diff --git a/CHANGELOG.md b/CHANGELOG.md
index 589492ae7..60b1780d7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,8 @@ BUG FIXES:
 
 * core: default user variable values don't need to be strings. [GH-456]
 * builder/amazon-chroot: Fix errors with waitin for state change. [GH-459]
+* communicator/ssh: SCP uploads now work properly when directories
+  contain symlinks. [GH-449]
 
 ## 0.3.8 (September 22, 2013)
 
diff --git a/communicator/ssh/communicator.go b/communicator/ssh/communicator.go
index 96de20de0..e2eea4b21 100644
--- a/communicator/ssh/communicator.go
+++ b/communicator/ssh/communicator.go
@@ -408,8 +408,27 @@ func scpUploadDir(root string, fs []os.FileInfo, w io.Writer, r *bufio.Reader) e
 	for _, fi := range fs {
 		realPath := filepath.Join(root, fi.Name())
 
-		if !fi.IsDir() {
-			// It is a regular file, just upload it
+		// Track if this is actually a symlink to a directory. If it is
+		// a symlink to a file we don't do any special behavior because uploading
+		// a file just works. If it is a directory, we need to know so we
+		// treat it as such.
+		isSymlinkToDir := false
+		if fi.Mode() & os.ModeSymlink == os.ModeSymlink {
+			symPath, err := filepath.EvalSymlinks(realPath)
+			if err != nil {
+				return err
+			}
+
+			symFi, err := os.Lstat(symPath)
+			if err != nil {
+				return err
+			}
+
+			isSymlinkToDir = symFi.IsDir()
+		}
+
+		if !fi.IsDir() && !isSymlinkToDir {
+			// It is a regular file (or symlink to a file), just upload it
 			f, err := os.Open(realPath)
 			if err != nil {
 				return err