diff --git a/AUTHORS b/AUTHORS
index 136ffd6c5ee..c20b4898fce 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -54,6 +54,7 @@ Anton Zhilin
 Antony Lee
 Arel Cordero
 Arias Emmanuel
+Ariel Even
 Ariel Pillemer
 Armin Rigo
 Aron Coyle
diff --git a/changelog/15310.bugfix.rst b/changelog/15310.bugfix.rst
new file mode 100644
index 00000000000..1ef38763231
--- /dev/null
+++ b/changelog/15310.bugfix.rst
@@ -0,0 +1 @@
+Fixed the assertion diff for mappings whose ``keys()`` returns a list, such as ``starlette.datastructures.Headers``, which failed with a ``TypeError`` since :pr:`14463`.
diff --git a/src/_pytest/assertion/_compare_mapping.py b/src/_pytest/assertion/_compare_mapping.py
index 9b7f392d9a9..31e1b71302e 100644
--- a/src/_pytest/assertion/_compare_mapping.py
+++ b/src/_pytest/assertion/_compare_mapping.py
@@ -2,7 +2,9 @@
 
 from collections.abc import Collection
 from collections.abc import Iterator
+from collections.abc import KeysView
 from collections.abc import Mapping
+from collections.abc import Set as AbstractSet
 import heapq
 import pprint
 
@@ -13,6 +15,17 @@
 from _pytest.assertion._typing import TruncationBudget
 
 
+def _keys_view(mapping: Mapping[object, object]) -> AbstractSet[object]:
+    """Return a set-like view of ``mapping``'s keys.
+
+    Some mappings override ``keys()`` to return a plain list (for example
+    ``starlette.datastructures.Headers``); wrap those in a ``KeysView``, which
+    still resolves membership through the mapping.
+    """
+    keys = mapping.keys()
+    return keys if isinstance(keys, AbstractSet) else KeysView(mapping)
+
+
 def _compare_eq_mapping(
     left: Mapping[object, object],
     right: Mapping[object, object],
@@ -24,8 +37,8 @@ def _compare_eq_mapping(
     # operations resolve membership through the mappings themselves, so a
     # mapping with its own key equivalence (case-insensitive keys, for
     # example) is compared the way it compares itself.
-    keys_left = left.keys()
-    keys_right = right.keys()
+    keys_left = _keys_view(left)
+    keys_right = _keys_view(right)
     common = keys_left & keys_right
     same = {k: left[k] for k in common if left[k] == right[k]}
     if same and verbose < 2:
diff --git a/testing/test_assertion.py b/testing/test_assertion.py
index 035aad31c54..4635d5cf28d 100644
--- a/testing/test_assertion.py
+++ b/testing/test_assertion.py
@@ -1116,6 +1116,44 @@ def __len__(self) -> int:  # pragma: no cover
             "Use -v to get more diff",
         ]
 
+    def test_mapping_with_list_keys(self) -> None:
+        """A mapping whose ``keys()`` returns a list still gets the mapping diff.
+
+        ``starlette.datastructures.Headers`` is such a mapping: it overrides
+        ``keys()`` to return a list, which has no set operations.
+        """
+
+        class ListKeysMapping(Mapping[str, int]):
+            def __init__(self, values: dict[str, int]) -> None:
+                self._values = values
+
+            def __getitem__(self, key: str) -> int:
+                return self._values[key]
+
+            def __iter__(self) -> Iterator[str]:
+                return iter(self._values)
+
+            def __len__(self) -> int:  # pragma: no cover
+                return len(self._values)
+
+            def keys(self) -> list[str]:  # type: ignore[override]
+                return list(self._values)
+
+        lines = callequal(
+            ListKeysMapping({"a": 0, "b": 1}),
+            ListKeysMapping({"a": 1, "b": 1, "c": 2}),
+        )
+
+        assert lines is not None
+        assert lines[2:] == [
+            "Omitting 1 identical items, use -vv to show",
+            "Differing items:",
+            "{'a': 0} != {'a': 1}",
+            "Right contains 1 more item:",
+            "{'c': 2}",
+            "Use -v to get more diff",
+        ]
+
     def test_sequence_different_items(self) -> None:
         lines = callequal((1, 2), (3, 4, 5), verbose=2)
         assert lines == [