diff --git a/docs/README.md b/docs/README.md
index 74ee21f39..ddd88d237 100644
--- a/docs/README.md
+++ b/docs/README.md
@@ -91,6 +91,9 @@ helm install capi-operator capi-operator/cluster-api-operator --create-namespace
 
 The operator Helm chart supports a "quickstart" option for bootstrapping a management cluster. The user experience is relatively similar to [clusterctl init](https://cluster-api.sigs.k8s.io/clusterctl/commands/init.html?highlight=init#clusterctl-init):
 
+> **Warning**
+> The `--wait` flag is REQUIRED for the helm install command to work with providers. If the --wait flag is not used, the helm install command will not wait for the resources to be created and will return immediately.
+
 ```bash
 helm install capi-operator capi-operator/cluster-api-operator --create-namespace -n capi-operator-system --set infrastructure=docker:v1.4.2  --wait --timeout 90s # core Cluster API with kubeadm bootstrap and control plane providers will also be installed
 ```
@@ -115,10 +118,13 @@ The operator Helm chart provides multiple ways to configure deployment. For inst
 
 #### Helm installation example
 
-The following command will install cert-manager, CAPI operator itself with modified log level, Core CAPI provider with kubeadm bootstrap and control plane, and Docker infrastructure.
+The following commands will install cert-manager, CAPI operator itself with modified log level, Core CAPI provider with kubeadm bootstrap and control plane, and Docker infrastructure.
 
 ```bash
-helm install capi-operator capi-operator/cluster-api-operator --create-namespace -n capi-operator-system --set infrastructure=docker:v1.5.0  --set cert-manager.enabled=true --set logLevel=4 --wait --timeout 90s
+helm repo add jetstack https://charts.jetstack.io --force-update
+helm repo update
+helm install cert-manager jetstack/cert-manager --namespace cert-manager --create-namespace --set installCRDs=true
+helm install capi-operator capi-operator/cluster-api-operator --create-namespace -n capi-operator-system --set infrastructure=docker:v1.5.0 --wait --timeout 90s
 ```
 
 ## Configuration
diff --git a/docs/book/src/01_user/02_quick-start.md b/docs/book/src/01_user/02_quick-start.md
index 7e8c61e04..ab6bf0466 100644
--- a/docs/book/src/01_user/02_quick-start.md
+++ b/docs/book/src/01_user/02_quick-start.md
@@ -28,14 +28,29 @@ kubectl create secret generic "${CREDENTIALS_SECRET_NAME}" --from-literal=AWS_B6
 
 ### Installing Cluster API Operator
 
-Add helm repository:
+Add CAPI Operator & cert manager helm repository:
 
 ```bash
 helm repo add capi-operator https://kubernetes-sigs.github.io/cluster-api-operator
+helm repo add jetstack https://charts.jetstack.io --force-update
 helm repo update
 ```
 
-Deploy Cluster API components with docker provider using a single command during operator installation
+Install cert manager:
+
+```bash
+helm install cert-manager jetstack/cert-manager --namespace cert-manager --create-namespace --set installCRDs=true
+```
+
+Deploy Cluster API components with docker provider using a single command during operator installation.
+
+<aside class="note warning">
+
+<h1> Warning </h1>
+
+The `--wait` flag is REQUIRED for the helm install command to work. If the --wait flag is not used, the helm install command will not wait for the resources to be created and will return immediately. This will cause the helm install command to fail because the webhooks will not be ready in time. The --timeout flag is optional and can be used to specify the amount of time to wait for the resources to be created.
+
+</aside>
 
 ```bash
 helm install capi-operator capi-operator/cluster-api-operator --create-namespace -n capi-operator-system --set infrastructure=docker --set configSecret.name=${CREDENTIALS_SECRET_NAME} --set configSecret.namespace=${CREDENTIALS_SECRET_NAMESPACE}  --wait --timeout 90s
diff --git a/docs/book/src/02_installation/04_helm-chart-installation.md b/docs/book/src/02_installation/04_helm-chart-installation.md
index 4a9594958..13d102488 100644
--- a/docs/book/src/02_installation/04_helm-chart-installation.md
+++ b/docs/book/src/02_installation/04_helm-chart-installation.md
@@ -12,6 +12,14 @@ helm install capi-operator capi-operator/cluster-api-operator --create-namespace
 
 The operator Helm chart supports a "quickstart" option for bootstrapping a management cluster. The user experience is relatively similar to [clusterctl init](https://cluster-api.sigs.k8s.io/clusterctl/commands/init.html?highlight=init#clusterctl-init):
 
+<aside class="note warning">
+
+<h1> Warning </h1>
+
+The `--wait` flag is REQUIRED for the helm install command to work with providers.
+
+</aside>
+
 ```bash
 helm install capi-operator capi-operator/cluster-api-operator --create-namespace -n capi-operator-system --set infrastructure=docker:v1.4.2  --wait --timeout 90s # core Cluster API with kubeadm bootstrap and control plane providers will also be installed
 ```
diff --git a/docs/quickstart.md b/docs/quickstart.md
index 85b78437a..72f0870b2 100644
--- a/docs/quickstart.md
+++ b/docs/quickstart.md
@@ -27,15 +27,30 @@ kubectl create secret generic "${CREDENTIALS_SECRET_NAME}" --from-literal=AWS_B6
 
 ### Installing Cluster API Operator
 
-Add helm repository:
+Add CAPI Operator & cert manager helm repository:
 
 ```bash
 helm repo add capi-operator https://kubernetes-sigs.github.io/cluster-api-operator
+helm repo add jetstack https://charts.jetstack.io --force-update
 helm repo update
 ```
 
+Install cert manager:
+
+```bash
+helm install cert-manager jetstack/cert-manager --namespace cert-manager --create-namespace --set installCRDs=true
+```
+
 Deploy Cluster API components with docker provider using a single command during operator installation
 
+<aside class="note warning">
+
+<h1> Warning </h1>
+
+The `--wait` flag is REQUIRED for the helm install command to work. If the --wait flag is not used, the helm install command will not wait for the resources to be created and will return immediately. This will cause the helm install command to fail because the webhooks will not be ready in time. The --timeout flag is optional and can be used to specify the amount of time to wait for the resources to be created.
+
+</aside>
+
 ```bash
 helm install capi-operator capi-operator/cluster-api-operator --create-namespace -n capi-operator-system --set infrastructure=docker --set cert-manager.enabled=true --set configSecret.name=${CREDENTIALS_SECRET_NAME} --set configSecret.namespace=${CREDENTIALS_SECRET_NAMESPACE}  --wait --timeout 90s
 ```