diff --git a/src/ubuntu/install/vpn/install_vpn.sh b/src/ubuntu/install/vpn/install_vpn.sh
index d954354..7b36ce1 100644
--- a/src/ubuntu/install/vpn/install_vpn.sh
+++ b/src/ubuntu/install/vpn/install_vpn.sh
@@ -9,37 +9,43 @@ if [[ "${DISTRO}" == @(ubuntu|kali|debian|parrotos5) ]]; then
     openvpn \
     resolvconf \
     wireguard-tools \
-    zenity
+    zenity \
+    jq
 elif [ "${DISTRO}" == "alpine" ]; then
   apk add --no-cache \
     openresolv \
     openvpn \
     tailscale \
     wireguard-tools \
-    zenity
+    zenity \
+    jq
 elif [[ "${DISTRO}" == @(oracle8|oracle9|rockylinux8|rockylinux9|almalinux8|almalinux9) ]] ; then
   dnf install -y epel-release
   dnf install -y \
     openvpn \
-    wireguard-tools
+    wireguard-tools \
+    jq
 elif [[ "${DISTRO}" == @(centos|oracle7) ]]; then
   yum install -y epel-release
   yum install -y \
     openvpn \
     wireguard-tools \
-    zenity
+    zenity \
+    jq
 elif [[ "${DISTRO}" == @(fedora37|fedora38) ]] ; then
   dnf install -y \
     openresolv \
     openvpn \
     wireguard-tools \
-    zenity
+    zenity \
+    jq
 elif [ "${DISTRO}" == "opensuse" ]; then
   zypper install -y \
     openresolv \
     openvpn \
     wireguard-tools \
-    zenity
+    zenity \
+    jq
 fi
 
 # Install tailscale
@@ -90,5 +96,5 @@ fi
 sed -i '/cmd sysctl -q/d' $(which wg-quick)
 
 # Copy startup script
-cp ${INST_DIR}/ubuntu/install/vpn/start_vpn.sh /
-chmod +x /start_vpn.sh
+cp ${INST_DIR}/ubuntu/install/vpn/start_vpn.sh /dockerstartup/start_vpn.sh
+chmod +x /dockerstartup/start_vpn.sh
diff --git a/src/ubuntu/install/vpn/start_vpn.sh b/src/ubuntu/install/vpn/start_vpn.sh
index 2b6eeae..d2504a2 100644
--- a/src/ubuntu/install/vpn/start_vpn.sh
+++ b/src/ubuntu/install/vpn/start_vpn.sh
@@ -1,11 +1,30 @@
 #!/usr/bin/env bash
+set -x
 
-set -ex
+ICON_SUCCESS="/usr/share/icons/ubuntu-mono-dark/status/22/nm-signal-100-secure.svg"
+ICON_ERROR="/usr/share/icons/ubuntu-mono-dark/status/22/network-error.svg"
+ICON_OFFLINE="/usr/share/icons/ubuntu-mono-dark/status/22/network-offline.svg"
+OPENVPN_STATUS_LOG="/tmp/openvpn-status.log"
+DEFAULT_OPENVPN_CONFIG="/dockerstartup/openvpn.conf"
+DEFAULT_OPENVPN_CREDS="/dockerstartup/openvpn-auth"
+DEFAULT_WIREGUARD_CONFIG="/dockerstartup/wireguard.conf"
+
+SHOW_VPN_STATUS_DEFAULT="1"
+SHOW_VPN_STAT=${SHOW_VPN_STATUS:-$SHOW_VPN_STATUS_DEFAULT}
+
+SHOW_IP_STATUS_DEFAULT="1"
+SHOW_IP_STAT=${SHOW_IP_STATUS:-$SHOW_IP_STATUS_DEFAULT}
 
 # Logging and trap
-LOGFILE="/vpn_start.log"
+LOGFILE="/dockerstartup/vpn_start.log"
 function notify_err() {
-  zenity --error --text="An error has occurred configuring the VPN please review the log at ${LOGFILE}"
+  local exit_code=$?
+  local failed_command="$BASH_COMMAND"
+  msg="An error occurred with exit code $exit_code while executing: $failed_command.\n\nPlease review the log at ${LOGFILE}"
+  echo msg
+  notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "${msg}"
+  exit $exit_code
+
 }
 function cleanup_log() {
   rm -f ${LOGFILE}
@@ -27,64 +46,178 @@ function get_set_creds() {
   VPN_CONFIG=/home/kasm-user/vpn.ovpn
 }
 
-# Start VPN based on content
-if [ ! -z ${VPN_CONFIG+x} ]; then
-  if [ "${VPN_CONFIG: -4}" == "conf" ]; then
-    echo "wireguard config detected checking for support"
-    if ip link add dev test type wireguard; then
-      echo "wireguard kernel module is present on this host continuing"
-      ip link del dev test
-    else
-      zenity --error --text="wireguard kernel module is not present on this host and a wireguard config was passed will not continue"
-      echo "wireguard kernel module is not present on this host and a wireguard config was passed will not continue"
-      exit 1
-    fi
-    wg-quick up ${VPN_CONFIG}
+function tailscale_status() {
+  if [ "$SHOW_VPN_STAT" == "1" ]; then
+    tailscale_status=$(tailscale status)
+    notify-send -u critical -t 0 -i "${ICON_SUCCESS}" "Tailscale Status" "${tailscale_status}"
   fi
-  if [ "${VPN_CONFIG: -4}" == "ovpn" ]; then
+}
+
+function ip_status(){
+  if [ "$SHOW_IP_STAT" == "1" ]; then
+    ip_status=$(curl https://ipinfo.io/json)
+    notify-send -u critical -t 0 -i "${ICON_SUCCESS}" "Public IP Status" "${ip_status}"
+  fi
+}
+
+function process_tailscale(){
+
+  local tailscale_key=$1
+
+  if [ ! -c /dev/net/tun ]; then
+    mkdir -p /dev/net
+    mknod /dev/net/tun c 10 200
+  fi
+  tailscaled &
+  sleep 2
+  set +e
+  tailscale up --authkey=${tailscale_key}
+  if [ $? -ne 0 ]; then
+      msg="Failed to establish tailscale connection. Please review the log at ${LOGFILE}"
+      echo msg
+      notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "${msg}"
+      exit 1
+  fi
+  set -e
+
+  notify-send -u critical -t 0 -i "${ICON_SUCCESS}" "VPN Connected!" "Tailscale VPN Connected Successfully"
+  tailscale_status
+  ip_status
+  cleanup_log
+  exit 0
+}
+
+
+function openvpn_status() {
+  if [ "$SHOW_VPN_STAT" == "1" ]; then
+    openvpn_status=$(cat ${OPENVPN_STATUS_LOG})
+    notify-send -u critical -t 0 -i "${ICON_SUCCESS}" "OpenVPN Status" "${openvpn_status}"
+  fi
+}
+
+
+function process_openvpn() {
+  local openvpn_config=$1
+
+   # Create tun device
+  if [ ! -c /dev/net/tun ]; then
+    mkdir -p /dev/net
+    mknod /dev/net/tun c 10 200
+  fi
+  if which resolvconf; then
+    openvpn --pull-filter ignore route-ipv6 --pull-filter ignore ifconfig-ipv6 --config "${openvpn_config}" --status ${OPENVPN_STATUS_LOG} &
+    sleep 10
+    if ! pgrep openvpn; then
+      msg="An error has occurred starting the VPN please review the log at ${LOGFILE}"
+      echo msg
+      notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "${msg}"
+      exit 1
+    else
+      notify-send -u critical -t 0 -i "${ICON_SUCCESS}" "VPN Connected!" "OpenVPN Connected Successfully"
+      openvpn_status
+      ip_status
+      cleanup_log
+      exit 0
+    fi
+  else
+    msg="Resolvconf is not found on this system this container is not compatible with OpenVPN"
+    echo msg
+    notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "${msg}"
+    exit 1
+  fi
+}
+
+function wireguard_status() {
+  if [ "$SHOW_VPN_STAT" == "1" ]; then
+    wg_show=$(wg show)
+    notify-send -u critical -t 0 -i "${ICON_SUCCESS}" "WireGuard Status" "${wg_show}"
+  fi
+}
+
+
+function process_wireguard() {
+
+  local wireguard_conf=$1
+  echo "WireGuard config detected checking for support"
+  if ip link add dev test type wireguard; then
+    echo "WireGuard kernel module is present on this host continuing"
+    ip link del dev test
+  else
+    msg="WireGuard kernel module is not present on this host and a WireGuard config was passed will not continue"
+    echo msg
+    notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "${msg}"
+    exit 1
+  fi
+
+  wg-quick up ${wireguard_conf}
+  if [ $? -ne 0 ]; then
+      msg="Failed to establish WireGuard connection. Please review the log at ${LOGFILE}"
+      echo msg
+      notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "${msg}"
+      exit 1
+  fi
+  notify-send -u critical -t 0 -i "${ICON_SUCCESS}" "VPN Connected!" "WireGuard VPN Connected Successfully"
+  wireguard_status
+  ip_status
+  cleanup_log
+  exit 0
+
+}
+
+notify-send -u critical -t 0  -i "${ICON_OFFLINE}" "Connecting to VPN" "Please wait while the VPN connection is being established..."
+
+VPN_LAUNCH_CONFIG='/dockerstartup/launch_selections.json'
+# Launch Config Based Workflow
+if [ -e ${VPN_LAUNCH_CONFIG} ]; then
+
+  VPN_SERVICE="$(jq -r '.vpn_service' ${VPN_LAUNCH_CONFIG})"
+
+  if [ "${VPN_SERVICE}" == "tailscale" ]; then
+    ts_key="$(jq -r '.tailscale_key' ${VPN_LAUNCH_CONFIG})"
+    process_tailscale $ts_key
+
+  elif [ "${VPN_SERVICE}" == "openvpn" ]; then
+    OPENVPN_USERNAME="$(jq -r '.openvpn_username' ${VPN_LAUNCH_CONFIG})"
+    OPENVPN_PASSWORD="$(jq -r '.openvpn_password' ${VPN_LAUNCH_CONFIG})"
+    echo ${OPENVPN_USERNAME} > ${DEFAULT_OPENVPN_CREDS}
+    echo ${OPENVPN_PASSWORD} >> ${DEFAULT_OPENVPN_CREDS}
+    jq -r '.openvpn_config' ${VPN_LAUNCH_CONFIG} > ${DEFAULT_OPENVPN_CONFIG}
+    sed -i "s#auth-user-pass#auth-user-pass ${DEFAULT_OPENVPN_CREDS}#g" ${DEFAULT_OPENVPN_CONFIG}
+    process_openvpn $DEFAULT_OPENVPN_CONFIG
+
+  elif [ "${VPN_SERVICE}" == "wireguard" ]; then
+    jq -r '.wireguard_config' ${VPN_LAUNCH_CONFIG} > /dockerstartup/wireguard.conf
+    process_wireguard "/dockerstartup/wireguard.conf"
+  else
+    notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "Unknown or missing vpn_service"
+    exit 1
+  fi
+
+else
+
+# File-Mapping/Env Based Workflow
+
+  ### Tailscale ###
+  if [ "${TAILSCALE_KEY:0:5}" == "tskey" ]; then
+    process_tailscale $TAILSCALE_KEY
+
+  ### WireGuard ###
+  elif [ -e ${DEFAULT_WIREGUARD_CONFIG} ]; then
+    process_wireguard $DEFAULT_WIREGUARD_CONFIG
+
+  ### OpenVPN ###
+  elif [ -e ${DEFAULT_OPENVPN_CONFIG} ]; then
+    VPN_CONFIG=$DEFAULT_OPENVPN_CONFIG
     # Check if we need user credentials
     if grep -x auth-user-pass ${VPN_CONFIG}; then
       get_set_creds
     fi
-    # Create tun device
-    if [ ! -c /dev/net/tun ]; then
-      mkdir -p /dev/net
-      mknod /dev/net/tun c 10 200
-    fi
-    if which resolvconf; then
-      openvpn --pull-filter ignore route-ipv6 --pull-filter ignore ifconfig-ipv6 --config "${VPN_CONFIG}" &
-      sleep 10
-      if ! pgrep openvpn; then
-        zenity --error --text="An error has occurred starting the VPN please review the log at ${LOGFILE}"
-	echo "An error has occurred starting the VPN please review the log at ${LOGFILE}"
-	exit 1
-      fi  
-    else
-      zenity --error --text="Resolvconf is not found on this system this container is not compatible with wireguard"
-      echo "Resolvconf is not found on this system this container is not compatible with wireguard"
-      exit 1
-    fi
-  fi
-  if [ "${VPN_CONFIG:0:5}" == "tskey" ]; then
-    # Create tun device
-    if [ ! -c /dev/net/tun ]; then
-      mkdir -p /dev/net
-      mknod /dev/net/tun c 10 200
-    fi
-    tailscaled &
-    sleep 2
-    tailscale up --authkey=${VPN_CONFIG} 
-  fi
-else
-  zenity --error --text="VPN_CONFIG is not defined there is no tunnel to start"
-  echo "VPN_CONFIG is not defined there is no tunnel to start"
-  exit 1
-fi
+    process_openvpn $VPN_CONFIG
 
-# Log success
-zenity \
-  --info \
-  --title "VPN configured" \
-  --text "VPN connected!"
-echo "VPN started using the config file ${VPN_CONFIG}"
-cleanup_log
+  else
+    msg="VPN Config File or TAILSCALE_KEY is not defined"
+    echo msg
+    notify-send -u critical -t 0 -i "${ICON_ERROR}" "VPN Configuration Failed" "${msg}"
+    exit 1
+  fi
+fi