Outlook office 2016 keeps asking for password for my personal email but not for my company email.

Outlook 2003 up to 2019 with a version less than (11601.10000) does not support Modern Authentication and as 16th Sept 2024 will not run.

Only way to get outlook to work is to download a copy of Office 2019 or 2021 from here: https://answers.microsoft.com/en-us/msoffice/forum/all/useful-microsoft-download-links-for-office-direct/7bcaa971-9493-44b6-a1ba-0db4c6957c47 and then purchase a licence key.

Or try this for both Office and Windows installation https://massgrave.dev/

You will need to delete your old profile in Outlook 2019 / 2021 then setup a new profile or you will still get the password error message. Office 2019 and 2021 will only run on Windows 10 or 11.

Windows 10 Media Creation Tool Download https://www.microsoft.com/en-us/software-download/windows10

Windows 11 Disk Image (ISO) Download https://www.microsoft.com/en-us/software-download/windows11?ranMID=24542&ranEAID=nOD/rLJHOac&ranSiteID=nOD_rLJHOac-XzuRXcfX5.4NEQjjeMWwVA&epi=nOD_rLJHOac-XzuRXcfX5.4NEQjjeMWwVA&irgwc=1&OCID=AIDcmm549zy227_aff_7593_1243925&tduid=%28ir__xalkf0mmbckfbzbfltppepyjd22xb39wbdnxhwfn00%29%287593%29%281243925%29%28nOD_rLJHOac-XzuRXcfX5.4NEQjjeMWwVA%29%28%29&irclickid=_xalkf0mmbckfbzbfltppepyjd22xb39wbdnxhwfn00

Both of the above are Microsoft sites.

Look here about how to enable modern authentication for office 2019. https://learn.microsoft.com/en-us/microsoft-365/enterprise/modern-auth-for-office-2013-and-2016? view=o365-worldwide

Any site that ends in (microsoft.com) is an official Microsoft site.

Outlook classic is not the same as Outlook 2016. Classic is a slimmed down version of the full Outlook desktop software. Outlook classic is being phased out soon and is being replace by outlook new. Both classic and new are slimed down versions of Outlook. Both of them are available to everyone who has windows 10 and 11.

That software looks just like the web version of Outlook too.

I had the same problem. I had disabled automatic updates right after installing and registering Office 2016 Pro Plus that I bought on a third party site. The seller labeled it as "Retail" but after registering the product it won't show on my Microsoft Account Services & Subscriptions. Anyhow, that was the least of my problems when I repeatedly got asked for a password trying to sign in into Outlook 2016.

I fixed it by enabling automatic updates inside Word. Office was updated successfully and now it replaced the Outlook 2016 client with a client called "Outlook(classic)". Now I can sign in and use Outlook. This was the fix for me.

Outlook 2003 up to 2019 with a version less than (11601.10000) does not support Modern Authentication and as off 3 weeks ago will not run. Only way to get outlook to work is to have windows 10 or 11 and download a copy of Office 2019 or 2021 from here and then purchase a licence key.

https://answers.microsoft.com/en-us/msoffice/forum/all/useful-microsoft-download-links-for-office-direct/7bcaa971-9493-44b6-a1ba-0db4c6957c47

Office 2019 and 2021 will not run on any other version of windows.

Look here about how to enable modern authentication for office 2019.

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

Any site that ends in (microsoft.com) is an official Microsoft site.