diff --git a/Changelog.md b/Changelog.md
index 70e7ebb0..36ff225d 100644
--- a/Changelog.md
+++ b/Changelog.md
@@ -2,6 +2,9 @@
 
 This file only reflects the changes that are made in the the docker image. Please refer to the upstream GitLab [CHANGELOG](https://github.com/gitlabhq/gitlabhq/blob/master/CHANGELOG) for the list of changes in GitLab.
 
+**latest**
+- Recompile assets when `GITLAB_RELATIVE_URL_ROOT` is used Fixes #481
+
 **8.1.0-1**
 - temporary fix for http/https cloning when `GITLAB_RELATIVE_URL_ROOT` is used
 
diff --git a/entrypoint.sh b/entrypoint.sh
index 5708f361..846c6bcf 100755
--- a/entrypoint.sh
+++ b/entrypoint.sh
@@ -789,6 +789,14 @@ fi
 # configure relative_url_root
 sed 's,{{GITLAB_RELATIVE_URL_ROOT}},'"${GITLAB_RELATIVE_URL_ROOT}"',' -i /etc/supervisor/conf.d/gitlab-git-http-server.conf
 if [[ -n ${GITLAB_RELATIVE_URL_ROOT} ]]; then
+  # create symlink to assets in tmp/cache
+  rm -rf tmp/cache
+  sudo -HEu ${GITLAB_USER} ln -s ${GITLAB_DATA_DIR}/tmp/cache tmp/cache
+
+  # create symlink to assets in public/assets
+  rm -rf public/assets
+  sudo -HEu ${GITLAB_USER} ln -s ${GITLAB_DATA_DIR}/tmp/public/assets public/assets
+
   sed 's,{{GITLAB_RELATIVE_URL_ROOT__with_trailing_slash}},'"${GITLAB_RELATIVE_URL_ROOT}/"',' -i /etc/nginx/sites-enabled/gitlab
   sed 's,# alias'"${GITLAB_INSTALL_DIR}"'/public,alias '"${GITLAB_INSTALL_DIR}"'/public,' -i /etc/nginx/sites-enabled/gitlab
 
@@ -923,8 +931,18 @@ appInit () {
     rm -rf ${GITLAB_DATA_DIR}/tmp
     sudo -HEu ${GITLAB_USER} mkdir -p ${GITLAB_DATA_DIR}/tmp/
 
-    # clear the cache
-    sudo -HEu ${GITLAB_USER} bundle exec rake cache:clear >/dev/null 2>&1
+    # assets need to be recompiled when GITLAB_RELATIVE_URL_ROOT is used
+    if [[ -n ${GITLAB_RELATIVE_URL_ROOT} ]]; then
+      # create the tmp/cache and tmp/public/assets directory
+      sudo -HEu ${GITLAB_USER} mkdir -p ${GITLAB_DATA_DIR}/tmp/cache/
+      sudo -HEu ${GITLAB_USER} mkdir -p ${GITLAB_DATA_DIR}/tmp/public/assets/
+
+      echo "GITLAB_RELATIVE_URL_ROOT in use, recompiling assets, this could take a while..."
+      sudo -HEu ${GITLAB_USER} bundle exec rake assets:clean assets:precompile cache:clear >/dev/null 2>&1
+    else
+      # clear the cache
+      sudo -HEu ${GITLAB_USER} bundle exec rake cache:clear >/dev/null 2>&1
+    fi
 
     # update VERSION information
     sudo -HEu ${GITLAB_USER} echo "${GITLAB_VERSION}" > ${GITLAB_DATA_DIR}/tmp/VERSION