diff --git a/README.md b/README.md
index 8330609..2da64fd 100644
--- a/README.md
+++ b/README.md
@@ -116,6 +116,7 @@ services:
       - PGID=1000
       - TZ=Etc/UTC
       - APP_URL=
+      - APP_KEY=
       - DB_HOST=
       - DB_PORT=3306
       - DB_USERNAME=
@@ -138,6 +139,7 @@ docker run -d \
   -e PGID=1000 \
   -e TZ=Etc/UTC \
   -e APP_URL= \
+  -e APP_KEY= \
   -e DB_HOST= \
   -e DB_PORT=3306 \
   -e DB_USERNAME= \
@@ -161,6 +163,7 @@ Containers are configured using parameters passed at runtime (such as those abov
 | `-e PGID=1000` | for GroupID - see below for explanation |
 | `-e TZ=Etc/UTC` | specify a timezone to use, see this [list](https://en.wikipedia.org/wiki/List_of_tz_database_time_zones#List). |
 | `-e APP_URL=` | The IP:port or URL your application will be accessed on (ie. `http://192.168.1.1:6875` or `https://bookstack.mydomain.com` |
+| `-e APP_KEY=` | Session encryption key. Can be generated with `docker run -it --rm --entrypoint /bin/bash lscr.io/linuxserver/bookstack:latest appkey` |
 | `-e DB_HOST=` | The database instance hostname |
 | `-e DB_PORT=3306` | Database port (default `3306`) |
 | `-e DB_USERNAME=` | Database user |
diff --git a/readme-vars.yml b/readme-vars.yml
index 3cc7bce..5c3f77d 100644
--- a/readme-vars.yml
+++ b/readme-vars.yml
@@ -25,6 +25,7 @@ param_volumes:
 param_usage_include_env: true
 param_env_vars:
   - { env_var: "APP_URL", env_value: "", desc: "The IP:port or URL your application will be accessed on (ie. `http://192.168.1.1:6875` or `https://bookstack.mydomain.com`"}
+  - { env_var: "APP_KEY", env_value: "", desc: "Session encryption key. Can be generated with `docker run -it --rm --entrypoint /bin/bash lscr.io/linuxserver/bookstack:latest appkey`"}
   - { env_var: "DB_HOST", env_value: "", desc: "The database instance hostname" }
   - { env_var: "DB_PORT", env_value: "3306", desc: "Database port (default `3306`)" }
   - { env_var: "DB_USERNAME", env_value: "", desc: "Database user" }
diff --git a/root/appkey b/root/appkey
new file mode 100755
index 0000000..2e689f6
--- /dev/null
+++ b/root/appkey
@@ -0,0 +1,3 @@
+#!/bin/bash
+
+php /app/www/artisan key:generate --show
diff --git a/root/etc/s6-overlay/s6-rc.d/init-bookstack-config/run b/root/etc/s6-overlay/s6-rc.d/init-bookstack-config/run
index ffabb69..8278406 100755
--- a/root/etc/s6-overlay/s6-rc.d/init-bookstack-config/run
+++ b/root/etc/s6-overlay/s6-rc.d/init-bookstack-config/run
@@ -46,9 +46,9 @@ fi
 
 # Check for app key
 if [[ -z ${APP_KEY} ]]; then
-    if ! grep -qE "APP_KEY=[0-9A-Za-z:+\/=]{1,}" /app/www/.env 2> /dev/null; then
+    if ! grep -qE "APP_KEY=[0-9A-Za-z:+\/=]{1,}" /app/www/.env 2> /dev/null || grep -qE "APP_KEY=SomeRandomString" /app/www/.env 2> /dev/null; then
         echo "An application key is missing, halting init!"
-        echo "You can generate a key with: docker exec -it bookstack php /app/www/artisan key:generate --show"
+        echo "You can generate a key with: docker run -it --rm --entrypoint /bin/bash lscr.io/linuxserver/bookstack:latest appkey"
         sleep infinity
     fi
 fi