diff --git a/.changeset/wet-cougars-invent.md b/.changeset/wet-cougars-invent.md
new file mode 100644
index 0000000000..5085b3765f
--- /dev/null
+++ b/.changeset/wet-cougars-invent.md
@@ -0,0 +1,8 @@
+---
+"@pnpm/global-bin-dir": patch
+---
+
+When looking for suitable directories for global executables, ignore case.
+
+When comparing to the currently running Node.js executable directory,
+ignore any trailing slash. `/foo/bar` is the same as `/foo/bar/`.
diff --git a/packages/global-bin-dir/src/index.ts b/packages/global-bin-dir/src/index.ts
index a198a427e5..2c2a8739a5 100644
--- a/packages/global-bin-dir/src/index.ts
+++ b/packages/global-bin-dir/src/index.ts
@@ -16,12 +16,13 @@ function pickBestGlobalBinDir (dirs: string[]) {
   const nodeBinDir = path.dirname(process.execPath)
   const noWriteAccessDirs = [] as string[]
   for (const dir of dirs) {
+    const lowCaseDir = dir.toLowerCase()
     if (
-      isUnderDir('node', dir) ||
-      isUnderDir('nodejs', dir) ||
-      isUnderDir('npm', dir) ||
-      isUnderDir('pnpm', dir) ||
-      nodeBinDir === dir
+      isUnderDir('node', lowCaseDir) ||
+      isUnderDir('nodejs', lowCaseDir) ||
+      isUnderDir('npm', lowCaseDir) ||
+      isUnderDir('pnpm', lowCaseDir) ||
+      path.relative(nodeBinDir, dir) === ''
     ) {
       if (canWriteToDirAndExists(dir)) return dir
       noWriteAccessDirs.push(dir)
diff --git a/packages/global-bin-dir/test/index.ts b/packages/global-bin-dir/test/index.ts
index 90ac706e42..14f95ef0b1 100644
--- a/packages/global-bin-dir/test/index.ts
+++ b/packages/global-bin-dir/test/index.ts
@@ -26,6 +26,7 @@ const npmGlobalBin = makePath('home', 'z', '.npm')
 const pnpmGlobalBin = makePath('home', 'z', '.pnpm')
 const otherDir = makePath('some', 'dir')
 const currentExecDir = makePath('current', 'exec')
+const dirWithTrailingSlash = `${makePath('current', 'slash')}${path.sep}`
 process.env[FAKE_PATH] = [
   userGlobalBin,
   nodeGlobalBin,
@@ -33,6 +34,7 @@ process.env[FAKE_PATH] = [
   pnpmGlobalBin,
   otherDir,
   currentExecDir,
+  dirWithTrailingSlash,
 ].join(path.delimiter)
 
 test('prefer a directory that has "nodejs", "npm", or "pnpm" in the path', (t) => {
@@ -66,6 +68,10 @@ test('prefer the directory of the currently executed nodejs command', (t) => {
   process.execPath = path.join(currentExecDir, 'n')
   canWriteToDir = (dir) => dir !== nodeGlobalBin && dir !== npmGlobalBin && dir !== pnpmGlobalBin
   t.equal(globalBinDir(), currentExecDir)
+
+  process.execPath = path.join(dirWithTrailingSlash, 'n')
+  t.equal(globalBinDir(), dirWithTrailingSlash)
+
   process.execPath = originalExecPath
   t.end()
 })
@@ -106,3 +112,15 @@ test('throw exception if PATH is not set', (t) => {
   process.env[FAKE_PATH] = pathEnv
   t.end()
 })
+
+test('prefer a directory that has "Node" in the path', (t) => {
+  const capitalizedNodeGlobalBin = makePath('home', 'z', '.nvs', 'Node', '12.0.0', 'x64', 'bin')
+  const pathEnv = process.env[FAKE_PATH]
+  process.env[FAKE_PATH] = capitalizedNodeGlobalBin
+
+  canWriteToDir = () => true
+  t.equal(globalBinDir(), capitalizedNodeGlobalBin)
+
+  process.env[FAKE_PATH] = pathEnv
+  t.end()
+})