diff --git a/GitLab/README.md b/GitLab/README.md
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+++ b/GitLab/README.md
@@ -3,4 +3,6 @@
 The Orka GitLab integration enables you to use [Orka by MacStadium][orka] in your GitLab CI/CI pipelines.  
 Learn how to configure the [GitLab Shell executor](shell-executor.md) or the [GitLab Custom executor](custom-executor.md).
 
+For common issues and solutions, see the [Troubleshooting guide](troubleshooting.md).
+
 [orka]: https://www.macstadium.com/orka
diff --git a/GitLab/troubleshooting.md b/GitLab/troubleshooting.md
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+# Troubleshooting the GitLab Orka Integration
+
+This guide covers common issues and solutions when using the GitLab [Custom executor][custom] with [Orka][orka].
+
+## Setting environment variables
+
+The integration reads configuration from environment variables. There are two ways to set them:
+
+**Option A — GitLab CI/CD Variables** (available to the build only)
+Go to Settings > CI/CD > Variables and add each variable. This is the right place for variables like `ORKA_TOKEN` and `ORKA_CONFIG_NAME` that the runner scripts need during job execution.
+
+**Option B — Docker container startup** (available inside the container)
+Pass variables when starting the runner container:
+```
+docker run --env ORKA_ENDPOINT="http://10.221.188.20" ...
+```
+Use this for variables that need to be present at the container level, like `ORKA_ENDPOINT`.
+
+For sensitive variables like `ORKA_TOKEN`, enable the **Masked** option in GitLab so the value is hidden in job logs.
+
+For `ORKA_SSH_KEY_FILE`, prefer mounting the key file directly into the runner container (Option B) rather than storing the private key contents as a GitLab variable.
+
+## Authentication issues
+
+### Error: "unauthorized" or "401"
+
+**Symptoms:**
+- VM deployment fails with authentication errors
+- `orka3` commands return "unauthorized"
+
+**Causes:**
+- `ORKA_TOKEN` is invalid or expired
+
+**Solutions:**
+
+1. Generate a new service account token:
+   ```bash
+   orka3 serviceaccount token <service-account-name>
+   ```
+
+2. Update `ORKA_TOKEN` with the new token. See [Setting environment variables](#setting-environment-variables).
+
+**Note:** Service account tokens are valid for 1 year by default. For custom duration, use `--duration` flag. Some Kubernetes control planes (e.g., EKS) do not allow long-lived tokens. In that case, use the `--no-expiration` flag instead.
+
+### Error: "config not found" or "no such host"
+
+**Symptoms:**
+- CLI commands fail before authentication
+- "dial tcp: lookup" errors
+
+**Causes:**
+- `ORKA_ENDPOINT` is not set or malformed
+- Network connectivity issues to Orka API
+
+**Solutions:**
+
+1. Verify the endpoint format (include protocol, no trailing slash). See [Setting environment variables](#setting-environment-variables).
+   ```
+   # Correct format
+   http://10.221.188.20
+
+   # Incorrect formats
+   10.221.188.20          # Missing protocol
+   http://10.221.188.20/  # Trailing slash
+   ```
+
+2. If the endpoint is correct but commands still fail, see [Runner cannot reach Orka endpoint](#runner-cannot-reach-orka-endpoint) for connectivity troubleshooting.
+
+## VM deployment failures
+
+### Error: "VM deployment failed"
+
+**Symptoms:**
+- prepare.sh exits with "VM deployment failed"
+- Deployment attempts exhausted
+
+**Causes:**
+- `ORKA_CONFIG_NAME` doesn't exist or is misspelled
+- No available nodes with sufficient resources
+
+**Solutions:**
+
+1. If the error says "config does not exist", check the spelling of `ORKA_CONFIG_NAME` in your GitLab CI/CD Variables. Create the config if needed:
+   ```bash
+   orka3 vm-config create <config-name> --image <image-name> --cpu <count>
+   ```
+
+2. Check available node resources:
+   ```bash
+   orka3 node list
+   ```
+
+3. Set `VM_DEPLOYMENT_ATTEMPTS` to your desired retry count. See [Setting environment variables](#setting-environment-variables).
+
+### Error: "Invalid ip" or "Invalid port"
+
+**Symptoms:**
+- VM deploys but connection info extraction fails
+- "Invalid ip: null" in logs
+
+**Causes:**
+- VM deployment returned unexpected JSON format
+- VM is in a failed state
+
+**Solutions:**
+
+This usually indicates a deeper infrastructure issue, not something the troubleshooting steps can directly fix.
+
+Deploy a VM manually and inspect the JSON output:
+```bash
+orka3 vm deploy test-vm --config "$ORKA_CONFIG_NAME" -o json
+```
+
+If the manual deploy also returns unexpected output or fails, contact [MacStadium Support][support] with the full error.
+
+Delete the test VM after inspection:
+```bash
+orka3 vm delete test-vm
+```
+
+## SSH connection issues
+
+### Error: "Waited 30 seconds for sshd to start"
+
+**Symptoms:**
+- VM deploys successfully
+- SSH connection times out after 30 seconds
+
+**Causes:**
+- SSH is not enabled on the base image
+- SSH key not configured on the VM
+- VM is still booting
+
+**Solutions:**
+
+Since the runner automatically deletes failed VMs, deploy a VM manually to troubleshoot:
+
+1. Deploy a test VM:
+   ```bash
+   # Connection details (IP and SSH port) are in the JSON output
+   orka3 vm deploy test-debug --config "$ORKA_CONFIG_NAME" -o json
+   ```
+
+2. Connect via Screen Sharing or VNC to check:
+   - System Preferences > Sharing > Remote Login is enabled
+   - Your public key is in `~/.ssh/authorized_keys`
+
+3. Test SSH manually:
+   ```bash
+   ssh -i ~/.ssh/orka_deployment_key -p <PORT> admin@<VM_IP> "echo ok"
+   ```
+
+4. Clean up:
+   ```bash
+   orka3 vm delete test-debug
+   ```
+
+### Error: "Permission denied (publickey)"
+
+**Symptoms:**
+- SSH connection is refused
+- "Permission denied" in logs
+
+**Causes:**
+- SSH key has a passphrase (not supported)
+- Wrong SSH user
+- SSH key not in VM's authorized_keys
+- SSH key doesn't match the one registered in the VM's authorized_keys
+
+**Solutions:**
+
+1. Verify the SSH key has no passphrase:
+   ```bash
+   # This should NOT prompt for a passphrase
+   ssh-keygen -y -f /path/to/key
+   ```
+
+2. If the key has a passphrase, generate a new one without:
+   ```bash
+   ssh-keygen -t ed25519 -f ~/.ssh/orka_key -N ""
+   ```
+
+3. Verify `ORKA_VM_USER` matches the user on the VM (default: `admin`). See [Setting environment variables](#setting-environment-variables).
+
+4. Deploy a test VM and verify the public key is in `~/.ssh/authorized_keys`.
+
+## Environment variable issues
+
+### Error: "unbound variable" or blank values
+
+**Symptoms:**
+- Script fails immediately
+- Variables are empty
+
+**Causes:**
+- Required environment variables not configured in GitLab
+
+**Solutions:**
+
+See [Setting environment variables](#setting-environment-variables) for how to configure these. Verify all required variables are set:
+
+| Variable | Required | Description |
+|----------|----------|-------------|
+| `ORKA_TOKEN` | Yes | Service account token |
+| `ORKA_ENDPOINT` | Yes | Orka API URL |
+| `ORKA_CONFIG_NAME` | Yes | VM config template name |
+| `ORKA_SSH_KEY_FILE` | Yes | Private SSH key contents. Recommended: mount the key file into the runner container rather than storing key contents as a GitLab variable. See [Setting environment variables](#setting-environment-variables). |
+| `ORKA_VM_USER` | No | SSH user (default: `admin`) |
+| `ORKA_VM_NAME_PREFIX` | No | VM name prefix (default: `gl-runner`) |
+| `VM_DEPLOYMENT_ATTEMPTS` | No | Retry count (default: `1`) |
+
+For sensitive variables like `ORKA_TOKEN` and `ORKA_SSH_KEY_FILE`, enable the "Masked" option.
+
+## Network and connectivity issues
+
+### Runner cannot reach Orka endpoint
+
+**Symptoms:**
+- "Connection refused" or "Connection timed out"
+- curl to endpoint fails
+
+**Causes:**
+- Runner is not on the same network as Orka
+- VPN not connected
+- Firewall blocking traffic
+
+**Solutions:**
+
+1. Test connectivity from the runner environment:
+   ```bash
+   curl -s -o /dev/null -w "%{http_code}" "$ORKA_ENDPOINT/api/v1/cluster-info"
+   ```
+
+2. If using VPN, verify your connection using your [IP plan][ip-plan] details.
+
+3. For Docker-based runners, ensure the container has network access to the Orka endpoint.
+
+### IP mapping issues
+
+**Symptoms:**
+- VM deploys but SSH connects to wrong IP
+- "No route to host" errors
+
+**Causes:**
+- Private/public IP mismatch
+- settings.json not configured for IP mapping
+
+**Solutions:**
+
+If your network requires IP mapping, create `/var/custom-executor/settings.json`:
+```json
+{
+  "mappings": [
+    {
+      "private_host": "10.221.188.100",
+      "public_host": "203.0.113.100"
+    }
+  ]
+}
+```
+
+See [template-settings.md](template-settings.md) for configuration details.
+
+## Job execution issues
+
+### Build script fails
+
+**Symptoms:**
+- Job fails during run.sh
+- Error is from your CI/CD script, not the integration
+
+**Note:** The integration distinguishes between:
+- **Build failures**: Your script failed (returns script exit code)
+- **System failures**: Infrastructure failed (returns exit code 1)
+
+If your build script fails, the issue is in your script, not the integration. Test your script on a standalone Orka VM.
+
+### Job hangs or times out
+
+**Symptoms:**
+- Job runs but never completes
+- GitLab times out the job
+
+**Causes:**
+- Long-running process without output
+- SSH connection dropped
+
+**Solutions:**
+
+1. For long jobs, add periodic output to prevent GitLab timeout.
+
+2. Consider breaking long jobs into smaller stages.
+
+3. Increase GitLab job timeout in project settings if needed.
+
+## Cleanup issues
+
+### Orphaned VMs
+
+**Symptoms:**
+- VMs remain after job completion
+
+**Causes:**
+- Runner crashed before cleanup
+- Network issue during cleanup
+
+**Solutions:**
+
+Delete orphaned VMs manually:
+```bash
+orka3 vm delete <vm-name>
+```
+
+## Getting help
+
+If you're still experiencing issues:
+
+1. Check the [Orka documentation][orka-docs] for platform-specific guidance
+2. Review GitLab Runner [logs][runner-logs]: `gitlab-runner --debug run`
+3. Contact [MacStadium Support][support] with:
+   - Error messages and logs
+   - Environment details (Runner version, Orka version)
+   - Steps to reproduce
+
+[custom]: https://docs.gitlab.com/runner/executors/custom.html
+[orka]: https://support.macstadium.com/hc/en-us/articles/29904434271387-Orka-Overview
+[orka-docs]: https://support.macstadium.com/hc/en-us
+[ip-plan]: https://support.macstadium.com/hc/en-us/articles/28230867289883-IP-Plan
+[masked-variables]: https://docs.gitlab.com/ee/ci/variables/#mask-a-cicd-variable
+[runner-logs]: https://docs.gitlab.com/runner/faq/#how-can-i-get-a-debug-log
+[support]: https://support.macstadium.com/