diff --git a/tsc/internal/fourslash/tests/autoImportIndexReExportPrefix_test.go b/tsc/internal/fourslash/tests/autoImportIndexReExportPrefix_test.go
new file mode 100644
index 0000000000000..c0934f80dc42d
--- /dev/null
+++ b/tsc/internal/fourslash/tests/autoImportIndexReExportPrefix_test.go
@@ -0,0 +1,26 @@
+package fourslash_test
+
+import (
+	"testing"
+
+	"github.com/microsoft/TypeScript/tsc/internal/fourslash"
+	"github.com/microsoft/TypeScript/tsc/internal/ls/lsutil"
+	"github.com/microsoft/TypeScript/tsc/internal/testutil"
+)
+
+func TestAutoImportIndexReExportPrefix(t *testing.T) {
+	t.Parallel()
+	defer testutil.RecoverAndFail(t, "Panic on fourslash test")
+	const content = `// @module: nodenext
+// @Filename: /package.json
+{ "type": "module" }
+// @Filename: /utils/sum/index.ts
+export { sum } from "./sum.js";
+// @Filename: /utils/sum/sum.ts
+export const sum = 0;
+// @Filename: /utils/sumAB.ts
+sum/**/`
+	f, done := fourslash.NewFourslash(t, nil /*capabilities*/, content)
+	defer done()
+	f.VerifyImportFixModuleSpecifiers(t, "", []string{"./sum/index.js", "./sum/sum.js"}, &lsutil.UserPreferences{ImportModuleSpecifierEnding: "js"})
+}
diff --git a/tsc/internal/ls/autoimport/fix.go b/tsc/internal/ls/autoimport/fix.go
index a035f305eaf1d..c8315b2fe3511 100644
--- a/tsc/internal/ls/autoimport/fix.go
+++ b/tsc/internal/ls/autoimport/fix.go
@@ -1097,7 +1097,7 @@ func (v *View) compareNodeCoreModuleSpecifiers(a, b string, importingFile *ast.S
 func isFixPossiblyReExportingImportingFile(fix *Fix, importingFileName string) bool {
 	if fix.IsReExport && isIndexFileName(fix.ModuleFileName) {
 		reExportDir := tspath.GetDirectoryPath(fix.ModuleFileName)
-		return strings.HasPrefix(importingFileName, reExportDir)
+		return strings.HasPrefix(importingFileName, tspath.EnsureTrailingDirectorySeparator(reExportDir))
 	}
 	return false
 }