diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 794a01d7d0..fb891aea8b 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -34,6 +34,8 @@ jobs:
           ./install.sh
           ./test.sh
           echo "Testing in-place upgrade"
+          # Also test plugin installation here
+          echo "sentry-auth-oidc" >> sentry/requirements.txt
           ./install.sh --minimize-downtime
           ./test.sh
 
diff --git a/docker-compose.yml b/docker-compose.yml
index d25e054498..4a2644c904 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -3,11 +3,7 @@ x-restart-policy: &restart_policy
   restart: unless-stopped
 x-sentry-defaults: &sentry_defaults
   <<: *restart_policy
-  build:
-    context: ./sentry
-    args:
-      - SENTRY_IMAGE
-  image: sentry-onpremise-local
+  image: "$SENTRY_IMAGE"
   depends_on:
     - redis
     - postgres
@@ -21,7 +17,10 @@ x-sentry-defaults: &sentry_defaults
     - snuba-replacer
     - symbolicator
     - kafka
+  entrypoint: "/etc/sentry/entrypoint.sh"
+  command: ["run", "web"]
   environment:
+    PYTHONUSERBASE: "/data/custom-packages"
     SENTRY_CONF: "/etc/sentry"
     SNUBA: "http://snuba-api:1218"
     # Leaving the value empty to just pass whatever is set
@@ -219,7 +218,7 @@ services:
     build:
       context: ./cron
       args:
-        BASE_IMAGE: "sentry-onpremise-local"
+        BASE_IMAGE: "$SENTRY_IMAGE"
     command: '"0 0 * * * gosu sentry sentry cleanup --days $SENTRY_EVENT_RETENTION_DAYS"'
   nginx:
     <<: *restart_policy
diff --git a/install.sh b/install.sh
index 4307b201b0..ab978185b4 100755
--- a/install.sh
+++ b/install.sh
@@ -247,8 +247,6 @@ echo "${_endgroup}"
 
 echo "${_group}Building and tagging Docker images ..."
 echo ""
-# Build the sentry onpremise image first as it is needed for the cron image
-$dc build --force-rm web
 $dc build --force-rm
 echo ""
 echo "Docker images built."
diff --git a/sentry/.dockerignore b/sentry/.dockerignore
deleted file mode 100644
index 693a7e0716..0000000000
--- a/sentry/.dockerignore
+++ /dev/null
@@ -1,5 +0,0 @@
-# Ignore everything
-*
-
-# Only allow requirements.txt
-!/requirements.txt
diff --git a/sentry/Dockerfile b/sentry/Dockerfile
deleted file mode 100644
index f9484f295b..0000000000
--- a/sentry/Dockerfile
+++ /dev/null
@@ -1,7 +0,0 @@
-ARG SENTRY_IMAGE
-FROM ${SENTRY_IMAGE}
-
-COPY . /usr/src/sentry
-
-# Hook for installing additional plugins
-RUN if [ -s /usr/src/sentry/requirements.txt ]; then pip install -r /usr/src/sentry/requirements.txt; fi
diff --git a/sentry/entrypoint.sh b/sentry/entrypoint.sh
new file mode 100755
index 0000000000..55c7e4141a
--- /dev/null
+++ b/sentry/entrypoint.sh
@@ -0,0 +1,16 @@
+#!/bin/bash
+set -e
+
+req_file="/etc/sentry/requirements.txt"
+plugins_dir="/data/custom-packages"
+checksum_file="$plugins_dir/.checksum"
+
+if [[ -s "$req_file" ]] && ! cat "$req_file" | grep '^[^#[:space:]]' | shasum -s -c "$checksum_file" 2>/dev/null; then
+    echo "Installing additional dependencies..."
+    mkdir -p "$plugins_dir"
+    pip install --user -r "$req_file"
+    cat "$req_file" | grep '^[^#[:space:]]' | shasum > "$checksum_file"
+    echo ""
+fi
+
+source /docker-entrypoint.sh