diff --git a/dist/index.js b/dist/index.js
index ac92e56..08a71b3 100644
--- a/dist/index.js
+++ b/dist/index.js
@@ -6463,6 +6463,7 @@ __webpack_require__.r(__webpack_exports__);
 // Most of this logic is from
 // https://github.com/MSP-Greg/actions-ruby/blob/master/lib/main.js
 
+const fs = __webpack_require__(747)
 const core = __webpack_require__(470)
 const exec = __webpack_require__(986)
 const tc = __webpack_require__(533)
@@ -6488,6 +6489,10 @@ async function downloadExtractAndSetPATH(ruby) {
   const newPath = setupPath(msys2, rubyPrefix)
   core.exportVariable('PATH', newPath)
 
+  if (!fs.existsSync(`${rubyPrefix}\\bin\\bundle.cmd`)) {
+    await exec.exec(`${rubyPrefix}\\bin\\gem install bundler --no-document`)
+  }
+
   return rubyPrefix
 }
 
diff --git a/windows.js b/windows.js
index bffa788..ce3e530 100644
--- a/windows.js
+++ b/windows.js
@@ -1,6 +1,7 @@
 // Most of this logic is from
 // https://github.com/MSP-Greg/actions-ruby/blob/master/lib/main.js
 
+const fs = require('fs')
 const core = require('@actions/core')
 const exec = require('@actions/exec')
 const tc = require('@actions/tool-cache')
@@ -26,6 +27,10 @@ export async function downloadExtractAndSetPATH(ruby) {
   const newPath = setupPath(msys2, rubyPrefix)
   core.exportVariable('PATH', newPath)
 
+  if (!fs.existsSync(`${rubyPrefix}\\bin\\bundle.cmd`)) {
+    await exec.exec(`${rubyPrefix}\\bin\\gem install bundler --no-document`)
+  }
+
   return rubyPrefix
 }