diff --git a/changelog/5404.bugfix.rst b/changelog/5404.bugfix.rst
new file mode 100644
index 00000000000..2187bed8b32
--- /dev/null
+++ b/changelog/5404.bugfix.rst
@@ -0,0 +1,2 @@
+Emit a warning when attempting to unwrap a broken object raises an exception,
+for easier debugging (`#5080 <https://github.com/pytest-dev/pytest/issues/5080>`__).
diff --git a/src/_pytest/doctest.py b/src/_pytest/doctest.py
index afb7ede4cc7..f40b59635e9 100644
--- a/src/_pytest/doctest.py
+++ b/src/_pytest/doctest.py
@@ -3,6 +3,7 @@
 import platform
 import sys
 import traceback
+import warnings
 from contextlib import contextmanager
 
 import pytest
@@ -12,6 +13,7 @@
 from _pytest.compat import safe_getattr
 from _pytest.fixtures import FixtureRequest
 from _pytest.outcomes import Skipped
+from _pytest.warning_types import PytestWarning
 
 DOCTEST_REPORT_CHOICE_NONE = "none"
 DOCTEST_REPORT_CHOICE_CDIFF = "cdiff"
@@ -368,10 +370,21 @@ def _patch_unwrap_mock_aware():
     else:
 
         def _mock_aware_unwrap(obj, stop=None):
-            if stop is None:
-                return real_unwrap(obj, stop=_is_mocked)
-            else:
-                return real_unwrap(obj, stop=lambda obj: _is_mocked(obj) or stop(obj))
+            try:
+                if stop is None or stop is _is_mocked:
+                    return real_unwrap(obj, stop=_is_mocked)
+                else:
+                    return real_unwrap(
+                        obj, stop=lambda obj: _is_mocked(obj) or stop(obj)
+                    )
+            except Exception as e:
+                warnings.warn(
+                    "Got %r when unwrapping %r.  This is usually caused "
+                    "by a violation of Python's object protocol; see e.g. "
+                    "https://github.com/pytest-dev/pytest/issues/5080" % (e, obj),
+                    PytestWarning,
+                )
+                raise
 
         inspect.unwrap = _mock_aware_unwrap
         try:
diff --git a/testing/test_doctest.py b/testing/test_doctest.py
index bf0405546bf..2c66bf6fe6a 100644
--- a/testing/test_doctest.py
+++ b/testing/test_doctest.py
@@ -1,7 +1,9 @@
+import inspect
 import textwrap
 
 import pytest
 from _pytest.compat import MODULE_NOT_FOUND_ERROR
+from _pytest.doctest import _patch_unwrap_mock_aware
 from _pytest.doctest import DoctestItem
 from _pytest.doctest import DoctestModule
 from _pytest.doctest import DoctestTextfile
@@ -1224,3 +1226,19 @@ class Example(object):
     )
     result = testdir.runpytest("--doctest-modules")
     result.stdout.fnmatch_lines(["* 1 passed *"])
+
+
+class Broken:
+    def __getattr__(self, _):
+        raise KeyError("This should be an AttributeError")
+
+
+@pytest.mark.parametrize(
+    "stop", [None, lambda f: None, lambda f: False, lambda f: True]
+)
+def test_warning_on_unwrap_of_broken_object(stop):
+    bad_instance = Broken()
+    with _patch_unwrap_mock_aware():
+        with pytest.raises(KeyError):
+            with pytest.warns(pytest.PytestWarning):
+                inspect.unwrap(bad_instance, stop=stop)