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Multiple MAPI accounts in the same Outlook profile
Problem reported by Nick Jansen - 10/5/2023 at 11:11 AM
Resolved
Hi, is anyone using more than one account on the same SmarterMail server via MAPI, in the same Outlook instance and profile, at the same time, with the Microsoft 365 version of Outlook?

I am having trouble with this where everything seems to work normally for a while (for about a day or so, even across Outlook restarts), but then suddenly Outlook will prompt for a password for one of the accounts, but with the username of one of the other accounts pre-filled. If I change it to the correct username and fill in the correct password, and check the box to remember the credentials, everything again works for a while. But then I get the same prompt again except for one of the other accounts, again with the username of a different account pre-filled. And so on in an infinite loop.

I'm not sure but my assumption is only one MAPI username and password combination for the whole server is actually being stored on this computer, and is getting overwritten every time I fill in the password prompt, causing the other MAPI accounts to lose their saved credentials and eventually the authentication token expires causing the prompt again.

I tried redoing all of the MAPI accounts for this user using these instructions from the knowledge base, but it didn't resolve the problem.

I also did Resync User Protocols for all this user's accounts, but that also didn't resolve the problem.

I have another user who is using the Office 2019 version of Outlook, also with multiple accounts (on the same SmarterMail server as each other, which is also the same SmarterMail server as the other user above) via MAPI in the same Outook profile, and this problem doesn't occur for this user. I don't know if the different version of Outlook is the key or if thers's something else going on with the first user.

Has anyone else been able to use multiple accounts via MAPI at the same time in Microsoft 365 Outlook?

I am using SmarterMail Enterprise build 8664, but I recently upgraded from 8451 and had the same issue then. Checking for Microsoft 365 updates on the first user says it's already the latest version.

17 Replies

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1
Kyle Kerst Replied
10/5/2023 at 12:09 PM
Employee Post
Hey Nick! Do the affected user's email addresses both reside on the same domain, or do they differ? I suspect one of them may have a missing autodiscover component or similar issue that is introducing hiccups into the whole process. 

When Outlook communicates with any given MAPI account it will constantly check several items and if these fail or generate security exceptions it can lead to that password prompt you are seeing there potentially: 
- Does https://mail.customer-domain.com terminate successfully on the SmarterMail web interface? 
- Does https://autodiscover.customer-domain.com terminate successfully on the SmarterMail web interface?
- Does the customer-domain.com DNS server contain an SRV record referencing mail.customer-domain.com on port 443?
- Do calls to https://customer-domain.com/autodiscover/autodiscover.xml get answered by the SmarterMail server, or are otherwise redirected to it?
This might be a good starting point just to make sure everything is working on that end. We're here in support if you need a hand tracking this down as well!
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
0
Nick Jansen Replied
10/5/2023 at 1:45 PM
Hi Kyle,

Thanks for your reply. All email addresses are on the same domain.

Yes to the first 3 questions in the box. For the last one, no, but I will see if I can set up a redirect on our main web server for that and test again and let you know the results.

Thanks!
1
Kyle Kerst Replied
10/5/2023 at 2:10 PM
Employee Post
You're very welcome Nick. Sounds like you're in pretty good shape on that front, but the autodiscover.xml redirect can be a problem all on its own sometimes. A lot of the time I see calls to that end up being captured by an old web/email server that used to offer similar services and this gets Outlook all sorts of turned around! Let me know how that goes and we can go from there. Have a good one Nick!
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
0
Nick Jansen Replied
10/6/2023 at 8:23 AM
I believe the redirect is set up now, with one exception: the SSL certificate on our main web server doesn't include the bare domain (without www) as a Subject Alt Name so the autodiscover URL there gives a certificate validation error.

Our web host manages the certificate themselves. I've asked them to add the bare domain as a Subject Alt Name in the past but didn't get anywhere (I may have sent the request to the wrong email address possibly though); trying again now.

I think worst case, I can set the additional accounts for this user up as IMAP/SMTP since they (other than the primary account) probably don't really have to be MAPI.
1
Kyle Kerst Replied
10/9/2023 at 9:45 AM
Employee Post
That's great to hear Nick, headed in the right direction! A good trick for the hostname addition might be leveraging Lets Encrypt/Certify the Web. With a DNS hint or other available methods in the client you can likely accomplish this from your end. It might take some troubleshooting to figure out what works best for your environment but that should help!
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
3
Brian Bjerring-Jensen Replied
10/9/2023 at 11:05 AM
This script works very well regarding autodiscovery on our systems.

Windows Registry Editor Version 5.00

[HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\Outlook\AutoDiscover]
"ExcludeExplicitO365Endpoint"=dword:00000001
"ExcludeHttpRedirect"=dword:00000001
"ExcludeHttpsRootDomain"=dword:00000001
"ExcludeScpLookup"=dword:00000001

[HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\Outlook\AutoDiscover\RedirectServers]
"yourmailserver.com"=hex(0):


We run it on all new users of our virtual desktops.
1
Antony Weaver Replied
10/10/2023 at 3:08 PM
I have the same problem, multiple smartermail  mapi email accounts (same domain) in Outlook 2021 that keep asking for the password.  Same email accounts on another computer on the same network in Outlook 2016  works flawlessly. I have a ticket 27B-2C948DFD-0B15 open but so far we haven't gotten it resolved. I just added the registry edit @Brian posted so we'll see if that makes a difference. 
0
Kyle Kerst Replied
10/10/2023 at 3:49 PM
Employee Post
@Antony: I just did a quick review of that ticket and what I can say is that the autodiscover environment for the domain you most recently replied referencing is in good shape at this point. You appear to be meeting all required pieces to keep Outlook happy, so you may be able to complete resyncs of the accounts under a fresh profile to resolve this for the user at this point. 
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
0
Antony Weaver Replied
10/11/2023 at 8:18 AM
I've already done a complete resync under a fresh profile.
1
Nick Jansen Replied
10/11/2023 at 9:59 AM
I fixed the SSL issue on our main website and the autodiscover URL redirect is set up. I will see if the username/password prompts continue to appear for this user.
0
Antony Weaver Replied
10/16/2023 at 4:27 PM
Outlook is still asking for passwords after adding the registry key @brian mentioned. Question.. I set the RedirectServers to mail.companyname.com Should it be autodiscover.companyname.com ?
2
Nick Jansen Replied
1/22/2024 at 9:29 AM
I continued having this problem after fixing the autodiscover URL redirect, and not only on this one user's computer. However, I think I figured out the solution, or at least what appears to have solved it in my case.

The original problem was, with more than one MAPI account in the same Outlook profile at the same time, both/all accounts would work for a short time, then I would get prompted for credentials for one account (sometimes with the wrong username pre-populated). I would enter the correct credentials and then both/all accounts would work again for a short time, then I would get prompted for credentials for a different account, and so on forever.

  1. Close Outlook.
  2. In Windows, open Credential Manager (either search for it on the Start menu, or go to Control Panel -> User Accounts -> Credential Manager).
  3. Click Windows Credentials.
  4. Look under Generic Credentials for entries starting with MicrosoftOffice16_Data:SSPI:. The number 16 may vary depending on your version of Office.
  5. Click the down arrow to the right of one of them. The User name: field is probably blank, which is probably normal if you only had one MAPI account. If it isn't blank, you might have a different problem.
  6. Click Edit near the bottom of this credential.
  7. Fill in User name with the same email address that's shown to the right of SSPI:.
  8. Click Save.
  9. Repeat steps 5-8 for all other MAPI accounts you have.
  10. Close Credential Manager.
  11. Open Outlook.
You may or may not have to reenter the credentials in Outlook one more time for one or more of your accounts, depending on if they were correctly saved last time.
1
Brian Bjerring-Jensen Replied
1/22/2024 at 10:38 AM
8776 has a similar issue and its reported on a ticket. No popups of credentials but calendars is going missing and you cannot view shared ressources.
0
Nick Jansen Replied
2/5/2024 at 3:48 PM
Correction, it appears the above steps don't actually fix it, just seems to make it take longer until I'm asked for credentials again. Does Outlook even actually support having multiple MAPI accounts in the same profile? I have the same issue in Outlook 2019 and Microsoft 365 Outlook and I get the impression that it isn't really a supported scenario.
1
Brian Bjerring-Jensen Replied
2/5/2024 at 8:27 PM
On exchange its not a problem. :)
0
Nick Jansen Replied
2/5/2024 at 10:33 PM
Oh hmm, good to know. Maybe something specific to my setup, or to SmarterMail in general then.
1
Antony Weaver Replied
4/2/2024 at 6:37 AM
@Nick Jansen I'm still having the same problem you are with one computer. Even did a factory reset and reinstall of windows and updated the Smarter Mail server to the latest version. I did the Generic Office credentials fix you mentioned and the next day it was prompting for the password again. I still have a ticket 178-2D4FD682-0B21 with support but so far we're not making any progress.
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