diff --git a/cmd/posix-errors.go b/cmd/posix-errors.go
new file mode 100644
index 000000000..0fc152822
--- /dev/null
+++ b/cmd/posix-errors.go
@@ -0,0 +1,89 @@
+/*
+ * Minio Cloud Storage, (C) 2016 Minio, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package cmd
+
+import (
+	"os"
+	"runtime"
+	"syscall"
+)
+
+// Check if the given error corresponds to ENOTDIR (is not a directory)
+func isSysErrNotDir(err error) bool {
+	if pathErr, ok := err.(*os.PathError); ok {
+		switch pathErr.Err {
+		case syscall.ENOTDIR:
+			return true
+		}
+	}
+	return false
+}
+
+// Check if the given error corresponds to EISDIR (is a directory)
+func isSysErrIsDir(err error) bool {
+	if pathErr, ok := err.(*os.PathError); ok {
+		switch pathErr.Err {
+		case syscall.EISDIR:
+			return true
+		}
+	}
+	return false
+}
+
+// Check if the given error corresponds to ENOTEMPTY for unix
+// and ERROR_DIR_NOT_EMPTY for windows (directory not empty)
+func isSysErrNotEmpty(err error) bool {
+	if pathErr, ok := err.(*os.PathError); ok {
+		if runtime.GOOS == "windows" {
+			if errno, _ok := pathErr.Err.(syscall.Errno); _ok && errno == 0x91 {
+				// ERROR_DIR_NOT_EMPTY
+				return true
+			}
+		}
+		switch pathErr.Err {
+		case syscall.ENOTEMPTY:
+			return true
+		}
+	}
+	return false
+}
+
+// Check if the given error corresponds to the specific ERROR_PATH_NOT_FOUND for windows
+func isSysErrPathNotFound(err error) bool {
+	if runtime.GOOS != "windows" {
+		return false
+	}
+	if pathErr, ok := err.(*os.PathError); ok {
+		if errno, _ok := pathErr.Err.(syscall.Errno); _ok && errno == 0x03 {
+			// ERROR_PATH_NOT_FOUND
+			return true
+		}
+	}
+	return false
+}
+
+// Check if the given error corresponds to the specific ERROR_INVALID_HANDLE for windows
+func isSysErrHandleInvalid(err error) bool {
+	if runtime.GOOS != "windows" {
+		return false
+	}
+	// Check if err contains ERROR_INVALID_HANDLE errno
+	if errno, ok := err.(syscall.Errno); ok && errno == 0x6 {
+		return true
+	}
+	return false
+}
diff --git a/cmd/posix.go b/cmd/posix.go
index e0ce58f11..8bf5bec3b 100644
--- a/cmd/posix.go
+++ b/cmd/posix.go
@@ -339,12 +339,7 @@ func (s *posix) DeleteVol(volume string) (err error) {
 	if err != nil {
 		if os.IsNotExist(err) {
 			return errVolumeNotFound
-		} else if strings.Contains(err.Error(), "directory is not empty") {
-			// On windows the string is slightly different, handle it here.
-			return errVolumeNotEmpty
-		} else if strings.Contains(err.Error(), "directory not empty") {
-			// Hopefully for all other operating systems, this is
-			// assumed to be consistent.
+		} else if isSysErrNotEmpty(err) {
 			return errVolumeNotEmpty
 		}
 		return err
@@ -439,7 +434,7 @@ func (s *posix) ReadAll(volume, path string) (buf []byte, err error) {
 			case syscall.ENOTDIR, syscall.EISDIR:
 				return nil, errFileNotFound
 			default:
-				if strings.Contains(pathErr.Err.Error(), "The handle is invalid") {
+				if isSysErrHandleInvalid(pathErr.Err) {
 					// This case is special and needs to be handled for windows.
 					return nil, errFileNotFound
 				}
@@ -498,7 +493,7 @@ func (s *posix) ReadFile(volume string, path string, offset int64, buf []byte) (
 			return 0, errFileNotFound
 		} else if os.IsPermission(err) {
 			return 0, errFileAccessDenied
-		} else if strings.Contains(err.Error(), "not a directory") {
+		} else if isSysErrNotDir(err) {
 			return 0, errFileAccessDenied
 		}
 		return 0, err
@@ -575,9 +570,9 @@ func (s *posix) AppendFile(volume, path string, buf []byte) (err error) {
 	// with mode 0777 mkdir honors system umask.
 	if err = mkdirAll(filepath.Dir(filePath), 0777); err != nil {
 		// File path cannot be verified since one of the parents is a file.
-		if strings.Contains(err.Error(), "not a directory") {
+		if isSysErrNotDir(err) {
 			return errFileAccessDenied
-		} else if runtime.GOOS == "windows" && strings.Contains(err.Error(), "system cannot find the path specified") {
+		} else if isSysErrPathNotFound(err) {
 			// Add specific case for windows.
 			return errFileAccessDenied
 		}
@@ -589,7 +584,7 @@ func (s *posix) AppendFile(volume, path string, buf []byte) (err error) {
 	w, err := os.OpenFile(preparePath(filePath), os.O_CREATE|os.O_APPEND|os.O_WRONLY, 0666)
 	if err != nil {
 		// File path cannot be verified since one of the parents is a file.
-		if strings.Contains(err.Error(), "not a directory") {
+		if isSysErrNotDir(err) {
 			return errFileAccessDenied
 		}
 		return err
@@ -645,7 +640,7 @@ func (s *posix) StatFile(volume, path string) (file FileInfo, err error) {
 		}
 
 		// File path cannot be verified since one of the parents is a file.
-		if strings.Contains(err.Error(), "not a directory") {
+		if isSysErrNotDir(err) {
 			return FileInfo{}, errFileNotFound
 		}
 
@@ -804,9 +799,9 @@ func (s *posix) RenameFile(srcVolume, srcPath, dstVolume, dstPath string) (err e
 	// Creates all the parent directories, with mode 0777 mkdir honors system umask.
 	if err = mkdirAll(preparePath(slashpath.Dir(dstFilePath)), 0777); err != nil {
 		// File path cannot be verified since one of the parents is a file.
-		if strings.Contains(err.Error(), "not a directory") {
+		if isSysErrNotDir(err) {
 			return errFileAccessDenied
-		} else if strings.Contains(err.Error(), "The system cannot find the path specified.") && runtime.GOOS == "windows" {
+		} else if isSysErrPathNotFound(err) {
 			// This is a special case should be handled only for
 			// windows, because windows API does not return "not a
 			// directory" error message. Handle this specifically here.
diff --git a/cmd/posix_test.go b/cmd/posix_test.go
index 25ac68b43..6bccb66cb 100644
--- a/cmd/posix_test.go
+++ b/cmd/posix_test.go
@@ -18,7 +18,6 @@ package cmd
 
 import (
 	"bytes"
-	"errors"
 	"io"
 	"io/ioutil"
 	"os"
@@ -901,7 +900,7 @@ func TestReadFile(t *testing.T) {
 					return &os.PathError{
 						Op:   "seek",
 						Path: preparePath(slashpath.Join(path, "success-vol", "myobject")),
-						Err:  errors.New("An attempt was made to move the file pointer before the beginning of the file."),
+						Err:  syscall.Errno(0x83), // ERROR_NEGATIVE_SEEK
 					}
 				}
 				return &os.PathError{
@@ -953,7 +952,24 @@ func TestReadFile(t *testing.T) {
 		if err != nil && testCase.expectedErr != nil {
 			// Validate if the type string of the errors are an exact match.
 			if err.Error() != testCase.expectedErr.Error() {
-				t.Errorf("Case: %d %#v, expected: %s, got: %s", i+1, testCase, testCase.expectedErr, err)
+				if runtime.GOOS != "windows" {
+					t.Errorf("Case: %d %#v, expected: %s, got: %s", i+1, testCase, testCase.expectedErr, err)
+				} else {
+					var resultErrno, expectErrno uintptr
+					if pathErr, ok := err.(*os.PathError); ok {
+						if errno, pok := pathErr.Err.(syscall.Errno); pok {
+							resultErrno = uintptr(errno)
+						}
+					}
+					if pathErr, ok := testCase.expectedErr.(*os.PathError); ok {
+						if errno, pok := pathErr.Err.(syscall.Errno); pok {
+							expectErrno = uintptr(errno)
+						}
+					}
+					if !(expectErrno != 0 && resultErrno != 0 && expectErrno == resultErrno) {
+						t.Errorf("Case: %d %#v, expected: %s, got: %s", i+1, testCase, testCase.expectedErr, err)
+					}
+				}
 			}
 			// Err unexpected EOF special case, where we verify we have provided a larger
 			// buffer than the data itself, but the results are in-fact valid. So we validate