Outlook 2016 doesn't accept password or app password

David --

Would you please explain why connections work for a few days and then stop working? Is Microsoft continuing to fix the mess it created with this ill-conceived change to authentication? Will MS provide compensation for the month+ that the services users pay for are unavailable to them via the devices and apps they (we/I) have used for years without issue? It would be helpful to know whether we can rely on MS to provide users their paid services or if we should find alternatives.

Thanks

Hi Frubbl - I totally understand your frustration with the changes. With that being said as a paying customer of Microsoft 365, nothing changes with those apps and services. Outlook that comes with Microsoft 365 continues to work and supports OAuth via Outlook.com Syncing. You also continue to get all of the added benefits like Ad Free experience and additional storage for your mailbox and OneDrive.

Sadly we are unable to comment or force a vendor to start using a more Modern Auth mechanism. This change that we are doing to eventually retire Basic Auth is not unique to Microsoft. In fact Google has already completed their deprecation of Basic auth/Less Secure Apps, and we know a variety of other ISPs that are in the same process. This change that all are going through is truly for the safety and benefit of all of the users.

So the best suggestion that I would have is to start discussions with BlackBerry to see if they are planning or will be supporting more current forms of Auth. This is the same way that apps like Apple Mail, Google Mail, and Thunderbird all have started to support OAuth in the past years.

@Jott Ell,

That version of Outlook 2016 MSI does not support OAuth for Outlook.com. Outlook 2016 MSI is out of mainstream support and is only getting security updates, Latest updates for versions of Office that use Windows Installer (MSI) - Office release notes | Microsoft Learn.

If you want to stay on Office Perpetual, you could go with Office 2021 which supports OAuth or wait a bit longer for Office 2024. I don't think there is a release date yet for Office 2024 though.

@flu8,

You are right there is a proxy of your Gmail, Yahoo, and iCloud mailbox that syncs to the Microsoft cloud when you add one of those accounts to New Outlook. The main reason the Outlook Team made this investment is to address prior feedback with using IMAP in Outlook Desktop. The main feedback was not being able to sync contacts and calendar, but other key features are not available in native IMAP. This article explains the main points of the functionality, Sync your account in Outlook to the Microsoft Cloud - Microsoft Support.

If you know of any issues with privacy with New Outlook, please let me know. I will share that back to the Outlook Team. At Microsoft all data is protected and locked down. Microsoft makes it so users control their own data, Data Protection with Microsoft Privacy Principles | Microsoft Trust Center.

I've been a very patient and non-complaining participant in this community and particularly this thread. This post by Frubbl is spot on.