Forum Discussion
telboy1965
Jun 14, 2026Copper Contributor
Outlook Desktop users continually prompted for credentials On-Prem Exchange SE
Battling ongoing issues with users being continually prompted for password using Outlook 2024 LTSC with on-prem Exchange 2019 SE. Removed Windows credentials, turned off cache mode, removed shared ca...
Ahmed_Masoud97
Sep 14, 2026Steel Contributor
Treat this as an Autodiscover or authentication failure, not an Outlook profile issue. While reproducing it, check Exchange IIS logs for 401 responses and use Outlook Test E-mail AutoConfiguration to confirm that every Autodiscover URL points on premises. Apply the latest Exchange SE and Office LTSC 2024 updates, then verify Kerberos SPNs, authentication methods, certificates, and load balancer consistency across all Exchange servers. Repeated prompts with HTTP 401 have previously been fixed through Exchange updates, so profile recreation only masks the underlying server response.