Hello @Gongada Bhanu ,
Welcome to Microsoft Q&A Platform. Thank you for reaching out & hope you are doing well.
I understand that you are using Azure Front Door Classic with App service built-in authentication and when accessing the website, sometimes you are not prompted to sign in due to Front Door cache, but it works if you clear the Front Door cache. You cannot disable the cache in the Front Door routing rules, as this is causing latency issues. So, you would like to know the possible solutions to such scenario.
You can find all the recommended considerations when using Azure Front Door with App service authentication in the below doc:
To make sure your website prompts for sign-in authentication every time it is opened, you should disable Caching for the authentication workflow:
See Disable cache for auth workflow to learn more on how to configure rules in Azure Front Door to disable caching for authentication and authorization-related pages.
Refer: https://learn.microsoft.com/en-us/azure/app-service/overview-authentication-authorization
https://azure.github.io/AppService/2021/03/26/Secure-resilient-site-with-custom-domain.html
Kindly let us know if the above helps or you need further assistance on this issue.
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