diff --git a/lib/irb/command/pushws.rb b/lib/irb/command/pushws.rb
index 0c2dd9e92..51ac07a1c 100644
--- a/lib/irb/command/pushws.rb
+++ b/lib/irb/command/pushws.rb
@@ -29,7 +29,12 @@ def truncated_inspect(obj)
         obj_inspection = obj.inspect
 
         if obj_inspection.size > threshold
-          obj_inspection = obj_inspection[0, threshold - 1] + "...>"
+          closing = obj_inspection[-1]
+          # Support closing characters for objects like:
+          # #<Object...>, [array...], {hash...}, (123/456...), "string...", /regexp.../
+          # Other objects will be truncated without a closing character.
+          closing = nil unless '>]})"/'.include?(closing)
+          obj_inspection = "#{obj_inspection[0, threshold - 1]}...#{closing}"
         end
 
         obj_inspection
diff --git a/test/irb/test_command.rb b/test/irb/test_command.rb
index fd98a5a1b..9091bbc81 100644
--- a/test/irb/test_command.rb
+++ b/test/irb/test_command.rb
@@ -535,6 +535,29 @@ def test_workspaces_returns_the_stack_of_workspaces
       assert_empty err
       assert_match(/\[#<TestIRB::Workspac...>, #<TestIRB::Workspac...>\]\n/, out)
     end
+
+    def test_workspaces_various_truncation
+      out, err = execute_lines(
+        'pushws { key: 123456789123456789 }',
+        'pushws "a" * 30',
+        'pushws [1] * 30',
+        'pushws /aaaaaaaaaaaaaaaaaaaaaaaaa/',
+        'pushws 1r/123456789123456789123456789',
+        'pushws 123456789123456789123456789',
+        'pushws Struct.new(:inspect).new("a" * 30)'
+      )
+      expected_truncations = [
+        '#<TestIRB::Workspac...>',
+        { key: 123456789123456789 }.inspect[0, 19] + '...}',
+        '"aaaaaaaaaaaaaaaaaa..."',
+        '[1, 1, 1, 1, 1, 1, ...]',
+        '/aaaaaaaaaaaaaaaaaa.../',
+        '(1/1234567891234567...)',
+        '1234567891234567891...',
+        'aaaaaaaaaaaaaaaaaaa...'
+      ]
+      assert_include(out, "[#{expected_truncations.join(", ")}]")
+    end
   end
 
   class PopwsTest < WorkspaceCommandTestCase