Some customers report that Outlook (2016) keep asking accounts passwords (Outlook is connected via MAPI to 2 accounts)

Problem reported by Gabriele Maoret - SERSIS - 10/14/2021 at 6:01 AM

Resolved

Some customers report that Outlook (2016) keep asking accounts passwords (Outlook is connected via MAPI to 2 accounts).

Smartermail is the latest version.

Theres's anyone that has this issue and have a solution?

Gabriele Maoret - Head of SysAdmins at SERSIS

Currently manages 6 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 5 on-premise for customers who prefer to have their mail server in-house)

7 Replies

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Kyle Kerst Replied

10/14/2021 at 6:37 AM

Employee Post

Hi Gabriele! Something I have seen cause recurring password prompts is missing autodiscover components, or problematic autodiscover components. When using MAPI/EAS/EWS, Outlook relies heavily on autodiscover, and so you'll want to verify the following criteria are met from the client PC:

https://mail.customer-domain.com should be reachable from a browser without security errors.

https://autodiscover.customer-domain.com should be reachable from a browser without security errors.

SRV record should be reachable in DNS and should reference mail.customer-domain.com on port 443.

Can you confirm these criteria are met for both usernames? Thanks Gabriele!

Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com

Gabriele Maoret - SERSIS Replied

10/14/2021 at 9:48 AM

yes these are OK.

I have to add that, in the same domain, the majority of users works flawlessy, only few ones have this issue (maybe 1 or 2 users per domain).

But there are users with this issue in differnet domains (only 3 domains right now)...

All other domains are OK...

Maybe is an Outlook issue?

Gabriele Maoret - Head of SysAdmins at SERSIS Currently manages 6 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 5 on-premise for customers who prefer to have their mail server in-house)

Kyle Kerst Replied

10/14/2021 at 10:12 AM

Employee Post

Thanks Gabriele, I appreciate you confirming this. In that case I wonder if this might be an issue involving one of a couple items:

1. Local DNS servers in use on these particular client machines are returning invalid results during the autodiscover routine.

2. Client PC has cached/saved credentials stored in Windows. You can try following this guide completely to resolve that: https://portal.smartertools.com/kb/a3487/how-to-thoroughly-replace-your-mapi-account.aspx

3. Outlook installation may be problematic. You can try a /scanpst on the OST file in question, and worst case, can try a repair or reinstallation of Outlook there.

I hope this helps! Have a great day Gabriele!

Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com

Michael Replied

10/15/2021 at 9:23 AM

Verrrrry interesting. After update to Build 7945 (Oct 2, 2021) we have had a handful of Outlook 20216 MAPI connected users have issues. One kept being prompted for password. The other did not get password prompt, but some email folders AND calendar did not sync. In both cases we removed the account from Outlook, restarted and re-added. Interesting to see this other report. We figured it was just some oddity locally. Guess not.

Both users had two accounts setup. One was a MAPI account (the one not syncing) and the other account was an IMAP group email box. Both accounts on the same server.

Kyle Kerst Replied

10/20/2021 at 4:59 PM

Employee Post

@Michael: I recommend submitting a ticket on this as there are no known/common issues surrounding sync issues or password prompts at this time.

@Gabriele: Were you able to circle back to this with the feedback I provided in my previous follow-up?

Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com

Gabriele Maoret - SERSIS Replied

10/20/2021 at 11:33 PM

Marked As Resolution

Hi all, the issue was resolved using this KB:

https://portal.smartertools.com/kb/a3496/outlook-for-windows-always-attempts-to-connect-to-office-365.aspx?KBSearchID=875845

In particular these are the settings I used for the .REG file:

Windows Registry Editor Version 5.00

[HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover]
"PreferLocalXML"=dword:00000000
“ExcludeLastKnownGood”=dword:000000
"ExcludeExplicitO365Endpoint"=dword:00000001
"ExcludeScpLookup"=dword:00000001
"ExcludeHttpsRootDomain"=dword:00000000
"ExcludeHttpsAutodiscoverDomain"=dword:00000000
"ExcludeHttpRedirect"=dword:00000000
"ExcludeSrvRecord"=dword:00000000

[HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover\RedirectServers]
"autodiscover-s.outlook.com"=hex(0):
"autodiscover-s.partner.outlook.cn"=hex(0):
"autodiscover-s.outlook.de"=hex(0):
"autodiscover-s.office365.us"=hex(0):
"autodiscover.hotmail.com"=hex(0):

"MYSERVER.MYDOMAIN.com"=hex(0):

NOTE: I do not use SERVER.CUSTOMER-DOMAIN.COM customized for every customer domain in autodiscover.

I only use a single MYSERVER.MYDOMAIN.COM for every customer domain, so I don't need to set up multiple settings... And it works really well!

Kyle Kerst Replied

10/21/2021 at 3:32 PM

Employee Post

Glad to hear that did the trick! The O365 redirect that takes place during account setup can be tricky to work around sometimes.

Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com

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