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SSL Handshake Failures when fetching Azure Entra URL in SSO configuration
Problem
When deploying MetaDefender Core with Docker Debian-based, SSL handshake failures related to certificate chain issues may occur while accessing the fetching Azure Entra URL (https://login.microsoftonline.com)
The server (https://login.microsoftonline.com) uses SSL certificates issued by DigCert Certificate Authority (CA) typically DigCert Global Root G2 and possibly intermediates like DigCert Global G2 TLS RSA SHA256 2020 CA1.
Since (https://login.microsoftonline.com) uses a Content Delivery Network (CDN), the certificate chain at your location may differ slightly from the one seen at OPSWAT Support.
How to fix it
- Access the Fetch URL in Your Browser
- Open a browser (e.g., Microsoft Edge or Chrome).
- Visit: https://login.microsoftonline.com
- Export the Certificates
- Click on the security lock icon next to the address bar.

- View Certificate details.

Export the first certificate (subject certificate)
- Select Base-64 encoded ASCII, single certificate (*.crt)
- Save it as →
stamp2.login.microsoftonline.com.crt

- Export the first certificate (subject certificate)
- In the certificate viewer, go to the Certification Path tab.

Select the second certificate (the intermediate CA), then click View Certificate.
Go to Details → Copy to File.
- Select Base-64 encoded X.509 (.CER) format.
- Save it as
Intermediate.crt(removed.cer)

Repeat the same process for the root certificate:
- Save it as
Root.crt(removed.cer) .
- Save it as
You should now have three certificate files:
stamp2.login.microsoftonline.com.crt(subject/leaf)Intermediate.crt(intermediate CA)Root.crt(root CA)

- Create a fullchain cert with the linux command:
cat Root.crt Intermediate.crt stamp2.login.microsoftonline.com.crt > azure-full-chain.crt
- Mount the volume for certificates into the trusted root certification authorities
- Given that the full chain certificate is stored at ./trusts-ca/azure-full-chain.crt, then we can mount it to the container with the following example:
docker run -d \ --name core \ ... -v ./trusts-ca/azure-full-chain.crt:/etc/ssl/certs/azure-full-chain.crt \ ... opswat/metadefendercore-debian-nonroot:5.17.1