diff --git a/CHANGELOG.md b/CHANGELOG.md
index f1ac49d51..abe58ce6e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ This document follows the conventions laid out in [Keep a CHANGELOG][].
 ### Added
 
 -   Extension methods declared in non-framework assemblies are bound to the type they extend, so they can be called from the instance like in C# (e.g. `order_status.is_open()`). Those marked `[EditorBrowsable(EditorBrowsableState.Never)]`, or declared in a class marked so, keep their static form only
+-   `repr()` of a .NET object whose type overrides `ToString()` returns that text (the Python-facing member name for enums), so containers of such objects print readably (e.g. `[SPY, AIG]`), unless the type declares a public `__repr__()`
 -   Types with an implicit conversion to a numeric type support Python arithmetic, comparisons, `float()` and `int()` through that conversion, behaving like a Python `int` for integral conversions and a `float` otherwise, unless they declare or inherit the operator
 -   Ability to instantiate new .NET arrays using `Array[T](dim1, dim2, ...)` syntax
 -   Python operator method will call C# operator method for supported binary and unary operators ([#1324][p1324]).
diff --git a/src/runtime/Types/ClassBase.cs b/src/runtime/Types/ClassBase.cs
index cdb00c548..3d08f8ca6 100644
--- a/src/runtime/Types/ClassBase.cs
+++ b/src/runtime/Types/ClassBase.cs
@@ -375,6 +375,45 @@ public static NewReference tp_repr(BorrowedReference ob)
                     return reprString is null ? new NewReference(Runtime.PyNone) : Runtime.PyString_FromString(reprString);
                 }
 
+                // show an overridden ToString() so containers of .NET objects print readably: [SPY, AIG].
+                // ValueType.ToString() only returns the type name, so structs without their own keep the default
+                var toStringOwner = instType;
+                if (co.inst is IPythonDerivedType)
+                {
+                    // the generated type of a Python subclass overrides every virtual method, so like
+                    // PythonDerivedType.InvokeMethod only count a ToString the Python class defines
+                    using var pyToString = Runtime.PyObject_GetAttrString(ob, "ToString");
+                    if (pyToString.IsNull())
+                    {
+                        Exceptions.Clear();
+                    }
+                    if (pyToString.IsNull() || GetManagedObject(pyToString.Borrow()) is not null)
+                    {
+                        while (typeof(IPythonDerivedType).IsAssignableFrom(toStringOwner))
+                        {
+                            toStringOwner = toStringOwner.BaseType;
+                        }
+                    }
+                }
+                var toStringType = toStringOwner.GetMethod("ToString", Type.EmptyTypes)?.DeclaringType;
+                if (toStringType != typeof(object) && toStringType != typeof(ValueType))
+                {
+                    string? text = null;
+                    try
+                    {
+                        // enums match their str(), the Python-facing member name
+                        text = co.inst is Enum enumValue ? EnumObject.ToPythonString(enumValue) : co.inst.ToString();
+                    }
+                    catch (Exception)
+                    {
+                        // repr() used to succeed for types whose ToString() throws, keep it that way
+                    }
+                    if (text is not null)
+                    {
+                        return Runtime.PyString_FromString(text);
+                    }
+                }
+
                 //otherwise use the standard object.__repr__(inst)
                 using var args = Runtime.PyTuple_New(1);
                 Runtime.PyTuple_SetItem(args.Borrow(), 0, ob);
diff --git a/src/testing/ReprTest.cs b/src/testing/ReprTest.cs
index 48e93683a..53f386989 100644
--- a/src/testing/ReprTest.cs
+++ b/src/testing/ReprTest.cs
@@ -68,6 +68,22 @@ public class Baz : BazMiddle
 
         }
 
+        public class NullToString
+        {
+            public override string ToString()
+            {
+                return null;
+            }
+        }
+
+        public class ThrowingToString
+        {
+            public override string ToString()
+            {
+                throw new InvalidOperationException("ToString() failed");
+            }
+        }
+
         public class Quux
         {
             public string ToString(string format)
diff --git a/tests/test_class.py b/tests/test_class.py
index c5d34ca51..b90dcc51a 100644
--- a/tests/test_class.py
+++ b/tests/test_class.py
@@ -45,8 +45,8 @@ def test_class_default_str():
 
 def test_class_default_repr():
     """Test the default __repr__ implementation for managed objects."""
-    s = System.String("this is a test")
-    assert repr(s).startswith("<System.String object")
+    o = System.Object()
+    assert repr(o).startswith("<System.Object object")
 
 
 def test_non_public_class():
diff --git a/tests/test_repr.py b/tests/test_repr.py
index 5131f5d88..1fce44228 100644
--- a/tests/test_repr.py
+++ b/tests/test_repr.py
@@ -17,27 +17,79 @@ def test_system_string():
     """Test system string"""
     ob = System.String("hello")
     assert str(ob) == "hello"
-    assert "<System.String object at " in ob.__repr__()
+    assert ob.__repr__() == "hello"
 
 def test_str_only():
     """Test class implementing ToString() but not __repr__()"""
     ob = ReprTest.Bar()
     assert str(ob) == "I implement ToString() but not __repr__()!"
-    assert "<Python.Test.Bar object at " in ob.__repr__()
+    assert ob.__repr__() == "I implement ToString() but not __repr__()!"
+
+def test_str_only_nested_in_list():
+    """Test containers show the ToString() of elements implementing ToString() but not __repr__()"""
+    obs = [ReprTest.Bar(), ReprTest.Bar()]
+    assert str(obs) == "[I implement ToString() but not __repr__()!, I implement ToString() but not __repr__()!]"
+
+def test_enum():
+    """Test enums show the same Python-facing member name as str()"""
+    from System import DayOfWeek
+    from System.IO import FileAccess
+    assert repr(DayOfWeek.Monday) == str(DayOfWeek.Monday) == "MONDAY"
+    assert str([DayOfWeek.Monday, FileAccess.ReadWrite]) == "[MONDAY, READ_WRITE]"
+
+def test_struct_without_tostring_override():
+    """Test struct not overriding ToString() keeps the default repr instead of ValueType's type name"""
+    from System.Collections.Generic import List
+    ob = List[int]().GetEnumerator()
+    assert repr(ob).startswith("<System.Collections.Generic.List")
+    assert " object at " in repr(ob)
+
+def test_namespace_subclass():
+    """Test Python subclasses with a __namespace__ only show a ToString() that is actually overridden"""
+    class ReprPlainNs(System.Object):
+        __namespace__ = "ReprTestNs"
+
+    class ReprBarNs(ReprTest.Bar):
+        __namespace__ = "ReprTestNs"
+
+    class ReprOverrideNs(System.Object):
+        __namespace__ = "ReprTestNs"
+
+        def ToString(self):
+            return "I implement ToString() in Python!"
+
+    assert " object at " in repr(ReprPlainNs())
+    assert repr(ReprBarNs()) == "I implement ToString() but not __repr__()!"
+    assert repr(ReprOverrideNs()) == "I implement ToString() in Python!"
+
+def test_no_tostring_override():
+    """Test object not overriding ToString() keeps the default repr"""
+    ob = System.Object()
+    assert repr(ob).startswith("<System.Object object at ")
+
+def test_tostring_returns_null():
+    """Test class whose ToString() returns null"""
+    ob = ReprTest.NullToString()
+    assert "<Python.Test.NullToString object at " in repr(ob)
+
+def test_tostring_throws():
+    """Test class whose ToString() throws"""
+    ob = ReprTest.ThrowingToString()
+    assert "<Python.Test.ThrowingToString object at " in repr(ob)
 
 def test_hierarchy1():
     """Test inheritance hierarchy with base & middle class implementing ToString"""
     ob1 = ReprTest.BazBase()
     assert str(ob1) == "Base class implementing ToString()!"
-    assert "<Python.Test.BazBase object at " in ob1.__repr__()
+    assert ob1.__repr__() == "Base class implementing ToString()!"
 
     ob2 = ReprTest.BazMiddle()
     assert str(ob2) == "Middle class implementing ToString()!"
-    assert "<Python.Test.BazMiddle object at " in ob2.__repr__()
+    assert ob2.__repr__() == "Middle class implementing ToString()!"
 
     ob3 = ReprTest.Baz()
     assert str(ob3) == "Middle class implementing ToString()!"
-    assert "<Python.Test.Baz object at " in ob3.__repr__()
+    assert ob3.__repr__() == "Middle class implementing ToString()!"
 
 def bad_tostring():
     """Test ToString that can't be used by str()"""