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Re:Microsoft Mishandling Example.com by gruez on Friday January 23, 2026 @09:07AM (#46732623)
>Microsoft's Autodiscover service misconfiguration can be confirmed via curl -v -u "[email protected]:password" "https://prod.autodetect.outlook.cloud.microsoft/autodetect/d...":

Hold up, does this mean outlook sends your full credentials to Microsoft when you try to set up an outlook account? I'm sure they pinky promise they keep your credentials secure, but this feels like it breaks all sorts of security/privacy expectations.

Re:Microsoft Mishandling Example.com by dspillett on Friday January 23, 2026 @10:07AM (#46733375)
> Hold up, does this mean outlook sends your full credentials to Microsoft when you try to set up an outlook account?

Not just an “outlook account” - any account in outlook, with default settings at least.

I run a mail server, mainly for me but a couple of friends have accounts on there too, and a while ago one friend reported apparently being locked out and it turned out that it was due to them switching Outlook versions and it was connecting via a completely different address to those that my whitelists expected sometimes at times when they weren't even actively using Outlook. Not only were active connections due to their interactive activity being proxied, but the IMAP credentials were stored so the MS server could login to check things whenever it wanted (I assume the intended value-add there is being able to send new mail notifications on phones/desktops even when not actively using mail?).

> but this feels like it breaks all sorts of security/privacy expectations.

It most certainly does. The behaviour can be tamed somewhat, but (unless there have been recent changes) is fully enabled by default in newer Outlook variants.

The above-mentioned friend migrated his mail to some other service in a huf as I refused to open my whitelist to “any old host run by MS” and he didn't want to dig in to how to return behaviour back to the previous “local connections only, not sending credentials off elsewhere where they might be stored”.

Re:Microsoft Mishandling Example.com by Grisu_FTP on Monday January 26, 2026 @08:53AM (#46765636)
I might be misremembering but i think it even copies all of your mails to their servers.
Re:Microsoft Mishandling Example.com by butvacuum on Friday January 23, 2026 @09:46AM (#46733091)
Basically everything microsoft makes that touches http will send your username and your password to any server that asks for Basic Authentication.

It looks like Microsoft Edge had the _ability to disable_ this added in 2020 or 2021, but it isn't currently the default and the Group Policy unintuitively only applies to unencrypted HTTP Connections.

Re:Microsoft Mishandling Example.com by gruez on Friday January 23, 2026 @09:58AM (#46733245)
>Basically everything microsoft makes that touches http will send your username and your password to any server that asks for Basic Authentication.

Are you talking about NTLM hashes? It's a weak hash, but not the same as "sending your password". The biggest difference is that even a weak hash can't be reversed if the password has high enough entropy.

Re:Microsoft Mishandling Example.com by butvacuum on Friday January 23, 2026 @11:58AM (#46734779)
yes, I meant to type hash. Not that it matters as even 10yr old integrated GPUs are enough to brute force 8 or 9 character NTLM(or any variant) passwords in a few hours. Not that you need to with Pass The Hash.
Re:Microsoft Mishandling Example.com by lazide on Friday January 23, 2026 @10:35AM (#46733731)
Not necessarily, the server can say it only supports basic auth and….
Re:Microsoft Mishandling Example.com by gruez on Friday January 23, 2026 @12:18PM (#46735029)
I don't think there's any evidence that windows sends cleartext passwords. The whole reason why NTLM is a thing is to avoid sending cleartext passwords.
Re:Microsoft Mishandling Example.com by lazide on Friday January 23, 2026 @12:37PM (#46735275)
Outlook appears to be
Re:Microsoft Mishandling Example.com by p_ing on Friday January 23, 2026 @12:42PM (#46735331)
The 'https://' disagrees with your 'sending clear text passwords' statement.
Re:Microsoft Mishandling Example.com by lazide on Friday January 23, 2026 @04:03PM (#46737889)
It’s clear text to the receiving server, which is what we’re talking about, not one way hashed.
Re:Microsoft Mishandling Example.com by brulx126 on Friday January 23, 2026 @09:44AM (#46733078)
Not just that, the new outlook app makes Microsoft a complete man-in-the-middle for your email account.

https://www.xda-developers.com/privacy-implications-new-micr...

Re:Microsoft Mishandling Example.com by donmcronald on Friday January 23, 2026 @12:01PM (#46734827)
They store passwords and proxy everything at the same time they’re pushing OAuth, authenticators, passkeys, etc. for their own services. Everyone should have revolted when they bought Acompli and started doing this kind of thing.
Re:Microsoft Mishandling Example.com by amluto on Friday January 23, 2026 @11:36AM (#46734520)
This seems like it would completely break any attempt to track access from unauthorized users or devices — any IT department using a backend other than Microsoft’s would need to pretend that all access from MS’s servers is safe.
Re:Microsoft Mishandling Example.com by fc417fc802 on Saturday January 24, 2026 @05:52AM (#46742522)
In response to discovering this any competent IT department would immediately move to ban the use of any offending apps and blacklist the MS servers from the relevant backends. Also I guess rather than drop the connections ideally you would want to accept the initial request, record the provided credentials, and then lock said account because the credentials have clearly been compromised and the user is now known to be making use of a banned app.
Re:Microsoft Mishandling Example.com by amluto on Saturday January 24, 2026 @02:30PM (#46746743)
It’s also the case that, of the major cloud providers, one of them is quite notably poor at securing its own systems. If I were a company that cared about security, I would not want Microsoft holding credentials to my system.
Re:Microsoft Mishandling Example.com by koakuma-chan on Friday January 23, 2026 @09:50AM (#46733152)
And? Do you think Gmail is end to end encrypted?
Re:Microsoft Mishandling Example.com by gruez on Friday January 23, 2026 @09:55AM (#46733204)
My bank isn't end to end encrypted either, but that doesn't mean it's suddenly ok for Microsoft (or any other company) to suddenly start MITMing my online banking connections.
Re:Microsoft Mishandling Example.com by brulx126 on Friday January 23, 2026 @09:55AM (#46733197)
I am talking about the fact that the new default email client on Windows will hand over all your email credentials to Microsoft. This has nothing to do with Gmail.
Re:Microsoft Mishandling Example.com by koakuma-chan on Friday January 23, 2026 @09:58AM (#46733244)
Oh you mean even if you don't use Microsoft's email? Now I get it.
Re:Microsoft Mishandling Example.com by delfinom on Friday January 23, 2026 @10:32AM (#46733682)
I think the concern is that it copies the emails of your non-Microsoft accounts that you added to the Outlook app, over to Microsoft servers
Re:Microsoft Mishandling Example.com by AlexandrB on Friday January 23, 2026 @10:02AM (#46733290)
Adding a bunch of middlemen that also see the data increases the risk.
Re:Microsoft Mishandling Example.com by kstrauser on Friday January 23, 2026 @02:35PM (#46736786)
I am so glad people are finally noticing and complaining about this. It's the same reason I won't use Spark or Superhuman. Those are neat services, but I can't abide storing the creds to perhaps the most security-sensitive service I use to a cloud provider. If they get hacked, then the attacker can access my email account, send phishing emails to my contacts, read and respond to password reset requests they make to other online services, etc. It would be disastrous.

No, I'll keep my credentials stored and used locally, thanks.

Re:Microsoft Mishandling Example.com by encom on Friday January 23, 2026 @04:35PM (#46738256)
So like Cloudflare for email.
Re:Microsoft Mishandling Example.com by Neil44 on Friday January 23, 2026 @11:36AM (#46734524)
I think the curl -u switch just requires the password field to be filled, there obviously isn't a legit user account [email protected] with a password of password either at microsoft or at the Japanese imap server.
Re:Microsoft Mishandling Example.com by gruez on Friday January 23, 2026 @12:17PM (#46735010)
>I think the curl -u switch just requires the password field to be filled

Yeah you're right, if you don't specify the password (eg. -u user), it prompts you for it

>there obviously isn't a legit user account [email protected] with a password of password either at microsoft or at the Japanese imap server.

But presumably the fact it's there at all suggests it's a required parameter? Maybe "password" is just a placeholder, but it's unclear based on the command line transcript alone.

Re:Microsoft Mishandling Example.com by thedanbob on Friday January 23, 2026 @09:18AM (#46732769)
It's more common than you might think. I know of at least one popular email client that stores your credentials on their servers to enable features like multi-account sync and scheduled sending.
Re:Microsoft Mishandling Example.com by RajT88 on Friday January 23, 2026 @10:02AM (#46733296)
I bought a hardware password manager a while back and the bulk load tool sent all your creds to a cloud service. I have not used it since, and sent the manufacturer a nasty note.

It was the Ethernom Beamu, company now defunct.

Re:Microsoft Mishandling Example.com by spiffyk on Friday January 23, 2026 @09:25AM (#46732847)
I would expect such a feature to use end-to-end encryption for the data, so that only the user can see the credentials. It does, right? Right?
Re:Microsoft Mishandling Example.com by gruez on Friday January 23, 2026 @09:27AM (#46732868)
>>multi-account sync and scheduled sending

>I would expect such a feature to use end-to-end encryption for the data

How would "end-to-end encryption" when such features by definition require the server to have access to the credentials to perform the required operations? If by "end to end" you actually mean it's encrypted all the way to the server, that's just "encryption in transit".

Re:Microsoft Mishandling Example.com by treyd on Friday January 23, 2026 @10:25AM (#46733599)
> If by "end to end" you actually mean it's encrypted all the way to the server, that's just "encryption in transit".

This is what Zoom claimed was e2ee for a little while before getting in trouble for it.

Re:Microsoft Mishandling Example.com by kingstnap on Friday January 23, 2026 @06:31PM (#46739404)
This is what Google also claims as end to end encrypted in their Gmail end to end thing. Many people including me mentioned this in the comments.

https://news.ycombinator.com/item?id=45458482

Its entirely their end to their end encrypted. You don't get any privacy.

Re:Microsoft Mishandling Example.com by fc417fc802 on Saturday January 24, 2026 @06:06AM (#46742592)
Use our new open source (modification and redistribution not permitted) app to exchange end-to-end encrypted (from your client to our server) messages with your friends! Having all your data on our service protects your data sovereignty (we do not provide for export or interop) by guaranteeing that you always have access to your full history! Usage also protects your privacy (we analyze your data for marketing purposes) by preventing unscrupulous third parties from analyzing your data for marketing purposes.

If we had competent regulators this sort of blatant willful negligence would constitute false advertising.

Re:Microsoft Mishandling Example.com by tom1337 on Friday January 23, 2026 @09:28AM (#46732876)
Do you mean Spark? I get why they need to do it that way but I also hate that they have to do it that way because it sucks for privacy.
Re:Microsoft Mishandling Example.com by thedanbob on Saturday January 24, 2026 @10:24PM (#46750385)
Yeah, Spark. Shame because I really liked their client, but I refused to use it anymore after I realized what they were doing.
Re:Microsoft Mishandling Example.com by tga on Friday January 23, 2026 @09:37AM (#46732990)
Most likely, and nobody cares.

Already many years ago I remember installing a firewall on my phone and noticing in surprise that Outlook was not connecting at all to my private mail server, but instead only sending my credentials to their cloud and downloading messages from there.

The only Android mail client not making random calls to cloud servers was (back then) K-9 Mail.

Re:Microsoft Mishandling Example.com by dec0dedab0de on Friday January 23, 2026 @09:34AM (#46732964)
I think outlook is pretty much a saas product these days.
Re:Microsoft Mishandling Example.com by DANmode on Saturday January 24, 2026 @12:48AM (#46741387)
What gave it away, the intrusive ads in your free inbox the last ten years,

or the “See Plans and Pricing” on the homepage?

Christ, my poor grandmother…

Re:Microsoft Mishandling Example.com by nhinck2 on Friday January 23, 2026 @09:43AM (#46733073)
Yeah since the Windows 11 2023h2 update.
Re:Microsoft Mishandling Example.com by 1718627440 on Friday January 23, 2026 @11:16AM (#46734275)
Always has been.
Re:Microsoft Mishandling Example.com by DANmode on Saturday January 24, 2026 @12:11AM (#46741261)
See also: Windows 11 telemetry