Intermittent "Chain validation failed" SSL error on Azure App Service (*.azurewebsites.net)

DCM 40 Reputation points
2025-11-12T06:45:15.87+00:00

Hello,

Since November 11, our Android app has started failing intermittently (around 70% of requests) when connecting to our Azure App Service endpoint. The app throws the following exception:

javax.net.ssl.SSLHandshakeException: Chain validation failed

Key facts:

  • The issue is intermittent — some requests succeed, others fail.
  • It affects multiple Android devices and carriers (mobile data).
  • The Android app hasn’t been updated in 6+ months and worked perfectly before Nov 11.
  • The App Service uses the default Azure SSL certificate (*.azurewebsites.net) — no custom SSL.
  • Tested with TLS 1.2.
  • Verified with openssl s_client:
verify error:num=20:unable to get local issuer certificate
  • The certificate chain observed:
*.azurewebsites.net
Microsoft Azure RSA TLS Issuing CA 04
DigiCert Global Root G2
  • Android SSL analyzer reports CRL errors (“IOException occurred”) on the intermediate CA.
  • SSL Report in SSL LabsUser's image

What we’ve already ruled out:

  • No app code or configuration changes.
  • Not device- or Android-version specific (tested on Android 13).
  • Not network/firewall-related (fails on public mobile data).
  • TLS version/cipher changes on App Service did not fix it.

Hypothesis: The intermediate certificate (“Microsoft Azure RSA TLS Issuing CA 04”) might not always be sent or its CRL/OCSP endpoints might be intermittently unreachable, causing Android’s certificate chain validation to fail.

Request: Could the Azure team please verify if there’s an ongoing issue with the *.azurewebsites.net certificate chain or with the CRL/OCSP availability of its intermediate CA? This behavior started suddenly on November 11 without any deployment changes on our side.

Environment details:

Resource: (Azure App Service, URL available privately if required)

  • Region: (West US)
  • TLS: 1.2 tested

Date/time first observed: November 11, 2025

  • Error reproducible in ~70% of attempts from Android clients.

Thank you!

Azure App Service
Azure App Service
Azure App Service is a service used to create and deploy scalable, mission-critical web apps.
{count} votes

3 answers

Sort by: Most helpful
  1. DCM 40 Reputation points
    2025-11-20T17:59:29.6266667+00:00

    It appears this was indeed a temporary platform-side issue with the Azure wildcard certificate (*.azurewebsites.net). The service returned to normal functionality on its own.

    1 person found this answer helpful.
    0 comments No comments

  2. Roccosco 10 Reputation points
    2025-11-13T16:45:28.76+00:00

    I'm using .NET Maui and the problem is related to the default HttpClientHandler. Using SocketsHttpHandler solved the problem.

    0 comments No comments

  3. Ankit 0 Reputation points
    2025-11-17T07:29:20.24+00:00

    I was getting issue because of socket app service inside http service but when we removed socket service from our backend then problem has been solved


Your answer

Answers can be marked as 'Accepted' by the question author and 'Recommended' by moderators, which helps users know the answer solved the author's problem.