diff --git a/bundle/file.go b/bundle/file.go
index ab1d1c72a2..183ab7532a 100644
--- a/bundle/file.go
+++ b/bundle/file.go
@@ -76,6 +76,20 @@ type dirLoader struct {
 // NewDirectoryLoader returns a basic DirectoryLoader implementation
 // that will load files from a given root directory path.
 func NewDirectoryLoader(root string) DirectoryLoader {
+
+	if len(root) > 1 {
+		// Normalize relative directories, ex "./src/bundle" -> "src/bundle"
+		// We don't need an absolute path, but this makes the joined/trimmed
+		// paths more uniform.
+		if root[0] == '.' && root[1] == filepath.Separator {
+			if len(root) == 2 {
+				root = root[:1] // "./" -> "."
+			} else {
+				root = root[2:] // remove leading "./"
+			}
+		}
+	}
+
 	d := dirLoader{
 		root: root,
 	}
diff --git a/bundle/file_test.go b/bundle/file_test.go
index 761ce8fd82..3b4f8b22ee 100644
--- a/bundle/file_test.go
+++ b/bundle/file_test.go
@@ -106,3 +106,67 @@ func testLoader(t *testing.T, loader DirectoryLoader, expectedFiles map[string]s
 		t.Fatalf("Expected to read %d files, read %d", len(expectedFiles), fileCount)
 	}
 }
+
+func TestNewDirectoryLoaderNormalizedRoot(t *testing.T) {
+	cases := []struct {
+		note     string
+		root     string
+		expected string
+	}{
+		{
+			note:     "abs",
+			root:     "/a/b/c",
+			expected: "/a/b/c",
+		},
+		{
+			note:     "trailing slash",
+			root:     "/a/b/c/",
+			expected: "/a/b/c/",
+		},
+		{
+			note:     "empty",
+			root:     "",
+			expected: "",
+		},
+		{
+			note:     "single abs",
+			root:     "/",
+			expected: "/",
+		},
+		{
+			note:     "single relative",
+			root:     "foo",
+			expected: "foo",
+		},
+		{
+			note:     "single relative dot",
+			root:     ".",
+			expected: ".",
+		},
+		{
+			note:     "single relative dot slash",
+			root:     "./",
+			expected: ".",
+		},
+		{
+			note:     "relative leading dot slash",
+			root:     "./a/b/c",
+			expected: "a/b/c",
+		},
+		{
+			note:     "relative",
+			root:     "a/b/c",
+			expected: "a/b/c",
+		},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.note, func(t *testing.T) {
+			l := NewDirectoryLoader(tc.root)
+			actual := l.(*dirLoader).root
+			if actual != tc.expected {
+				t.Fatalf("Expected root %s got %s", tc.expected, actual)
+			}
+		})
+	}
+}