diff --git a/fs/operations/operations.go b/fs/operations/operations.go
index b97fade44..ec2be9290 100644
--- a/fs/operations/operations.go
+++ b/fs/operations/operations.go
@@ -10,6 +10,7 @@ import (
 	"io/ioutil"
 	"net/http"
 	"path"
+	"path/filepath"
 	"sort"
 	"strconv"
 	"strings"
@@ -543,7 +544,7 @@ func Overlapping(fdst, fsrc fs.Info) bool {
 	}
 	// Return the Root with a trailing / if not empty
 	fixedRoot := func(f fs.Info) string {
-		s := strings.Trim(f.Root(), "/")
+		s := strings.Trim(filepath.ToSlash(f.Root()), "/")
 		if s != "" {
 			s += "/"
 		}
diff --git a/fs/operations/operations_test.go b/fs/operations/operations_test.go
index 1ee69ee6a..72749fdaa 100644
--- a/fs/operations/operations_test.go
+++ b/fs/operations/operations_test.go
@@ -777,6 +777,7 @@ func TestSame(t *testing.T) {
 
 func TestOverlapping(t *testing.T) {
 	a := &testFsInfo{name: "name", root: "root"}
+	slash := string(os.PathSeparator) // native path separator
 	for _, test := range []struct {
 		name     string
 		root     string
@@ -789,6 +790,8 @@ func TestOverlapping(t *testing.T) {
 		{"name", "roo", false},
 		{"name", "root/toot", true},
 		{"name", "root/toot/", true},
+		{"name", "root" + slash + "toot", true},
+		{"name", "root" + slash + "toot" + slash, true},
 		{"name", "", true},
 		{"name", "/", true},
 	} {
diff --git a/fs/sync/sync_test.go b/fs/sync/sync_test.go
index ab8522ce4..ab013cc81 100644
--- a/fs/sync/sync_test.go
+++ b/fs/sync/sync_test.go
@@ -1124,8 +1124,9 @@ func TestSyncOverlap(t *testing.T) {
 	require.NoError(t, err)
 
 	checkErr := func(err error) {
+		require.Error(t, err)
 		assert.True(t, fserrors.IsFatalError(err))
-		assert.Equal(t, err.Error(), fs.ErrorOverlapping.Error())
+		assert.Equal(t, fs.ErrorOverlapping.Error(), err.Error())
 	}
 
 	checkErr(Sync(FremoteSync, r.Fremote))