diff --git a/h11/_headers.py b/h11/_headers.py
index 31da3e2..0d4cd23 100644
--- a/h11/_headers.py
+++ b/h11/_headers.py
@@ -108,6 +108,9 @@ def __bool__(self) -> bool:
         return bool(self._full_items)
 
     def __eq__(self, other: object) -> bool:
+        other_type = type(other)
+        if not (hasattr(other_type, "__iter__") or hasattr(other_type, "__getitem__")):
+            return NotImplemented
         return list(self) == list(other)  # type: ignore
 
     def __len__(self) -> int:
diff --git a/h11/tests/test_headers.py b/h11/tests/test_headers.py
index b57274c..d3d1956 100644
--- a/h11/tests/test_headers.py
+++ b/h11/tests/test_headers.py
@@ -1,3 +1,6 @@
+from typing import Iterator, Tuple
+from unittest.mock import ANY
+
 import pytest
 
 from .._events import Request
@@ -94,6 +97,71 @@ def test_normalize_and_validate() -> None:
     assert excinfo.value.error_status_hint == 501  # Not Implemented
 
 
+@pytest.mark.parametrize("other", [None, 42, object()])
+def test_headers_compare_unequal_to_non_iterables(other: object) -> None:
+    headers = Request(
+        method="GET", target="/", headers=[("Host", "example.com")]
+    ).headers
+
+    assert not (headers == other)
+    assert not (other == headers)
+    assert headers != other
+    assert other != headers
+
+
+def test_headers_allow_reflected_equality() -> None:
+    headers = Request(
+        method="GET", target="/", headers=[("Host", "example.com")]
+    ).headers
+
+    assert headers == ANY
+    assert ANY == headers
+    assert not (headers != ANY)
+    assert not (ANY != headers)
+
+
+def test_headers_compare_with_iterables() -> None:
+    headers = normalize_and_validate([("Host", "example.com")])
+
+    assert headers == [(b"host", b"example.com")]
+    assert headers == ((b"host", b"example.com"),)
+    assert headers == iter([(b"host", b"example.com")])
+    assert headers == normalize_and_validate([("HOST", "example.com")])
+    assert headers != [(b"host", b"different.com")]
+
+
+def test_headers_compare_with_sequence_protocol() -> None:
+    class HeaderSequence:
+        def __getitem__(self, index: int) -> Tuple[bytes, bytes]:
+            return [(b"host", b"example.com")][index]
+
+    headers = normalize_and_validate([("Host", "example.com")])
+
+    assert headers == HeaderSequence()
+
+
+def test_headers_equality_propagates_iterator_setup_errors() -> None:
+    class BrokenIterable:
+        def __iter__(self) -> Iterator[Tuple[bytes, bytes]]:
+            raise TypeError("iterator setup failed")
+
+    headers = normalize_and_validate([("Host", "example.com")])
+
+    with pytest.raises(TypeError, match="iterator setup failed"):
+        headers == BrokenIterable()
+
+
+def test_headers_equality_propagates_iteration_errors() -> None:
+    def broken_iterator() -> Iterator[Tuple[bytes, bytes]]:
+        yield (b"host", b"example.com")
+        raise TypeError("broken iterator")
+
+    headers = normalize_and_validate([("Host", "example.com")])
+
+    with pytest.raises(TypeError, match="broken iterator"):
+        headers == broken_iterator()
+
+
 def test_get_set_comma_header() -> None:
     headers = normalize_and_validate(
         [
diff --git a/newsfragments/214.bugfix.rst b/newsfragments/214.bugfix.rst
new file mode 100644
index 0000000..280545d
--- /dev/null
+++ b/newsfragments/214.bugfix.rst
@@ -0,0 +1 @@
+Comparing event headers with non-iterable objects now follows Python's equality fallback instead of raising ``TypeError``, allowing sentinel comparisons and reflected equality such as ``unittest.mock.ANY``.