diff --git a/.azure-pipelines/templates/jobs/standard-tests-jobs.yml b/.azure-pipelines/templates/jobs/standard-tests-jobs.yml
index 045abcddb..e1474b152 100644
--- a/.azure-pipelines/templates/jobs/standard-tests-jobs.yml
+++ b/.azure-pipelines/templates/jobs/standard-tests-jobs.yml
@@ -4,20 +4,12 @@ jobs:
       PYTHON_VERSION: 3.12
     strategy:
       matrix:
-        macos-py38-cover:
-          # mac unit+cover tests with the oldest python we support
+        macos-cover:
           IMAGE_NAME: macOS-15
-          PYTHON_VERSION: 3.8
           TOXENV: cover
           # As of pip 23.1.0, builds started failing on macOS unless this flag was set.
           # See https://github.com/certbot/certbot/pull/9717#issuecomment-1610861794.
           PIP_USE_PEP517: "true"
-        macos-cover:
-          # mac unit+cover tests with the newest python we support
-          IMAGE_NAME: macOS-15
-          TOXENV: cover
-          # See explanation under macos-py38-cover.
-          PIP_USE_PEP517: "true"
         linux-oldest:
           IMAGE_NAME: ubuntu-22.04
           PYTHON_VERSION: 3.8
diff --git a/certbot/CHANGELOG.md b/certbot/CHANGELOG.md
index 425a8d587..33563d54e 100644
--- a/certbot/CHANGELOG.md
+++ b/certbot/CHANGELOG.md
@@ -1,4 +1,3 @@
-
 # Certbot change log
 
 Certbot adheres to [Semantic Versioning](https://semver.org/).
@@ -11,7 +10,7 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
 
 ### Changed
 
-*
+* Updated our Docker images to be based on Alpine Linux 3.20.
 
 ### Fixed
 
@@ -19,7 +18,6 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
 
 More details about these changes can be found on our GitHub repo.
 
-
 ## 3.0.1 - 2024-11-14
 
 ### Fixed
diff --git a/tools/docker/Dockerfile b/tools/docker/Dockerfile
index 6ea546906..760c65b98 100644
--- a/tools/docker/Dockerfile
+++ b/tools/docker/Dockerfile
@@ -1,5 +1,5 @@
 #base image
-FROM python:3.12-alpine3.18 AS certbot
+FROM python:3.12-alpine3.20 AS certbot
 
 ENTRYPOINT [ "certbot" ]
 EXPOSE 80 443
@@ -15,7 +15,7 @@ COPY certbot src/certbot
 # Install certbot runtime dependencies
 RUN apk add --no-cache --virtual .certbot-deps \
         libffi \
-        libssl1.1 \
+        libssl3 \
         openssl \
         ca-certificates \
         binutils