diff --git a/lib/irb/ext/eval_history.rb b/lib/irb/ext/eval_history.rb
index 6c21ff00e..dd1173382 100644
--- a/lib/irb/ext/eval_history.rb
+++ b/lib/irb/ext/eval_history.rb
@@ -97,8 +97,8 @@ def initialize(size = 16)  # :nodoc:
     end
 
     def size(size) # :nodoc:
-      if size != 0 && size < @size
-        @contents = @contents[@size - size .. @size]
+      if size.positive? && @contents.size > size
+        @contents = @contents.last(size)
       end
       @size = size
     end
diff --git a/test/irb/test_eval_history.rb b/test/irb/test_eval_history.rb
index 685ad679a..b1d480636 100644
--- a/test/irb/test_eval_history.rb
+++ b/test/irb/test_eval_history.rb
@@ -49,5 +49,16 @@ def test_eval_history_respects_given_limit
       # Because eval_history injects `__` into the history AND decide to ignore it, we only get <limit> - 1 results
       assert_match("2 \"bar\"\n" + "3 \"baz\"\n" + "4 \"xyz\"\n", out)
     end
+
+    def test_eval_history_can_shrink_before_reaching_configured_limit
+      out, err = execute_lines(
+        "IRB.CurrentContext.eval_history = 2",
+        "__",
+        conf: { EVAL_HISTORY: 5 }
+      )
+
+      assert_empty(err)
+      assert_match("=> 2\n" + "=> 1 2\n", out)
+    end
   end
 end