diff --git a/lib/strip-absolute-path.js b/lib/strip-absolute-path.js
new file mode 100644
index 00000000..49161ddc
--- /dev/null
+++ b/lib/strip-absolute-path.js
@@ -0,0 +1,14 @@
+// unix absolute paths are also absolute on win32, so we use this for both
+const { isAbsolute, parse } = require('path').win32
+
+// returns [root, stripped]
+module.exports = path => {
+  let r = ''
+  while (isAbsolute(path)) {
+    // windows will think that //x/y/z has a "root" of //x/y/
+    const root = path.charAt(0) === '/' ? '/' : parse(path).root
+    path = path.substr(root.length)
+    r += root
+  }
+  return [r, path]
+}
diff --git a/lib/unpack.js b/lib/unpack.js
index 7d4b79d9..216fa71b 100644
--- a/lib/unpack.js
+++ b/lib/unpack.js
@@ -14,6 +14,7 @@ const path = require('path')
 const mkdir = require('./mkdir.js')
 const wc = require('./winchars.js')
 const pathReservations = require('./path-reservations.js')
+const stripAbsolutePath = require('./strip-absolute-path.js')
 
 const ONENTRY = Symbol('onEntry')
 const CHECKFS = Symbol('checkFs')
@@ -224,11 +225,10 @@ class Unpack extends Parser {
 
       // absolutes on posix are also absolutes on win32
       // so we only need to test this one to get both
-      if (path.win32.isAbsolute(p)) {
-        const parsed = path.win32.parse(p)
-        entry.path = p.substr(parsed.root.length)
-        const r = parsed.root
-        this.warn('TAR_ENTRY_INFO', `stripping ${r} from absolute path`, {
+      const [root, stripped] = stripAbsolutePath(p)
+      if (root) {
+        entry.path = stripped
+        this.warn('TAR_ENTRY_INFO', `stripping ${root} from absolute path`, {
           entry,
           path: p,
         })
diff --git a/lib/write-entry.js b/lib/write-entry.js
index 1d0b746c..0301759a 100644
--- a/lib/write-entry.js
+++ b/lib/write-entry.js
@@ -23,6 +23,7 @@ const CLOSE = Symbol('close')
 const MODE = Symbol('mode')
 const warner = require('./warn-mixin.js')
 const winchars = require('./winchars.js')
+const stripAbsolutePath = require('./strip-absolute-path.js')
 
 const modeFix = require('./mode-fix.js')
 
@@ -52,12 +53,12 @@ const WriteEntry = warner(class WriteEntry extends MiniPass {
       this.on('warn', opt.onwarn)
 
     let pathWarn = false
-    if (!this.preservePaths && path.win32.isAbsolute(p)) {
-      // absolutes on posix are also absolutes on win32
-      // so we only need to test this one to get both
-      const parsed = path.win32.parse(p)
-      this.path = p.substr(parsed.root.length)
-      pathWarn = parsed.root
+    if (!this.preservePaths) {
+      const [root, stripped] = stripAbsolutePath(this.path)
+      if (root) {
+        this.path = stripped
+        pathWarn = root
+      }
     }
 
     this.win32 = !!opt.win32 || process.platform === 'win32'
@@ -351,10 +352,12 @@ const WriteEntryTar = warner(class WriteEntryTar extends MiniPass {
       this.on('warn', opt.onwarn)
 
     let pathWarn = false
-    if (path.isAbsolute(this.path) && !this.preservePaths) {
-      const parsed = path.parse(this.path)
-      pathWarn = parsed.root
-      this.path = this.path.substr(parsed.root.length)
+    if (!this.preservePaths) {
+      const [root, stripped] = stripAbsolutePath(this.path)
+      if (root) {
+        this.path = stripped
+        pathWarn = root
+      }
     }
 
     this.remain = readEntry.size
diff --git a/test/strip-absolute-path.js b/test/strip-absolute-path.js
new file mode 100644
index 00000000..beb057ff
--- /dev/null
+++ b/test/strip-absolute-path.js
@@ -0,0 +1,14 @@
+const t = require('tap')
+const stripAbsolutePath = require('../lib/strip-absolute-path.js')
+
+const cases = {
+  '/': ['/', ''],
+  '////': ['////', ''],
+  'c:///a/b/c': ['c:///', 'a/b/c'],
+  '\\\\foo\\bar\\baz': ['\\\\foo\\bar\\', 'baz'],
+  '//foo//bar//baz': ['//', 'foo//bar//baz'],
+  'c:\\c:\\c:\\c:\\\\d:\\e/f/g': ['c:\\c:\\c:\\c:\\\\d:\\', 'e/f/g'],
+}
+
+for (const [input, [root, stripped]] of Object.entries(cases))
+  t.strictSame(stripAbsolutePath(input), [root, stripped], input)
diff --git a/test/unpack.js b/test/unpack.js
index cc3538ae..1b2a0334 100644
--- a/test/unpack.js
+++ b/test/unpack.js
@@ -776,6 +776,9 @@ t.test('absolute paths', t => {
   })
 
   const absolute = path.resolve(dir, 'd/i/r/absolute')
+  const root = path.parse(absolute).root
+  const extraAbsolute = root + root + root + absolute
+  t.ok(path.isAbsolute(extraAbsolute))
   t.ok(path.isAbsolute(absolute))
   const parsed = path.parse(absolute)
   const relative = absolute.substr(parsed.root.length)
@@ -783,7 +786,7 @@ t.test('absolute paths', t => {
 
   const data = makeTar([
     {
-      path: absolute,
+      path: extraAbsolute,
       type: 'File',
       size: 1,
       atime: new Date('1979-07-01T19:10:00.000Z'),
@@ -798,7 +801,7 @@ t.test('absolute paths', t => {
   t.test('warn and correct', t => {
     const check = t => {
       t.match(warnings, [[
-        'stripping / from absolute path',
+        `stripping ${root}${root}${root}${root} from absolute path`,
         { path: absolute, code: 'TAR_ENTRY_INFO' },
       ]])
       t.ok(fs.lstatSync(path.resolve(dir, relative)).isFile(), 'is file')
diff --git a/test/write-entry.js b/test/write-entry.js
index 89ddcc89..c177f89e 100644
--- a/test/write-entry.js
+++ b/test/write-entry.js
@@ -385,7 +385,10 @@ t.test('nonexistent file', t => {
 })
 
 t.test('absolute path', t => {
-  const f = path.resolve(files, '512-bytes.txt')
+  const absolute = path.resolve(files, '512-bytes.txt')
+  const { root } = path.parse(absolute)
+  const f = root + root + root + absolute
+  const warn = root + root + root + root
   t.test('preservePaths=false strict=false', t => {
     const warnings = []
     const ws = new WriteEntry(f, {
@@ -398,13 +401,13 @@ t.test('absolute path', t => {
       out = Buffer.concat(out)
       t.equal(out.length, 1024)
       t.match(warnings, [[
-        'TAR_ENTRY_INFO', /stripping .* from absolute path/, { path: f },
+        'TAR_ENTRY_INFO', `stripping ${warn} from absolute path`, { path: f },
       ]])
 
       t.match(ws.header, {
         cksumValid: true,
         needPax: false,
-        path: f.replace(/^(\/|[a-z]:\\\\)/, ''),
+        path: f.replace(/^(\/|[a-z]:\\\\){4}/, ''),
         mode: 0o644,
         size: 512,
         linkpath: null,