Outlook.exe won't accept correct password

Forums › Microsoft Windows › Outlook.exe won't accept correct password

allan

2044 posts

Uber Geek

ID Verified

Lifetime subscriber

#311176 20-Dec-2023 21:20

Trying to assist a friend who has an Exchange Online account which has been working successfully in the Outlook application on Windows 10, but as of about a week ago is suddenly started prompting him for his password whenever he opens Outlook. Here's what I know/have tried:

Same password works successfully for his Exchange Online email on his iPhone
Web browsing to https://outlook.office365.com also works with the same password
Creating a new account on an Android device in the Outlook app works with the same password
Attempting to create a new Outlook profile on his Windows 10 device does not work as it immediately prompts for a password
Ditto attempting to create an Outlook profile on a Windows machine that he has never logged into before

My friend is not the admin for the 365/Exchange Online account, that person is unfortunately on the other side of the world and difficult to contact.

My online searching has turned up suggestions like turning off "Always prompt for logon credentials", but that is not ticked anyway and clearing credentials from Windows credential manager - done that, made no difference.

Any ideas or pointers to go looking for?

1 | 2

Hammered
8344 posts

Uber Geek

Moderator

ID Verified

Trusted

Lifetime subscriber

#3173843 20-Dec-2023 21:44

Could be wrong, but try looking up generating an App Specific Password. Not sure if that's still a thing, it's been a while.

People often mistake me for an adult because of my age.

Keep calm, and carry on posting.

Referral Links: Sharesies - Backblaze -

Are you happy with what you get from Geekzone? If so, please consider supporting us by subscribing.

No matter where you go, there you are.

gehenna

8514 posts

Uber Geek

Moderator

Trusted

Lifetime subscriber

#3173907 20-Dec-2023 23:04

Definitely still a thing when adding iCloud to a non Apple app. Not sure about what's being described here though.

SATTV

1648 posts

Uber Geek

ID Verified

#3173926 21-Dec-2023 07:39

What version of Outlook?

This is an older artcle I found.

John

I know enough to be dangerous

SATTV

1648 posts

Uber Geek

ID Verified

#3173927 21-Dec-2023 07:42

Oh,

The other thing, enable modern autentication.

Uses Microsoft SARA https://www.microsoft.com/en-us/download/details.aspx?id=100607 if you have not already done so.

Again it may have taken some time for MS to catch up with that tennant.

John

I know enough to be dangerous

ANglEAUT

2326 posts

Uber Geek

Trusted

Lifetime subscriber

#3173935 21-Dec-2023 08:36

allan: ... in the Outlook application on Windows 10, ...

Nothing immediately obvious here at the Windows release health page about Outlook issues... Sorry, no idea

Please keep this GZ community vibrant by contributing in a constructive & respectful manner.

robjg63

4098 posts

Uber Geek

Subscriber

#3173960 21-Dec-2023 09:21

Seem to recall seeing that occassionally over the years.

I think it was often something like a corrupted profile.

This link has quite a lot of things to try.

I would suggest maybe the "7. Create new Outlook profile to resolve the corrupt profile issue" section.

Nothing is impossible for the man who doesn't have to do it himself - A. H. Weiler

allan

2044 posts

Uber Geek

ID Verified

Lifetime subscriber

#3174017 21-Dec-2023 12:22

@SATTV Outlook version is Outlook 365 v2311, so no issues there

I ran the SARA tool which indicated the tenant was set up for modern authentication, but Outlook needed configuring, so let it do its thing, which auto-discovered the correct user details etc and said it had reconfigured Outlook, but still failed to accept the password. Then let it create a new profile (which I had already manually tried as per my original post), but same issue with password not being accepted. However, interestingly, while SARA said it could auto-discover the account details, if I run the "Microsoft Outlook Connectivity Tester" for Office365 & Outlook Connectivity, it fails with the following:

So I'm now thinking DNS auto-discovery record has possibly been removed? Not something I can fix for him. I think he is going to have to track down the 365 administrator for the account, which is what the SARA tool finally got to as well - unless anyone has any other suggestions?

@robjg63 - Already tried creating a new profile as per bullet point 4 of my original post.

Sharesies

Trade NZ and US shares and funds with Sharesies (affiliate link).

SATTV

1648 posts

Uber Geek

ID Verified

#3174039 21-Dec-2023 13:05

That does not look good, you are right it does look like a DNS thing

Can you pin autodiscover.domain.com

John

I know enough to be dangerous

Ruphus

465 posts

Ultimate Geek

#3174081 21-Dec-2023 15:23

Something to look into for sure but wouldn't the removal of Autodiscover cause issues with everyone? Also with an Exchange Online mailbox, isn't https://outlook.office365.com/<tenant> used for connection?

I'd look at the sign-in logs in Entra if you have access to them. Also if they're able get into Outlook, they could try holding down the CTRL key while right clicking on the Outlook icon in the task tray and selecting Test Email AutoConfiguration.

If you could connect the computer through another network connection (phone hotspot) to test if there's any blocked ports etc with the current network, it's something else to try.

Do you know if this managed corporate device or a BYOD device?

networkn

Networkn
32354 posts

Uber Geek

ID Verified

Trusted

Lifetime subscriber

#3174086 21-Dec-2023 15:33

What happens if you create a new user profile on the same computer?

Rickles

2938 posts

Uber Geek

Trusted

#3174981 23-Dec-2023 11:39

Try Outlook/Office Repair? (Start-Settings-Apps etc)

Might cure a corrupt file and/or setting particularly if running fine until now.

allan

2044 posts

Uber Geek

ID Verified

Lifetime subscriber

#3175210 24-Dec-2023 13:47

Just got back to this again.

@Ruphus - Turns out there is more than one person affected by this issue. This is a BYOD device. It is a very small organisation, but just happen to have people on opposite sides of the world. I've done the Outlook autoconfiguration test, which failed and have also tried recreating the my friend's 365 email login on my own device with the same failed result as my original post.

However, in pursuing my hunch re DNS (I'm probably out of my depth here) there is something really screwy with how their DNS records are being handled. Their domain is registered with Domainz and has an SOA record and three nameserver records to various servers at nsserver.net.nz, all have TTL values of 3600 - but there is no A record.

However, if I use something like https://www.broadbandsearch.net/ to query their DNS, it is returning an A record, another SOA record, an MX record for Exchange Online email, plus a couple of associated TXT records and two further nameserver records pointing to siteground.net - who appear to be their website host. All of these, except the A record, have TTL values of 0 which I am assuming would in most cases be seen in preference to the records at Domainz. Is that a valid assumption? All of which probably means Outlook is getting very confused when attempting to connect...

Rickles

2938 posts

Uber Geek

Trusted

#3175212 24-Dec-2023 13:59

I'd be tempted to find out all the correct settings for Exchange in the Outlook client, and completely delete then re-enter them ... if you are copying the existing settings to another computer then you may simply be carrying the fault forward?

networkn

Networkn
32354 posts

Uber Geek

ID Verified

Trusted

Lifetime subscriber

#3175227 24-Dec-2023 15:22

Removal of autodiscover record won't stop existing setups, but will prevent new devices being configured in many cases.

If you want to DM me I can take a look at your 365 records and setup. The number of ways this can go wrong are fairly limited, so it should be relatively easy to fix.

Primarily I'd need to know the domain name it's under and I can probably tell you what's wrong.

Alternatively, you can read through this.

https://learn.microsoft.com/en-us/microsoft-365/admin/get-help-with-domains/create-dns-records-at-any-dns-hosting-provider?view=o365-worldwide

allan

2044 posts

Uber Geek

ID Verified

Lifetime subscriber

#3176111 29-Dec-2023 10:09

networkn:

Removal of autodiscover record won't stop existing setups, but will prevent new devices being configured in many cases.

If you want to DM me I can take a look at your 365 records and setup. The number of ways this can go wrong are fairly limited, so it should be relatively easy to fix.

Primarily I'd need to know the domain name it's under and I can probably tell you what's wrong.

...

Thanks @networkn, I've DMed you.

1 | 2