diff --git a/assets/runtime/functions b/assets/runtime/functions
index 60dd0f76..52335880 100644
--- a/assets/runtime/functions
+++ b/assets/runtime/functions
@@ -960,6 +960,25 @@ initialize_datadir() {
   chmod 700 ${GITLAB_DATA_DIR}/.ssh
   chmod 600 ${GITLAB_DATA_DIR}/.ssh/authorized_keys
   chown -R ${GITLAB_USER}: ${GITLAB_DATA_DIR}/.ssh
+
+  # recompile and persist assets when relative_url is in use
+  if [[ -n ${GITLAB_RELATIVE_URL_ROOT} ]]; then
+    mkdir -p ${GITLAB_TEMP_DIR}/cache
+    chmod 755 ${GITLAB_TEMP_DIR}/cache
+    chown ${GITLAB_USER}: ${GITLAB_TEMP_DIR}/cache
+
+    mkdir -p ${GITLAB_TEMP_DIR}/assets
+    chmod 755 ${GITLAB_TEMP_DIR}/assets
+    chown ${GITLAB_USER}: ${GITLAB_TEMP_DIR}/assets
+
+    # symlink ${GITLAB_INSTALL_DIR}/tmp/cache -> ${GITLAB_TEMP_DIR}/cache
+    rm -rf ${GITLAB_INSTALL_DIR}/tmp/cache
+    exec_as_git ln -s ${GITLAB_TEMP_DIR}/cache ${GITLAB_INSTALL_DIR}/tmp/cache
+
+    # symlink ${GITLAB_INSTALL_DIR}/public/assets -> ${GITLAB_TEMP_DIR}/assets
+    rm -rf ${GITLAB_INSTALL_DIR}/public/assets
+    exec_as_git ln -s ${GITLAB_TEMP_DIR}/assets ${GITLAB_INSTALL_DIR}/public/assets
+  fi
 }
 
 sanitize_datadir() {
@@ -1190,8 +1209,14 @@ migrate_database() {
   fi
 
   # clear cache if relative_url has changed.
-  [[ -f ${GITLAB_DATA_DIR}/tmp/GITLAB_RELATIVE_URL_ROOT ]] && CACHE_GITLAB_RELATIVE_URL_ROOT=$(cat ${GITLAB_DATA_DIR}/tmp/GITLAB_RELATIVE_URL_ROOT)
-  if [[ ! -f ${GITLAB_DATA_DIR}/tmp/GITLAB_RELATIVE_URL_ROOT || ${GITLAB_RELATIVE_URL_ROOT} != ${CACHE_GITLAB_RELATIVE_URL_ROOT} ]]; then
+  [[ -f ${GITLAB_TEMP_DIR}/GITLAB_RELATIVE_URL_ROOT ]] && CACHE_GITLAB_RELATIVE_URL_ROOT=$(cat ${GITLAB_TEMP_DIR}/GITLAB_RELATIVE_URL_ROOT)
+  if [[ ! -f ${GITLAB_TEMP_DIR}/GITLAB_RELATIVE_URL_ROOT || ${GITLAB_RELATIVE_URL_ROOT} != ${CACHE_GITLAB_RELATIVE_URL_ROOT} ]]; then
+    # assets need to be recompiled when GITLAB_RELATIVE_URL_ROOT is used
+    if [[ -n ${GITLAB_RELATIVE_URL_ROOT} ]]; then
+      echo "Recompiling assets (relative_url in use), this could take a while..."
+      exec_as_git bundle exec rake assets:clean assets:precompile >/dev/null 2>&1
+    fi
+
     echo "Clearing cache..."
     exec_as_git bundle exec rake cache:clear >/dev/null 2>&1
     echo "${GITLAB_RELATIVE_URL_ROOT}" > ${GITLAB_TEMP_DIR}/GITLAB_RELATIVE_URL_ROOT