Yeah, good luck googling for “outlook does not ask for password”! It’s the exact opposite of what used to torment most Outlook users with Exchange accounts for quite a few years after RPC over HTTPS (Outlook Anywhere) was first introduced.
This is Outlook version 2111 Build 16.0.14701.20240 (365 subscription) on Windows 10. a.k.a. Outlook 2019 to 2021 ish.
My customer has a number of mailboxes, all full accounts (added to Outlook as accounts, rather than via delegation), and one of those accounts has quite a few aliases (proxy SMTP addresses). She wants one of those aliases putting as a separate mailbox.
I removed the alias email address, then created a new mailbox with that email address, with an Exchange Online Plan 1 license. Everything went OK server/cloud side, and I could log in via OWA, but any attempt to add the account to Outlook resulted in no prompt for the credentials. It just said ‘done’, but then when trying to access the mailbox, I would get “The attempt to log on to Microsoft Exchange has failed”.
Much faffing around with new Outlook profiles, checking of Saved Credentials in the credential manager, didn’t work.
The solution was to go to Access work or school, and then remove the Workplace or school account of the original account (the one that used to have the problem-address as an alias).
Then, I tried to add in the new account as a Work or School account, but that didn’t work. This may be because it’s an Exchange Online Plan 1 license rather than a full 365 Business Basic license. I stopped using Exchange Online Plan 1 for my customers a while ago and was giving everyone Business Basic licenses, since it was only 80p per month extra in cost, but these licenses are due a 20% price increase soon, amongst other Microsoft price increases and increased minimum-term commitments, so Exchange Plan 1 is back on the cards for basic email requirements.
After the failure to add this new account as a Work or School account, I instead added it to Email & accounts in Windows 10. This then magically added it as a Workplace account as well. I then removed the Email account from Windows 10, because I don’t want to use the Mail app and the Windows 10 notifications. Happily, the Workplace account remained in place.
I reopened Outlook. Outlook prompted for credentials for the original Workplace account that I removed earlier. I gave the credentials and allowed it to add the account back in to Windows as a Workplace account (‘use this account everywhere’. ‘allow my organisation to manage my device’).
I then proceeded to add the new ex-alias problem-account into Outlook. Outlook did not prompt for credentials, but things took a touch longer than last time (when it didn’t work), and this is fine, because the credentials are stored with the Workplace account already. After closing and reopening Outlook, all is well.