diff --git a/pkg/utils/file.go b/pkg/utils/file.go
index 9e0368db7ce..21bb00697b7 100644
--- a/pkg/utils/file.go
+++ b/pkg/utils/file.go
@@ -276,7 +276,7 @@ func IsPathInDir(dir, pathToCheck string) bool {
 	rel, err := filepath.Rel(dir, pathToCheck)
 
 	if err == nil {
-		if !strings.HasPrefix(rel, ".."+string(filepath.Separator)) {
+		if !strings.HasPrefix(rel, "..") { // if path is the parent no separator is returned
 			return true
 		}
 	}
diff --git a/pkg/utils/file_linux_test.go b/pkg/utils/file_linux_test.go
new file mode 100644
index 00000000000..7f106ae14a5
--- /dev/null
+++ b/pkg/utils/file_linux_test.go
@@ -0,0 +1,35 @@
+// +build linux
+
+package utils
+
+import (
+	"strconv"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+// Due to the way some functions work some tests need to be run
+// with data for the running OS
+
+// linux path tests for IsPathInDir (path separator is evaluated at runtime)
+var linuxTestPaths = []struct {
+	basePath string
+	path     string
+	isInDir  bool
+}{
+	{"/media/.previews", "/media", false}, //1
+	{"/media", "/media/.previews", true},
+	{"/", "/my/media/path", true},
+	{"/opt/stash/media", "/opt/media", false},
+	{"/opt/", "/opt/stash/media", true},
+	{"/opt/stash/", "/opt/stash", true}, // 6
+}
+
+func TestIsPathInDirLinux(t *testing.T) {
+	assert := assert.New(t)
+
+	for i, tp := range linuxTestPaths {
+		assert.Equal(tp.isInDir, IsPathInDir(tp.basePath, tp.path), "Test "+strconv.Itoa(i+1)+":"+tp.basePath+"... failed")
+	}
+}
diff --git a/pkg/utils/file_windows_test.go b/pkg/utils/file_windows_test.go
new file mode 100644
index 00000000000..a258483dd2e
--- /dev/null
+++ b/pkg/utils/file_windows_test.go
@@ -0,0 +1,35 @@
+// +build windows
+
+package utils
+
+import (
+	"strconv"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+// Due to the way some functions work some tests need to be run
+// with data for the running OS
+
+// windows path tests for IsPathInDir (path separator is evaluated at runtime)
+var windowsTestPaths = []struct {
+	basePath string
+	path     string
+	isInDir  bool
+}{
+	{"c:\\media\\.previews", "c:\\media", false}, //1
+	{"c:\\media", "c:\\media\\.previews", true},
+	{"c:\\", "c:\\my\\media\\path", true},
+	{"\\\\netshare\\stash\\media", "\\\\netshare\\opt\\media", false},
+	{"\\\\netshare", "\\\\netshare\\stash\\media", true},
+	{"c:\\user\\data\\2", "c:\\user\\data\\2", true}, // 6
+}
+
+func TestIsPathInDirWindows(t *testing.T) {
+	assert := assert.New(t)
+
+	for i, tp := range windowsTestPaths {
+		assert.Equal(tp.isInDir, IsPathInDir(tp.basePath, tp.path), "Test "+strconv.Itoa(i+1)+":"+tp.basePath+"... failed")
+	}
+}