diff --git a/README.md b/README.md
index d4d2c61..c80cf91 100644
--- a/README.md
+++ b/README.md
@@ -45,6 +45,8 @@ File.isCustomProp('path'); // false -> internal getter/setter
 Read more in [Extending Vinyl](#extending-vinyl).
 
 ### constructor(options)
+All internally managed paths (`cwd`, `base`, `path`, `[history]`) are normalized and remove a trailing separator.
+
 #### options.cwd
 Type: `String`<br><br>Default: `process.cwd()`
 
@@ -64,7 +66,7 @@ Path history. Has no effect if `options.path` is passed.
 Type: `Array`<br><br>Default: `options.path ? [options.path] : []`
 
 #### options.stat
-The result of an fs.stat call. See [fs.Stats](http://nodejs.org/api/fs.html#fs_class_fs_stats) for more information.
+The result of an fs.stat call. This is how you mark the file as a directory. See [isDirectory()](#isDirectory) and [fs.Stats](http://nodejs.org/api/fs.html#fs_class_fs_stats) for more information.
 
 Type: `fs.Stats`<br><br>Default: `null`
 
@@ -92,6 +94,15 @@ Returns true if file.contents is a Stream.
 ### isNull()
 Returns true if file.contents is null.
 
+### isDirectory()
+Returns true if file is a directory. File is considered a directory when:
+
+- `file.isNull()` is `true`
+- `file.stat` is an object
+- `file.stat.isDirectory()` returns `true`
+
+When constructing a Vinyl object, pass in a valid `fs.Stats` object via `options.stat`. Some operations in Vinyl might need to know the file is a directory from the get go. If you are mocking the `fs.Stats` object, ensure it has the `isDirectory()` method.
+
 ### clone([opt])
 Returns a new File object with all attributes cloned.<br>By default custom attributes are deep-cloned.
 
@@ -124,8 +135,14 @@ if (file.isBuffer()) {
 }
 ```
 
+### cwd
+Gets and sets current working directory. Defaults to `process.cwd`. Will always be normalized and remove a trailing separator.
+
+### base
+Gets and sets base directory. Used for relative pathing (typically where a glob starts). When `null` or `undefined`, it simply proxies the `file.cwd` property. Will always be normalized and remove a trailing separator.
+
 ### path
-Absolute pathname string or `undefined`. Setting to a different value pushes the old value to `history`.
+Absolute pathname string or `undefined`. Setting to a different value pushes the old value to `history`. All new values are normalized and remove a trailing separator.
 
 ### history
 Array of `path` values the file object has had, from `history[0]` (original) through `history[history.length - 1]` (current). `history` and its elements should normally be treated as read-only and only altered indirectly by setting `path`.
@@ -146,7 +163,7 @@ console.log(file.relative); // file.coffee
 ```
 
 ### dirname
-Gets and sets path.dirname for the file path.
+Gets and sets path.dirname for the file path. Will always be normalized and remove a trailing separator.
 
 Example:
 
@@ -225,6 +242,24 @@ console.log(file.extname); // .js
 console.log(file.path); // /test/file.js
 ```
 
+### symlink
+Path where the file points to in case it's a symbolic link. Will always be normalized and remove a trailing separator.
+
+## Normalization and concatenation
+Since all properties are normalized in their setters, you can just concatenate with `/`, and normalization takes care of it properly on all platforms.
+
+Example:
+
+```javascript
+var file = new File();
+file.path = '/' + 'test' + '/' + 'foo.bar';
+console.log(file.path);
+// posix => /test/foo.bar
+// win32 => \\test\\foo.bar
+```
+
+But never concatenate with `\`, since that is a valid filename character on posix system.
+
 ## Extending Vinyl
 When extending Vinyl into your own class with extra features, you need to think about a few things.
 
diff --git a/index.js b/index.js
index 0cdbdb3..975f36c 100644
--- a/index.js
+++ b/index.js
@@ -2,15 +2,18 @@ var path = require('path');
 var clone = require('clone');
 var cloneStats = require('clone-stats');
 var cloneBuffer = require('./lib/cloneBuffer');
+var stripTrailingSep = require('./lib/stripTrailingSep');
 var isBuffer = require('./lib/isBuffer');
 var isStream = require('./lib/isStream');
 var isNull = require('./lib/isNull');
 var inspectStream = require('./lib/inspectStream');
+var normalize = require('./lib/normalize');
 var Stream = require('stream');
 var replaceExt = require('replace-ext');
 
 var builtInFields = [
-  '_contents', '_symlink', 'contents', 'stat', 'history', 'path', 'base', 'cwd',
+  '_contents', '_symlink', 'contents', 'stat', 'history', 'path',
+  '_base', 'base', '_cwd', 'cwd',
 ];
 
 function File(file) {
@@ -20,19 +23,22 @@ function File(file) {
     file = {};
   }
 
-  // Record path change
-  var history = file.path ? [file.path] : file.history;
-  this.history = history || [];
-
-  this.cwd = file.cwd || process.cwd();
-  this.base = file.base || this.cwd;
-
   // Stat = files stats object
   this.stat = file.stat || null;
 
   // Contents = stream, buffer, or null if not read
   this.contents = file.contents || null;
 
+  // Replay path history to ensure proper normalization and trailing sep
+  var history = file.path ? [file.path] : file.history || [];
+  this.history = [];
+  history.forEach(function(path) {
+    self.path = path;
+  });
+
+  this.cwd = file.cwd || process.cwd();
+  this.base = file.base;
+
   this._isVinyl = true;
 
   this._symlink = null;
@@ -156,7 +162,7 @@ File.prototype.inspect = function() {
   var inspect = [];
 
   // Use relative path if possible
-  var filePath = (this.base && this.path) ? this.relative : this.path;
+  var filePath = this.path ? this.relative : null;
 
   if (filePath) {
     inspect.push('"' + filePath + '"');
@@ -195,12 +201,40 @@ Object.defineProperty(File.prototype, 'contents', {
   },
 });
 
+Object.defineProperty(File.prototype, 'cwd', {
+  get: function() {
+    return this._cwd;
+  },
+  set: function(cwd) {
+    if (!cwd || typeof cwd !== 'string') {
+      throw new Error('cwd must be a non-empty string.');
+    }
+    this._cwd = stripTrailingSep(normalize(cwd));
+  },
+});
+
+Object.defineProperty(File.prototype, 'base', {
+  get: function() {
+    return this._base || this._cwd;
+  },
+  set: function(base) {
+    if (base == null) {
+      delete this._base;
+      return;
+    }
+    if (typeof base !== 'string' || !base) {
+      throw new Error('base must be a non-empty string, or null/undefined.');
+    }
+    base = stripTrailingSep(normalize(base));
+    if (base !== this._cwd) {
+      this._base = base;
+    }
+  },
+});
+
 // TODO: Should this be moved to vinyl-fs?
 Object.defineProperty(File.prototype, 'relative', {
   get: function() {
-    if (!this.base) {
-      throw new Error('No base specified! Can not get relative.');
-    }
     if (!this.path) {
       throw new Error('No path specified! Can not get relative.');
     }
@@ -222,7 +256,7 @@ Object.defineProperty(File.prototype, 'dirname', {
     if (!this.path) {
       throw new Error('No path specified! Can not set dirname.');
     }
-    this.path = path.join(dirname, path.basename(this.path));
+    this.path = path.join(dirname, this.basename);
   },
 });
 
@@ -237,7 +271,7 @@ Object.defineProperty(File.prototype, 'basename', {
     if (!this.path) {
       throw new Error('No path specified! Can not set basename.');
     }
-    this.path = path.join(path.dirname(this.path), basename);
+    this.path = path.join(this.dirname, basename);
   },
 });
 
@@ -253,7 +287,7 @@ Object.defineProperty(File.prototype, 'stem', {
     if (!this.path) {
       throw new Error('No path specified! Can not set stem.');
     }
-    this.path = path.join(path.dirname(this.path), stem + this.extname);
+    this.path = path.join(this.dirname, stem + this.extname);
   },
 });
 
@@ -278,8 +312,9 @@ Object.defineProperty(File.prototype, 'path', {
   },
   set: function(path) {
     if (typeof path !== 'string') {
-      throw new Error('path should be string');
+      throw new Error('path should be a string.');
     }
+    path = stripTrailingSep(normalize(path));
 
     // Record history only when path changed
     if (path && path !== this.path) {
@@ -298,7 +333,7 @@ Object.defineProperty(File.prototype, 'symlink', {
       throw new Error('symlink should be a string');
     }
 
-    this._symlink = symlink;
+    this._symlink = stripTrailingSep(normalize(symlink));
   },
 });
 
diff --git a/lib/normalize.js b/lib/normalize.js
new file mode 100644
index 0000000..5bb5537
--- /dev/null
+++ b/lib/normalize.js
@@ -0,0 +1,5 @@
+var normalize = require('path').normalize;
+
+module.exports = function(str) {
+  return str === '' ? str : normalize(str);
+};
diff --git a/lib/stripTrailingSep.js b/lib/stripTrailingSep.js
new file mode 100644
index 0000000..ecc3765
--- /dev/null
+++ b/lib/stripTrailingSep.js
@@ -0,0 +1,11 @@
+module.exports = function(str) {
+  while (endsInSeparator(str)) {
+    str = str.slice(0, -1);
+  }
+  return str;
+};
+
+function endsInSeparator(str) {
+  var last = str[str.length - 1];
+  return str.length > 1 && (last === '/' || last === '\\');
+}
diff --git a/test/File.js b/test/File.js
index 1aaebc7..351f147 100644
--- a/test/File.js
+++ b/test/File.js
@@ -31,7 +31,7 @@ describe('File', function() {
     });
 
     it('should default base to cwd', function(done) {
-      var cwd = '/';
+      var cwd = path.normalize('/');
       var file = new File({ cwd: cwd });
       file.base.should.equal(cwd);
       done();
@@ -68,21 +68,21 @@ describe('File', function() {
     });
 
     it('should set base to given value', function(done) {
-      var val = '/';
+      var val = path.normalize('/');
       var file = new File({ base: val });
       file.base.should.equal(val);
       done();
     });
 
     it('should set cwd to given value', function(done) {
-      var val = '/';
+      var val = path.normalize('/');
       var file = new File({ cwd: val });
       file.cwd.should.equal(val);
       done();
     });
 
     it('should set path to given value', function(done) {
-      var val = '/test.coffee';
+      var val = path.normalize('/test.coffee');
       var file = new File({ path: val });
       file.path.should.equal(val);
       file.history.should.eql([val]);
@@ -90,7 +90,7 @@ describe('File', function() {
     });
 
     it('should set history to given value', function(done) {
-      var val = '/test.coffee';
+      var val = path.normalize('/test.coffee');
       var file = new File({ history: [val] });
       file.path.should.equal(val);
       file.history.should.eql([val]);
@@ -117,6 +117,71 @@ describe('File', function() {
       file.sourceMap.should.equal(sourceMap);
       done();
     });
+
+    it('should normalize path', function() {
+      var file = new File({ path: '/test/foo/../test.coffee' });
+
+      if (process.platform === 'win32') {
+        file.path.should.equal('\\test\\test.coffee');
+        file.history.should.eql(['\\test\\test.coffee']);
+      } else {
+        file.path.should.equal('/test/test.coffee');
+        file.history.should.eql(['/test/test.coffee']);
+      }
+    });
+
+    it('should correctly normalize and strip trailing sep from path', function() {
+      var file = new File({ path: '/test/foo/../foo/' });
+
+      if (process.platform === 'win32') {
+        file.path.should.equal('\\test\\foo');
+      } else {
+        file.path.should.equal('/test/foo');
+      }
+    });
+
+    it('should correctly normalize and strip trailing sep from history', function() {
+      var file = new File({
+        history: [
+          '/test/foo/../foo/',
+          '/test/bar/../bar/',
+        ],
+      });
+
+      if (process.platform === 'win32') {
+        file.history.should.eql([
+          '\\test\\foo',
+          '\\test\\bar',
+        ]);
+      } else {
+        file.history.should.eql([
+          '/test/foo',
+          '/test/bar',
+        ]);
+      }
+    });
+
+    it('should normalize history', function() {
+      var history = [
+        '/test/bar/../bar/test.coffee',
+        '/test/foo/../test.coffee',
+      ];
+      var file = new File({ history: history });
+
+      if (process.platform === 'win32') {
+        file.path.should.equal('\\test\\test.coffee');
+        file.history.should.eql([
+          '\\test\\bar\\test.coffee',
+          '\\test\\test.coffee',
+        ]);
+      } else {
+        file.path.should.equal('/test/test.coffee');
+        file.history.should.eql([
+          '/test/bar/test.coffee',
+          '/test/test.coffee',
+        ]);
+      }
+    });
   });
 
   describe('isBuffer()', function() {
@@ -367,9 +432,9 @@ describe('File', function() {
 
     it('should properly clone the `history` property', function(done) {
       var options = {
-        cwd: '/',
-        base: '/test/',
-        path: '/test/test.js',
+        cwd: path.normalize('/'),
+        base: path.normalize('/test/'),
+        path: path.normalize('/test/test.js'),
         contents: new Buffer('test'),
         stat: fs.statSync(__filename),
       };
@@ -413,23 +478,20 @@ describe('File', function() {
         path: '/test/test.coffee',
         contents: null,
       };
+      var history = [
+        path.normalize('/test/test.coffee'),
+        path.normalize('/test/test.js'),
+        path.normalize('/test/test-938di2s.js'),
+      ];
 
       var file = new File(options);
-      file.path = '/test/test.js';
-      file.path = '/test/test-938di2s.js';
+      file.path = history[1];
+      file.path = history[2];
       var file2 = file.clone();
 
-      file2.history.should.eql([
-        '/test/test.coffee',
-        '/test/test.js',
-        '/test/test-938di2s.js',
-      ]);
-      file2.history.should.not.equal([
-        '/test/test.coffee',
-        '/test/test.js',
-        '/test/test-938di2s.js',
-      ]);
-      file2.path.should.eql('/test/test-938di2s.js');
+      file2.history.should.eql(history);
+      file2.history.should.not.equal(history);
+      file2.path.should.eql(history[2]);
 
       done();
     });
@@ -652,18 +714,6 @@ describe('File', function() {
       done();
     });
 
-    it('should return correct format when Buffer and only path and no base', function(done) {
-      var val = new Buffer('test');
-      var file = new File({
-        cwd: '/',
-        path: '/test/test.coffee',
-        contents: val,
-      });
-      delete file.base;
-      file.inspect().should.equal('<File "/test/test.coffee" <Buffer 74 65 73 74>>');
-      done();
-    });
-
     it('should return correct format when Stream and relative path', function(done) {
       var file = new File({
         cwd: '/',
@@ -724,23 +774,136 @@ describe('File', function() {
     });
   });
 
-  describe('relative get/set', function() {
-    it('should error on set', function(done) {
+  describe('cwd get/set', function() {
+    it('should return _cwd', function() {
       var file = new File();
-      try {
-        file.relative = 'test';
-      } catch (err) {
-        should.exist(err);
-        done();
+      file.cwd = '/test';
+      file.cwd.should.equal(file._cwd);
+    });
+
+    it('should set cwd', function() {
+      var file = new File();
+      file.cwd = '/test';
+      file._cwd.should.equal(path.normalize('/test'));
+    });
+
+    it('should normalize and strip trailing sep on set', function() {
+      var file = new File();
+
+      file.cwd = '/test/foo/../foo/';
+
+      if (process.platform === 'win32') {
+        file.cwd.should.equal('\\test\\foo');
+      } else {
+        file.cwd.should.equal('/test/foo');
+      }
+
+      file.cwd = '\\test\\foo\\..\\foo\\';
+
+      if (process.platform === 'win32') {
+        file.cwd.should.equal('\\test\\foo');
+      } else {
+        file.cwd.should.equal('\\test\\foo\\..\\foo');
       }
     });
 
-    it('should error on get when no base', function(done) {
-      var a;
+    it('should throw on set when value is empty or not a string', function() {
+      var notAllowed = [
+        '', null, undefined, true, false, 0, Infinity, NaN, {}, [],
+      ];
+      notAllowed.forEach(function(val) {
+        (function() {
+          new File().cwd = val;
+        }).should.throw('cwd must be a non-empty string.');
+      });
+    });
+  });
+
+  describe('base get/set', function() {
+    it('should proxy to cwd when omitted', function() {
+      var file = new File({
+        cwd: '/test',
+      });
+      file.base.should.equal(path.normalize('/test'));
+    });
+
+    it('should proxy to cwd when same', function() {
+      var file = new File({
+        cwd: '/test',
+        base: '/test',
+      });
+      file.cwd = '/foo/';
+      file.base.should.equal(path.normalize('/foo'));
+
+      var file2 = new File({
+        cwd: '/test',
+      });
+      file2.base = '/test/';
+      file2.cwd = '/foo/';
+      file2.base.should.equal(path.normalize('/foo'));
+    });
+
+    it('should proxy to cwd when null or undefined', function() {
+      var file = new File({
+        cwd: '/foo',
+        base: '/bar',
+      });
+      file.base.should.equal(path.normalize('/bar'));
+      file.base = null;
+      file.base.should.equal(path.normalize('/foo'));
+      file.base = '/bar/';
+      file.base.should.equal(path.normalize('/bar'));
+      file.base = undefined;
+      file.base.should.equal(path.normalize('/foo'));
+    });
+
+    it('should return _base', function() {
+      var file = new File();
+      file._base = '/test/';
+      file.base.should.equal('/test/');
+    });
+
+    it('should set base', function() {
+      var file = new File();
+      file.base = '/test/foo';
+      file.base.should.equal(path.normalize('/test/foo'));
+    });
+
+    it('should normalize and strip trailing sep on set', function() {
+      var file = new File();
+
+      file.base = '/test/foo/../foo/';
+
+      if (process.platform === 'win32') {
+        file.base.should.equal('\\test\\foo');
+      } else {
+        file.base.should.equal('/test/foo');
+      }
+
+      file.base = '\\test\\foo\\..\\foo\\';
+
+      if (process.platform === 'win32') {
+        file.base.should.equal('\\test\\foo');
+      } else {
+        file.base.should.equal('\\test\\foo\\..\\foo');
+      }
+    });
+
+    it('should throw on set when not null/undefined or a non-empty string', function() {
+      var notStrings = [true, false, 1, 0, Infinity, NaN, '', {}, []];
+      notStrings.forEach(function(val) {
+        (function() {
+          new File().base = val;
+        }).should.throw('base must be a non-empty string, or null/undefined.');
+      });
+    });
+  });
+
+  describe('relative get/set', function() {
+    it('should error on set', function(done) {
       var file = new File();
-      delete file.base;
       try {
-        a = file.relative;
+        file.relative = 'test';
       } catch (err) {
         should.exist(err);
         done();
@@ -776,6 +939,35 @@ describe('File', function() {
       file.relative.should.equal(path.join('test','test.coffee'));
       done();
     });
+
+    it('should not append sep when directory', function() {
+      var file = new File({
+        base: '/test',
+        path: '/test/foo/bar',
+        stat: {
+          isDirectory: function() {
+            return true;
+          },
+        },
+      });
+      file.relative.should.equal(path.normalize('foo/bar'));
+    });
+
+    it('should not append sep when directory & simlink', function() {
+      var file = new File({
+        base: '/test',
+        path: '/test/foo/bar',
+        stat: {
+          isDirectory: function() {
+            return true;
+          },
+          isSymbolicLink: function() {
+            return true;
+          },
+        },
+      });
+      file.relative.should.equal(path.normalize('foo/bar'));
+    });
   });
 
   describe('dirname get/set', function() {
@@ -790,13 +982,13 @@ describe('File', function() {
       }
     });
 
-    it('should return the dirname of the path', function(done) {
+    it('should return the path without trailing sep', function(done) {
       var file = new File({
         cwd: '/',
-        base: '/test/',
+        base: '/test',
         path: '/test/test.coffee',
       });
-      file.dirname.should.equal('/test');
+      file.dirname.should.equal(path.normalize('/test'));
       done();
     });
 
@@ -817,7 +1009,7 @@ describe('File', function() {
         path: '/test/test.coffee',
       });
       file.dirname = '/test/foo';
-      file.path.should.equal('/test/foo/test.coffee');
+      file.path.should.equal(path.normalize('/test/foo/test.coffee'));
       done();
     });
   });
@@ -844,6 +1036,41 @@ describe('File', function() {
       done();
     });
 
+    it('should not append trailing sep', function() {
+      var file = new File({
+        path: '/test/foo',
+        stat: {
+          isDirectory: function() {
+            return true;
+          },
+        },
+      });
+      file.basename.should.equal('foo');
+
+      var file2 = new File({
+        path: '/test/foo',
+        stat: {
+          isSymbolicLink: function() {
+            return true;
+          },
+        },
+      });
+      file2.basename.should.equal('foo');
+
+      var file3 = new File({
+        path: '/test/foo',
+        stat: {
+          isDirectory: function() {
+            return true;
+          },
+          isSymbolicLink: function() {
+            return true;
+          },
+        },
+      });
+      file3.basename.should.equal('foo');
+    });
+
     it('should error on set when no path', function(done) {
       var file = new File();
       try {
@@ -861,7 +1088,7 @@ describe('File', function() {
         path: '/test/test.coffee',
       });
       file.basename = 'foo.png';
-      file.path.should.equal('/test/foo.png');
+      file.path.should.equal(path.normalize('/test/foo.png'));
       done();
     });
   });
@@ -905,7 +1132,7 @@ describe('File', function() {
         path: '/test/test.coffee',
       });
       file.stem = 'foo';
-      file.path.should.equal('/test/foo.coffee');
+      file.path.should.equal(path.normalize('/test/foo.coffee'));
       done();
     });
   });
@@ -949,21 +1176,21 @@ describe('File', function() {
         path: '/test/test.coffee',
       });
       file.extname = '.png';
-      file.path.should.equal('/test/test.png');
+      file.path.should.equal(path.normalize('/test/test.png'));
       done();
     });
   });
 
   describe('path get/set', function() {
-
     it('should record history when instantiation', function() {
       var file = new File({
         cwd: '/',
         path: '/test/test.coffee',
       });
+      var history = [path.normalize('/test/test.coffee')];
 
-      file.path.should.eql('/test/test.coffee');
-      file.history.should.eql(['/test/test.coffee']);
+      file.path.should.eql(history[0]);
+      file.history.should.eql(history);
     });
 
     it('should record history when path change', function() {
@@ -971,31 +1198,38 @@ describe('File', function() {
         cwd: '/',
         path: '/test/test.coffee',
       });
+      var history = [
+        path.normalize('/test/test.coffee'),
+        path.normalize('/test/test.js'),
+      ];
+
+      file.path = history[history.length - 1];
+      file.path.should.eql(history[history.length - 1]);
+      file.history.should.eql(history);
 
-      file.path = '/test/test.js';
-      file.path.should.eql('/test/test.js');
-      file.history.should.eql(['/test/test.coffee', '/test/test.js']);
+      history.push(path.normalize('/test/test.es6'));
 
-      file.path = '/test/test.coffee';
-      file.path.should.eql('/test/test.coffee');
-      file.history.should.eql(['/test/test.coffee', '/test/test.js', '/test/test.coffee']);
+      file.path = history[history.length - 1];
+      file.path.should.eql(history[history.length - 1]);
+      file.history.should.eql(history);
     });
 
     it('should not record history when set the same path', function() {
+      var val = path.normalize('/test/test.coffee');
       var file = new File({
         cwd: '/',
-        path: '/test/test.coffee',
+        path: val,
       });
 
-      file.path = '/test/test.coffee';
-      file.path = '/test/test.coffee';
-      file.path.should.eql('/test/test.coffee');
-      file.history.should.eql(['/test/test.coffee']);
+      file.path = val;
+      file.path = val;
+      file.path.should.eql(val);
+      file.history.should.eql([val]);
 
       // Ignore when set empty string
       file.path = '';
-      file.path.should.eql('/test/test.coffee');
-      file.history.should.eql(['/test/test.coffee']);
+      file.path.should.eql(val);
+      file.history.should.eql([val]);
     });
 
     it('should throw when set path null', function() {
@@ -1009,7 +1243,39 @@ describe('File', function() {
 
       (function() {
         file.path = null;
-      }).should.throw('path should be string');
+      }).should.throw('path should be a string.');
+    });
+
+    it('should normalize the path on set', function() {
+      var file = new File();
+
+      file.path = '/test/foo/../test.coffee';
+
+      if (process.platform === 'win32') {
+        file.path.should.equal('\\test\\test.coffee');
+        file.history.should.eql(['\\test\\test.coffee']);
+      } else {
+        file.path.should.equal('/test/test.coffee');
+        file.history.should.eql(['/test/test.coffee']);
+      }
+    });
+
+    it('should strip trailing sep', function() {
+      var file = new File();
+      file.path = '/test/';
+      file.path.should.eql(path.normalize('/test'));
+      file.history.should.eql([path.normalize('/test')]);
+
+      var file2 = new File({
+        stat: {
+          isDirectory: function() {
+            return true;
+          },
+        },
+      });
+      file2.path = '/test/';
+      file2.path.should.eql(path.normalize('/test'));
+      file2.history.should.eql([path.normalize('/test')]);
     });
   });
 
@@ -1025,7 +1291,7 @@ describe('File', function() {
       var file = new File({
         symlink: '/test/test.coffee',
       });
-      file.symlink.should.equal('/test/test.coffee');
+      file.symlink.should.equal(path.normalize('/test/test.coffee'));
       done();
     });
 
@@ -1042,15 +1308,27 @@ describe('File', function() {
     it('should set the symlink', function(done) {
       var file = new File();
       file.symlink = '/test/test.coffee';
-      file.symlink.should.equal('/test/test.coffee');
+      file.symlink.should.equal(path.normalize('/test/test.coffee'));
       done();
     });
 
     it('should set the relative symlink', function(done) {
       var file = new File();
-      file.symlink = './test.coffee';
-      file.symlink.should.equal('./test.coffee');
+      file.symlink = 'test.coffee';
+      file.symlink.should.equal('test.coffee');
       done();
     });
+
+    it('should be normalized and stripped off a trailing sep on set', function() {
+      var file = new File();
+
+      file.symlink = '/test/foo/../bar/';
+
+      if (process.platform === 'win32') {
+        file.symlink.should.equal('\\test\\bar');
+      } else {
+        file.symlink.should.equal('/test/bar');
+      }
+    });
   });
 });
diff --git a/test/normalize.js b/test/normalize.js
new file mode 100644
index 0000000..2bfa9a2
--- /dev/null
+++ b/test/normalize.js
@@ -0,0 +1,15 @@
+var normalize = require('../lib/normalize');
+var path = require('path');
+require('should');
+require('mocha');
+
+describe('normalize()', function() {
+  it('should leave empty strings unmodified', function() {
+    normalize('').should.equal('');
+  });
+
+  it('should apply path.normalize for everything else', function() {
+    var str = '/foo//../bar/baz';
+    normalize(str).should.equal(path.normalize(str));
+  });
+});
diff --git a/test/stripTrailingSep.js b/test/stripTrailingSep.js
new file mode 100644
index 0000000..2a432ce
--- /dev/null
+++ b/test/stripTrailingSep.js
@@ -0,0 +1,36 @@
+var stripTrailingSep = require('../lib/stripTrailingSep');
+require('should');
+require('mocha');
+
+describe('stripTrailingSep()', function() {
+  it('should strip trailing separator', function() {
+    stripTrailingSep('foo/').should.equal('foo');
+    stripTrailingSep('foo\\').should.equal('foo');
+  });
+
+  it('should not strip when the only char in the string', function() {
+    stripTrailingSep('/').should.equal('/');
+    stripTrailingSep('\\').should.equal('\\');
+  });
+
+  it('should strip only the trailing separator', function() {
+    stripTrailingSep('/test/foo/bar/').should.equal('/test/foo/bar');
+    stripTrailingSep('\\test\\foo\\bar\\').should.equal('\\test\\foo\\bar');
+  });
+
+  it('should strip multiple trailing separators', function() {
+    stripTrailingSep('/test//').should.equal('/test');
+    stripTrailingSep('\\test\\\\').should.equal('\\test');
+  });
+
+  it('should leave 1st separator in a string of only separators', function() {
+    stripTrailingSep('//').should.equal('/');
+    stripTrailingSep('////').should.equal('/');
+    stripTrailingSep('\\\\').should.equal('\\');
+    stripTrailingSep('\\\\\\\\').should.equal('\\');
+  });
+
+  it('should return back empty string', function() {
+    stripTrailingSep('').should.equal('');
+  });
+});