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Foiler

Outlook prompts for password every day - Office 365 mail - Eset Endpoint Antivirus version 5

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A business with only two Windows 7 computers on the network both have the same problem ..  Outlook prompts for re-entry of password almost every day.

Microsoft support are suggesting we have "network problems".  However, this is a very unsophisticated setup, just a simple network and an inexpensive router with default setup.  The mail setup is Office 365. The only "network" filtering possible would be the antivirus perhaps?  Windows Firewall is disabled.

The antivirus is Eset Endpoint Antivirus version 5. Is it possible there is a setting in that which is blocking port 443 or access to Microsoft Certificates?

Just wondering if anyone else has had similar problems?

 

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Does the problem go away after uninstalling EEA? Since Endpoint v5 is in basic support phase, I'd strongly recommend upgrading to EEA v7 first before troubleshooting the issue further. Basic support means:

  • Availability of regular engine module updates
  • Availability of module updates is not guaranteed
  • Product is no longer available for download from ESET download servers
  • technical support is no longer available, no bugs will be fixed

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Thank you Marcos .. sensible suggestion to uninstall and test, but I am a  bit nervous to do that given that we would have an unprotected workstation for a day or two while waiting for a password prompt, or not. Also not a conclusive test by the nature of the beast unless we uninstalled it permanently.

Microsoft have a product called SARA https://support.microsoft.com/en-nz/help/4098558/how-to-scan-outlook-by-using-the-sara-tool and this failed so we could test that with Eset uninstalled.

There is some suggestion by Microsoft that port 443 is being interfered with - could Eset possibly be guilty of that and is there any way of disabling that component?

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11 hours ago, Foiler said:

Thank you Marcos .. sensible suggestion to uninstall and test, but I am a  bit nervous to do that given that we would have an unprotected workstation for a day or two while waiting for a password prompt, or not. Also not a conclusive test by the nature of the beast unless we uninstalled it permanently.

Microsoft have a product called SARA https://support.microsoft.com/en-nz/help/4098558/how-to-scan-outlook-by-using-the-sara-tool and this failed so we could test that with Eset uninstalled.

There is some suggestion by Microsoft that port 443 is being interfered with - could Eset possibly be guilty of that and is there any way of disabling that component?

Hi Foiler,

We have 140 endpoints using Office 365 Mail and all of them have ESET installed and we have no issues.

Does the password prompt specifically appear once a day or every time you restart the machine?

If it was blocking port 443 then you wouldn't be able to receive any mail traffic in the first place so it cannot be that. 

Try updating your ESET client to a newer version?

Regards,

Kieran Barry

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23 hours ago, Foiler said:

A business with only two Windows 7 computers on the network both have the same problem ..  Outlook prompts for re-entry of password almost every day.

Microsoft support are suggesting we have "network problems".  However, this is a very unsophisticated setup, just a simple network and an inexpensive router with default setup.  The mail setup is Office 365. The only "network" filtering possible would be the antivirus perhaps?  Windows Firewall is disabled.

The antivirus is Eset Endpoint Antivirus version 5. Is it possible there is a setting in that which is blocking port 443 or access to Microsoft Certificates?

Just wondering if anyone else has had similar problems?

 

You could check policy settings: Windows desktop v5 > Personal firewall > Settings > SSL > SSL protocol checking

We had similar situation but it was due UTM settings.

 

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Though not related to ESET - check Credential Manager on you Windows computers.   Delete anything that that mentions email, Outlook, etc.

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I am having this exact same issue on Office 365 +  ESET Endpoint AV 7.0.2073.1.

We use modern authentication and outlook is prompting for password several times a day for no reason.  closing and reopening outlook resolves the issue.

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Further update .. we still have this problem. Microsoft have been unable to solve this one after 34 emails from them, and countless hours on the phone with shared sessions.

Here is what Microsoft have done so far, but the problem persists. 

    1    Created a new Outlook profile.
    2    Re-installed Office with Easy Fix Tool.
    3    Cleared cached credentials.
    4    Created a new Windows Profile.
    5    Ran Autodiscover regkey fix.
    6    Disable IPV6
    7    Made sure Network is set to Work instead of Public.
    8    Deleted OST file.
    9    Disable MFA.
    10    Ran SaRA, but it gave a certificate issue which might be related to your Network.
    11    installed a 64bit version of Office.

 

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Our next step would be to temporarily change the Eset antivirus to something else eg AVG free .. but unfortunately the end user is now completely fed up and would prefer to have to enter the O365 password frequently than to make any further changes. This project is hence on hold.

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2 hours ago, Foiler said:

Our next step would be to temporarily change the Eset antivirus to something else eg AVG free .. but unfortunately the end user is now completely fed up and would prefer to have to enter the O365 password frequently than to make any further changes. This project is hence on hold.

Just out of curiosity, which protocol you use to communicate with O365 servers?

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I doubt it's ESET Endpoint at fault here. We use v5 and O365 (and also MAPI over HTTP) and don't have any problems. 

Can you check this option on clients:

1.jpg?psid=1

Also, regarding 10. Ran SaRA, but it gave a certificate issue which might be related to your Network. Could you post message about certificate? 

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This is something I've been seeing more and more often.  ESET interferes with the Office 365 authentication process, which causes a password request loop of authentication failures.  Removing ESET is the only permanent solution.  Latest version.  I've been seeing this for 2 months on 1 home customer computer, now on a domain account business customer today, between both systems, one brand new.

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Quote

ESET interferes with the Office 365 authentication process, which causes a password request loop of authentication failures

Does the issue occur with the "Always prompt for logon credentials" option disabled?

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1 minute ago, Marcos said:

Does the issue occur with the "Always prompt for logon credentials" option disabled?

Yes. 

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