Question: I have a docker image building through a circle.ci pipeline, it's pulling an ECR image from AWS and hosted on EB/EC2 and its failing to build continuously with this error: #5 0.329 Get:1 http://deb.debian.org/debian bookworm InRelease [147 kB] #5 0.339 Get:2 http://deb.debian.org/debian bookworm-updates InRelease [52.1 kB] #5 0.339 Get:3 http://deb.debian.org/debian-security bookworm-security InRelease [48.0 kB] #5 0.401 Get:4 http://deb.debian.org/debian bookworm/main amd64 Packages [8904 kB] #5 0.548 Get:5 http://deb.debian.org/debian-security bookworm-security/main amd64 Packages [27.7 kB] #5 1.597 Fetched 9179 kB in 1s (7185 kB/s) #5 1.597 Reading package lists... #5 2.165 E: Problem executing scripts APT::Update::Post-Invoke 'rm -f /var/cache/apt/archives/*.deb /var/cache/apt/archives/partial/*.deb /var/cache/apt/*.bin || true' #5 2.165 E: Sub-process returned an error code #5 ERROR: executor failed running [/bin/sh -c apt-get update]: exit code: 100 ------ > [dev 2/7] RUN apt-get update: ------ error: failed to solve: rpc error: code = Unknown desc = executor failed running [/bin/sh -c apt-get update]: exit code: 100  My Docker file FROM python:3.9-slim as dev ENV DEBIAN_FRONTEND=noninteractive # Custom cache invalidation ARG CACHEBUST=1 RUN apt-get update RUN apt-get install -y pipenv default-libmysqlclient-dev libcurl4-openssl-dev libssl-dev COPY Pipfile* ./ RUN pipenv install --system --deploy --dev ENV APP_DIR=/app/withinhealth RUN mkdir -p ${APP_DIR} WORKDIR ${APP_DIR} FROM dev as prod COPY . ./ 

Answer: Looks like the version of docker being used needs updating. I was also having this problem using an old version of docker (20.10.6 - don't ask). There was a Debian release a few days ago. python:3.9-slim derives from this new Debian version and there are some issues with running images based on this Debian version with older versions of docker (certificates and/or keys, updated version of glibc perhaps). Minimal steps to reproduce (with docker version 20.10.6): $ docker run --rm -it python:3.9-slim bash root@f350ecdf0140:/# apt update Get:1 http://deb.debian.org/debian bookworm InRelease [147 kB] Get:2 http://deb.debian.org/debian bookworm-updates InRelease [52.1 kB] Get:3 http://deb.debian.org/debian-security bookworm-security InRelease [48.0 kB] Get:4 http://deb.debian.org/debian bookworm/main amd64 Packages [8904 kB] Get:5 http://deb.debian.org/debian-security bookworm-security/main amd64 Packages [28.3 kB] Fetched 9180 kB in 2s (5210 kB/s) Reading package lists... Done E: Problem executing scripts APT::Update::Post-Invoke 'rm -f /var/cache/apt/archives/*.deb /var/cache/apt/archives/partial/*.deb /var/cache/apt/*.bin || true' E: Sub-process returned an error code  Following upgrade of docker to 24.0.2: $ docker run --rm -it python:3.9-slim bash root@6824359f6240:/# apt update Get:1 http://deb.debian.org/debian bookworm InRelease [147 kB] Get:2 http://deb.debian.org/debian bookworm-updates InRelease [52.1 kB] Get:3 http://deb.debian.org/debian-security bookworm-security InRelease [48.0 kB] Get:4 http://deb.debian.org/debian bookworm/main amd64 Packages [8904 kB] Get:5 http://deb.debian.org/debian-security bookworm-security/main amd64 Packages [28.3 kB] Fetched 9180 kB in 2s (5248 kB/s) Reading package lists... Done Building dependency tree... Done Reading state information... Done All packages are up to date.