diff --git a/load.c b/load.c
index 00ccb6c..580b9f1 100644
--- a/load.c
+++ b/load.c
@@ -380,9 +380,9 @@ search_required(VALUE fname, volatile VALUE *path)
 	    if ((tmp = rb_find_file(fname)) != 0) {
 		tmp = rb_file_expand_path(tmp, Qnil);
 		ext = strrchr(ftptr = RSTRING_PTR(tmp), '.');
-//		if (!rb_feature_p(ftptr, ext, Qtrue, Qtrue, 0)) {
+    // if (!rb_feature_p(ftptr, ext, Qtrue, Qtrue, 0)) {
 		    *path = tmp;
-//		}
+    // }
 		return 'r';
 	    }
 	    return 0;
diff --git a/objc.m b/objc.m
index e098a86..a0bccc8 100644
--- a/objc.m
+++ b/objc.m
@@ -192,13 +192,42 @@ rb_objc_symbolize_address(void *addr, void **start, char *name,
 VALUE
 rb_file_expand_path(VALUE fname, VALUE dname)
 {
-    NSString *res = [(NSString *)fname stringByExpandingTildeInPath];
-    if (![res isAbsolutePath]) {
-	NSString *dir = dname != Qnil
-	    	? (NSString *)dname
-		: [[NSFileManager defaultManager] currentDirectoryPath];
-	res = [dir stringByAppendingPathComponent:res];
+    NSString *res = (NSString *)StringValue(fname);
+
+    // If the original path starts with "/private", stringByStandardizingPath:
+    // and stringByResolvingSymlinksInPath: remove the "/private" prefix if that path resolves
+    // to a directory in "/". MRI, however, doesn't do that. So we replace the prefix with our own
+    // so the Cocoa methods won't treat it as "/private" and replace it again in the end _if_
+    // the expanded path still has our prefix.
+    BOOL private = [res hasPrefix:@"/private"];
+    if (private) {
+      res = [@"/__mr_private__" stringByAppendingPathComponent:[res substringFromIndex:8]];
     }
+
+    if ([res isAbsolutePath]) {
+      res = [res stringByResolvingSymlinksInPath];
+    } else {
+      NSString *dir = dname != Qnil ?
+        (NSString *)dname : [[NSFileManager defaultManager] currentDirectoryPath];
+
+      if (![dir isAbsolutePath]) {
+        dir = (NSString *)rb_file_expand_path((VALUE)dir, Qnil);
+      }
+
+      // stringByStandardizingPath does not expand "/." to "/"
+      if ([res isEqualTo:@"."] && [dir isEqualTo:@"/"]) {
+        return (VALUE)[@"/" mutableCopy];
+      } else {
+        res = [dir stringByAppendingPathComponent:res];
+      }
+
+      res = [res stringByStandardizingPath];
+    }
+
+    if (private && [res hasPrefix:@"/__mr_private__"]) {
+      res = [@"/private" stringByAppendingPathComponent:[res substringFromIndex:15]];
+    }
+
     return (VALUE)[res mutableCopy];
 }

diff --git a/spec/frozen/core/file/expand_path_spec.rb b/spec/frozen/core/file/expand_path_spec.rb
index e896ac4..f07868e 100644
--- a/spec/frozen/core/file/expand_path_spec.rb
+++ b/spec/frozen/core/file/expand_path_spec.rb
@@ -67,10 +67,16 @@ describe "File.expand_path" do
       File.expand_path('~/').should == ENV['HOME']
       File.expand_path('~/..badfilename').should == "#{ENV['HOME']}/..badfilename"
       File.expand_path('..').should == Dir.pwd.split('/')[0...-1].join("/")
-      File.expand_path('//').should == '//'
       File.expand_path('~/a','~/b').should == "#{ENV['HOME']}/a"
     end

+    not_compliant_on :macruby do
+      it "leaves multiple prefixed slashes untouched" do
+        File.expand_path('//').should == '//'
+        File.expand_path('////').should == '////'
+      end
+    end
+
     it "raises an ArgumentError if the path is not valid" do
       lambda { File.expand_path("~a_fake_file") }.should raise_error(ArgumentError)
     end
@@ -85,7 +91,7 @@ describe "File.expand_path" do
     end
   end

-  it "raises an ArgumentError is not passed one or two arguments" do
+  it "raises an ArgumentError if not passed one or two arguments" do
     lambda { File.expand_path }.should raise_error(ArgumentError)
     lambda { File.expand_path '../', 'tmp', 'foo' }.should raise_error(ArgumentError)
   end
diff --git a/spec/frozen/tags/macruby/core/file/expand_path_tags.txt b/spec/frozen/tags/macruby/core/file/expand_path_tags.txt
index 26a751e..b33331c 100644
--- a/spec/frozen/tags/macruby/core/file/expand_path_tags.txt
+++ b/spec/frozen/tags/macruby/core/file/expand_path_tags.txt
@@ -1,7 +1,2 @@
-critical:File.expand_path raises an ArgumentError is not passed one or two arguments
 critical:File.expand_path raises a TypeError if not passed a String type
-fails:File.expand_path converts a pathname to an absolute pathname, using a complete path
-fails:File.expand_path expand path with
-fails:File.expand_path expand_path for commoms unix path  give a full path
-fails:File.expand_path raises an ArgumentError if the path is not valid
-fails:File.expand_path expands /./dir to /dir
+fails:File.expand_path raises an ArgumentError if the path is not valid
\ No newline at end of file
diff --git a/spec/macruby/core/file_spec.rb b/spec/macruby/core/file_spec.rb
new file mode 100644
index 0000000..47c1696
--- /dev/null
+++ b/spec/macruby/core/file_spec.rb
@@ -0,0 +1,26 @@
+# TODO
+# require File.expand_path('../spec_helper', __FILE__)
+# require File.expand_path('../spec_helper.rb', __FILE__)
+
+require File.dirname(__FILE__) + "/../spec_helper"
+
+describe "File#expand_path" do
+  it "returns path prefixed with '/private/tmp' if the original path has the '/private' prefix and expands to '/tmp'" do
+    File.expand_path('/private/tmp').should == '/private/tmp'
+    File.expand_path('/private/bin').should == '/private/bin'
+    File.expand_path('/private/foo').should == '/private/foo'
+    File.expand_path('/private/../foo').should == '/foo'
+    File.expand_path('/private/tmp/foo').should == '/private/tmp/foo'
+    File.expand_path('/private/bin/foo').should == '/private/bin/foo'
+    File.expand_path('/private/foo/../tmp').should == '/private/tmp'
+    File.expand_path('/private/private').should == '/private/private'
+    File.expand_path('/private/private/private').should == '/private/private/private'
+  end
+
+  it "removes prefixed slashes, which isn't done by MRI" do
+    File.expand_path('//').should == '/'
+    File.expand_path('////').should == '/'
+    File.expand_path('////foo').should == '/foo'
+    File.expand_path('////foo//bar').should == '/foo/bar'
+  end
+end
\ No newline at end of file