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Outlook continuously prompts user for password

ecar13

We have an on-prem Exchange Server, and all computers on the local network use Outlook 2013. Right after we deployed our XG Firewall (SFOS 18.0.4) seemingly at random, users will get a pop-up box in Outlook asking them to sign in. Even if they enter the correct credentials the box will pop up again and again. If they click cancel, Outlook immediately reconnects to the Exchange server anyway, and Outlook works just fine.  This could have nothing to do with XG but I can tell you this started happening right after we deployed our XG Firewall. I am wondering if traffic is getting blocked and is causing this unexpected behavior. Nothing else has changed on the network. Has anyone else experienced this and/or do you have any recommendations on how I can troubleshoot this?



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  • 0

    HI,

    is the server on the same network as the users?

    Sound like some of the user setups have a bypass the local server for some mail sites?

    Ian

    XG115W - v20 GA - Home

    XG on VM 8 - v20 GA

    If a post solves your question please use the 'Verify Answer' button.

  • 0 in reply to rfcat_vk

    Exchange server is in the DMZ. All workstations are on the main network. There is a plain vanilla firewall rule that allows traffic between the Exchange server and the main network. All users are on the domain. Most users have Outlook 2013. Some have Outlook 2019 and some have Office 365. Not all users are getting prompted with the Outlook login popup box. And it's not limited to a specific version of Outlook. (At least one user from each version gets this pop-up box). Each installation of Outlook is ONLY configured to connect to the Exchange server. No POP3 or IMAP or gmail or anything like that. Strictly Exchange connection for company email. 

    I have another thread on this forum that appears to be a completely different topic > https://community.sophos.com/xg-firewall/f/discussions/125297/internal-traffic-blocked-by-authentication-ntlmauth

    However I am thinking the 2 issues are related. Somehow the XG firewall is having trouble with Kerberos and NTLM authentication EVEN between subnets on the private network and as a result, internal communication across VLANs (subnets) is getting blocked. I am hoping that once this issue gets resolved it will also take care of this Outlook issue.

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  • 0 in reply to rfcat_vk

    Exchange server is in the DMZ. All workstations are on the main network. There is a plain vanilla firewall rule that allows traffic between the Exchange server and the main network. All users are on the domain. Most users have Outlook 2013. Some have Outlook 2019 and some have Office 365. Not all users are getting prompted with the Outlook login popup box. And it's not limited to a specific version of Outlook. (At least one user from each version gets this pop-up box). Each installation of Outlook is ONLY configured to connect to the Exchange server. No POP3 or IMAP or gmail or anything like that. Strictly Exchange connection for company email. 

    I have another thread on this forum that appears to be a completely different topic > https://community.sophos.com/xg-firewall/f/discussions/125297/internal-traffic-blocked-by-authentication-ntlmauth

    However I am thinking the 2 issues are related. Somehow the XG firewall is having trouble with Kerberos and NTLM authentication EVEN between subnets on the private network and as a result, internal communication across VLANs (subnets) is getting blocked. I am hoping that once this issue gets resolved it will also take care of this Outlook issue.

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