outlook, outlook, outlook issue

[discoveranother]

Hi all,

 

Not sure if anyone else has encountered this but I'm sure they must have. Had a situation today trying to sort out the latest Outlook issues throwing up the password box linking to O365. Nightmare. Here is what happened.

 

Got some clients on Outlook 2013. I upgraded these to 2016 (will explain shortly why not 2019 or 2021) and some clients it went fine. I just had to add in the update as follows after 2016 upgrade.:-

 

https://support.microsoft.com/en-us/topic/march-2-2021-update-for-outlook-2016-kb4493226-8bb9c555-a33f-906f-3366-3ac20c4055cd

 

However, other clients after the upgrade from 2013 to 2016, it removed their email accounts completely from control panel>mail which was massively frustrating, so the user had to 'attempt' to add their email addresses in manually.

 

Anyway, adding the email accounts in manually did not work as Outlook 2016 would not connect to O365 like Outlook 2013 does, due to the error below:-

 

 

Then had to try and setup Outlook 2016 through manual settings below, but it would not work as the first option highlighted on the screenshot below was not available, only the other 2 options were showing:-

 

 

The clients domains all have autodiscover DNS record setup for their domains.

 

Instead, tried installing office 2019 and office 2021 and kept getting the following errors

 

https://www.winchatsupport.com/error-code-0-20390-for-office-2021-get-fixed-here/#:~:text=Error%20code%200%2D2039%20(0)%20occurs%20when%20installing%20or,system%20file%20errors%20or%20corruption

 

I believe this however is down to the Smoothwall firewalls onsite.

 

What a nightmare day. Any thoughts would be most welcome.

 

Thanks all

[gaz350b]

Could be anything from ssl interception to domains being blocked. It could also be failing authentication to Smoothwall.

 

Get m365 domains added to white lists, allow unauthenticated users and finally add it them to the bypass ssl interception.

 

Mix and match to find if any helps.

[jmak]

I've seen the first error at my (still quite new) place. I've been told it's quite normal and just go back the next day and try again.

 

Alternatively, I'm finding far fewer problems using the O365 client.

[MYK-IT]

Possible suggestions...

 

Ensure Modern Authentication is enabled. (Legacy authentication is, or has been disabled by now - varies by Microsoft tennacy). Can't remember atm, but may require a registry tweak when upgrading from older version(s) of Outlook, as it's not enabled by default on 2016 etc.

 

TLS version. Ensure using and enabled (at least) v1.2

Edited November 1, 2022 by MYK-IT

[andy_b]

We had Modern Authentication turned on this weekend.

 

For Outlook 2013 you need these reg keys: https://learn.microsoft.com/en-us/microsoft-365/admin/security-and-compliance/enable-modern-authentication?view=o365-worldwide

 

Also had to update our Mosyle email profile for iPads - tick OAuth and get staff to re-login.

[free780]

Make sure you are not SSL/TLS inspecting any Office 365 domains. Ideally don’t proxy any Office 365 traffic given the amount of persistent connections.

[chaplic]

You cannot manually setup the connection to O365, it MUST be via autodiscover.

 

Just because you have a cname of autodiscover.yourname.uk > autodiscover.outlook.com does not mean everything is going to work.

 

Newer versions of oultook 2016 onwards basically to connect to O365 first directly which would probably work around your issue should you actually get it installed, but there's no reason we cannot make the current version work.

 

The 'there is not an encrypted connection' error is largely misleading in my experience, it means 'uh, something went wrong'

 

Theres a multi step process that outlook tries to find it's exchange server. If any of these steps fail in an expected way, it will contine to the next step

However I've seen circusmtances where, for example, when outlook does a root domain query https://yourdomain.co.uk/autodiscover/autodiscover.xml the webserver answers or asks for auth which screw outlook up.

 

Follow the process here

 

Outlook 2016 implementation of Autodiscover (microsoft.com)

 

 

Or create an outlook profile with no mail connection, ctrl right click on outlook icon bottom right and click test autodiscover. Untick both guesssmart boxes and fill in email address. This will give you some clues, post it here redacted as you wish.