diff --git a/elasticsearch/examples/upgrade/Makefile b/elasticsearch/examples/upgrade/Makefile
index 9e1e6fd5e..f890d502c 100644
--- a/elasticsearch/examples/upgrade/Makefile
+++ b/elasticsearch/examples/upgrade/Makefile
@@ -4,17 +4,8 @@ include ../../../helpers/examples.mk
 
 RELEASE := helm-es-upgrade
 
-# Right now the version is hardcoded because helm install will ignore
-# anything with an alpha tag when trying to install the latest release
-# This hardcoding can be removed once we drop the alpha tag
-# The "--set terminationGracePeriod=121" always makes sure that a rolling
-# upgrade is forced for this test
 install:
-	helm repo add elastic https://helm.elastic.co && \
-	helm upgrade --wait --timeout=600 --install $(RELEASE) elastic/elasticsearch --version 7.0.0-alpha1 --set clusterName=upgrade ; \
-	kubectl rollout status sts/upgrade-master --timeout=600s
-	helm upgrade --wait --timeout=600 --set terminationGracePeriod=121 --install $(RELEASE) ../../ --set clusterName=upgrade ; \
-	kubectl rollout status sts/upgrade-master --timeout=600s
+	./scripts/upgrade.sh --release $(RELEASE)
 
 init:
 	helm init --client-only
diff --git a/elasticsearch/examples/upgrade/README.md b/elasticsearch/examples/upgrade/README.md
index adc82ebb1..402979b55 100644
--- a/elasticsearch/examples/upgrade/README.md
+++ b/elasticsearch/examples/upgrade/README.md
@@ -1,19 +1,27 @@
 # Upgrade
 
-This example deploy a 3 nodes Elasticsearch cluster using [7.0.0-alpha1][] chart
-version, then upgrade it to 7.8.0-SNAPSHOT version.
+This example will deploy a 3 node Elasticsearch cluster using an old chart version,
+then upgrade it to version 7.8.0-SNAPSHOT.
+
+The following upgrades are tested:
+- Upgrade from [7.0.0-alpha1][] version on K8S <1.16
+- Upgrade from [7.4.0][] version on K8S >=1.16 (Elasticsearch chart < 7.4.0 are
+not compatible with K8S >= 1.16)
 
 
 ## Usage
 
-Running `make install` command will do both 7.0.0-alpha1 install and 7.8.0-SNAPSHOT
-upgrade
+Running `make install` command will do first install and 7.8.0-SNAPSHOT upgrade.
+
+Note: [jq][] is a requirement for this make target.
 
 
 ## Testing
 
-You can also run [goss integration tests][] using `make test`
+You can also run [goss integration tests][] using `make test`.
 
 
 [7.0.0-alpha1]: https://github.com/elastic/helm-charts/releases/tag/7.0.0-alpha1
+[7.4.0]: https://github.com/elastic/helm-charts/releases/tag/7.4.0
 [goss integration tests]: https://github.com/elastic/helm-charts/tree/7.x/elasticsearch/examples/upgrade/test/goss.yaml
+[jq]: https://stedolan.github.io/jq/
diff --git a/elasticsearch/examples/upgrade/scripts/upgrade.sh b/elasticsearch/examples/upgrade/scripts/upgrade.sh
new file mode 100755
index 000000000..6d0aa9ffc
--- /dev/null
+++ b/elasticsearch/examples/upgrade/scripts/upgrade.sh
@@ -0,0 +1,76 @@
+#!/usr/bin/env bash
+
+set -euo pipefail
+
+usage() {
+  cat <<-EOF
+	USAGE:
+	  $0 [--release <release-name>] [--from <elasticsearch-version>]
+	  $0 --help
+
+	OPTIONS:
+	  --release <release-name>
+	    Name of the Helm release to install
+	  --from <elasticsearch-version>
+	    Elasticsearch version to use for first install
+	EOF
+  exit 1
+}
+
+RELEASE="helm-es-upgrade"
+FROM=""
+
+while [[ $# -gt 0 ]]
+do
+  key="$1"
+
+  case $key in
+    --help)
+      usage
+    ;;
+    --release)
+      RELEASE="$2"
+      shift 2
+    ;;
+    --from)
+      FROM="$2"
+      shift 2
+    ;;
+    *)
+      log "Unrecognized argument: '$key'"
+      usage
+    ;;
+  esac
+done
+
+if ! command -v jq > /dev/null
+then
+  echo 'jq is required to use this script'
+  echo 'please check https://stedolan.github.io/jq/download/ to install it'
+  exit 1
+fi
+
+# Elasticsearch chart < 7.4.0 are not compatible with K8S >= 1.16)
+if [[ -z $FROM ]]
+then
+  KUBE_MINOR_VERSION=$(kubectl version -o json | jq --raw-output --exit-status '.serverVersion.minor' | sed 's/[^0-9]*//g')
+
+  if [ "$KUBE_MINOR_VERSION" -lt 16 ]
+  then
+    FROM="7.0.0-alpha1"
+  else
+    FROM="7.4.0"
+  fi
+fi
+
+helm repo add elastic https://helm.elastic.co
+
+# Initial install
+printf "Installing Elasticsearch chart %s\n" "$FROM"
+helm upgrade --wait --timeout=600 --install "$RELEASE" elastic/elasticsearch --version "$FROM" --set clusterName=upgrade
+kubectl rollout status sts/upgrade-master --timeout=600s
+
+# Upgrade
+printf "Upgrading Elasticsearch chart\n"
+helm upgrade --wait --timeout=600 --set terminationGracePeriod=121 --install "$RELEASE" ../../ --set clusterName=upgrade
+kubectl rollout status sts/upgrade-master --timeout=600s
diff --git a/helpers/matrix.yml b/helpers/matrix.yml
index 3a5871aad..aaba651f9 100644
--- a/helpers/matrix.yml
+++ b/helpers/matrix.yml
@@ -34,3 +34,4 @@ APM_SERVER_SUITE:
 KUBERNETES_VERSION:
   - '1.14'
   - '1.15'
+  - '1.16'
diff --git a/helpers/terraform/Dockerfile b/helpers/terraform/Dockerfile
index 3c0294060..09057aca0 100644
--- a/helpers/terraform/Dockerfile
+++ b/helpers/terraform/Dockerfile
@@ -2,9 +2,10 @@ FROM centos:7
 
 ENV VAULT_VERSION 0.9.3
 ENV TERRAFORM_VERSION=0.11.7
-ENV KUBECTL_VERSION=1.15.4
+ENV KUBECTL_VERSION=1.16.10
 ENV HELM_VERSION=2.16.7
 ENV DOCKER_VERSION=18.09.7
+ENV JQ_VERSION=1.6
 
 RUN yum -y install \
     make \
@@ -44,3 +45,8 @@ RUN curl -O https://download.docker.com/linux/static/stable/x86_64/docker-${DOCK
     mv docker/docker /usr/local/bin && \
     rm -rf docker/ && \
     docker
+
+RUN curl -O -L https://github.com/stedolan/jq/releases/download/jq-${JQ_VERSION}/jq-linux64 && \
+    mv jq-linux64 /usr/local/bin/jq && \
+    chmod a+x /usr/local/bin/jq && \
+    jq --version