Outlook 2016 doesn't accept password or app password

@Gabriel

Again, you are using IMAP... not EAS or similar protocol. Several of us are saying the same thing that we prefer EAS or Exchange, so we can sync contacts and calendar in addition to email. If you add 1 of the 2 common plug-ins to do EAS, you will then have the issue Rob is talking about.

I am seeing exactly the same issue as I have been exploring alternatives. Perhaps this is something you can bring back to your team. As much as it pains me, you now have life-long MS supporters seriously looking at alternatives.

Rob,

I just installed Thunderbird on a new machine and followed the instructions in the Known Issue and it added my @Hotmail account with OAuth, Outlook and other apps are unable to connect to Outlook.com when using Basic authentication - Microsoft Support. Its working so far with no issues. Please double check if you might need to remove the account and add it back using the OAuth settings.

If you are using Outlook 2013 you will keep having the random password prompt issue. As MS representatives have explained on this thread, Outlook 2013 and other version older than Outlook 2021 and up doesn't support the newly MS authentication implementation OAuth 2.0.

The only solution is to upgrade to an Outlook version (or any other email client) that support OAuth. It is hard and frustrating having to accept that, but this is the current reality, I was using Outlook 2013 as well for years for all my accounts including MS, Gmail accounts etc.. and I have now, like you and many others, to deal with the password prompt issue for almost a month, until I discovered in this thread why this is happening.

To make things worst, while now you have just to enter your password a million times when prompted, at one point in time (which haven't been specified yet) Microsoft will completely deny access to email accounts from clients that use basic authentication instead of OAuth, Please someone correct me if I'm wrong.

I hated having to ditch Outlook 2013 since it was working fine until now, but the reality is that now it doesn't, and if you think that you will still be able to use Outlook 2013 with Gmail you are wrong, Gmail starting September this year will implement exclusively OAuth as their authentication like Microsoft and you will not be able to use your Outlook 2013 to access Gmail accounts as well.

I'm not using any of my personal email accounts at work or for work, so for me the easy choice was to install the new free Outlook (I still have the old Outlook 2013 installed just in case) and so far I didn't have any problem or password prompt or else. It's a pretty decent client. The downside is that the free version drop just 1 advertising email once you start your client, otherwise if you keep it open it doesn't send you any advertising email, it does that only when you start up the email app, and I repeat its just 1 ad email, and you will receive the ad only on your Microsoft account, not on other non Microsoft ones like Gmail or other providers.

Those are just my 2 cents, I know some here hate that client and that's fine, there are other options out there free and not free. I had the opportunity to buy a 30% discounted license for MS 365 with my employee Microsoft Workplace Discount Program, but I really don't need that, and I really didn't want to pay for a subscription. I think for my personal email the free Outlook is just fine and I was honestly surprised on how easy is to setup your email accounts and how fast the app is, it definitely exceeded my expectations. About the privacy, it is as private as any other email client, or email service. Office 365 have over 400 million users worldwide from 500 fortune companies, Military, Government, Health Care, Education and on and on, you think they will risk their reputation to look at or use your email for some obscure reason? I don't think so, but that's just my opinion. You are probably using Windows or macOS as your OS, you think your privacy is safe? Well there is not way to tell if Windows or macOS are...nothing today is private or safe. If you want privacy stay off line and don't use a pc or a phone. You will still get plenty of phone scam call out of nowhere over your landline.

I tried to add it within confine of Outlook for Android, and I was getting credential prompt frequently.

The next round I tried is to add the account credentials at the OS level, so the sync would apply to email, contacts, and calendar (the 3 types of data supported by Hotmail for sync). Technically, this would have sync'ed and added data to your phone's phone-wide email/contact/calendar storage. This was working well for years until 1/23/2024; I did get the occasional server can't be reached error but it never lasted as long as this time. As of last few days, when I attempt to add the account (after deleting it), it would get not able to reach server error. It's a common error if you Google it. According to MS' own articles, the auto-discovery function of MS accounts is done by MS, so regardless if Outlook for Android try to resolve it, or if OS' Exchange Service try to resolve it, it should be going through similar or even the same mechanism.

Again, my main concern is that I want least amount of "clients" on my mobile device. Every email client will sync data on its own cycle, and running multiple clients would mean using extra battery, and have separate notifications and so on. The battery issue is particularly noticeable when you have push turned on.

You can argue I could just use Outlook for Android for everything but this triggers another set of concerns. Outlook for Android uses similar architecture as "New Outlook" for Windows. It uses Microsoft Cloud as proxy to access email. According to numerous MS' own articles I read, the proxy mode is even used for Exchange on-premise accounts. Your company's legal/IT team may jump all over this because many NDA agreements indicate you cannot allow certain information to sit on 3rd party system, namely Microsoft Cloud in this case. In my situation, since Hotmail is hosted on MS infrastructure, it always has my data, so it's OK for me. BUT, accessing other emails not on MS infrastructure would then need to be stored on MS system - and this is not OK for me. Therefore, I cannot use Outlook for Android or Outlook Lite for Android for all of my emails and calendar. And if you read more about MS' terms and conditions, your data, even in this cached state, is subject to government/state level orders, so even non-US countries can technically issue a subpoena or order to have MS dump out any and all data it has on you - this then by extension, touches ALL data including those 3rd party you accessed via Outlook for Android/iOS or "New Outlook for Windows.

Hi, I am not 100 % sure, but maybe there is a little misunderstandig. It seems like Gabriel is talking about using autodiscovery in -Outlook- on Android (and support button within Outlook) but you are using GMail on Android?