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Cannot connect Microsoft Exchange to Outlook 365

Hi Experts,


I just migrated 15 users to Microsoft Exchange Online, and for about 7-8 users I had to login to their computers and connect their Exchange  accounts to Outlook. This took me about 5 minutes to do for each user - with my eyes closed.


However, with one particular user, I just cannot connect. The user has admitted that he is suspicious of Microsoft (he’s on Win 10) and all IT, he has also turned off some default settings, but doesn’t know which.  Fun! 


Based on the above, my first suspension was that he disabled Autodiscover, but the user does not have the AlwaysUseMSOAuthForAutoDiscover entry.
 User generated image
I still need to add his Exchange account to his Outlook 365, and he has never used Outlook before (as he says). So, when he opens his Outlook and/or adds a new Profile through Control Panel > Mail, he keeps looping between these 2 screens.


User generated image 
The user indicated that he has already run and accepted all Windows updates. 


I will be logging into his computer, is there anything specific what I need to look for, or do in  this situation? Firewall?


Any help would be appreciated.


Thank you!

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Rodney Barnhardt
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Since he may have been messing around with the system, try downloading the Outlook Test and Recovery tool. It maybe able to either diagnose or correct the issue. 

https://support.microsoft.com/en-us/office/resolve-outlook-for-windows-issues-with-automated-troubleshooting-tools-38e2342d-3527-4190-8754-a82d8b970fe2
Download the Office uninstall support tool. Click here scroll to the bottom and expand option 2. This will clean out every aspect of MS Office including the registry. Make sure to restart after and install MS Office afterwards.

What does ipconfig /all show? Maybe he put in a DNS entry or changed something here.

Do ipconfig /flushdns then nslookup to check if the computer is resolving Microsoft 365 servers.

Firewall is easy enough to test, either completely reset or disable while testing.


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ASKER

What am I looking for with ipconfig /all ?

What is the Exchange Online server that I can ping against?

Side note, he is able to access OWA through www.office.com
With option 2 in the Office Uninstall tool, will his files remain?
What am I looking for with ipconfig /all ?
probably nothing since you confirmed he can access through the portal. Which is a good indication DNS is working correctly. I wanted to make sure he didn't put in a secondary DNS.

What is the Exchange Online server that I can ping against?
not ping I'd recommend doing nslookup from a DOS command prompt. Make sure DNS is resolving, which it appears to be fine since you can access via the portal. Oh, ipconfig /flush dns flushes out the DNS cache.

With option 2...
all your data is fine, just make sure to close out and save first. It only removes MS Office and the registry settings. Microsoft has had allot of complaints over the years when MS Office ends up having serious issues due to all the different versions, they created a pretty good mess so it's nice they made a tool to clean it up. 
Look at the Windows Acccounts, be sure he doesn't have a personal MS and business account logged in. Happens a lot.
Lisa - what do you mean? I have a lot of users - actually all, with Office being registered to their personal MS Acounts, but are using their Exchange work emaiil.
So, the client did the diagnostics on his own, and this is what he sent me...

Following a prompt from the Microsoft troubleshooting page, I downloaded and tried their Support and Recovery Assistant.
It ran some checks, did some diagnostics and seemed to think everything was fine.
Here is the window it displayed when finished its troubleshooting. Note that the Autodiscover item is checked. (?)
 
---------------------------------------
1. We're ready to set up your Office 365 email in Outlook. Click Yes when you're ready. Click No to skip.

User generated image

---------------------------------------
 
I clicked, "yes", that I was ready to set up Outlook, and it gave me the following window to Choose Profile:
 
User generated image
 
 
I tried using "outlook" as suggested, I tried creating new profile from this "New" button, I tried "Properties" (which led to me to that larger window that you directed me to before where I can select "New" to make a new profile).  
All actions led to same message that says Outlook could not set up the account.
 
For what it's worth, I attached the log file that the SARA made.

SaraLog-20220309-0-0.log

~~~~~~~~

As well, user states that he has a Custom toolbar in Excel, will he loose that if we do the Option #2 Removal?
I would export it, I believe it will be removed.

Click here for info. 
You may want to look for a cached Exchange OST file in the following path and delete it if it exist. Even with a new profile, I have seen Outlook reconnect to an existing one and cause issues. It will be recreated with the new profile. 

C:\Users\<username>\AppData\Local\Microsoft\Outlook
I deleted all profiles from Control Panel>Mail

I deleted all *.ost files, and even renamed

C:\Users\<username>\AppData\Local\Microsoft\Outlook

to

C:\Users\<username>\AppData\Local\Microsoft\Outlook.bak

after, I added a new profile, and of course it created blank Outlook folder. When I tried adding the Exchange address it gave me the below screen


User generated image

This is, of course, the POP3/IMAP dialog, and the server points to the old server. When I add his account on my computer, I get the following pop up, which I never get on his computer.

User generated image

Of course, on my computer his Exchange account works normally. But somehow, his computer is preset to the old server.
Since you mentioned the users had been making changes to Windows 10 and Outlook does not seem to even try to connect to M365, you may want to check and see if they disabled the ability to connect to it in Windows 10.

  1. Go to your Registry Editor
  2. Go to Computer\HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Internet\UseOnlineContent
  3. Set the value to 0.
Should be set to 1 for enabled or not exist at all. 

So,...

=============
Computer\HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Internet\UseOnlineContent 

Does not exist

============
HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\AutoDiscover

Has only one entry (Default) with no value.

============
HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\x.0\Outlook\AutoDiscover

Has only one entry (Default) with no value.

HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\AutoDiscover
HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\x.0\Outlook\AutoDiscover

Has only one entry (Default) with no value.
0 = Disabled
1 = Enabled

From the article:
To resolve this problem, review the Autodiscover-related registry data you may have on your Outlook client, and ensure the data is configured correctly. Also, if you are unsure if the registry data is needed, consider changing the data for any of these registry values to zero (0), and then test Outlook to see if you experience a difference in Autodiscover. 
Make sure to restart after making registry changes.
From the user...

 
Per your email, I changed the first registry key (shows new value):
User generated image
but the second one you listed, I don't have.
User generated image

Is it an issue that the user does not have the 2nd?
BTW, the user added his @hotmail.com account to Outlook without issue.
hotmail.com, now known as Outlook.com are entirely different than Microsoft 365, especially the way they each connect to services on the backend.  
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WORKS2011
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