diff --git a/.github/workflows/linux-builder-update.yml b/.github/workflows/linux-builder-update.yml
index a68baee..0154ab4 100644
--- a/.github/workflows/linux-builder-update.yml
+++ b/.github/workflows/linux-builder-update.yml
@@ -38,40 +38,6 @@ jobs:
           topic: ${{ github.repository }} scheduled job failure
           content: ${{ github.server_url}}/${{ github.repository }}/actions/runs/${{ github.run_id }} failed.
 
-  x86-64-unknown-linux-builder-with-libressl_3_5_3:
-    needs:
-      - x86-64-unknown-linux-builder
-
-    name: Update x86-64-unknown-linux-builder-with-libressl-3.5.3
-    runs-on: ubuntu-latest
-    steps:
-      - uses: actions/checkout@v3
-      - name: Login to DockerHub
-        run: docker login -u "$DOCKER_USERNAME" -p "$DOCKER_PASSWORD"
-        env:
-          DOCKER_PASSWORD: ${{ secrets.DOCKER_PASSWORD }}
-          DOCKER_USERNAME: ${{ secrets.DOCKER_USERNAME }}
-      - name: Login to GitHub Container Registry
-        # v2.2.0
-        uses: docker/login-action@465a07811f14bebb1938fbed4728c6a1ff8901fc
-        with:
-          registry: ghcr.io
-          username: ${{ github.repository_owner }}
-          password: ${{ secrets.GITHUB_TOKEN }}
-      - name: Build and push
-        run: bash x86-64-unknown-linux-builder-with-libressl-3.5.3/build-and-push.bash
-      - name: Send alert on failure
-        if: ${{ failure() }}
-        uses: zulip/github-actions-zulip/send-message@b62d5a0e48a4d984ea4fce5dd65ba691963d4db4
-        with:
-          api-key: ${{ secrets.ZULIP_SCHEDULED_JOB_FAILURE_API_KEY }}
-          email: ${{ secrets.ZULIP_SCHEDULED_JOB_FAILURE_EMAIL }}
-          organization-url: 'https://ponylang.zulipchat.com/'
-          to: notifications
-          type: stream
-          topic: ${{ github.repository }} scheduled job failure
-          content: ${{ github.server_url}}/${{ github.repository }}/actions/runs/${{ github.run_id }} failed.
-
   x86-64-unknown-linux-builder-with-libressl_3_7_2:
     needs:
       - x86-64-unknown-linux-builder
@@ -313,7 +279,6 @@ jobs:
   send-linux-builders-updated-event:
     needs:
       - x86-64-unknown-linux-builder
-      - x86-64-unknown-linux-builder-with-libressl_3_5_3
       - x86-64-unknown-linux-builder-with-libressl_3_7_2
       - x86-64-unknown-linux-builder-with-libressl_3_7_3
       - x86-64-unknown-linux-builder-with-openssl_1_1_1q
@@ -387,7 +352,6 @@ jobs:
       matrix:
         image:
           - shared-docker-ci-x86-64-unknown-linux-builder
-          - shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.5.3
           - shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.7.2
           - shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.7.3
           - shared-docker-ci-x86-64-unknown-linux-builder-with-openssl_1.1.1q
diff --git a/.github/workflows/pr.yml b/.github/workflows/pr.yml
index 41ae417..90f1563 100644
--- a/.github/workflows/pr.yml
+++ b/.github/workflows/pr.yml
@@ -46,14 +46,6 @@ jobs:
       - name: Docker build
         run: "docker build --pull --file=x86-64-unknown-linux-builder/Dockerfile ."
 
-  validate-x86-64-unknown-linux-builder-with-libressl-3_5_3-image-builds:
-    name: Validate x86-64-unknown-linux-builder-with-libressl-3.5.3 Docker image builds
-    runs-on: ubuntu-latest
-    steps:
-      - uses: actions/checkout@v3
-      - name: Docker build
-        run: "docker build --pull --file=x86-64-unknown-linux-builder-with-libressl-3.5.3/Dockerfile ."
-
   validate-x86-64-unknown-linux-builder-with-libressl-3_7_2-image-builds:
     name: Validate x86-64-unknown-linux-builder-with-libressl-3.7.2 Docker image builds
     runs-on: ubuntu-latest
diff --git a/x86-64-unknown-linux-builder-with-libressl-3.5.3/Dockerfile b/x86-64-unknown-linux-builder-with-libressl-3.5.3/Dockerfile
deleted file mode 100644
index 49a61ac..0000000
--- a/x86-64-unknown-linux-builder-with-libressl-3.5.3/Dockerfile
+++ /dev/null
@@ -1,11 +0,0 @@
-ARG FROM_TAG=release
-FROM ghcr.io/ponylang/shared-docker-ci-x86-64-unknown-linux-builder:${FROM_TAG}
-
-RUN cd /tmp && \
-  wget https://cdn.openbsd.org/pub/OpenBSD/LibreSSL/libressl-3.5.3.tar.gz && \
-  tar xf libressl-3.5.3.tar.gz && \
-  cd libressl-3.5.3/ && \
-  ./configure && \
-  make install && \
-  cd /tmp && \
-  rm -rf libressl*
diff --git a/x86-64-unknown-linux-builder-with-libressl-3.5.3/README.md b/x86-64-unknown-linux-builder-with-libressl-3.5.3/README.md
deleted file mode 100644
index 02c8e2a..0000000
--- a/x86-64-unknown-linux-builder-with-libressl-3.5.3/README.md
+++ /dev/null
@@ -1,3 +0,0 @@
-# x86-64-unknown-linux-builder-with-libressl-3.5.3
-
-The x86-64-unknown-linux-builder with libressl 3.5.3 SSL implementation installed as well. Rebuilt daily.
diff --git a/x86-64-unknown-linux-builder-with-libressl-3.5.3/build-and-push.bash b/x86-64-unknown-linux-builder-with-libressl-3.5.3/build-and-push.bash
deleted file mode 100644
index 9676ee2..0000000
--- a/x86-64-unknown-linux-builder-with-libressl-3.5.3/build-and-push.bash
+++ /dev/null
@@ -1,47 +0,0 @@
-#!/bin/bash
-
-set -o errexit
-set -o nounset
-
-#
-# *** You should already be logged in to DockerHub
-#     and GitHub Container Registry when you run this ***
-#
-
-DOCKERFILE_DIR="$(dirname "$0")"
-
-## DockerHub
-
-NAME="ponylang/shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.5.3"
-
-# built from x86-64-unknown-linux-builder release tag
-FROM_TAG=release
-TAG_AS=release
-docker build --pull --build-arg FROM_TAG="${FROM_TAG}" \
-  -t "${NAME}:${TAG_AS}" "${DOCKERFILE_DIR}"
-docker push "${NAME}:${TAG_AS}"
-
-# built from x86-64-unknown-linux-builder latest tag
-FROM_TAG=latest
-TAG_AS=latest
-docker build --pull --build-arg FROM_TAG="${FROM_TAG}" \
-  -t "${NAME}:${TAG_AS}" "${DOCKERFILE_DIR}"
-docker push "${NAME}:${TAG_AS}"
-
-## GitHub Container Registry
-
-NAME="ghcr.io/ponylang/shared-docker-ci-x86-64-unknown-linux-builder-with-libressl-3.5.3"
-
-# built from x86-64-unknown-linux-builder release tag
-FROM_TAG=release
-TAG_AS=release
-docker build --pull --build-arg FROM_TAG="${FROM_TAG}" \
-  -t "${NAME}:${TAG_AS}" "${DOCKERFILE_DIR}"
-docker push "${NAME}:${TAG_AS}"
-
-# built from x86-64-unknown-linux-builder latest tag
-FROM_TAG=latest
-TAG_AS=latest
-docker build --pull --build-arg FROM_TAG="${FROM_TAG}" \
-  -t "${NAME}:${TAG_AS}" "${DOCKERFILE_DIR}"
-docker push "${NAME}:${TAG_AS}"