diff --git a/lib/strip-absolute-path.js b/lib/strip-absolute-path.js
index 49161ddc..1aa2d2ae 100644
--- a/lib/strip-absolute-path.js
+++ b/lib/strip-absolute-path.js
@@ -2,13 +2,23 @@
 const { isAbsolute, parse } = require('path').win32
 
 // returns [root, stripped]
+// Note that windows will think that //x/y/z/a has a "root" of //x/y, and in
+// those cases, we want to sanitize it to x/y/z/a, not z/a, so we strip /
+// explicitly if it's the first character.
+// drive-specific relative paths on Windows get their root stripped off even
+// though they are not absolute, so `c:../foo` becomes ['c:', '../foo']
 module.exports = path => {
   let r = ''
-  while (isAbsolute(path)) {
+
+  let parsed = parse(path)
+  while (isAbsolute(path) || parsed.root) {
     // windows will think that //x/y/z has a "root" of //x/y/
-    const root = path.charAt(0) === '/' ? '/' : parse(path).root
+    // but strip the //?/C:/ off of //?/C:/path
+    const root = path.charAt(0) === '/' && path.slice(0, 4) !== '//?/' ? '/'
+      : parsed.root
     path = path.substr(root.length)
     r += root
+    parsed = parse(path)
   }
   return [r, path]
 }
diff --git a/lib/unpack.js b/lib/unpack.js
index 4bc2fae0..6034110d 100644
--- a/lib/unpack.js
+++ b/lib/unpack.js
@@ -236,13 +236,13 @@ class Unpack extends Parser {
 
     if (!this.preservePaths) {
       const p = normPath(entry.path)
-      if (p.split('/').includes('..')) {
+      const parts = p.split('/')
+      if (parts.includes('..') || isWindows && /^[a-z]:\.\.$/i.test(parts[0])) {
         this.warn(`path contains '..'`, p)
         return false
       }
 
-      // absolutes on posix are also absolutes on win32
-      // so we only need to test this one to get both
+      // strip off the root
       const s = stripAbsolutePath(p)
       if (s[0]) {
         entry.path = s[1]
@@ -255,6 +255,22 @@ class Unpack extends Parser {
     else
       entry.absolute = normPath(path.resolve(this.cwd, entry.path))
 
+    // if we somehow ended up with a path that escapes the cwd, and we are
+    // not in preservePaths mode, then something is fishy!  This should have
+    // been prevented above, so ignore this for coverage.
+    /* istanbul ignore if - defense in depth */
+    if (!this.preservePaths &&
+        entry.absolute.indexOf(this.cwd + '/') !== 0 &&
+        entry.absolute !== this.cwd) {
+      this.warn('TAR_ENTRY_ERROR', 'path escaped extraction target', {
+        entry,
+        path: normPath(entry.path),
+        resolvedPath: entry.absolute,
+        cwd: this.cwd,
+      })
+      return false
+    }
+
     // an archive can set properties on the extraction directory, but it
     // may not replace the cwd with a different kind of thing entirely.
     if (entry.absolute === this.cwd &&
diff --git a/test/strip-absolute-path.js b/test/strip-absolute-path.js
index beb057ff..c50e2858 100644
--- a/test/strip-absolute-path.js
+++ b/test/strip-absolute-path.js
@@ -1,14 +1,52 @@
 const t = require('tap')
 const stripAbsolutePath = require('../lib/strip-absolute-path.js')
+const cwd = process.cwd()
+const requireInject = require('require-inject')
 
-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'],
-}
+t.test('basic', t => {
+  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)
+  for (const [input, [root, stripped]] of Object.entries(cases))
+    t.strictSame(stripAbsolutePath(input, cwd), [root, stripped], input)
+  t.end()
+})
+
+t.test('drive-local paths', t => {
+  const env = process.env
+  t.teardown(() => process.env = env)
+  const cwd = 'D:\\safety\\land'
+  const realPath = require('path')
+  // be windowsy
+  const path = {
+    ...realPath.win32,
+    win32: realPath.win32,
+    posix: realPath.posix,
+  }
+  const stripAbsolutePath = requireInject('../lib/strip-absolute-path.js', { path })
+  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'],
+    'c:..\\system\\explorer.exe': ['c:', '..\\system\\explorer.exe'],
+    'd:..\\..\\unsafe\\land': ['d:', '..\\..\\unsafe\\land'],
+    'c:foo': ['c:', 'foo'],
+    'D:mark': ['D:', 'mark'],
+    '//?/X:/y/z': ['//?/X:/', 'y/z'],
+    '\\\\?\\X:\\y\\z': ['\\\\?\\X:\\', 'y\\z'],
+  }
+  for (const [input, [root, stripped]] of Object.entries(cases)) {
+    if (!t.strictSame(stripAbsolutePath(input, cwd), [root, stripped], input))
+      break
+  }
+  t.end()
+})