diff --git a/check/response_writer.go b/check/response_writer.go
index 40bb7bf..be80d31 100644
--- a/check/response_writer.go
+++ b/check/response_writer.go
@@ -339,8 +339,11 @@ func getFileLocationForAddAnnotationOptions(
 		if !ok {
 			return nil, fmt.Errorf("cannot add annotation for unknown file: %q", fileName)
 		}
-		if len(path) > 0 {
+		for ; len(path) > 0; path = path[:len(path)-1] {
 			sourceLocation = fileDescriptor.ProtoreflectFileDescriptor().SourceLocations().ByPath(path)
+			if len(sourceLocation.Path) > 0 {
+				break
+			}
 		}
 		return descriptor.NewFileLocation(fileDescriptor, sourceLocation), nil
 	}
diff --git a/check/response_writer_test.go b/check/response_writer_test.go
new file mode 100644
index 0000000..594fe41
--- /dev/null
+++ b/check/response_writer_test.go
@@ -0,0 +1,132 @@
+package check_test
+
+import (
+	"context"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"buf.build/go/bufplugin/check"
+	"buf.build/go/bufplugin/check/checktest"
+	"buf.build/go/bufplugin/check/checkutil"
+	"buf.build/go/bufplugin/descriptor"
+	"github.com/stretchr/testify/require"
+)
+
+const protoFile = `
+syntax = "proto3";
+import "google/protobuf/descriptor.proto";
+extend google.protobuf.MessageOptions {
+  X x = 5000;
+}
+message X {
+  string y = 1;
+}
+message Foo {
+  option deprecated = true;
+  option (x).y = "z";
+}
+`
+
+// TestIssue20 checks that an annotation by source path points to the nearest parent if the original one is missing.
+func TestIssue20(t *testing.T) {
+	t.Parallel()
+	dir := t.TempDir()
+	const fileName = "file.proto"
+	const ruleID = "TEST_MISSING_SOURCE_LOCATION"
+	require.NoError(t, os.WriteFile(filepath.Join(dir, fileName), []byte(protoFile), 0666))
+	checktest.CheckTest{
+		Request: &checktest.RequestSpec{
+			Files: &checktest.ProtoFileSpec{
+				DirPaths:  []string{dir},
+				FilePaths: []string{fileName},
+			},
+			RuleIDs: []string{ruleID},
+		},
+		Spec: &check.Spec{
+			Rules: []*check.RuleSpec{{
+				ID:      ruleID,
+				Purpose: "Purpose.",
+				Type:    check.RuleTypeLint,
+				Handler: checkutil.NewFileRuleHandler(
+					func(
+						_ context.Context,
+						writer check.ResponseWriter,
+						_ check.Request,
+						file descriptor.FileDescriptor,
+					) error {
+						foo := file.ProtoreflectFileDescriptor().Messages().ByName("Foo")
+						fooPath := file.ProtoreflectFileDescriptor().SourceLocations().ByDescriptor(foo).Path
+						writer.AddAnnotation(
+							check.WithMessage("Annotation for message"),
+							check.WithFileNameAndSourcePath(
+								fileName,
+								fooPath,
+							),
+						)
+						writer.AddAnnotation(
+							check.WithMessage("Annotation for option (x).y"),
+							check.WithFileNameAndSourcePath(
+								fileName,
+								append(
+									fooPath,
+									7,    // google.protobuf.DescriptorProto.options
+									5000, // x
+									1,    // X.y
+								),
+							),
+						)
+						writer.AddAnnotation(
+							check.WithMessage("Annotation for option (x) points to first message option"),
+							check.WithFileNameAndSourcePath(
+								fileName,
+								append(
+									fooPath,
+									7,    // google.protobuf.DescriptorProto.options
+									5000, // x
+								),
+							),
+						)
+						return nil
+					},
+					checkutil.WithoutImports(),
+				),
+			}},
+		},
+		ExpectedAnnotations: []checktest.ExpectedAnnotation{
+			{
+				RuleID:  ruleID,
+				Message: "Annotation for message",
+				FileLocation: &checktest.ExpectedFileLocation{
+					FileName:    fileName,
+					StartLine:   9,
+					StartColumn: 0,
+					EndLine:     12,
+					EndColumn:   1,
+				},
+			},
+			{
+				RuleID:  ruleID,
+				Message: "Annotation for option (x) points to first message option",
+				FileLocation: &checktest.ExpectedFileLocation{
+					FileName:    fileName,
+					StartLine:   10,
+					StartColumn: 2,
+					EndLine:     10,
+					EndColumn:   27,
+				},
+			},
+			{
+				RuleID:  ruleID,
+				Message: "Annotation for option (x).y",
+				FileLocation: &checktest.ExpectedFileLocation{
+					FileName:    fileName,
+					StartLine:   11,
+					StartColumn: 2,
+					EndLine:     11,
+					EndColumn:   21,
+				},
+			},
+		},
+	}.Run(t)
+}