diff --git a/lib/path-reservations.js b/lib/path-reservations.js
index 48c750e3..b7f6c916 100644
--- a/lib/path-reservations.js
+++ b/lib/path-reservations.js
@@ -8,8 +8,12 @@
 
 const assert = require('assert')
 const normPath = require('./normalize-windows-path.js')
+const stripSlashes = require('./strip-trailing-slashes.js')
 const { join } = require('path')
 
+const platform = process.env.TESTING_TAR_FAKE_PLATFORM || process.platform
+const isWindows = platform === 'win32'
+
 module.exports = () => {
   // path => [function or Set]
   // A Set object means a directory reservation
@@ -20,10 +24,16 @@ module.exports = () => {
   const reservations = new Map()
 
   // return a set of parent dirs for a given path
-  const getDirs = path =>
-    path.split('/').slice(0, -1).reduce((set, path) =>
-      set.length ? set.concat(normPath(join(set[set.length - 1], path)))
-      : [path], [])
+  // '/a/b/c/d' -> ['/', '/a', '/a/b', '/a/b/c', '/a/b/c/d']
+  const getDirs = path => {
+    const dirs = path.split('/').slice(0, -1).reduce((set, path) => {
+      if (set.length)
+        path = normPath(join(set[set.length - 1], path))
+      set.push(path || '/')
+      return set
+    }, [])
+    return dirs
+  }
 
   // functions currently running
   const running = new Set()
@@ -99,7 +109,18 @@ module.exports = () => {
   }
 
   const reserve = (paths, fn) => {
-    paths = paths.map(p => normPath(join(p)).toLowerCase())
+    // collide on matches across case and unicode normalization
+    // On windows, thanks to the magic of 8.3 shortnames, it is fundamentally
+    // impossible to determine whether two paths refer to the same thing on
+    // disk, without asking the kernel for a shortname.
+    // So, we just pretend that every path matches every other path here,
+    // effectively removing all parallelization on windows.
+    paths = isWindows ? ['win32 parallelization disabled'] : paths.map(p => {
+      return stripSlashes(normPath(join(p)))
+        .normalize('NFKD')
+        .toLowerCase()
+    })
+
     const dirs = new Set(
       paths.map(path => getDirs(path)).reduce((a, b) => a.concat(b))
     )
diff --git a/test/path-reservations.js b/test/path-reservations.js
index 9ce46b80..c495f310 100644
--- a/test/path-reservations.js
+++ b/test/path-reservations.js
@@ -1,5 +1,14 @@
 const t = require('tap')
+const requireInject = require('require-inject')
+
+// load up the posix and windows versions of the reserver
+if (process.platform === 'win32')
+  process.env.TESTING_TAR_FAKE_PLATFORM = 'posix'
 const { reserve } = require('../lib/path-reservations.js')()
+delete process.env.TESTING_TAR_FAKE_PLATFORM
+if (process.platform !== 'win32')
+  process.env.TESTING_TAR_FAKE_PLATFORM = 'win32'
+const { reserve: winReserve } = requireInject('../lib/path-reservations.js')()
 
 t.test('basic race', t => {
   // simulate the race conditions we care about
@@ -54,3 +63,87 @@ t.test('basic race', t => {
   t.notOk(reserve(['a/b'], dir2), 'dir2 waits')
   t.notOk(reserve(['a/b/x'], dir3), 'dir3 waits')
 })
+
+t.test('unicode shenanigans', t => {
+  const e1 = Buffer.from([0xc3, 0xa9])
+  const e2 = Buffer.from([0x65, 0xcc, 0x81])
+  let didCafe1 = false
+  const cafe1 = done => {
+    t.equal(didCafe1, false, 'did cafe1 only once')
+    t.equal(didCafe2, false, 'did cafe1 before cafe2')
+    didCafe1 = true
+    setTimeout(done)
+  }
+  let didCafe2 = false
+  const cafe2 = done => {
+    t.equal(didCafe1, true, 'did cafe1 before cafe2')
+    t.equal(didCafe2, false, 'did cafe2 only once')
+    didCafe2 = true
+    done()
+    t.end()
+  }
+  const cafePath1 = `c/a/f/${e1}`
+  const cafePath2 = `c/a/f/${e2}`
+  t.ok(reserve([cafePath1], cafe1))
+  t.notOk(reserve([cafePath2], cafe2))
+})
+
+t.test('absolute paths and trailing slash', t => {
+  let calledA1 = false
+  let calledA2 = false
+  const a1 = done => {
+    t.equal(calledA1, false, 'called a1 only once')
+    t.equal(calledA2, false, 'called a1 before 2')
+    calledA1 = true
+    setTimeout(done)
+  }
+  const a2 = done => {
+    t.equal(calledA1, true, 'called a1 before 2')
+    t.equal(calledA2, false, 'called a2 only once')
+    calledA2 = true
+    done()
+    if (calledR2)
+      t.end()
+  }
+  let calledR1 = false
+  let calledR2 = false
+  const r1 = done => {
+    t.equal(calledR1, false, 'called r1 only once')
+    t.equal(calledR2, false, 'called r1 before 2')
+    calledR1 = true
+    setTimeout(done)
+  }
+  const r2 = done => {
+    t.equal(calledR1, true, 'called r1 before 2')
+    t.equal(calledR2, false, 'called r1 only once')
+    calledR2 = true
+    done()
+    if (calledA2)
+      t.end()
+  }
+  t.ok(reserve(['/p/a/t/h'], a1))
+  t.notOk(reserve(['/p/a/t/h/'], a2))
+  t.ok(reserve(['p/a/t/h'], r1))
+  t.notOk(reserve(['p/a/t/h/'], r2))
+})
+
+t.test('on windows, everything collides with everything', t => {
+  const reserve = winReserve
+  let called1 = false
+  let called2 = false
+  const f1 = done => {
+    t.equal(called1, false, 'only call 1 once')
+    t.equal(called2, false, 'call 1 before 2')
+    called1 = true
+    setTimeout(done)
+  }
+  const f2 = done => {
+    t.equal(called1, true, 'call 1 before 2')
+    t.equal(called2, false, 'only call 2 once')
+    called2 = true
+    done()
+    t.end()
+  }
+  t.equal(reserve(['some/path'], f1), true)
+  t.equal(reserve(['other/path'], f2), false)
+})