diff --git a/Userland/Utilities/headless-browser.cpp b/Userland/Utilities/headless-browser.cpp
index d6f5f758a3..58858ef559 100644
--- a/Userland/Utilities/headless-browser.cpp
+++ b/Userland/Utilities/headless-browser.cpp
@@ -240,7 +240,14 @@ static ErrorOr<TestResult> run_test(HeadlessWebContentView& view, StringView inp
     if (result.is_error())
         return result.release_error();
 
-    auto expectation_file = TRY(Core::File::open(expectation_path, Core::File::OpenMode::Read));
+    auto expectation_file_or_error = Core::File::open(expectation_path, Core::File::OpenMode::Read);
+    if (expectation_file_or_error.is_error()) {
+        warnln("Failed opening '{}': {}", expectation_path, expectation_file_or_error.error());
+        return expectation_file_or_error.release_error();
+    }
+
+    auto expectation_file = expectation_file_or_error.release_value();
+
     auto expectation = TRY(String::from_utf8(StringView(TRY(expectation_file->read_until_eof()).bytes())));
 
     auto actual = result.release_value();