diff --git a/beets/dbcore/sort.py b/beets/dbcore/sort.py
index 65079b22b..d45577ea6 100644
--- a/beets/dbcore/sort.py
+++ b/beets/dbcore/sort.py
@@ -111,9 +111,8 @@ class FieldSort(Sort):
         self.case_insensitive = case_insensitive
 
     def sort(self, objs: list[AnyModel]) -> list[AnyModel]:
-        # TODO: Conversion and null-detection here. In Python 3,
-        # comparisons with None fail. We should also support flexible
-        # attributes with different types without falling over.
+        # TODO: Support flexible attributes with different types (e.g. a mix
+        # of strings and numbers) without falling over.
 
         def key(obj: Model) -> Any:
             field_val = obj.get(self.field, None)
@@ -126,7 +125,13 @@ class FieldSort(Sort):
                     field_val = ""
             if self.case_insensitive and isinstance(field_val, str):
                 field_val = field_val.lower()
-            return field_val
+            # Nullable types (e.g. ``NullInteger``/``NullFloat``) use ``None``
+            # as their null value, so a field may be missing on some objects
+            # and present on others. Comparing ``None`` with a real value
+            # raises a ``TypeError``, so group all missing values together:
+            # this places them first when sorting ascending and last when
+            # descending, matching SQLite's default ordering of NULLs.
+            return (field_val is not None, field_val)
 
         return sorted(objs, key=key, reverse=not self.ascending)
 
diff --git a/docs/changelog.rst b/docs/changelog.rst
index 1ffa1d9e3..b87b369b3 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -55,6 +55,11 @@ Bug fixes
   instrumental track, and store that state in ``lyrics_instrumental`` flexible
   attribute. Existing ``[Instrumental]`` lyrics are migrated automatically.
   :bug:`6719`
+- Sorting by a nullable field (for example a flexible attribute with a declared
+  type whose null value is ``None``) that is present on only some items no
+  longer crashes with a ``TypeError``. Missing values are now grouped together,
+  ordered before present ones when sorting ascending and after them when
+  descending. :bug:`3461`
 
 ..
     For plugin developers
diff --git a/test/dbcore/test_sort.py b/test/dbcore/test_sort.py
index 876ab9019..0edd16397 100644
--- a/test/dbcore/test_sort.py
+++ b/test/dbcore/test_sort.py
@@ -253,6 +253,34 @@ class TestNonExistingField:
         assert ids_asc == [*null_values_ids, lower_item.id, higher_item.id]
         assert ids_desc == [higher_item.id, lower_item.id, *null_values_ids]
 
+    @pytest.mark.parametrize(
+        "field_type,lower,higher",
+        [
+            _p(types.NullInteger(), 2, 10, id="null-integer"),
+            _p(types.NullFloat(), 2.5, 10.5, id="null-float"),
+        ],
+    )
+    def test_nullable_field_present_in_some_items(
+        self, monkeypatch, field_type, lower, higher
+    ):
+        """Ordering by a nullable-typed field (whose null value is ``None``)
+        that is present on only some items should not raise. See #3461.
+        """
+        monkeypatch.setitem(Item._types, "mynull", field_type)
+
+        lower_item, higher_item, *items_without_val = self.lib.items("id+")
+        for item, value in zip((lower_item, higher_item), (lower, higher)):
+            item.mynull = value
+            item.store()
+
+        null_values_ids = [i.id for i in items_without_val]
+
+        ids_asc = [i.id for i in self.lib.items("mynull+ id+")]
+        ids_desc = [i.id for i in self.lib.items("mynull- id+")]
+
+        assert ids_asc == [*null_values_ids, lower_item.id, higher_item.id]
+        assert ids_desc == [higher_item.id, lower_item.id, *null_values_ids]
+
     def test_negation_interaction(self):
         """Test the handling of negation and sorting together.