diff --git a/Makefile b/Makefile
index f439b5f4517..84d55eddee7 100644
--- a/Makefile
+++ b/Makefile
@@ -190,10 +190,12 @@ install_antlr_cli: ## Install antlr CLI locally
.PHONY: docker-docs
docker-docs: ## Runs the OM docs in docker passing openmetadata-docs as volume for content and images
+ docker pull openmetadata/docs:latest
docker run --name openmetadata-docs -p 3000:3000 -v ${PWD}/openmetadata-docs/content:/docs/content/ -v ${PWD}/openmetadata-docs/images:/docs/public/images openmetadata/docs:latest
.PHONY: docker-docs-validate
docker-docs-validate: ## Runs the OM docs in docker passing openmetadata-docs as volume for content and images
+ docker pull openmetadata/docs:latest
docker run --entrypoint '/bin/sh' -v ${PWD}/openmetadata-docs/content:/docs/content/ -v ${PWD}/openmetadata-docs/images:/docs/public/images openmetadata/docs:latest -c 'npm run export'
.PHONY: docker-docs-local
diff --git a/openmetadata-docs/content/deployment/security/enable-ssl/openmetadata-server.md b/openmetadata-docs/content/deployment/security/enable-ssl/openmetadata-server.md
index d8a583ce6ea..ccdb0202d49 100644
--- a/openmetadata-docs/content/deployment/security/enable-ssl/openmetadata-server.md
+++ b/openmetadata-docs/content/deployment/security/enable-ssl/openmetadata-server.md
@@ -91,18 +91,3 @@ Click on `Trust` to open and set `Always Trust`:
Once the above steps are finished, all the browsers will allow you to visit the OpenMetadata server using HTTPS.
However, you'll still a warning in the address bar. All of these steps are not necessary with an X509 certificate issued
by a trusted authority and one should always use that in production.
-
-### Import public cert into Java Keystore
-
-This step is required in case you have configured a `bot` with a JWT Token as authentication mechanism and your server
-has SSL enabled.
-
-From your terminal:
-
-1. Go to your $JAVA_HOME/lib/security where the **cacerts** keystore is located.
-
-2. Run the following command once in the directory:
-
-```bash
-keytool -import -trustcacerts -keystore cacerts -storepass changeit -noprompt -alias localhost -file /path/to/public.cert
-```
diff --git a/openmetadata-docs/content/deployment/security/enable-ssl/ssl-troubleshooting.md b/openmetadata-docs/content/deployment/security/enable-ssl/ssl-troubleshooting.md
new file mode 100644
index 00000000000..6ecc438f6a8
--- /dev/null
+++ b/openmetadata-docs/content/deployment/security/enable-ssl/ssl-troubleshooting.md
@@ -0,0 +1,144 @@
+---
+title: SSL Troubleshooting
+slug: /deployment/security/enable-ssl/ssl-troubleshooting
+---
+
+# SSL Troubleshooting
+
+In this section we comment common issues that the user can face when enabling SSL in OpenMetadata.
+
+## Bot using JWT as authentication mechanism
+
+After enabling SSL on the OM server, we have to update also the public keys URL for the validation of the JWT tokens by
+updating to the secured URL: `https://{server_domain}:{port}/api/v1/config/jwks`.
+
+In case we are using a self-signed certificate, it will fail with the error below:
+
+
+
+To avoid this error, you must import your public certificate into the Java Keystore of the OM server. If your OM
+deployment is done with Docker or Kubernetes, you must copy the cert into the `openmetadata_server` container or pod.
+After that, you can proceed with the following steps from your terminal:
+
+1. Go to your $JAVA_HOME/lib/security where the **cacerts** keystore is located.
+
+2. Run the following command once in the directory:
+
+```bash
+keytool -import -trustcacerts -keystore cacerts -storepass changeit -noprompt -alias localhost -file /path/to/public.cert
+```
+
+After that, you can restart the server, and the error 500 will disappear.
+
+## Deploying workflows in Airflow
+
+One common issue after enabling SSL with a self-signed certificate is that our workflows in Airflow will fail or will
+not be deployed. We can notice it because the following error will be shown in the UI when deploying or re-deploying:
+
+
+
+This can be solved in two different ways:
+
+#### 1. Validate the certificate using the public certificate (recommended):
+
+We specify which public certificate must be used to validate the OM server connection.
+
+1. Copy the public certificate into our Airflow instance.
+2. Update the configuration of our OM server so that each time a workflow is deployed, we send the new configuration.
+
+- In **docker**:
+
+```yaml
+AIRFLOW_VERIFY_SSL=validate
+AIRFLOW_SSL_CERT_PATH=/path/to/certificate/in/airflow
+```
+
+- In **bare metal**:
+
+Edit the `conf/openmetadata.yaml` file:
+
+```yaml
+airflowConfiguration:
+ verifySSL: "validate"
+ sslConfig:
+ validate:
+ certificatePath: "/path/to/certificate/in/airflow"
+```
+
+- In **K8s**:
+
+We have to update in the `values.yaml` file with:
+
+```yaml
+global:
+ airflow:
+ verifySsl: "validate"
+ sslCertificatePath: "/path/to/certificate/in/airflow"
+```
+
+#### 2. Ignore the certification validation (not recommended for production):
+
+When doing any call to the secured OM server, the certificate validation will be ignored.
+
+- In **docker**:
+
+```yaml
+AIRFLOW_VERIFY_SSL=ignore
+```
+
+- In **bare metal**:
+
+Edit the `conf/openmetadata.yaml` file:
+
+```yaml
+airflowConfiguration:
+ verifySSL: "ignore"
+```
+
+- In **K8s**:
+
+We have to update in the `values.yaml` file with:
+
+```yaml
+global:
+ airflow:
+ verifySsl: "ignore"
+```
+
+Once one of the configurations is set, we can restart our OM server and deploy or redeploy without any issues.
+
+## Ingesting from CLI
+
+Similar to what happens when deploying workflows in Airflow, we have to update our workflow config file with one of
+these options:
+
+- To validate our certificate:
+
+```yaml
+workflowConfig:
+ openMetadataServerConfig:
+ verifySSL: validate
+ sslConfig:
+ certificatePath: /local/path/to/certificate
+```
+
+- To ignore certificate validation:
+
+```yaml
+workflowConfig:
+ openMetadataServerConfig:
+ verifySSL: ignore
+```
+
+## Demo of SSL enabled with an SSO and JWT token configured
+
+In case you are looking for a full dockerized demo of how JWT tokens, SSO configuration, and SSL enabled work together,
+please visit our demo repository [here](https://github.com/open-metadata/openmetadata-demo/tree/main/sso-with-ssl).
\ No newline at end of file
diff --git a/openmetadata-docs/content/menu.md b/openmetadata-docs/content/menu.md
index 847a377a19a..2808ceb5c75 100644
--- a/openmetadata-docs/content/menu.md
+++ b/openmetadata-docs/content/menu.md
@@ -133,6 +133,8 @@ site_menu:
url: /deployment/security/enable-ssl/nginx
- category: Deployment / Enable Security / Enable SSL / Use the OpenMetadata Server
url: /deployment/security/enable-ssl/openmetadata-server
+ - category: Deployment / Enable Security / Enable SSL / SSL Troubleshooting
+ url: /deployment/security/enable-ssl/ssl-troubleshooting
- category: Deployment / Enable Security / Enable JWT Tokens
url: /deployment/security/enable-jwt-tokens
- category: Deployment / Enable Security / JWT Troubleshooting
diff --git a/openmetadata-docs/images/deployment/enable-ssl/500-error-ssl.png b/openmetadata-docs/images/deployment/enable-ssl/500-error-ssl.png
new file mode 100644
index 00000000000..f7da56a4904
Binary files /dev/null and b/openmetadata-docs/images/deployment/enable-ssl/500-error-ssl.png differ
diff --git a/openmetadata-docs/images/deployment/enable-ssl/handshake-error-ssl.png b/openmetadata-docs/images/deployment/enable-ssl/handshake-error-ssl.png
new file mode 100644
index 00000000000..1a24154de46
Binary files /dev/null and b/openmetadata-docs/images/deployment/enable-ssl/handshake-error-ssl.png differ