diff --git a/roles/docker-discourse/Debug.md b/roles/docker-discourse/Debug.md
new file mode 100644
index 00000000..c0713f9b
--- /dev/null
+++ b/roles/docker-discourse/Debug.md
@@ -0,0 +1,106 @@
+## Discourse Debugging Guide for Docker Role
+
+This document explains how to locate and use key log file paths on both the host and inside the container for a Docker-based Discourse installation deployed via the `docker-discourse` role.
+
+### 1. Host Paths
+
+Discourse log files are stored in the Docker volume named `discourse_data`. On the host, you can find them at:
+
+* **Rails Production Log**:
+
+  ```bash
+  cat /var/lib/docker/volumes/discourse_data/_data/log/rails/production.log | grep -i mail
+  ```
+
+  Filters for email-related entries:
+
+  * **Queued emails**: `Email::Sender: queued mail to user@example.com`
+  * **Errors**: e.g. `Net::SMTPAuthenticationError`, `SMTPConnectionError`
+
+* **Sidekiq Log**:
+
+  ```bash
+  cat /var/lib/docker/volumes/discourse_data/_data/log/sidekiq.log | grep -i mail
+  ```
+
+  Shows asynchronous mail job executions, retries, and failures.
+
+### 2. Inside the Container
+
+To inspect logs within the container, enter it:
+
+```bash
+cd /var/discourse
+./launcher enter app
+```
+
+Logs are mounted under `/var/log` inside the container:
+
+* **Rails Production Log**:
+
+  ```bash
+  tail -n 200 /var/log/rails/production.log | grep -i mail
+  ```
+
+  * **Info**: `I, [timestamp] INFO -- : Email::Sender: queued mail to ...`
+  * **Error**: `E, [timestamp] ERROR -- : Net::SMTPSyntaxError ...`
+
+* **Sidekiq Log**:
+
+  ```bash
+  tail -n 200 /var/log/sidekiq.log | grep -i mail
+  ```
+
+  * **Execution**: `Mail::MessageJob JID-...`
+  * **Retries/Exceptions** on delivery failure.
+
+### 3. Live Streaming Logs
+
+For real-time monitoring while reproducing an issue:
+
+```bash
+# On host:
+
+tail -f \
+  /var/lib/docker/volumes/discourse_data/_data/log/rails/production.log \
+  /var/lib/docker/volumes/discourse_data/_data/log/sidekiq.log | grep -i mail
+
+# Or inside container:
+tail -f /var/log/rails/production.log /var/log/sidekiq.log | grep -i mail
+```
+
+### 4. Enabling Verbose Email Debugging
+
+For detailed SMTP conversation logging:
+
+```bash
+# Inside container
+rails c
+> Discourse.debug_email = true
+```
+
+Send a test email:
+
+```bash
+rails c
+> UserMailer.test_email("you@example.com").deliver_now
+```
+
+Then check logs for the full SMTP handshake details.
+
+### 5. Flushing Redis Cache
+
+After configuration changes, clear Redis to remove stale session or cached data:
+
+```bash
+# Inside container
+rails r "Redis.new.flushall"
+```
+
+### 6. Sidekiq Web UI
+
+In the Admin UI under **Plugins → Sidekiq**, monitor queues, retries, and failed jobs for additional context.
+
+---
+
+Use this guide to quickly locate and interpret Discourse logs on both host and container, enabling efficient debugging of email delivery and background job issues in a Docker deployment managed by the `docker-discourse` role.
diff --git a/roles/docker-discourse/templates/discourse_application.yml.j2 b/roles/docker-discourse/templates/discourse_application.yml.j2
index aad39d9c..bf8fa903 100644
--- a/roles/docker-discourse/templates/discourse_application.yml.j2
+++ b/roles/docker-discourse/templates/discourse_application.yml.j2
@@ -62,7 +62,8 @@ env:
   DISCOURSE_SMTP_PORT:              {{ system_email.port }}
   DISCOURSE_SMTP_USER_NAME:         {{ users['no-reply'].email }}
   DISCOURSE_SMTP_PASSWORD:          {{ users['no-reply'].mailu_token }}
-  DISCOURSE_SMTP_ENABLE_START_TLS:  {{ system_email.start_tls | upper }}
+  DISCOURSE_SMTP_ENABLE_START_TLS:  {{ system_email.start_tls }}
+  DISCOURSE_SMTP_FORCE_TLS:         {{ system_email.tls }}
   DISCOURSE_SMTP_DOMAIN:            {{ system_email.domain }}
   DISCOURSE_NOTIFICATION_EMAIL:     {{ users['no-reply'].email }}