diff --git a/README.md b/README.md
index 4853a7b684..f0a92e066a 100644
--- a/README.md
+++ b/README.md
@@ -142,5 +142,15 @@ To upload more PDFs, put them in the data/ folder and run `./scripts/prepdocs.sh
 
 ### Troubleshooting
 
-If the web app fails to deploy and you receive a '404 Not Found' message in your browser, run `azd deploy`. If you still encounter errors with the deployed app, consult these [tips for debugging Flask app deployments](http://blog.pamelafox.org/2023/06/tips-for-debugging-flask-deployments-to.html)
-and file an issue if the error logs don't help you resolve the issue.
\ No newline at end of file
+Here are the most common failure scenarios and solutions:
+
+1. The subscription (`AZURE_SUBSCRIPTION_ID`) doesn't have access to the Azure OpenAI service. Please ensure `AZURE_SUBSCRIPTION_ID` matches the ID specified in the [OpenAI access request process](https://aka.ms/oai/access).
+
+1. You're attempting to create resources in regions not enabled for Azure OpenAI (e.g. East US 2 instead of East US), or where the model you're trying to use isn't enabled. See [this matrix of model availability](https://aka.ms/oai/models).
+
+1. You've exceeded a quota, most often number of resources per region. See [this article on quotas and limits](https://aka.ms/oai/quotas).
+
+1. You're getting "same resource name not allowed" conflicts. That's likely because you've run the sample multiple times and deleted the resources you've been creating each time, but are forgetting to purge them. Azure keeps resources for 48 hours unless you purge from soft delete. See [this article on purging resources](https://learn.microsoft.com/azure/cognitive-services/manage-resources?tabs=azure-portal#purge-a-deleted-resource).
+
+1. After running `azd up` and visiting the website, you see a '404 Not Found' in the browser. First, try running `azd deploy`. If you still encounter errors with the deployed app, consult these [tips for debugging Flask app deployments](http://blog.pamelafox.org/2023/06/tips-for-debugging-flask-deployments-to.html)
+and file an issue if the error logs don't help you resolve the issue.