diff --git a/lib/path.js b/lib/path.js
index 2d09eb595a2e2a..bbe5f0b5be0716 100644
--- a/lib/path.js
+++ b/lib/path.js
@@ -11,10 +11,10 @@ function assertPath(path) {
 // Resolves . and .. elements in a path with directory names
 function normalizeStringWin32(path, allowAboveRoot) {
   var res = '';
+  var lastSegmentLength = 0;
   var lastSlash = -1;
   var dots = 0;
   var code;
-  var isAboveRoot = false;
   for (var i = 0; i <= path.length; ++i) {
     if (i < path.length)
       code = path.charCodeAt(i);
@@ -26,7 +26,7 @@ function normalizeStringWin32(path, allowAboveRoot) {
       if (lastSlash === i - 1 || dots === 1) {
         // NOOP
       } else if (lastSlash !== i - 1 && dots === 2) {
-        if (res.length < 2 || !isAboveRoot ||
+        if (res.length < 2 || lastSegmentLength !== 2 ||
             res.charCodeAt(res.length - 1) !== 46/*.*/ ||
             res.charCodeAt(res.length - 2) !== 46/*.*/) {
           if (res.length > 2) {
@@ -37,20 +37,22 @@ function normalizeStringWin32(path, allowAboveRoot) {
                 break;
             }
             if (j !== start) {
-              if (j === -1)
+              if (j === -1) {
                 res = '';
-              else
+                lastSegmentLength = 0;
+              } else {
                 res = res.slice(0, j);
+                lastSegmentLength = j;
+              }
               lastSlash = i;
               dots = 0;
-              isAboveRoot = false;
               continue;
             }
           } else if (res.length === 2 || res.length === 1) {
             res = '';
+            lastSegmentLength = 0;
             lastSlash = i;
             dots = 0;
-            isAboveRoot = false;
             continue;
           }
         }
@@ -59,14 +61,14 @@ function normalizeStringWin32(path, allowAboveRoot) {
             res += '\\..';
           else
             res = '..';
-          isAboveRoot = true;
+          lastSegmentLength = 2;
         }
       } else {
         if (res.length > 0)
           res += '\\' + path.slice(lastSlash + 1, i);
         else
           res = path.slice(lastSlash + 1, i);
-        isAboveRoot = false;
+        lastSegmentLength = i - lastSlash - 1;
       }
       lastSlash = i;
       dots = 0;
@@ -82,10 +84,10 @@ function normalizeStringWin32(path, allowAboveRoot) {
 // Resolves . and .. elements in a path with directory names
 function normalizeStringPosix(path, allowAboveRoot) {
   var res = '';
+  var lastSegmentLength = 0;
   var lastSlash = -1;
   var dots = 0;
   var code;
-  var isAboveRoot = false;
   for (var i = 0; i <= path.length; ++i) {
     if (i < path.length)
       code = path.charCodeAt(i);
@@ -97,7 +99,7 @@ function normalizeStringPosix(path, allowAboveRoot) {
       if (lastSlash === i - 1 || dots === 1) {
         // NOOP
       } else if (lastSlash !== i - 1 && dots === 2) {
-        if (res.length < 2 || !isAboveRoot ||
+        if (res.length < 2 || lastSegmentLength !== 2 ||
             res.charCodeAt(res.length - 1) !== 46/*.*/ ||
             res.charCodeAt(res.length - 2) !== 46/*.*/) {
           if (res.length > 2) {
@@ -108,20 +110,22 @@ function normalizeStringPosix(path, allowAboveRoot) {
                 break;
             }
             if (j !== start) {
-              if (j === -1)
+              if (j === -1) {
                 res = '';
-              else
+                lastSegmentLength = 0;
+              } else {
                 res = res.slice(0, j);
+                lastSegmentLength = j;
+              }
               lastSlash = i;
               dots = 0;
-              isAboveRoot = false;
               continue;
             }
           } else if (res.length === 2 || res.length === 1) {
             res = '';
+            lastSegmentLength = 0;
             lastSlash = i;
             dots = 0;
-            isAboveRoot = false;
             continue;
           }
         }
@@ -130,14 +134,14 @@ function normalizeStringPosix(path, allowAboveRoot) {
             res += '/..';
           else
             res = '..';
-          isAboveRoot = true;
+          lastSegmentLength = 2;
         }
       } else {
         if (res.length > 0)
           res += '/' + path.slice(lastSlash + 1, i);
         else
           res = path.slice(lastSlash + 1, i);
-        isAboveRoot = false;
+        lastSegmentLength = i - lastSlash - 1;
       }
       lastSlash = i;
       dots = 0;
diff --git a/test/parallel/test-path-normalize.js b/test/parallel/test-path-normalize.js
index db91432b3e0955..0820052446367e 100644
--- a/test/parallel/test-path-normalize.js
+++ b/test/parallel/test-path-normalize.js
@@ -23,6 +23,10 @@ assert.strictEqual(path.win32.normalize('bar\\foo..\\..'), 'bar');
 assert.strictEqual(path.win32.normalize('bar\\foo..\\..\\baz'), 'bar\\baz');
 assert.strictEqual(path.win32.normalize('bar\\foo..\\'), 'bar\\foo..\\');
 assert.strictEqual(path.win32.normalize('bar\\foo..'), 'bar\\foo..');
+assert.strictEqual(path.win32.normalize('..\\foo..\\..\\..\\bar'),
+                   '..\\..\\bar');
+assert.strictEqual(path.win32.normalize('..\\...\\..\\.\\...\\..\\..\\bar'),
+                   '..\\..\\bar');
 
 assert.strictEqual(path.posix.normalize('./fixtures///b/../b/c.js'),
                    'fixtures/b/c.js');
@@ -37,3 +41,6 @@ assert.strictEqual(path.posix.normalize('bar/foo../..'), 'bar');
 assert.strictEqual(path.posix.normalize('bar/foo../../baz'), 'bar/baz');
 assert.strictEqual(path.posix.normalize('bar/foo../'), 'bar/foo../');
 assert.strictEqual(path.posix.normalize('bar/foo..'), 'bar/foo..');
+assert.strictEqual(path.posix.normalize('../foo../../../bar'), '../../bar');
+assert.strictEqual(path.posix.normalize('../.../.././.../../../bar'),
+                   '../../bar');