diff --git a/app/models/clusters/concerns/application_status.rb b/app/models/clusters/concerns/application_status.rb
index 93bdf9c223d..712dc901795 100644
--- a/app/models/clusters/concerns/application_status.rb
+++ b/app/models/clusters/concerns/application_status.rb
@@ -64,6 +64,10 @@ module Clusters
             status_reason = transition.args.first
             app_status.status_reason = status_reason if status_reason
           end
+
+          before_transition any => [:installed, :updated] do |app_status, _|
+            app_status.cluster.application_helm.update!(version: Gitlab::Kubernetes::Helm::HELM_VERSION)
+          end
         end
       end
 
diff --git a/changelogs/unreleased/49726-upgrade-helm-to-2-11.yml b/changelogs/unreleased/49726-upgrade-helm-to-2-11.yml
new file mode 100644
index 00000000000..dd26af875f5
--- /dev/null
+++ b/changelogs/unreleased/49726-upgrade-helm-to-2-11.yml
@@ -0,0 +1,5 @@
+---
+title: Upgrade helm to 2.11.0 and upgrade on every install
+merge_request: 22693
+author:
+type: added
diff --git a/doc/user/project/clusters/index.md b/doc/user/project/clusters/index.md
index 3fbd4c21eab..1d1de01c120 100644
--- a/doc/user/project/clusters/index.md
+++ b/doc/user/project/clusters/index.md
@@ -230,6 +230,10 @@ twice, which can lead to confusion during deployments.
 | [JupyterHub](http://jupyter.org/) | 11.0+ | [JupyterHub](https://jupyterhub.readthedocs.io/en/stable/) is a multi-user service for managing notebooks across a team. [Jupyter Notebooks](https://jupyter-notebook.readthedocs.io/en/latest/) provide a web-based interactive programming environment used for data analysis, visualization, and machine learning. We use [this](https://gitlab.com/gitlab-org/jupyterhub-user-image/blob/master/Dockerfile) custom Jupyter image that installs additional useful packages on top of the base Jupyter. You will also see ready-to-use DevOps Runbooks built with Nurtch's [Rubix library](https://github.com/amit1rrr/rubix). More information on creating executable runbooks can be found at [Nurtch Documentation](http://docs.nurtch.com/en/latest).  **Note**: Authentication will be enabled for any user of the GitLab server via OAuth2. HTTPS will be supported in a future release. | [jupyter/jupyterhub](https://jupyterhub.github.io/helm-chart/) |
 | [Knative](https://cloud.google.com/knative) | 0.1.2 | Knative provides a platform to create, deploy, and manage serverless workloads from a Kubernetes cluster. It is used in conjunction with, and includes [Istio](https://istio.io) to provide an external IP address for all programs hosted by Knative. You will be prompted to enter a wildcard domain where your applications will be exposed. Configure your DNS server to use the external IP address for that domain. For any application created and installed, they will be accessible as <program_name>.<kubernetes_namespace>.<domain_name>.  **Note**: This will require your kubernetes cluster to have RBAC enabled. | [knative/knative](https://storage.googleapis.com/triggermesh-charts)
 
+NOTE: **Note:**
+As of GitLab 11.6 Helm Tiller will be upgraded to the latest version supported
+by GitLab before installing any of the above applications.
+
 ## Getting the external IP address
 
 NOTE: **Note:**
diff --git a/lib/gitlab/kubernetes/helm.rb b/lib/gitlab/kubernetes/helm.rb
index 1cd4f9e17b7..5a22b5e3364 100644
--- a/lib/gitlab/kubernetes/helm.rb
+++ b/lib/gitlab/kubernetes/helm.rb
@@ -1,7 +1,7 @@
 module Gitlab
   module Kubernetes
     module Helm
-      HELM_VERSION = '2.7.2'.freeze
+      HELM_VERSION = '2.11.0'.freeze
       KUBECTL_VERSION = '1.11.0'.freeze
       NAMESPACE = 'gitlab-managed-apps'.freeze
       SERVICE_ACCOUNT = 'tiller'.freeze
diff --git a/lib/gitlab/kubernetes/helm/install_command.rb b/lib/gitlab/kubernetes/helm/install_command.rb
index ff1c1657b98..5c7b6d6cb75 100644
--- a/lib/gitlab/kubernetes/helm/install_command.rb
+++ b/lib/gitlab/kubernetes/helm/install_command.rb
@@ -20,6 +20,10 @@ module Gitlab
         def generate_script
           super + [
             init_command,
+            # Sleep is necessary to give Tiller time to restart after upgrade.
+            # Ideally we'd be able to use --wait but cannot because of
+            # https://github.com/helm/helm/issues/4855
+            sleep_command,
             repository_command,
             repository_update_command,
             preinstall_command,
@@ -35,7 +39,11 @@ module Gitlab
         private
 
         def init_command
-          'helm init --client-only'
+          'helm init --upgrade --tiller-namespace gitlab-managed-apps'
+        end
+
+        def sleep_command
+          'sleep 30'
         end
 
         def repository_command
diff --git a/lib/gitlab/kubernetes/helm/upgrade_command.rb b/lib/gitlab/kubernetes/helm/upgrade_command.rb
index b36315f7a82..5b47944e5e6 100644
--- a/lib/gitlab/kubernetes/helm/upgrade_command.rb
+++ b/lib/gitlab/kubernetes/helm/upgrade_command.rb
@@ -20,6 +20,10 @@ module Gitlab
         def generate_script
           super + [
             init_command,
+            # Sleep is necessary to give Tiller time to restart after upgrade.
+            # Ideally we'd be able to use --wait but cannot because of
+            # https://github.com/helm/helm/issues/4855
+            sleep_command,
             repository_command,
             script_command
           ].compact.join("\n")
@@ -36,7 +40,11 @@ module Gitlab
         private
 
         def init_command
-          'helm init --client-only'
+          'helm init --upgrade --tiller-namespace gitlab-managed-apps'
+        end
+
+        def sleep_command
+          'sleep 30'
         end
 
         def repository_command
diff --git a/spec/lib/gitlab/kubernetes/helm/install_command_spec.rb b/spec/lib/gitlab/kubernetes/helm/install_command_spec.rb
index 2b7e3ea6def..9fa47f9a264 100644
--- a/spec/lib/gitlab/kubernetes/helm/install_command_spec.rb
+++ b/spec/lib/gitlab/kubernetes/helm/install_command_spec.rb
@@ -26,7 +26,8 @@ describe Gitlab::Kubernetes::Helm::InstallCommand do
   it_behaves_like 'helm commands' do
     let(:commands) do
       <<~EOS
-      helm init --client-only
+      helm init --upgrade --tiller-namespace gitlab-managed-apps
+      sleep 30
       helm repo add app-name https://repository.example.com
       helm repo update
       #{helm_install_comand}
@@ -54,7 +55,8 @@ describe Gitlab::Kubernetes::Helm::InstallCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-        helm init --client-only
+        helm init --upgrade --tiller-namespace gitlab-managed-apps
+        sleep 30
         helm repo add app-name https://repository.example.com
         helm repo update
         #{helm_install_command}
@@ -84,7 +86,8 @@ describe Gitlab::Kubernetes::Helm::InstallCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-        helm init --client-only
+        helm init --upgrade --tiller-namespace gitlab-managed-apps
+        sleep 30
         #{helm_install_command}
         EOS
       end
@@ -111,7 +114,8 @@ describe Gitlab::Kubernetes::Helm::InstallCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-        helm init --client-only
+        helm init --upgrade --tiller-namespace gitlab-managed-apps
+        sleep 30
         helm repo add app-name https://repository.example.com
         helm repo update
         #{helm_install_command}
@@ -134,7 +138,8 @@ describe Gitlab::Kubernetes::Helm::InstallCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-        helm init --client-only
+        helm init --upgrade --tiller-namespace gitlab-managed-apps
+        sleep 30
         helm repo add app-name https://repository.example.com
         helm repo update
         #{helm_install_command}
@@ -157,7 +162,8 @@ describe Gitlab::Kubernetes::Helm::InstallCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-        helm init --client-only
+        helm init --upgrade --tiller-namespace gitlab-managed-apps
+        sleep 30
         helm repo add app-name https://repository.example.com
         helm repo update
         #{helm_install_command}
@@ -182,7 +188,8 @@ describe Gitlab::Kubernetes::Helm::InstallCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-        helm init --client-only
+        helm init --upgrade --tiller-namespace gitlab-managed-apps
+        sleep 30
         helm repo add app-name https://repository.example.com
         helm repo update
         #{helm_install_command}
diff --git a/spec/lib/gitlab/kubernetes/helm/pod_spec.rb b/spec/lib/gitlab/kubernetes/helm/pod_spec.rb
index c92bc92c42d..2dd3a570a1d 100644
--- a/spec/lib/gitlab/kubernetes/helm/pod_spec.rb
+++ b/spec/lib/gitlab/kubernetes/helm/pod_spec.rb
@@ -30,7 +30,7 @@ describe Gitlab::Kubernetes::Helm::Pod do
       it 'should generate the appropriate specifications for the container' do
         container = subject.generate.spec.containers.first
         expect(container.name).to eq('helm')
-        expect(container.image).to eq('registry.gitlab.com/gitlab-org/cluster-integration/helm-install-image/releases/2.7.2-kube-1.11.0')
+        expect(container.image).to eq('registry.gitlab.com/gitlab-org/cluster-integration/helm-install-image/releases/2.11.0-kube-1.11.0')
         expect(container.env.count).to eq(3)
         expect(container.env.map(&:name)).to match_array([:HELM_VERSION, :TILLER_NAMESPACE, :COMMAND_SCRIPT])
         expect(container.command).to match_array(["/bin/sh"])
diff --git a/spec/lib/gitlab/kubernetes/helm/upgrade_command_spec.rb b/spec/lib/gitlab/kubernetes/helm/upgrade_command_spec.rb
index 9c9fc91ef3c..afc926abc27 100644
--- a/spec/lib/gitlab/kubernetes/helm/upgrade_command_spec.rb
+++ b/spec/lib/gitlab/kubernetes/helm/upgrade_command_spec.rb
@@ -21,7 +21,8 @@ describe Gitlab::Kubernetes::Helm::UpgradeCommand do
   it_behaves_like 'helm commands' do
     let(:commands) do
       <<~EOS
-         helm init --client-only
+         helm init --upgrade --tiller-namespace gitlab-managed-apps
+         sleep 30
          helm upgrade #{application.name} #{application.chart} --tls --tls-ca-cert /data/helm/#{application.name}/config/ca.pem --tls-cert /data/helm/#{application.name}/config/cert.pem --tls-key /data/helm/#{application.name}/config/key.pem --reset-values --install --namespace #{namespace} -f /data/helm/#{application.name}/config/values.yaml
       EOS
     end
@@ -33,7 +34,8 @@ describe Gitlab::Kubernetes::Helm::UpgradeCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-         helm init --client-only
+         helm init --upgrade --tiller-namespace gitlab-managed-apps
+         sleep 30
          helm upgrade #{application.name} #{application.chart} --tls --tls-ca-cert /data/helm/#{application.name}/config/ca.pem --tls-cert /data/helm/#{application.name}/config/cert.pem --tls-key /data/helm/#{application.name}/config/key.pem --reset-values --install --namespace #{namespace} -f /data/helm/#{application.name}/config/values.yaml
         EOS
       end
@@ -56,7 +58,8 @@ describe Gitlab::Kubernetes::Helm::UpgradeCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-           helm init --client-only
+           helm init --upgrade --tiller-namespace gitlab-managed-apps
+           sleep 30
            helm repo add #{application.name} #{application.repository}
            helm upgrade #{application.name} #{application.chart} --tls --tls-ca-cert /data/helm/#{application.name}/config/ca.pem --tls-cert /data/helm/#{application.name}/config/cert.pem --tls-key /data/helm/#{application.name}/config/key.pem --reset-values --install --namespace #{namespace} -f /data/helm/#{application.name}/config/values.yaml
         EOS
@@ -70,7 +73,8 @@ describe Gitlab::Kubernetes::Helm::UpgradeCommand do
     it_behaves_like 'helm commands' do
       let(:commands) do
         <<~EOS
-         helm init --client-only
+         helm init --upgrade --tiller-namespace gitlab-managed-apps
+         sleep 30
          helm upgrade #{application.name} #{application.chart} --reset-values --install --namespace #{namespace} -f /data/helm/#{application.name}/config/values.yaml
         EOS
       end
diff --git a/spec/models/clusters/applications/prometheus_spec.rb b/spec/models/clusters/applications/prometheus_spec.rb
index 86de9dc60f2..b5aa1dcece5 100644
--- a/spec/models/clusters/applications/prometheus_spec.rb
+++ b/spec/models/clusters/applications/prometheus_spec.rb
@@ -35,7 +35,7 @@ describe Clusters::Applications::Prometheus do
 
   describe 'transition to installed' do
     let(:project) { create(:project) }
-    let(:cluster) { create(:cluster, projects: [project]) }
+    let(:cluster) { create(:cluster, :with_installed_helm, projects: [project]) }
     let(:prometheus_service) { double('prometheus_service') }
 
     subject { create(:clusters_applications_prometheus, :installing, cluster: cluster) }
diff --git a/spec/support/shared_examples/models/cluster_application_status_shared_examples.rb b/spec/support/shared_examples/models/cluster_application_status_shared_examples.rb
index 82f0dd5d00f..c391cc48f4e 100644
--- a/spec/support/shared_examples/models/cluster_application_status_shared_examples.rb
+++ b/spec/support/shared_examples/models/cluster_application_status_shared_examples.rb
@@ -44,10 +44,40 @@ shared_examples 'cluster application status specs' do |application_name|
       subject { create(application_name, :installing) }
 
       it 'is installed' do
-        subject.make_installed
+        subject.make_installed!
 
         expect(subject).to be_installed
       end
+
+      it 'updates helm version' do
+        subject.cluster.application_helm.update!(version: '1.2.3')
+
+        subject.make_installed!
+
+        subject.cluster.application_helm.reload
+
+        expect(subject.cluster.application_helm.version).to eq(Gitlab::Kubernetes::Helm::HELM_VERSION)
+      end
+    end
+
+    describe '#make_updated' do
+      subject { create(application_name, :updating) }
+
+      it 'is updated' do
+        subject.make_updated!
+
+        expect(subject).to be_updated
+      end
+
+      it 'updates helm version' do
+        subject.cluster.application_helm.update!(version: '1.2.3')
+
+        subject.make_updated!
+
+        subject.cluster.application_helm.reload
+
+        expect(subject.cluster.application_helm.version).to eq(Gitlab::Kubernetes::Helm::HELM_VERSION)
+      end
     end
 
     describe '#make_errored' do