diff --git a/acme/acme/__init__.py b/acme/acme/__init__.py
index 1e21b5896..51034a301 100644
--- a/acme/acme/__init__.py
+++ b/acme/acme/__init__.py
@@ -6,6 +6,7 @@ This module is an implementation of the `ACME protocol`_.
 
 """
 import sys
+import warnings
 
 # This code exists to keep backwards compatibility with people using acme.jose
 # before it became the standalone josepy package.
@@ -19,3 +20,10 @@ for mod in list(sys.modules):
     # preserved (acme.jose.* is josepy.*)
     if mod == 'josepy' or mod.startswith('josepy.'):
         sys.modules['acme.' + mod.replace('josepy', 'jose', 1)] = sys.modules[mod]
+
+if sys.version_info[:2] == (3, 8):
+    warnings.warn(
+            "Python 3.8 support will be dropped in the next planned release of "
+            "acme. Please upgrade your Python version.",
+            PendingDeprecationWarning,
+    )  # pragma: no cover
diff --git a/certbot/CHANGELOG.md b/certbot/CHANGELOG.md
index dd682d0ba..39251a40e 100644
--- a/certbot/CHANGELOG.md
+++ b/certbot/CHANGELOG.md
@@ -18,6 +18,8 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
 * The `certbot_dns_route53.authenticator` module has been removed. This should
   not affect any users of the plugin and instead would only affect developers
   trying to develop on top of the old code.
+* Support for Python 3.8 was deprecated and will be removed in our next planned
+  release.
 
 ### Fixed
 
diff --git a/certbot/certbot/__init__.py b/certbot/certbot/__init__.py
index cf4ffab00..83099c370 100644
--- a/certbot/certbot/__init__.py
+++ b/certbot/certbot/__init__.py
@@ -1,4 +1,13 @@
 """Certbot client."""
+import sys
+import warnings
 
 # version number like 1.2.3a0, must have at least 2 parts, like 1.2
 __version__ = '2.12.0.dev0'
+
+if sys.version_info[:2] == (3, 8):
+    warnings.warn(
+            "Python 3.8 support will be dropped in the next planned release of "
+            "certbot. Please upgrade your Python version.",
+            PendingDeprecationWarning,
+    )  # pragma: no cover
diff --git a/certbot/certbot/_internal/main.py b/certbot/certbot/_internal/main.py
index 2fa80e364..107443b5f 100644
--- a/certbot/certbot/_internal/main.py
+++ b/certbot/certbot/_internal/main.py
@@ -1866,6 +1866,10 @@ def main(cli_args: Optional[List[str]] = None) -> Optional[Union[str, int]]:
         if config.func != plugins_cmd:  # pylint: disable=comparison-with-callable
             raise
 
+    if sys.version_info[:2] == (3, 8):
+        logger.warning("Python 3.8 support will be dropped in the next planned release "
+                       "of Certbot - please upgrade your Python version.")
+
     with make_displayer(config) as displayer:
         display_obj.set_display(displayer)
 
diff --git a/pytest.ini b/pytest.ini
index 65932b071..55c8435fd 100644
--- a/pytest.ini
+++ b/pytest.ini
@@ -25,6 +25,7 @@
 #    dependencies) until https://github.com/certbot/certbot/issues/9828 is resolved.
 # 6) Similarly to 6), CSR support is deprecated in pyOpenSSL since 24.2, we silence
 #    the warning until https://github.com/certbot/certbot/issues/9992 is resolved.
+# 7) Ignore our own PendingDeprecationWarning about Python 3.8 soon to be dropped.
 filterwarnings =
     error
     ignore:decodestring\(\) is a deprecated alias:DeprecationWarning:dns
@@ -33,3 +34,4 @@ filterwarnings =
     ignore:.*datetime.utcfromtimestamp\(\) is deprecated:DeprecationWarning:dateutil
     ignore:X509Extension support in pyOpenSSL is deprecated:DeprecationWarning
     ignore:CSR support in pyOpenSSL is deprecated:DeprecationWarning
+    ignore:Python 3.8 support will be dropped:PendingDeprecationWarning