diff --git a/command_line/dash_r_spec.rb b/command_line/dash_r_spec.rb
index 0de9ba2e2..052ad5e63 100644
--- a/command_line/dash_r_spec.rb
+++ b/command_line/dash_r_spec.rb
@@ -25,4 +25,9 @@
     out.should_not.include?("REQUIRED")
     out.should.include?("No such file or directory")
   end
+
+  it "requires in order when given multiple times" do
+    ruby_exe("", options: "-r#{fixture(__FILE__, "test_file.rb")} -r#{fixture(__FILE__, "verbose.rb")}").
+      should == "REQUIRED\nfalse\n"
+  end
 end
diff --git a/command_line/rubyopt_spec.rb b/command_line/rubyopt_spec.rb
index eb297cd6f..7ac875774 100644
--- a/command_line/rubyopt_spec.rb
+++ b/command_line/rubyopt_spec.rb
@@ -83,6 +83,12 @@
     ruby_exe("0", args: '2>&1').should =~ /^rubyopt.rb required/
   end
 
+  it "requires from CLI -r first and then from RUBYOPT -r" do
+    ENV["RUBYOPT"] = "-r#{fixture(__FILE__, "rubyopt.rb")}"
+    ruby_exe("", options: "-r#{fixture(__FILE__, "test_file.rb")}").
+      should == "REQUIRED\nrubyopt.rb required\n"
+  end
+
   it "raises a RuntimeError for '-a'" do
     ENV["RUBYOPT"] = '-a'
     ruby_exe("", args: '2>&1', exit_status: 1).should =~ /RuntimeError/