diff --git a/CHANGELOG.md b/CHANGELOG.md
index d3472bcdcf7..26d3eee80e6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -19,6 +19,7 @@ BUG FIXES:
  * client/artifact: Honor netrc [GH-2524]
  * client/artifact: Handle tars where file in directory is listed before
    directory [GH-2524]
+ * driver/exec: Properly set file/dir ownership in chroots [GH-2552]
  * server: Reject non-TLS clients when TLS enabled [GH-2525]
  * server: Fix a panic in plan evaluation with partial failures and all_at_once
    set [GH-2544]
diff --git a/client/allocdir/alloc_dir.go b/client/allocdir/alloc_dir.go
index bbdb6431798..dd665926112 100644
--- a/client/allocdir/alloc_dir.go
+++ b/client/allocdir/alloc_dir.go
@@ -17,6 +17,12 @@ import (
 	"github.com/hpcloud/tail/watch"
 )
 
+const (
+	// idUnsupported is what the uid/gid will be set to on platforms (eg
+	// Windows) that don't support integer ownership identifiers.
+	idUnsupported = -1
+)
+
 var (
 	// The name of the directory that is shared across tasks in a task group.
 	SharedAllocName = "alloc"
@@ -385,7 +391,9 @@ func getFileWatcher(path string) watch.FileWatcher {
 	return watch.NewPollingFileWatcher(path)
 }
 
-func fileCopy(src, dst string, perm os.FileMode) error {
+// fileCopy from src to dst setting the permissions and owner (if uid & gid are
+// both greater than 0)
+func fileCopy(src, dst string, uid, gid int, perm os.FileMode) error {
 	// Do a simple copy.
 	srcFile, err := os.Open(src)
 	if err != nil {
@@ -400,7 +408,13 @@ func fileCopy(src, dst string, perm os.FileMode) error {
 	defer dstFile.Close()
 
 	if _, err := io.Copy(dstFile, srcFile); err != nil {
-		return fmt.Errorf("Couldn't copy %v to %v: %v", src, dst, err)
+		return fmt.Errorf("Couldn't copy %q to %q: %v", src, dst, err)
+	}
+
+	if uid != idUnsupported && gid != idUnsupported {
+		if err := dstFile.Chown(uid, gid); err != nil {
+			return fmt.Errorf("Couldn't copy %q to %q: %v", src, dst, err)
+		}
 	}
 
 	return nil
@@ -448,6 +462,12 @@ func createDir(basePath, relPath string) error {
 		if err := os.MkdirAll(destDir, fi.Perm); err != nil {
 			return err
 		}
+
+		if fi.Uid != idUnsupported && fi.Gid != idUnsupported {
+			if err := os.Chown(destDir, fi.Uid, fi.Gid); err != nil {
+				return err
+			}
+		}
 	}
 	return nil
 }
@@ -456,6 +476,10 @@ func createDir(basePath, relPath string) error {
 type fileInfo struct {
 	Name string
 	Perm os.FileMode
+
+	// Uid and Gid are unsupported on Windows
+	Uid int
+	Gid int
 }
 
 // splitPath stats each subdirectory of a path. The first element of the array
@@ -463,17 +487,19 @@ type fileInfo struct {
 // path.
 func splitPath(path string) ([]fileInfo, error) {
 	var mode os.FileMode
-	i, err := os.Stat(path)
+	fi, err := os.Stat(path)
 
 	// If the path is not present in the host then we respond with the most
 	// flexible permission.
+	uid, gid := idUnsupported, idUnsupported
 	if err != nil {
 		mode = os.ModePerm
 	} else {
-		mode = i.Mode()
+		uid, gid = getOwner(fi)
+		mode = fi.Mode()
 	}
 	var dirs []fileInfo
-	dirs = append(dirs, fileInfo{Name: path, Perm: mode})
+	dirs = append(dirs, fileInfo{Name: path, Perm: mode, Uid: uid, Gid: gid})
 	currentDir := path
 	for {
 		dir := filepath.Dir(filepath.Clean(currentDir))
@@ -483,13 +509,15 @@ func splitPath(path string) ([]fileInfo, error) {
 
 		// We try to find the permission of the file in the host. If the path is not
 		// present in the host then we respond with the most flexible permission.
-		i, err = os.Stat(dir)
+		uid, gid := idUnsupported, idUnsupported
+		fi, err := os.Stat(dir)
 		if err != nil {
 			mode = os.ModePerm
 		} else {
-			mode = i.Mode()
+			uid, gid = getOwner(fi)
+			mode = fi.Mode()
 		}
-		dirs = append(dirs, fileInfo{Name: dir, Perm: mode})
+		dirs = append(dirs, fileInfo{Name: dir, Perm: mode, Uid: uid, Gid: gid})
 		currentDir = dir
 	}
 	return dirs, nil
diff --git a/client/allocdir/fs_unix.go b/client/allocdir/fs_unix.go
index 648fce1adb6..77447a32f7f 100644
--- a/client/allocdir/fs_unix.go
+++ b/client/allocdir/fs_unix.go
@@ -8,6 +8,7 @@ import (
 	"os/user"
 	"path/filepath"
 	"strconv"
+	"syscall"
 
 	"golang.org/x/sys/unix"
 )
@@ -82,7 +83,7 @@ func getGid(u *user.User) (int, error) {
 
 // linkOrCopy attempts to hardlink dst to src and fallsback to copying if the
 // hardlink fails.
-func linkOrCopy(src, dst string, perm os.FileMode) error {
+func linkOrCopy(src, dst string, uid, gid int, perm os.FileMode) error {
 	// Avoid link/copy if the file already exists in the chroot
 	// TODO 0.6 clean this up. This was needed because chroot creation fails
 	// when a process restarts.
@@ -94,5 +95,13 @@ func linkOrCopy(src, dst string, perm os.FileMode) error {
 		return nil
 	}
 
-	return fileCopy(src, dst, perm)
+	return fileCopy(src, dst, uid, gid, perm)
+}
+
+func getOwner(fi os.FileInfo) (int, int) {
+	stat, ok := fi.Sys().(*syscall.Stat_t)
+	if !ok {
+		return -1, -1
+	}
+	return int(stat.Uid), int(stat.Gid)
 }
diff --git a/client/allocdir/fs_windows.go b/client/allocdir/fs_windows.go
index de0fcec898c..3667c1953bb 100644
--- a/client/allocdir/fs_windows.go
+++ b/client/allocdir/fs_windows.go
@@ -21,8 +21,8 @@ var (
 )
 
 // linkOrCopy is always copies dst to src on Windows.
-func linkOrCopy(src, dst string, perm os.FileMode) error {
-	return fileCopy(src, dst, perm)
+func linkOrCopy(src, dst string, uid, gid int, perm os.FileMode) error {
+	return fileCopy(src, dst, uid, gid, perm)
 }
 
 // The windows version does nothing currently.
@@ -70,3 +70,8 @@ func MountSpecialDirs(taskDir string) error {
 func unmountSpecialDirs(taskDir string) error {
 	return nil
 }
+
+// getOwner doesn't work on Windows as Windows doesn't use int user IDs
+func getOwner(os.FileInfo) (int, int) {
+	return idUnsupported, idUnsupported
+}
diff --git a/client/allocdir/task_dir.go b/client/allocdir/task_dir.go
index 4f2817e625c..b4376057213 100644
--- a/client/allocdir/task_dir.go
+++ b/client/allocdir/task_dir.go
@@ -163,7 +163,8 @@ func (t *TaskDir) embedDirs(entries map[string]string) error {
 
 			// Copy the file.
 			taskEntry := filepath.Join(t.Dir, dest)
-			if err := linkOrCopy(source, taskEntry, s.Mode().Perm()); err != nil {
+			uid, gid := getOwner(s)
+			if err := linkOrCopy(source, taskEntry, uid, gid, s.Mode().Perm()); err != nil {
 				return err
 			}
 
@@ -217,7 +218,8 @@ func (t *TaskDir) embedDirs(entries map[string]string) error {
 				continue
 			}
 
-			if err := linkOrCopy(hostEntry, taskEntry, entry.Mode().Perm()); err != nil {
+			uid, gid := getOwner(entry)
+			if err := linkOrCopy(hostEntry, taskEntry, uid, gid, entry.Mode().Perm()); err != nil {
 				return err
 			}
 		}