Outlook 2016 Authentication Issues

[discoveranother]

Hi all,

 

Further to a previous thread below :

 

http://www.edugeek.net/forums/office-software/230166-outlook-outlook-outlook-issue.html#post1972769

 

Some. not all of our clients have had issues authenticating to M365 mailboxes from Outlook 2016 on their PCs.

 

These clients have an A1 license with M365, so this license does not include the Microsoft Apps for Business license which normally comes with an A3 license.

 

I queried with Microsoft support that many clients Outlook 2016 still works connecting to M365 and that this particular client has the same A1 license as the others. Here is Microsoft's response below. I would welcome your guys feedback. Many thanks for any feedback.

 

"Accessing a Microsoft 365 mailbox (whose license does not include the desktop client application features) via outlook 2016 is not consistent as the mailbox is not licensed to be accessed via a desktop client application.

 

An account assigned the Office A1 faculty license is not authorized to access its mailbox via a desktop client application. If eventually a user is lucky enough to bypass authentication and access the mailbox through any version of outlook desktop application, it is only a matter of time before that connection to that mailbox via desktop client application fails as it is not consistent, hence, when situation like this arises there is limited support Microsoft can provide as the license assigned to that account does not include a desktop client application feature.

 

Please keep in mind that I am not doubting your claim that you have other businesses with exactly the same licenses who also use outlook 2016 without any problems. However, connection to the mailboxes using this method is not consistent and authentication could fail at any time."

[Koldov]

This is interesting to me as I had some recent issues with Outlook 2016 and connecting to what I think is an O365 account.

 

I'm not sure if it is the same issue you're describing and it seems that authenticating is not the main issue as it DOES authenticate. The issue was that they needed to at all, because they certainly didn't in the same way previously. I am wondering if we are one of the 'lucky' tenants that hasn't been 'upgraded' to maybe modern auth or whatever it is they've moved to now...?

 

We have a 3rd party email provider (who have set up a tenant in O365 and use various licenses ranging from A1 to Exchange Online).... bit of a mess really...

 

 

Previously you could access email by providing your credentials in a little grey 'Win 95' style box through Outlook 2016. Unfortunately some (most) users tick 'remember me' and that is the last time they'll need to authenticate.

 

I didn't do that and authenticated in that little box for all my accounts every time, but at some point a few months ago that little box didn't come up anymore... instead it took me to the webpage for the 3rd party email provider, I asked our provider if anything had changed in their set-up and got this reply:

 

"Our technical team has looked into this, and unfortunately there isn’t much we can do about this because this pop-up is generated by a third-party application.

 

In general, when a product in the Microsoft suite has to open a webpage like this it has a hard-coded 'backdoor' to use the MS owned web browser that existed when it was made. That means this is almost certainly using an old version of edge from before they switched it to be chromium based, which hasn't been updated for several years at this point.

 

The popup is meant for authenticating and everything within Outlook will work as expected."

 

It kind of made sense in some respects and not others...

 

Anyway, I upgraded my machine to Office 2019 and then 2021 LTSC and the issue went away (not sure exactly why)...

[discoveranother]

Thank you for the reply.

 

This is interesting also, as I did hear the odd story about upgrading to Office 2019 or 2021 LTSC and it may work, so I will give that a go as well.

 

Thanks

[chaplic]

**BS CLAXON**

 

A1 does not include a license for Office, I think we all know that. But if you have a fully licensed modern-auth-aware outlook client (say via a KMS key) I do not believe there is a block on any clients connecting, and ‘sometimes it works sometimes it doesn’t is a nonsense.

 

I think the agent responding to that is making stuff up, or at best not understanding that office can be licensed in other ways than through an office365 license. If you really want to dispel this and have a client that regularly fails, just buy an A3 license and apply it to the client (and watch it still fail!).

[chaplic]

This is interesting to me as I had some recent issues with Outlook 2016 and connecting to what I think is an O365 account.

 

"Our technical team has looked into this, and unfortunately there isn’t much we can do about this because this pop-up is generated by a third-party application.

Anyway, I upgraded my machine to Office 2019 and then 2021 LTSC and the issue went away (not sure exactly why)...

 

BS CLAXON 2, this is a nonsense, a little gray box is basic authentication hence not working.

 

 

2019 has a feature that reaches directly to office365 first and ignores any autodiscover configuration issues, that’s likely why it’s working.

[Michael]

I've not seen or observed any issues with Outlook 2016, but I know if you installed a fresh copy of Outlook, it'd require updates before successfully connecting to Exchange Online.

 

As for what happens if you updated Outlook so far, blocked updates and then Microsoft increased the minimum (with an existing/working setup), maybe it's something along these lines!?

[Oaktech]

I've not seen or observed any issues with Outlook 2016, but I know if you installed a fresh copy of Outlook, it'd require updates before successfully connecting to Exchange Online.

 

As for what happens if you updated Outlook so far, blocked updates and then Microsoft increased the minimum (with an existing/working setup), maybe it's something along these lines!?

 

There was a specific update to Outlook that enabled modern auth, I've been out to 3 schools and 2 companies now where that update was either missed or actively blocked and connection carnage has resulted.

 

On each site I've either followed the guidance included here:

 

https://learn.microsoft.com/en-us/microsoft-365/enterprise/modern-auth-for-office-2013-and-2016?view=o365-worldwide and installed the specific update mentioned

 

Or I've tweaked WSUS and it's supporting GPOs to include MS product updates then reinstalled office from the 'repair install' option and ensured that all updates had run and installed before trying to use it.

[Michael]

That makes sense, if WSUS isn't set to approve updates automatically.

 

I use WUfB so all updates are approved, so long as they've been published for 30+ days (the way I have things setup).

[chaplic]

Modern auth has always been on by default in Outlook 2016, the code is in Outlook 2013 but not enabled by default. Outlook 2013 + Modern Auth will still connect happily today, as will Outlook 2016RTM if you were daft enough to be unpatched. What's changed is later versions of outlook ignoring any misconfigurations of autodiscover and going 'hmm, bet they are on office365' and connecting directly.