diff --git a/Dockerfile b/Dockerfile
index 5465787..8b65d7b 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -147,8 +147,9 @@ RUN find -exec sh -c 'file "{}" | grep -q ELF && strip --strip-debug "{}"' \; \
  && mv usr/bin/curl /output/usr/bin \
  && mv usr/bin/xml /output/usr/bin/xmlstarlet
 
-ADD start_pms /output/usr/sbin/start_pms
-RUN chmod +x /output/usr/sbin/start_pms
+ADD entrypoint /output/usr/local/bin/
+ADD *.sh /output/usr/local/bin/
+RUN chmod +x /output/usr/local/bin/*
 
 #=========================
 
@@ -172,16 +173,26 @@ LABEL maintainer="Spritsail <plex@spritsail.io>" \
       io.spritsail.version.libstdcpp=${LIBSTDCPP_VER} \
       io.spritsail.version.xmlstarlet=${XMLSTAR_VER}
 
-ENV SUID=900 SGID=900
+WORKDIR /usr/lib/plexmediaserver
 
 COPY --from=builder /output/ /
 
+ENV SUID=900 SGID=900 \
+    PLEX_MEDIA_SERVER_MAX_PLUGIN_PROCS="6" \
+    PLEX_MEDIA_SERVER_MAX_STACK_SIZE="3000" \
+    PLEX_MEDIA_SERVER_TMPDIR="/tmp" \
+    PLEX_MEDIA_SERVER_HOME="/usr/lib/plexmediaserver" \
+    PLEX_MEDIA_SERVER_APPLICATION_SUPPORT_DIR="/var/lib/plexmediaserver"
+
 HEALTHCHECK --interval=10s --timeout=5s \
     CMD [ "wget", "-O", "/dev/null", "-T", "10", "-q", "localhost:32400/identity" ]
 
-WORKDIR /usr/lib/plexmediaserver
-
 EXPOSE 32400
 
+VOLUME ["/config", "/transcode"]
+
+RUN mkdir -p "$PLEX_MEDIA_SERVER_APPLICATION_SUPPORT_DIR" \
+ && ln -sfv /config "$PLEX_MEDIA_SERVER_APPLICATION_SUPPORT_DIR/Plex Media Server"
+
 ENTRYPOINT ["/sbin/tini", "--"]
-CMD ["/usr/sbin/start_pms"]
+CMD ["/usr/local/bin/entrypoint"]
diff --git a/entrypoint b/entrypoint
new file mode 100755
index 0000000..37175de
--- /dev/null
+++ b/entrypoint
@@ -0,0 +1,28 @@
+#!/bin/sh
+set -e
+
+if su-exec -e [ ! -w "/config" ]; then
+    2>&1 echo "Warning: No permission to write in '/config' directory."
+    2>&1 echo "         Correcting permissions to prevent a crash"
+    2>&1 echo
+    (
+    set -x
+    chown $SUID:$SGID /config
+    chmod o+rw /config
+    )
+fi
+
+exec su-exec -e sh <<EOF
+# Generate a default configuration, including some user-specified values
+if [ ! -e "/config/Preferences.xml" ]; then
+    gen-config.sh
+fi
+
+# Duplicate the Plex logs to stdout (docker logs)
+tail -Fn 0 "/config/Logs/Plex Media Server.log" 2>/dev/null &
+
+# Use a random pidfile
+export PLEX_MEDIA_SERVER_PIDFILE="\$(mktemp -ut pms-pid.XXXXXX)"
+
+exec "\$PLEX_MEDIA_SERVER_HOME/Plex Media Server"
+EOF
diff --git a/gen-config.sh b/gen-config.sh
new file mode 100755
index 0000000..48046ae
--- /dev/null
+++ b/gen-config.sh
@@ -0,0 +1,64 @@
+#!/bin/sh
+set -e
+
+PREF_FILE="${1:-/config/Preferences.xml}"
+
+getPref() {
+    xmlstarlet sel -T -t -m "/Preferences" -v "@$1" -n "${PREF_FILE}"
+}
+setPref() {
+    count="$(xmlstarlet sel -t -v "count(/Preferences/@$1)" "${PREF_FILE}")"
+    if [ $(($count + 0)) -gt 0 ]; then
+        xmlstarlet ed --inplace --update "/Preferences/@$1" -v "$2" "${PREF_FILE}" 2>/dev/null
+    else
+        xmlstarlet ed --inplace --insert "/Preferences"  --type attr -n "$1" -v "$2" "${PREF_FILE}" 2>/dev/null
+    fi
+}
+
+# Create a default config file allowing external access
+echo -e $'<?xml version="1.0" encoding="utf-8"?>\n<Preferences />' > "/config/Preferences.xml"
+
+# Enforced defaults. These can be changed manually afterwards.
+setPref "AcceptedEULA" "1"
+setPref "TranscoderTempDirectory" "/transcode"
+
+# The following below is ripped directly from the official (inferior) Plex container:
+# https://github.com/plexinc/pms-docker/blob/155f00c71b50f94c73ffea0aae16cc61ef957df7/root/etc/cont-init.d/40-plex-first-run
+
+# Setup Server's client identifier
+serial="$(getPref "MachineIdentifier")"
+if [ -z "${serial}" ]; then
+    serial="$(cat /proc/sys/kernel/random/uuid)"
+    setPref "MachineIdentifier" "${serial}"
+fi
+clientId="$(getPref "ProcessedMachineIdentifier")"
+if [ -z "${clientId}" ]; then
+    clientId="$(echo -n "${serial}- Plex Media Server" | sha1sum | cut -b 1-40)"
+    setPref "ProcessedMachineIdentifier" "${clientId}"
+fi
+
+# Get server token and only turn claim token into server token if we have former but not latter.
+token="$(getPref "PlexOnlineToken")"
+if [ ! -z "${PLEX_CLAIM}" ] && [ -z "${token}" ]; then
+    echo "Attempting to obtain server token from claim token"
+    loginInfo="$(curl -X POST \
+        -H 'X-Plex-Client-Identifier: '${clientId} \
+        -H 'X-Plex-Product: Plex Media Server'\
+        -H 'X-Plex-Version: 1.1' \
+        -H 'X-Plex-Provides: server' \
+        -H 'X-Plex-Platform: Linux' \
+        -H 'X-Plex-Platform-Version: 1.0' \
+        -H 'X-Plex-Device-Name: PlexMediaServer' \
+        -H 'X-Plex-Device: Linux' \
+        "https://plex.tv/api/claim/exchange?token=${PLEX_CLAIM}")"
+    token="$(echo "$loginInfo" | sed -n 's/.*<authentication-token>\(.*\)<\/authentication-token>.*/\1/p')"
+
+    if [ "$token" ]; then
+        echo "Token obtained successfully"
+        setPref "PlexOnlineToken" "${token}"
+    fi
+fi
+
+test -n "${ADVERTISE_IP}"       && setPref "customConnections" "${ADVERTISE_IP}"
+test -n "${ALLOWED_NETWORKS}"   && setPref "allowedNetworks" "${ALLOWED_NETWORKS}"
+test -n "${DISABLE_REMOTE_SEC}" && setPref "disableRemoteSecurity" "1"
diff --git a/start_pms b/start_pms
deleted file mode 100755
index 720b17c..0000000
--- a/start_pms
+++ /dev/null
@@ -1,43 +0,0 @@
-#!/bin/sh
-
-# Default values
-export PLEX_MEDIA_SERVER_MAX_PLUGIN_PROCS="${PLEX_MEDIA_SERVER_MAX_PLUGIN_PROCS:-6}"
-export PLEX_MEDIA_SERVER_HOME="${PLEX_MEDIA_SERVER_HOME:-/usr/lib/plexmediaserver}"
-export PLEX_MEDIA_SERVER_MAX_STACK_SIZE="${PLEX_MEDIA_SERVER_MAX_STACK_SIZE:-3000}"
-export PLEX_MEDIA_SERVER_TMPDIR="${PLEX_MEDIA_SERVER_TMPDIR:-/tmp}"
-export PLEX_MEDIA_SERVER_APPLICATION_SUPPORT_DIR="${PLEX_MEDIA_SERVER_APPLICATION_SUPPORT_DIR:-/config}"
-export PLEX_MEDIA_SERVER_CONFIG_DIR="${PLEX_MEDIA_SERVER_APPLICATION_SUPPORT_DIR}/Plex Media Server"
-export TMPDIR="${PLEX_MEDIA_SERVER_TMPDIR}"
-
-if [ ! -d "$PLEX_MEDIA_SERVER_CONFIG_DIR" ]; then
-  mkdir -p "$PLEX_MEDIA_SERVER_CONFIG_DIR" && \
-  chown $SUID:$SGID "$PLEX_MEDIA_SERVER_CONFIG_DIR"
-  if [ ! $? -eq 0 ]; then
-    echo "WARNING COULDN'T CREATE $PLEX_MEDIA_SERVER_CONFIG_DIR, MAKE SURE I HAVE PERMISSON TO DO THAT!"
-    exit 1
-  fi
-fi
-
-if su-exec -e [ ! -w "$PLEX_MEDIA_SERVER_CONFIG_DIR" ]; then
-  echo "ERROR: CANNOT WRITE IN $PLEX_MEDIA_SERVER_CONFIG_DIR, MAKE SURE I HAVE PERMISSION TO DO THAT!"
-  exit 2
-fi
-
-if [ ! -e "$PLEX_MEDIA_SERVER_CONFIG_DIR/Preferences.xml" ]; then
-    # Create a default config file allowing external access
-    echo -e '<?xml version="1.0" encoding="utf-8"?>\n<Preferences disableRemoteSecurity="1" />' \
-        >> "$PLEX_MEDIA_SERVER_CONFIG_DIR/Preferences.xml"
-fi
-
-# Allow Plex group to write to tmpdir
-chgrp $SGID "$TMPDIR"
-chmod g+rwx "$TMPDIR"
-
-PIDFILE="${PLEX_MEDIA_SERVER_CONFIG_DIR}/plexmediaserver.pid"
-if [ -f "$PIDFILE" ]; then
-    rm -f "$PIDFILE"
-fi
-
-tail -F "$PLEX_MEDIA_SERVER_CONFIG_DIR/Logs/Plex Media Server.log" >/proc/1/fd/1 2>/dev/null &
-
-exec su-exec -e "$PLEX_MEDIA_SERVER_HOME/Plex Media Server"