Outlook 2016 doesn't accept password or app password

(see here for issues on Apple's platforms:

https://answers.microsoft.com/en-us/msoffice/forum/all/app-specific-passwords-not-working-why/59120e3b-7cbe-48e7-9e1c-d398932763b8?page=2&messageId=1717a28c-8dae-4ad4-8bd9-f1e30bd51dc0 )

On my M365 Outlook, which is on my work system, I added my Hotmail account just to see if it worked better. It was added via both methods of auto discovery and manually creating it as EAS and I was still getting the prompts in both cases. The connection status showed my work account under "Bearer*" and Hotmail under "Clear*". The prompt was so frequent and as I mentioned in another comment, it would take away the cursor/pointer focus suddenly, resulted in my workflow being constantly disrupted, so I removed the account to gain back my productivity. I did add it back a few times to see if things progressed differently, but was still getting the prompt.

I also spoke to our IT folks (pretty friendly with them), and they have no desire to work on my personal account issue as they are knee deep in other MS related issues such as problems from the recent Patch Tuesday rounds.

Just to be clear, my Hotmail issue was never with IMAP or POP3. I do not use those protocols with Hotmail. I always set the account as Exchange/EAS or Outlook.com. To be frank, I've noticed Outlook.com account type to be slower. Exchange type on desktop and EAS on mobile were the gold standard for fast and accurate sync and it was the case up until 1/23/2024. I do use POP3 for non-Microsoft mail and it has been fine during this period. POP3 and offline PST is an important consideration for me.

Also, I pored through your peers' postings on "New Outlook", including people claiming they are product manager for Outlook. What was said is that POP3 and PST are in the plan. However, no firm date and comment that address the elephant in the room, of using Microsoft cloud as proxy to access and store non-Microsoft 3rd-party data. I honestly don't know how POP3/PST and proxy architecture means for each other and its scary to even think about this. Is Microsoft cloud will suck up the entire PST during its processing for import in the future and POP3 will also morph into a proxy architecture? None of this is clear enough... But I will leave it to regulators in EU to address that issue with Microsoft.

I saw that article as well. I think Microsoft's real desire is to gain access to our data that are not currently in Microsoft ecosystem. There is nothing stopping them for continuing Outlook desktop, and have a lite/feature-removed version for free, for consumers. Instead, some wisdom in Redmond decided to merge everything together. The "New Outlook"s product managers posted about adding POP3 and PST support, and a slew of very important features that are currently missing. Given "New Outlook" is a PWA, it's POP3 protocol will likely be implemented as a proxy service as well and perhaps PST only done as a file write to your local file system (just like how doc/xls/ppt are done with online Office) or stored in OneDrive.

It would be really good to have a solid alternative like Thurderbird for Exchange support, especially Microsoft seem to be abandoning that market for consumers.

AnotherBug,

Clear* connecting to Outlook.com means basic auth. If you are connecting Outlook Desktop to Outlook.com make sure to use the default Add Account experience that will add it as an Exchange account. This is different than EAS and is the only connection option that will connect from Outlook Desktop to Outlook.com with OAuth. Please do not use EAS in Outlook Desktop for Outlook.com or M365.

Concerning the proxy also known as cloud cache there is nothing nefarious about it. If Microsoft abused customer data in any way it would have issues with regulators. Because of this it's actually easier to get into Fort Knox than to access customer data. No one at Microsoft can go look at your email data and no one has any interest in that. The only reason for cloud cache is to make it so Outlook is connecting to your third-party mailbox so that it appears as an Exchange account so that Outlook can provide you with all the features that come with it. This article explains what all cloud cache is for, Sync your account in Outlook to the Microsoft Cloud - Microsoft Support.