diff --git a/mypy/stubtest.py b/mypy/stubtest.py
index 7915e14f1551..f0fb16900bde 100644
--- a/mypy/stubtest.py
+++ b/mypy/stubtest.py
@@ -202,6 +202,13 @@ def verify_mypyfile(
     if isinstance(runtime, Missing):
         yield Error(object_path, "is not present at runtime", stub, runtime)
         return
+
+    # Workaround for pyOpenSSL that has its module objects wrapped.
+    # See https://github.com/python/typeshed/pull/5657 for details.
+    if f"{type(runtime).__module__}.{type(runtime).__qualname__}" \
+            == "cryptography.utils._ModuleWithDeprecations":
+        runtime = runtime._module # type: ignore[attr-defined]
+
     if not isinstance(runtime, types.ModuleType):
         yield Error(object_path, "is not a module", stub, runtime)
         return
@@ -652,6 +659,12 @@ def verify_funcitem(
         yield Error(object_path, "is not present at runtime", stub, runtime)
         return
 
+    # Workaround for pyOpenSSL that has some of its function objects wrapped.
+    # See https://github.com/python/typeshed/pull/5657 for details.
+    if f"{type(runtime).__module__}.{type(runtime).__qualname__}" \
+            == "cryptography.utils._DeprecatedValue":
+        runtime = runtime.value
+
     if (
         not isinstance(runtime, (types.FunctionType, types.BuiltinFunctionType))
         and not isinstance(runtime, (types.MethodType, types.BuiltinMethodType))