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I have configured an application behind my application gateway V2 and it is providing multiple logins prompts. I Have enabled cookie-based affinity on my HTTP settings as outlined in the Azure Application Gateway Documentation, Application Gateway supports cookie-based affinity enabling which it can direct subsequent traffic from a user session to the same server for processing. Also I have moved out 1 server from the backend pool leaving only 1 server behind. We are still facing same issues.

Afolabi
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Please use Application Gateway V1. I have seen this issue where the server sends negotiate and NTLM and with AppGW V2 the auth fallsback to NTLM where it promts for login for each and every request(CSS file loading).

msrini-MSIT
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NTLM / Kerberos is not supported on V2 gateways. No idea why.

https://learn.microsoft.com/en-us/azure/application-gateway/application-gateway-faq#does-application-gateway-v2-support-proxying-requests-with-ntlm-authentication

pgbfnf
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