diff --git a/AUTHORS.md b/AUTHORS.md
index 7ea639059..ade78d714 100644
--- a/AUTHORS.md
+++ b/AUTHORS.md
@@ -23,6 +23,7 @@
 -   Avinash Maddikonda ([@SFM61319](https://github.com/SFM61319))
 -   Benoît Hudson ([@benoithudson](https://github.com/benoithudson))
 -   Bradley Friedman ([@leith-bartrich](https://github.com/leith-bartrich))
+-   Brandon Carpenter ([@brandon-avantus](https://github.com/brandon-avantus))
 -   Callum Noble ([@callumnoble](https://github.com/callumnoble))
 -   Christabella Irwanto([@christabella](https://github.com/christabella))
 -   Christian Heimes ([@tiran](https://github.com/tiran))
diff --git a/CHANGELOG.md b/CHANGELOG.md
index df68fbb39..3cbe9e230 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -16,6 +16,7 @@ This document follows the conventions laid out in [Keep a CHANGELOG][].
 
 -  Fixed crash when trying to `del clrObj[...]` for non-arrays
 - ci: properly exclude job (#2542)
+-  Fixed conversion of elements when iterating non-generic containers (#2679)
 
 ## [3.0.5](https://github.com/pythonnet/pythonnet/releases/tag/v3.0.5) - 2024-12-13
 
diff --git a/src/runtime/Types/Iterator.cs b/src/runtime/Types/Iterator.cs
index 49145d2c3..2170f0684 100644
--- a/src/runtime/Types/Iterator.cs
+++ b/src/runtime/Types/Iterator.cs
@@ -43,7 +43,12 @@ public static NewReference tp_iternext(BorrowedReference ob)
                 return default;
             }
             object item = self.iter.Current;
-            return Converter.ToPython(item, self.elemType);
+            // Non-generic enumerator elements are typed as System.Object,
+            // in which case the actual object type should be converted.
+            Type elemType = item is null || self.elemType != typeof(object)
+                ? self.elemType
+                : item.GetType();
+            return Converter.ToPython(item, elemType);
         }
 
         public static NewReference tp_iter(BorrowedReference ob) => new (ob);
diff --git a/tests/test_conversion.py b/tests/test_conversion.py
index dd70f900a..3b48d9dbe 100644
--- a/tests/test_conversion.py
+++ b/tests/test_conversion.py
@@ -5,7 +5,7 @@
 
 import System
 from Python.Test import ConversionTest, MethodResolutionInt, UnicodeString, CodecResetter
-from Python.Runtime import PyObjectConversions
+from Python.Runtime import IPyObjectEncoder, PyObjectConversions
 from Python.Runtime.Codecs import RawProxyEncoder
 
 
@@ -755,3 +755,35 @@ def test_explicit_conversion():
         assert int(t(123.4)) == 123
         with pytest.raises(TypeError):
             index(t(123.4))
+
+@pytest.mark.parametrize('container_type', ['generic', 'non-generic'])
+def test_iterator_element_conversion(container_type):
+    """Test iterator element conversion from Python."""
+    from Python.Test import Spam
+
+    try:
+        from Python.Test import IteratorElementEncoder
+    except ImportError:
+        class IteratorElementEncoder(IPyObjectEncoder):
+            __namespace__ = "Python.Test"
+            def CanEncode(self, clr_type):
+                return clr_type.Name == "Spam" and clr_type.Namespace == "Python.Test"
+            def TryEncode(self, clr_object):
+                return clr_object.GetValue()
+
+    spam_encoder = IteratorElementEncoder()
+    PyObjectConversions.RegisterEncoder(spam_encoder)
+
+    values = ["first", "second", "third"]
+    if container_type == 'generic':
+        container = System.Collections.Generic.List[Spam]()
+        for value in values:
+            container.Add(Spam(value))
+    else:
+        container = System.Array[Spam](Spam(v) for v in values)
+
+    assert type(container[0]) is str
+    assert next(iter(container.GetEnumerator())) == container[0]
+    assert list(container.GetEnumerator()) == values
+
+    CodecResetter.Reset()