diff --git a/lib/irb/debug.rb b/lib/irb/debug.rb
index cd64b77ad..59be1365b 100644
--- a/lib/irb/debug.rb
+++ b/lib/irb/debug.rb
@@ -81,6 +81,7 @@ def configure_irb_for_debugger(irb)
         IRB.instance_variable_set(:@debugger_irb, irb)
         irb.context.with_debugger = true
         irb.context.irb_name += ":rdbg"
+        irb.context.io.load_history if irb.context.io.class < HistorySavingAbility
       end
 
       module SkipPathHelperForIRB
diff --git a/test/irb/test_history.rb b/test/irb/test_history.rb
index 15c16ed89..021bb682c 100644
--- a/test/irb/test_history.rb
+++ b/test/irb/test_history.rb
@@ -488,6 +488,36 @@ def foo
       HISTORY
     end
 
+    def test_direct_debug_session_loads_history
+      @envs['RUBY_DEBUG_IRB_CONSOLE'] = "1"
+      write_history <<~HISTORY
+        old_history_1
+        old_history_2
+        old_history_3
+      HISTORY
+
+      write_ruby <<~'RUBY'
+        require 'debug'
+        debugger
+        binding.irb # needed to satisfy run_ruby_file
+      RUBY
+
+      output = run_ruby_file do
+        type "history"
+        type "puts 'foo'"
+        type "history"
+        type "exit!"
+      end
+
+      assert_include(output, "irb:rdbg(main):002") # assert that we're in an irb:rdbg session
+      assert_include(output, "5: history")
+      assert_include(output, "4: puts 'foo'")
+      assert_include(output, "3: history")
+      assert_include(output, "2: old_history_3")
+      assert_include(output, "1: old_history_2")
+      assert_include(output, "0: old_history_1")
+    end
+
     private
 
     def write_history(history)