diff --git a/spec/spec_with_project.rb b/spec/spec_with_project.rb
index 541c6f90f..182636037 100644
--- a/spec/spec_with_project.rb
+++ b/spec/spec_with_project.rb
@@ -104,6 +104,13 @@ def assert_project_file_exist(path)
       assert(@project.file?(path))
     end
 
+    # Assert that `path` exists inside project.
+    # `Path` can include patterns such as `*`, useful for testing RBIs for real gems
+    sig { params(path: String).void }
+    def assert_project_file_match(path)
+      assert(Dir[path].any?)
+    end
+
     # Refute that `path` exists inside `@project`
     sig { params(path: String).void }
     def refute_project_file_exist(path)
diff --git a/spec/tapioca/cli/gem_spec.rb b/spec/tapioca/cli/gem_spec.rb
index cbca14aa7..80495571d 100644
--- a/spec/tapioca/cli/gem_spec.rb
+++ b/spec/tapioca/cli/gem_spec.rb
@@ -800,7 +800,7 @@ class Secret; end
           assert_project_file_exist("sorbet/rbi/gems/foo@0.0.1.rbi")
           assert_project_file_exist("sorbet/rbi/gems/bar@0.3.0.rbi")
           assert_project_file_exist("sorbet/rbi/gems/actionpack@7.0.6.rbi")
-          assert_project_file_exist("sorbet/rbi/gems/rack@2.2.10.rbi")
+          assert_project_file_match("sorbet/rbi/gems/rack@*.rbi")
           refute_project_file_exist("sorbet/rbi/gems/baz@0.0.2.rbi")
 
           assert_empty_stderr(result)