diff --git a/.gitlab-ci.yml b/.gitlab-ci.yml
index 309043e..16cae83 100644
--- a/.gitlab-ci.yml
+++ b/.gitlab-ci.yml
@@ -67,9 +67,12 @@ ruby-2.6-golang-1.14-git-2.28-pgbouncer-1.14 test: *test_custom
 # Used by GitLab: https://gitlab.com/gitlab-org/gitlab/blob/master/.gitlab-ci.yml
 ruby-2.6.6-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-11-graphicsmagick-1.3.34 test: *test_custom
 ruby-2.6.6-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-12-graphicsmagick-1.3.34 test: *test_custom
+ruby-2.7.1-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-11-graphicsmagick-1.3.34 test: *test_custom
+ruby-2.7.1-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-12-graphicsmagick-1.3.34 test: *test_custom
 
 # Used by GitLab's compile-production-assets and compile-test-assets jobs
 ruby-2.6.6-git-2.28-lfs-2.9-node-12.x-yarn-1.21-graphicsmagick-1.3.34 test: *test_custom
+ruby-2.7.1-git-2.28-lfs-2.9-node-12.x-yarn-1.21-graphicsmagick-1.3.34 test: *test_custom
 
 # Used by www-gitlab-com's rspec job: https://gitlab.com/gitlab-com/www-gitlab-com/blob/master/.gitlab-ci.yml
 ruby-2.6.5-git-2.28-chrome-74.0-node-12.x-yarn-1.21-docker-19.03.1 test: *test_custom
@@ -125,9 +128,12 @@ ruby-2.6-golang-1.14-git-2.28-pgbouncer-1.14: *build_and_deploy_custom
 # Used by GitLab CE/EE: https://gitlab.com/gitlab-org/gitlab-ee/blob/master/.gitlab-ci.yml
 ruby-2.6.6-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-11-graphicsmagick-1.3.34: *build_and_deploy_custom
 ruby-2.6.6-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-12-graphicsmagick-1.3.34: *build_and_deploy_custom
+ruby-2.7.1-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-11-graphicsmagick-1.3.34: *build_and_deploy_custom
+ruby-2.7.1-golang-1.14-git-2.28-lfs-2.9-chrome-84-node-12.x-yarn-1.21-postgresql-12-graphicsmagick-1.3.34: *build_and_deploy_custom
 
 # Used by GitLab's compile-production-assets and compile-test-assets jobs
 ruby-2.6.6-git-2.28-lfs-2.9-node-12.x-yarn-1.21-graphicsmagick-1.3.34: *build_and_deploy_custom
+ruby-2.7.1-git-2.28-lfs-2.9-node-12.x-yarn-1.21-graphicsmagick-1.3.34: *build_and_deploy_custom
 
 # Used by www-gitlab-com's rspec job: https://gitlab.com/gitlab-com/www-gitlab-com/blob/master/.gitlab-ci.yml
 ruby-2.6.5-git-2.28-chrome-74.0-node-12.x-yarn-1.21-docker-19.03.1: *build_and_deploy_custom
diff --git a/scripts/custom-docker-build b/scripts/custom-docker-build
index f541a96..050cf51 100755
--- a/scripts/custom-docker-build
+++ b/scripts/custom-docker-build
@@ -213,9 +213,17 @@ function parse_arguments() {
     read base
     read base_version
 
-    # Lock Ruby to Debian stretch
+    # Lock Ruby to Debian version to pin OpenSSL version
     case "$base" in
-        ruby) base_version="$base_version-stretch" ;;
+        ruby)
+            case "$base_version" in
+                2.6.*)
+                    base_version="$base_version-stretch"
+                    ;;
+                *)
+                    base_version="$base_version-buster"
+                    ;;
+            esac
     esac
 
     printf -- "-f Dockerfile.custom " "$base"
diff --git a/scripts/install-essentials b/scripts/install-essentials
index 17692c3..ea0d473 100755
--- a/scripts/install-essentials
+++ b/scripts/install-essentials
@@ -6,15 +6,31 @@ IFS=$'\n\t'
 export DEBIAN_FRONTEND=noninteractive
 
 apt-get update
-apt-get install -y \
-	curl wget build-essential apt-utils locales \
-	libssl-dev libyaml-dev libreadline6-dev zlib1g-dev \
-	libncurses5-dev libffi-dev libgdbm3 libgdbm-dev \
-	ca-certificates libyaml-dev checkinstall libxml2-dev \
-	libxslt-dev libcurl4-openssl-dev libicu-dev \
-	logrotate python-docutils pkg-config cmake nodejs \
-	libkrb5-dev postgresql-client mysql-client unzip \
-	libre2-dev gettext rsync \
+
+EXIT_CODE=0
+grep "Debian GNU/Linux 9" /etc/issue || EXIT_CODE=$?
+
+if [ $EXIT_CODE -eq 0 ]
+then
+    apt-get install -y \
+            curl wget build-essential apt-utils locales \
+            libssl-dev libyaml-dev libreadline6-dev zlib1g-dev \
+            libncurses5-dev libffi-dev libgdbm3 libgdbm-dev \
+            ca-certificates libyaml-dev checkinstall libxml2-dev \
+            libxslt-dev libcurl4-openssl-dev libicu-dev \
+            logrotate python-docutils pkg-config cmake nodejs \
+            libkrb5-dev postgresql-client mysql-client unzip \
+            libre2-dev gettext rsync
+else
+    apt-get install -y \
+            curl wget build-essential apt-utils locales \
+            libssl-dev libyaml-dev libreadline-dev zlib1g-dev \
+            libncurses5-dev libffi-dev ca-certificates libyaml-dev libxml2-dev \
+            libxslt1-dev libcurl4-openssl-dev libicu-dev \
+            logrotate python-docutils pkg-config cmake \
+            libkrb5-dev postgresql-client unzip \
+            libre2-dev gettext rsync
+fi
 
 # Set UTF-8
 # http://stackoverflow.com/a/3182519/2137281