Ol16 desktopT suddenly can't connect with Exchange

astro46

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
OL16, desktop version. win10 2019.
Turned on desktop computer today, opened Outlook. greeted with a request about connecting to internet. Never saw that before. Then I am getting requests for microsoft password, which eventually I figured out was for outlook.com and its syncing calendar. Desktop was working ok last night.

My phone calendar, and laptop Outlook are working fine. Calendars sync.

After web search, I tried deleting all certificates relating to Office. Didn't help.

I have tried deleting the outlook.com account in Outlook. Now I can't create a new one. At best it will create an 'active exchange' account, using the password, which won't sync calendar. But I can not create an Exchange account. Keeps asking for password. I have copy of password in spreadsheet, and in pw manager. So I am pretty sure I am using the correct one. I don't want to use the 'forgot my password', since I don't think that this is the problem, and I am afraid that my laptop and phone will then be locked out of Exchange.

I have tried restoring an image from 2 weeks ago. It had the same problem, asking to connect with internet , then repeatedly asking for password. I have put it back to image from today. This computer was ok last night.

Any ideas about what is happening here?
 

astro46

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
I notice that if i enter a knowingly wrong password, it immediately tells me that it is wrong.
If i enter what i believe is the correct password, it keeps recycling asking for password. i've tried entering 5 times, it keeps recycling.
 

astro46

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
and, I have tried deleting the control panel>mail>profiles>'outlook profile'. Opening outlook, it asked to create a profile and a email account. as before , it couldn't login to the outlook.com site. around and around about asking for password.

I have restored the image that I wisely created before deleting the profile, since I didn't want to have to reinstall all email accounts on the long shot that this would fix it.
 

astro46

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
I manually synced the desktop pst to laptop . I have done this for years without a problem. today, as soon as i opened Outlook is asked for login to outlook.com. So, now the problem exists on 2 computers.

Went to an desktop image, from 4/17/20, moved the outlook.pst to both desktop and laptop. Makes no difference. still wants, but won't accept password.
I have no idea what is going on here, or, obviously, how to fix it.
 

astro46

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
I just logged into my outlook.com online, through browser. I know the pw is correct.
 

astro46

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
since thur I have also tried: make a new profile, turning on 2 step verification and generating an app password (gets immediate 'wrong password'response), MS remote connectivity analyzer (tells me "autodiscovery failed"), Support and Recoveryi Asst> "solution isn't supported for yoru office environment". Created an alias. can send email to the alias, but it also won't establish an Exchange account. I can set up AES accounts all day, but not Exchange.

Again, this problem exists on 2 win10 computers. But so far not on my iphone, which connects to exchange calendar.
 
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