diff --git a/django/utils/autoreload.py b/django/utils/autoreload.py
index 99812979d73c..13019f7214b7 100644
--- a/django/utils/autoreload.py
+++ b/django/utils/autoreload.py
@@ -33,6 +33,8 @@
 # file paths to allow watching them in the future.
 _error_files = []
 _exception = None
+# Exception raised while loading the URLConf.
+_url_module_exception = None
 
 try:
     import termios
@@ -62,7 +64,7 @@ def wrapper(*args, **kwargs):
         global _exception
         try:
             fn(*args, **kwargs)
-        except Exception:
+        except Exception as e:
             _exception = sys.exc_info()
 
             et, ev, tb = _exception
@@ -75,8 +77,10 @@ def wrapper(*args, **kwargs):
 
             if filename not in _error_files:
                 _error_files.append(filename)
+            if _url_module_exception is not None:
+                raise e from _url_module_exception
 
-            raise
+            raise e
 
     return wrapper
 
@@ -339,6 +343,7 @@ def wait_for_apps_ready(self, app_reg, django_main_thread):
             return False
 
     def run(self, django_main_thread):
+        global _url_module_exception
         logger.debug("Waiting for apps ready_event.")
         self.wait_for_apps_ready(apps, django_main_thread)
         from django.urls import get_resolver
@@ -347,10 +352,10 @@ def run(self, django_main_thread):
         # reloader starts by accessing the urlconf_module property.
         try:
             get_resolver().urlconf_module
-        except Exception:
+        except Exception as e:
             # Loading the urlconf can result in errors during development.
-            # If this occurs then swallow the error and continue.
-            pass
+            # If this occurs then store the error and continue.
+            _url_module_exception = e
         logger.debug("Apps ready_event triggered. Sending autoreload_started signal.")
         autoreload_started.send(sender=self)
         self.run_loop()
diff --git a/docs/topics/db/sql.txt b/docs/topics/db/sql.txt
index bd34df8bb73a..da26f433472b 100644
--- a/docs/topics/db/sql.txt
+++ b/docs/topics/db/sql.txt
@@ -4,9 +4,11 @@ Performing raw SQL queries
 
 .. currentmodule:: django.db.models
 
-Django gives you two ways of performing raw SQL queries: you can use
-:meth:`Manager.raw` to `perform raw queries and return model instances`__, or
-you can avoid the model layer entirely and `execute custom SQL directly`__.
+Django gives you three ways of performing raw SQL queries: you can embed raw
+SQL fragments into ORM queries using
+:class:`~django.db.models.expressions.RawSQL` (see :ref:`raw-sql-fragments`),
+use :meth:`Manager.raw` to `perform raw queries and return model instances`__,
+or avoid the model layer entirely and `execute custom SQL directly`__.
 
 __ `performing raw queries`_
 __ `executing custom SQL directly`_
@@ -34,6 +36,19 @@ __ `executing custom SQL directly`_
     Please read more about :ref:`SQL injection protection
     <sql-injection-protection>`.
 
+.. _raw-sql-fragments:
+
+Raw SQL fragments
+=================
+
+In some cases, you may need to embed raw SQL fragments directly into ORM
+queries — for example, in :meth:`~django.db.models.query.QuerySet.annotate` or
+:meth:`~django.db.models.query.QuerySet.filter` calls. Use :ref:`Func()
+expressions <func-expressions>` for calling database functions across
+backends, or
+:class:`~django.db.models.expressions.RawSQL` for arbitrary parameterized SQL
+fragments.
+
 .. _executing-raw-queries:
 
 Performing raw queries
@@ -195,28 +210,6 @@ must always be included in a raw query. A
 :class:`~django.core.exceptions.FieldDoesNotExist` exception will be raised if
 you forget to include the primary key.
 
-Adding annotations
-------------------
-
-You can also execute queries containing fields that aren't defined on the
-model. For example, we could use `PostgreSQL's age() function`__ to get a list
-of people with their ages calculated by the database:
-
-.. code-block:: pycon
-
-    >>> people = Person.objects.raw("SELECT *, age(birth_date) AS age FROM myapp_person")
-    >>> for p in people:
-    ...     print("%s is %s." % (p.first_name, p.age))
-    ...
-    John is 37.
-    Jane is 42.
-    ...
-
-You can often avoid using raw SQL to compute annotations by instead using a
-:ref:`Func() expression <func-expressions>`.
-
-__ https://www.postgresql.org/docs/current/functions-datetime.html
-
 Passing parameters into ``raw()``
 ---------------------------------
 
diff --git a/tests/utils_tests/test_autoreload.py b/tests/utils_tests/test_autoreload.py
index c9e6443c6fbf..2033728da809 100644
--- a/tests/utils_tests/test_autoreload.py
+++ b/tests/utils_tests/test_autoreload.py
@@ -434,6 +434,18 @@ def test_mutates_error_files(self):
                 autoreload._exception = None
         self.assertEqual(mocked_error_files.append.call_count, 1)
 
+    def test_urlconf_exception_is_used_as_cause(self):
+        urlconf_exc = ValueError("Error")
+        fake_method = mock.MagicMock(side_effect=RuntimeError())
+        wrapped = autoreload.check_errors(fake_method)
+        with mock.patch.object(autoreload, "_url_module_exception", urlconf_exc):
+            try:
+                with self.assertRaises(RuntimeError) as cm:
+                    wrapped()
+            finally:
+                autoreload._exception = None
+        self.assertIs(cm.exception.__cause__, urlconf_exc)
+
 
 class TestRaiseLastException(SimpleTestCase):
     @mock.patch("django.utils.autoreload._exception", None)