builds = (await response.json()).builds.filter(build => build.channel === 'dev' && build.platform === platform)
+  if (builds.length === 0) {
+    throw new Error(`No mswin head build for ${platform} in ${indexURL}`)
+  }
+
+  // The index is sorted by name, and the date in the name can differ from the date it was published
+  return builds.reduce((latest, build) => build.published_at > latest.published_at ? build : latest).url
+}
+
 async function downloadAndExtract(engine, version, url, base, rubyPrefix) {
   const downloadPath = await common.measure('Downloading Ruby', async () => {
     console.log(url)
@@ -148,15 +186,22 @@ async function installMSYS2(url, rubyPrefix = process.env.RUNNER_TEMP) {
   return [`${msys2Path}\\${msys2Type}\\bin`, `${msys2Path}\\usr\\bin`]
 }
 
-async function installMSYS1(url) {
+// DevKit and mswin Rubies have no usable CA certificates on runners, so they use the bundle of Git for Windows
+function findGitCertFile() {
   const certFile = [
     'C:\\Program Files\\Git\\ucrt64\\etc\\ssl\\cert.pem',
     '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',
   ].find(file => fs.existsSync(file))
   if (certFile === undefined) {
     throw new Error("Cannot find Git's cert file")
   }
+  return certFile
+}
+
+async function installMSYS1(url) {
+  const certFile = findGitCertFile()
 
   const downloadPath = await common.measure('Downloading msys1 build tools', async () => {
     console.log(url)