diff --git a/docker-compose.yml b/docker-compose.yml
index c31e71404..b2316da09 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -23,11 +23,13 @@ services:
     build:
       context: .
       dockerfile: docker/Dockerfile.rails
-    command: bundle exec thin start -p 3000 --ssl --ssl-key-file dev_server_keys/server.key --ssl-cert-file dev_server_keys/server.crt
+    command: bash docker/rails_entry.sh
+    environment:
+       BUNDLE_PATH: "/bundle"
     ports:
       - "3000:3000"
     volumes:
-      - rails-app-sync:/app/app:nocopy
+      - rails-app-sync:/project_root:nocopy
     depends_on:
       - mysql
       - jetty
diff --git a/docker-sync.yml b/docker-sync.yml
index 1b546fbbe..197e4ef86 100644
--- a/docker-sync.yml
+++ b/docker-sync.yml
@@ -4,6 +4,5 @@ options:
   verbose: true
 syncs:
   rails-app-sync: # tip: add -sync and you keep consistent names as a convention
-    src: './app'
-    # sync_strategy: 'native_osx' # not needed, this is the default now
-    sync_excludes: ['ignored_folder', '.ignored_dot_folder']
+    src: '.'
+    sync_excludes: ['.git', 'tmp', 'jetty', 'vendor/bundle']
diff --git a/docker/Dockerfile.rails b/docker/Dockerfile.rails
index 621a33278..62d1e2e64 100644
--- a/docker/Dockerfile.rails
+++ b/docker/Dockerfile.rails
@@ -1,9 +1,17 @@
 FROM ruby:2.1.10
 
 RUN apt-get update -qq && apt-get install -y build-essential libpq-dev nodejs
-RUN mkdir /app
 
-WORKDIR /app
-COPY . /app
+# Put the installed gems outside of project_root so that the sync volume won't interfere
+RUN mkdir /bundle
+COPY Gemfile /bundle
+COPY Gemfile.lock /bundle
+WORKDIR /bundle
+RUN bundle install  --without headless --path /bundle
 
-RUN bundle install  --without headless
+RUN mkdir /project_root
+WORKDIR /project_root
+COPY . /project_root
+
+# Gemfile.lock may have changed after bundling, copy it back into the project_root
+RUN cp /bundle/Gemfile.lock /project_root/
diff --git a/docker/rails_entry.sh b/docker/rails_entry.sh
new file mode 100755
index 000000000..039fa9b23
--- /dev/null
+++ b/docker/rails_entry.sh
@@ -0,0 +1,7 @@
+# All the things that will execute when starting the rails service
+# Copy the generated lock file back into the project root. This is to sync this change back to the
+# application after the container has mounted the sync volume
+cp /bundle/Gemfile.lock ./
+bash docker/wait-for-it.sh mysql:3306
+bundle exec rake db:schema:load
+bundle exec thin start -p 3000 --ssl --ssl-key-file dev_server_keys/server.key --ssl-cert-file dev_server_keys/server.crt
diff --git a/docker/wait-for-it.sh b/docker/wait-for-it.sh
new file mode 100755
index 000000000..bbe404324
--- /dev/null
+++ b/docker/wait-for-it.sh
@@ -0,0 +1,177 @@
+#!/usr/bin/env bash
+#   Use this script to test if a given TCP host/port are available
+
+cmdname=$(basename $0)
+
+echoerr() { if [[ $QUIET -ne 1 ]]; then echo "$@" 1>&2; fi }
+
+usage()
+{
+    cat << USAGE >&2
+Usage:
+    $cmdname host:port [-s] [-t timeout] [-- command args]
+    -h HOST | --host=HOST       Host or IP under test
+    -p PORT | --port=PORT       TCP port under test
+                                Alternatively, you specify the host and port as host:port
+    -s | --strict               Only execute subcommand if the test succeeds
+    -q | --quiet                Don't output any status messages
+    -t TIMEOUT | --timeout=TIMEOUT
+                                Timeout in seconds, zero for no timeout
+    -- COMMAND ARGS             Execute command with args after the test finishes
+USAGE
+    exit 1
+}
+
+wait_for()
+{
+    if [[ $TIMEOUT -gt 0 ]]; then
+        echoerr "$cmdname: waiting $TIMEOUT seconds for $HOST:$PORT"
+    else
+        echoerr "$cmdname: waiting for $HOST:$PORT without a timeout"
+    fi
+    start_ts=$(date +%s)
+    while :
+    do
+        if [[ $ISBUSY -eq 1 ]]; then
+            nc -z $HOST $PORT
+            result=$?
+        else
+            (echo > /dev/tcp/$HOST/$PORT) >/dev/null 2>&1
+            result=$?
+        fi
+        if [[ $result -eq 0 ]]; then
+            end_ts=$(date +%s)
+            echoerr "$cmdname: $HOST:$PORT is available after $((end_ts - start_ts)) seconds"
+            break
+        fi
+        sleep 1
+    done
+    return $result
+}
+
+wait_for_wrapper()
+{
+    # In order to support SIGINT during timeout: http://unix.stackexchange.com/a/57692
+    if [[ $QUIET -eq 1 ]]; then
+        timeout $BUSYTIMEFLAG $TIMEOUT $0 --quiet --child --host=$HOST --port=$PORT --timeout=$TIMEOUT &
+    else
+        timeout $BUSYTIMEFLAG $TIMEOUT $0 --child --host=$HOST --port=$PORT --timeout=$TIMEOUT &
+    fi
+    PID=$!
+    trap "kill -INT -$PID" INT
+    wait $PID
+    RESULT=$?
+    if [[ $RESULT -ne 0 ]]; then
+        echoerr "$cmdname: timeout occurred after waiting $TIMEOUT seconds for $HOST:$PORT"
+    fi
+    return $RESULT
+}
+
+# process arguments
+while [[ $# -gt 0 ]]
+do
+    case "$1" in
+        *:* )
+        hostport=(${1//:/ })
+        HOST=${hostport[0]}
+        PORT=${hostport[1]}
+        shift 1
+        ;;
+        --child)
+        CHILD=1
+        shift 1
+        ;;
+        -q | --quiet)
+        QUIET=1
+        shift 1
+        ;;
+        -s | --strict)
+        STRICT=1
+        shift 1
+        ;;
+        -h)
+        HOST="$2"
+        if [[ $HOST == "" ]]; then break; fi
+        shift 2
+        ;;
+        --host=*)
+        HOST="${1#*=}"
+        shift 1
+        ;;
+        -p)
+        PORT="$2"
+        if [[ $PORT == "" ]]; then break; fi
+        shift 2
+        ;;
+        --port=*)
+        PORT="${1#*=}"
+        shift 1
+        ;;
+        -t)
+        TIMEOUT="$2"
+        if [[ $TIMEOUT == "" ]]; then break; fi
+        shift 2
+        ;;
+        --timeout=*)
+        TIMEOUT="${1#*=}"
+        shift 1
+        ;;
+        --)
+        shift
+        CLI=("$@")
+        break
+        ;;
+        --help)
+        usage
+        ;;
+        *)
+        echoerr "Unknown argument: $1"
+        usage
+        ;;
+    esac
+done
+
+if [[ "$HOST" == "" || "$PORT" == "" ]]; then
+    echoerr "Error: you need to provide a host and port to test."
+    usage
+fi
+
+TIMEOUT=${TIMEOUT:-15}
+STRICT=${STRICT:-0}
+CHILD=${CHILD:-0}
+QUIET=${QUIET:-0}
+
+# check to see if timeout is from busybox?
+# check to see if timeout is from busybox?
+TIMEOUT_PATH=$(realpath $(which timeout))
+if [[ $TIMEOUT_PATH =~ "busybox" ]]; then
+        ISBUSY=1
+        BUSYTIMEFLAG="-t"
+else
+        ISBUSY=0
+        BUSYTIMEFLAG=""
+fi
+
+if [[ $CHILD -gt 0 ]]; then
+    wait_for
+    RESULT=$?
+    exit $RESULT
+else
+    if [[ $TIMEOUT -gt 0 ]]; then
+        wait_for_wrapper
+        RESULT=$?
+    else
+        wait_for
+        RESULT=$?
+    fi
+fi
+
+if [[ $CLI != "" ]]; then
+    if [[ $RESULT -ne 0 && $STRICT -eq 1 ]]; then
+        echoerr "$cmdname: strict mode, refusing to execute subprocess"
+        exit $RESULT
+    fi
+    exec "${CLI[@]}"
+else
+    exit $RESULT
+fi