diff --git a/internal/datafs/reader.go b/internal/datafs/reader.go
index a7c00d34c..68d5d37f7 100644
--- a/internal/datafs/reader.go
+++ b/internal/datafs/reader.go
@@ -188,8 +188,6 @@ func (d *dsReader) readFileContent(ctx context.Context, u *url.URL, hdr http.Hea
 	return &content{contentType: mimeType, b: data}, nil
 }
 
-// COPIED FROM /data/datasource.go
-//
 // resolveURL parses the relative URL rel against base, and returns the
 // resolved URL. Differs from url.ResolveReference in that query parameters are
 // added. In case of duplicates, params from rel are used.
@@ -232,9 +230,18 @@ func resolveURL(base *url.URL, rel string) (*url.URL, error) {
 	// URL.ResolveReference requires (or assumes, at least) that the base is
 	// absolute. We want to support relative URLs too though, so we need to
 	// correct for that.
-	out := base.ResolveReference(relURL)
-	if out.Scheme == "" && out.Path[0] == '/' {
+	var out *url.URL
+	switch {
+	case rel == "":
+		out = base
+	case base.IsAbs():
+		out = base.ResolveReference(relURL)
+	case base.Scheme == "" && base.Path[0] == '/':
+		// absolute path, no scheme or volume
+		out = base.ResolveReference(relURL)
 		out.Path = out.Path[1:]
+	default:
+		out = resolveRelativeURL(base, relURL)
 	}
 
 	if base.RawQuery != "" {
@@ -248,3 +255,22 @@ func resolveURL(base *url.URL, rel string) (*url.URL, error) {
 
 	return out, nil
 }
+
+// relative path, might even involve .. or . in the path
+func resolveRelativeURL(base, relURL *url.URL) *url.URL {
+	// first find the difference between base and what base would be if it
+	// were absolute
+	emptyURL, _ := url.Parse("")
+	absBase := base.ResolveReference(emptyURL)
+	absBase.Path = strings.TrimPrefix(absBase.Path, "/")
+
+	diff := strings.TrimSuffix(base.Path, absBase.Path)
+	diff = strings.TrimSuffix(diff, "/")
+
+	out := base.ResolveReference(relURL)
+
+	// now correct the path by adding the prefix back in
+	out.Path = diff + out.Path
+
+	return out
+}
diff --git a/internal/datafs/reader_test.go b/internal/datafs/reader_test.go
index 588592fd0..05472642c 100644
--- a/internal/datafs/reader_test.go
+++ b/internal/datafs/reader_test.go
@@ -61,10 +61,24 @@ func TestResolveURL(t *testing.T) {
 	_, err = resolveURL(mustParseURL("git+ssh://git@example.com/foo//bar"), "baz//myfile")
 	require.Error(t, err)
 
-	// relative urls must remain relative
+	// relative base URLs must remain relative
 	out, err = resolveURL(mustParseURL("tmp/foo.json"), "")
 	require.NoError(t, err)
 	assert.Equal(t, "tmp/foo.json", out.String())
+
+	// relative implicit file URLs without volume or scheme are OK
+	out, err = resolveURL(mustParseURL("/tmp/"), "foo.json")
+	require.NoError(t, err)
+	assert.Equal(t, "tmp/foo.json", out.String())
+
+	// relative base URLs in parent directories are OK
+	out, err = resolveURL(mustParseURL("../../tmp/foo.json"), "")
+	require.NoError(t, err)
+	assert.Equal(t, "../../tmp/foo.json", out.String())
+
+	out, err = resolveURL(mustParseURL("../../tmp/"), "sub/foo.json")
+	require.NoError(t, err)
+	assert.Equal(t, "../../tmp/sub/foo.json", out.String())
 }
 
 func TestReadFileContent(t *testing.T) {
diff --git a/internal/tests/integration/datasources_file_test.go b/internal/tests/integration/datasources_file_test.go
index 37e65a0fc..ea4f02592 100644
--- a/internal/tests/integration/datasources_file_test.go
+++ b/internal/tests/integration/datasources_file_test.go
@@ -189,3 +189,36 @@ func TestDatasources_File_Directory(t *testing.T) {
 		withDir(tmpDir.Path()).run()
 	assertSuccess(t, o, e, err, "core.yaml root key: cloud")
 }
+
+func TestDatsources_File_RelativePath(t *testing.T) {
+	// regression test for #2230
+	tmpDir := fs.NewDir(t, "gomplate-inttests",
+		fs.WithDir("root",
+			fs.WithDir("foo",
+				fs.WithDir("bar",
+					fs.WithFiles(map[string]string{
+						".gomplate.yaml": `
+context:
+  qux:
+    url: "../../baz/qux.yaml"
+`,
+					}),
+				),
+			),
+			fs.WithDir("baz",
+				fs.WithFiles(map[string]string{
+					"qux.yaml": `values:
+- value1
+- value2
+`,
+				}),
+			),
+		),
+	)
+	t.Cleanup(tmpDir.Remove)
+
+	o, e, err := cmd(t, "--config", ".gomplate.yaml", "-i", "{{ .qux.values }}").
+		withDir(tmpDir.Join("root", "foo", "bar")).run()
+
+	assertSuccess(t, o, e, err, "[value1 value2]")
+}