An error occured executing configure AAD sync task: AN error occured while sending the request

Question

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Answer 1

@Dale Spalvieri ,

To add to Andy's answer, if the issue isn't related to the TLS 1.2 enablement, it's possible that there's an issue with the certificate.

It sounds like the certificate isn't valid during that specific cycle or the TLS connection is being dropped (some kind of reverse proxy).

I would recommend checking these questions:

1. Is the server in question behind a web proxy? If so, have you configured the AADConnectProvisioningAgent.exe.config to use this proxy?  See: https://learn.microsoft.com/en-us/entra/identity/app-provisioning/on-premises-application-provisioning-architecture#how-do-i-configure-the-provisioning-agent-to-use-a-proxy-server-for-outbound-http-communication
2. I would suggest also enabling the verbose logs while reproducing the issue:
3. In addition, I would recommend capturing a network trace from the agent server during the repro.

If you don't get the information you need from checking these options, you can also share these details over a private message. This may require a support case for deeper troubleshooting though.

Answer 2

I would verify no one disabled TLS 1.2 on that server:

https://learn.microsoft.com/en-us/entra/identity/hybrid/connect/reference-connect-tls-enforcement