diff --git a/cron/Dockerfile b/cron/Dockerfile
index 14b901fd0d1..edb6407fdb3 100644
--- a/cron/Dockerfile
+++ b/cron/Dockerfile
@@ -1,6 +1,8 @@
 ARG BASE_IMAGE
 FROM ${BASE_IMAGE}
 USER 0
+RUN if [ -z "${http_proxy}" ]; then echo "Acquire::http::proxy \"${http_proxy}\";" >> /etc/apt/apt.conf; fi
+RUN if [ -z "${https_proxy}" ]; then echo "Acquire::https::proxy \"${https_proxy}\";" >> /etc/apt/apt.conf; fi
 RUN apt-get update && apt-get install -y --no-install-recommends cron && \
     rm -r /var/lib/apt/lists/*
 COPY entrypoint.sh /entrypoint.sh
diff --git a/docker-compose.yml b/docker-compose.yml
index a38d1158ea4..cfb9bb5d3d4 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -211,7 +211,10 @@ services:
       test:
         [
           "CMD-SHELL",
-          "wget -nv -t1 --spider 'http://localhost:8123/' || exit 1",
+          # Manually override any http_proxy envvar that might be set, because
+          # this wget does not support no_proxy. See:
+          # https://github.com/getsentry/self-hosted/issues/1537
+          "http_proxy='' wget -nv -t1 --spider 'http://localhost:8123/' || exit 1",
         ]
       interval: 3s
       timeout: 600s
diff --git a/install/build-docker-images.sh b/install/build-docker-images.sh
index 63bb0dac429..671597eec46 100644
--- a/install/build-docker-images.sh
+++ b/install/build-docker-images.sh
@@ -3,8 +3,8 @@ echo "${_group}Building and tagging Docker images ..."
 echo ""
 # Build any service that provides the image sentry-self-hosted-local first,
 # as it is used as the base image for sentry-cleanup-self-hosted-local.
-$dc build --force-rm web
-$dc build --force-rm
+$dc build --build-arg "http_proxy=${http_proxy:-}" --build-arg "https_proxy=${https_proxy:-}" --build-arg "no_proxy=${no_proxy:-}" --force-rm web
+$dc build --build-arg "http_proxy=${http_proxy:-}" --build-arg "https_proxy=${https_proxy:-}" --build-arg "no_proxy=${no_proxy:-}" --force-rm
 echo ""
 echo "Docker images built."