diff --git a/examples/docker/aiohttp/Dockerfile b/examples/docker/aiohttp/Dockerfile
index a7b78ed12..7ebb18246 100644
--- a/examples/docker/aiohttp/Dockerfile
+++ b/examples/docker/aiohttp/Dockerfile
@@ -1,13 +1,17 @@
 #
 # docker build . -t your-repo/hello-bolt
 #
-FROM python:3.8.5-slim-buster as builder
+FROM python:3.8-slim-bookworm as builder
 RUN apt-get update && apt-get clean
 COPY requirements.txt /build/
 WORKDIR /build/
 RUN pip install -U pip && pip install -r requirements.txt
 
-FROM python:3.8.5-slim-buster as app
+FROM python:3.8-slim-bookworm as app
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 COPY --from=builder /build/ /app/
 COPY --from=builder /usr/local/lib/ /usr/local/lib/
 WORKDIR /app/
diff --git a/examples/docker/asgi/Dockerfile b/examples/docker/asgi/Dockerfile
index cef704967..0334461ba 100644
--- a/examples/docker/asgi/Dockerfile
+++ b/examples/docker/asgi/Dockerfile
@@ -1,12 +1,14 @@
 #
 # docker build . -t your-repo/hello-bolt
 #
-FROM python:3.11-alpine3.17 as builder
+FROM python:3.11-alpine3.20 as builder
 COPY requirements.txt /build/
 WORKDIR /build/
 RUN pip install -U pip && pip install -r requirements.txt
 
-FROM python:3.11-alpine3.17 as app
+FROM python:3.11-alpine3.20 as app
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apk add --no-cache --upgrade ca-certificates ca-certificates-bundle
 WORKDIR /app/
 COPY --from=builder /usr/local/bin/ /usr/local/bin/
 COPY --from=builder /usr/local/lib/ /usr/local/lib/
diff --git a/examples/docker/fastapi-gunicorn/Dockerfile b/examples/docker/fastapi-gunicorn/Dockerfile
index c8f8b94e3..4938b4b5b 100644
--- a/examples/docker/fastapi-gunicorn/Dockerfile
+++ b/examples/docker/fastapi-gunicorn/Dockerfile
@@ -2,6 +2,10 @@
 # docker build . -t your-repo/hello-bolt
 #
 FROM tiangolo/uvicorn-gunicorn:python3.8-slim
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 WORKDIR /app/
 COPY *.py /app/
 COPY requirements.txt /app/
diff --git a/examples/docker/flask-gunicorn/Dockerfile b/examples/docker/flask-gunicorn/Dockerfile
index e788cb388..a7a0f2362 100644
--- a/examples/docker/flask-gunicorn/Dockerfile
+++ b/examples/docker/flask-gunicorn/Dockerfile
@@ -1,12 +1,16 @@
 #
 # docker build . -t your-repo/hello-bolt
 #
-FROM python:3.8.5-slim-buster as builder
+FROM python:3.8-slim-bookworm as builder
 COPY requirements.txt /build/
 WORKDIR /build/
 RUN pip install -U pip && pip install -r requirements.txt
 
-FROM python:3.8.5-slim-buster as app
+FROM python:3.8-slim-bookworm as app
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 WORKDIR /app/
 COPY --from=builder /usr/local/bin/ /usr/local/bin/
 COPY --from=builder /usr/local/lib/ /usr/local/lib/
diff --git a/examples/docker/flask-uwsgi/Dockerfile b/examples/docker/flask-uwsgi/Dockerfile
index 14ddfb41b..f5d7e6863 100644
--- a/examples/docker/flask-uwsgi/Dockerfile
+++ b/examples/docker/flask-uwsgi/Dockerfile
@@ -1,15 +1,19 @@
 #
 # docker build . -t your-repo/hello-bolt
 #
-FROM python:3.8.5-slim-buster as builder
+FROM python:3.8-slim-bookworm as builder
 RUN apt-get update \
-    && apt-get -y install build-essential libpcre3-dev \
+    && apt-get -y install build-essential libpcre2-dev \
     && apt-get clean
 COPY requirements.txt /build/
 WORKDIR /build/
 RUN pip install -U pip && pip install -r requirements.txt
 
-FROM python:3.8.5-slim-buster as app
+FROM python:3.8-slim-bookworm as app
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 WORKDIR /app/
 COPY --from=builder /usr/local/bin/ /usr/local/bin/
 COPY --from=builder /usr/local/lib/ /usr/local/lib/
diff --git a/examples/docker/sanic/Dockerfile b/examples/docker/sanic/Dockerfile
index 4606e68bd..c24d81b5c 100644
--- a/examples/docker/sanic/Dockerfile
+++ b/examples/docker/sanic/Dockerfile
@@ -1,12 +1,16 @@
 #
 # docker build . -t your-repo/hello-bolt
 #
-FROM python:3.8.5-slim-buster as builder
+FROM python:3.8-slim-bookworm as builder
 COPY requirements.txt /build/
 WORKDIR /build/
 RUN pip install -U pip && pip install -r requirements.txt
 
-FROM python:3.8.5-slim-buster as app
+FROM python:3.8-slim-bookworm as app
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 WORKDIR /app/
 COPY *.py /app/
 COPY --from=builder /usr/local/bin/ /usr/local/bin/
diff --git a/examples/google_cloud_run/aiohttp/Dockerfile b/examples/google_cloud_run/aiohttp/Dockerfile
index e4432e3a2..77a656180 100644
--- a/examples/google_cloud_run/aiohttp/Dockerfile
+++ b/examples/google_cloud_run/aiohttp/Dockerfile
@@ -11,7 +11,12 @@
 # ----------------------------------------------
 # Use the official lightweight Python image.
 # https://hub.docker.com/_/python
-FROM python:3.8.5-slim-buster
+FROM python:3.8-slim-bookworm
+
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 
 # Allow statements and log messages to immediately appear in the Knative logs
 ENV PYTHONUNBUFFERED True
diff --git a/examples/google_cloud_run/flask-gunicorn/Dockerfile b/examples/google_cloud_run/flask-gunicorn/Dockerfile
index 8342e3a8b..01dd32523 100644
--- a/examples/google_cloud_run/flask-gunicorn/Dockerfile
+++ b/examples/google_cloud_run/flask-gunicorn/Dockerfile
@@ -11,7 +11,12 @@
 # ----------------------------------------------
 # Use the official lightweight Python image.
 # https://hub.docker.com/_/python
-FROM python:3.8.5-slim-buster
+FROM python:3.8-slim-bookworm
+
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 
 # Allow statements and log messages to immediately appear in the Knative logs
 ENV PYTHONUNBUFFERED True
diff --git a/examples/google_cloud_run/sanic/Dockerfile b/examples/google_cloud_run/sanic/Dockerfile
index d71ddef67..15c38fe1e 100644
--- a/examples/google_cloud_run/sanic/Dockerfile
+++ b/examples/google_cloud_run/sanic/Dockerfile
@@ -11,7 +11,12 @@
 # ----------------------------------------------
 # Use the official lightweight Python image.
 # https://hub.docker.com/_/python
-FROM python:3.8.5-slim-buster
+FROM python:3.8-slim-bookworm
+
+# Refresh the OS trust store so the image gets the latest ca-certificates.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates \
+    && rm -rf /var/lib/apt/lists/*
 
 # Allow statements and log messages to immediately appear in the Knative logs
 ENV PYTHONUNBUFFERED True