diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index 61d3c6c..7f092c3 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -30,6 +30,13 @@ vNext
 
 *Unreleased changes*
 
+Features
+~~~~~~~~
+
+* Support customizing the requests.Session for requests-based backends,
+  and document how this can be used to mount an adapter that simplifies
+  automatic retry logic. (Thanks to `@dgilmanAIDENTIFIED`_.)
+
 Fixes
 ~~~~~
 
@@ -1340,6 +1347,7 @@ Features
 .. _@costela: https://github.com/costela
 .. _@coupa-anya: https://github.com/coupa-anya
 .. _@decibyte: https://github.com/decibyte
+.. _@dgilmanAIDENTIFIED: https://github.com/dgilmanAIDENTIFIED
 .. _@dominik-lekse: https://github.com/dominik-lekse
 .. _@erikdrums: https://github.com/erikdrums
 .. _@ewingrj: https://github.com/ewingrj
diff --git a/anymail/backends/base_requests.py b/anymail/backends/base_requests.py
index 64848b6..c0b9ff9 100644
--- a/anymail/backends/base_requests.py
+++ b/anymail/backends/base_requests.py
@@ -25,17 +25,12 @@ class AnymailRequestsBackend(AnymailBaseBackend):
             return False  # already exists
 
         try:
-            self.session = requests.Session()
-        except requests.RequestException:
+            self.session = self.create_session()
+        except Exception:
             if not self.fail_silently:
                 raise
-        else:
-            self.session.headers["User-Agent"] = "django-anymail/{version}-{esp} {orig}".format(
-                esp=self.esp_name.lower(), version=__version__,
-                orig=self.session.headers.get("User-Agent", ""))
-            if self.debug_api_requests:
-                self.session.hooks['response'].append(self._dump_api_request)
-            return True
+
+        return True
 
     def close(self):
         if self.session is None:
@@ -57,6 +52,23 @@ class AnymailRequestsBackend(AnymailBaseBackend):
                 "or you are incorrectly calling _send directly.)".format(class_name=class_name))
         return super()._send(message)
 
+    def create_session(self):
+        """Create the requests.Session object used by this instance of the backend.
+        If subclassed, you can modify the Session returned from super() to give
+        it your own configuration.
+
+        This must return an instance of requests.Session."""
+        session = requests.Session()
+
+        session.headers["User-Agent"] = "django-anymail/{version}-{esp} {orig}".format(
+            esp=self.esp_name.lower(), version=__version__,
+            orig=session.headers.get("User-Agent", ""))
+
+        if self.debug_api_requests:
+            session.hooks['response'].append(self._dump_api_request)
+
+        return session
+
     def post_to_esp(self, payload, message):
         """Post payload to ESP send API endpoint, and return the raw response.
 
diff --git a/docs/conf.py b/docs/conf.py
index 9d1738e..ac36fa5 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -276,6 +276,7 @@ intersphinx_mapping = {
     'python': ('https://docs.python.org/3.10', None),
     'django': ('https://docs.djangoproject.com/en/stable/', 'https://docs.djangoproject.com/en/stable/_objects/'),
     'requests': ('https://requests.readthedocs.io/en/stable/', None),
+    'urllib3': ('https://urllib3.readthedocs.io/en/stable/', None),
 }
 
 
diff --git a/docs/tips/transient_errors.rst b/docs/tips/transient_errors.rst
index ad2f15a..e5bae86 100644
--- a/docs/tips/transient_errors.rst
+++ b/docs/tips/transient_errors.rst
@@ -23,3 +23,46 @@ transient ESP errors depends on your Django project:
 In addition to handling connectivity issues, either of these approaches also has the advantage
 of moving email sending to a background thread. This is a best practice for sending email from
 Django, as it allows your web views to respond faster.
+
+Automatic retries
+-----------------
+
+Backends that use :pypi:`requests` for network calls can configure its built-in retry
+functionality. Subclass the Anymail backend and mount instances of
+:class:`~requests.adapters.HTTPAdapter` and :class:`~urllib3.util.Retry` configured with
+your settings on the :class:`~requests.Session` object in `create_session()`.
+
+Automatic retries aren't a substitute for sending emails in a background thread, they're
+a way to simplify your retry logic within the worker. Be aware that retrying `read` and `other`
+failures may result in sending duplicate emails. Requests will only attempt to retry idempotent
+HTTP verbs by default, you may need to whitelist the verbs used by your backend's API in
+`allowed_methods` to actually get any retries. It can also automatically retry error HTTP
+status codes for you but you may need to configure `status_forcelist` with the error HTTP status
+codes used by your backend provider.
+
+   .. code-block:: python
+
+      import anymail.backends.mandrill
+      from django.conf import settings
+      import requests.adapters
+
+
+      class RetryableMandrillEmailBackend(anymail.backends.mandrill.EmailBackend):
+          def __init__(self, *args, **kwargs):
+              super().__init__(*args, **kwargs)
+              retry = requests.adapters.Retry(
+                  total=settings.EMAIL_TOTAL_RETRIES,
+                  connect=settings.EMAIL_CONNECT_RETRIES,
+                  read=settings.EMAIL_READ_RETRIES,
+                  status=settings.EMAIL_HTTP_STATUS_RETRIES,
+                  other=settings.EMAIL_OTHER_RETRIES,
+                  allowed_methods=False,  # Retry all HTTP verbs
+                  status_forcelist=settings.EMAIL_HTTP_STATUS_RETRYABLE,
+                  backoff_factor=settings.EMAIL_RETRY_BACKOFF_FACTOR,
+              )
+              self.retryable_adapter = requests.adapters.HTTPAdapter(max_retries=retry)
+
+          def create_session(self):
+              session = super().create_session()
+              session.mount("https://", self.retryable_adapter)
+              return session