Hello @Kaz1
It’s very likely that the issue is related to where the HTTPS request originates — whether it’s coming from the Databricks control plane or your data plane (your own AWS VPC).
When you run a local script or call the Teams webhook from a cluster in your own VPC, the request goes out through your network egress, which typically has full Internet access. That’s why it works fine locally.
However, when Databricks services such as notification destinations or workspace-level alerts send a webhook, those requests are made from the Databricks control plane, which lives in a Databricks-managed VPC, not yours.
If Microsoft Teams (or the Azure Logic App endpoint) restricts inbound traffic by IP or region, or only accepts certain TLS configurations, the control-plane traffic can be blocked or rejected, resulting in the SSLEOFError you’re seeing..
You can confirm this by checking whether the request originates from a cluster (data plane) or a workspace feature (control plane). If it’s the latter, make sure your Teams webhook allow-lists the Databricks control-plane IP ranges for your region, as described-> Docs Networking Requirements
In case this request is sent from your data plane you should try a newer version of DBR (e.g 13.3) to make sure everything is ok with modern Microsoft endpoints.
Hope this helps 🙂
Isi