Outlook SMTP Oauth2 error

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sgeneris
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Outlook SMTP Oauth2 error

Post by sgeneris »

I have a MS live.com acct which was working fine with Oauth2.
Yesterday I started receiving the attached error, after which the messages do go thru.
Very weird.

???????
error.png
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Last edited by Jeff on Fri Mar 17, 2023 6:55 pm, edited 1 time in total.
Reason: Change subject for better visibility
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Jeff
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Re: Weird error

Post by Jeff »

Use the password method instead of Oauth2 -- see the details here:
https://www.esumsoft.com/news/outlook-s ... th2-error/
sgeneris
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Re: Weird error

Post by sgeneris »

Looks like MS fixed it -- sent email to myself and got thru, no error.
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mjs
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Re: Weird error

Post by mjs »

sgeneris wrote: Thu Feb 09, 2023 2:42 am But Oauth2 has worked until now -- why would I go back to pasword?
Because at this time as stated in the link Jeff provided: "Outlook’s SMTP server currently has an issue with Oauth2.". Using the "Password" authentication is a way around the problem with Outlook at this time (please refer to the link Jeff previously posted for more details).
sgeneris wrote: Thu Feb 09, 2023 2:42 am And why disappear from the outbox and is recorded in the Sent mail AFTER the error?
Does it go through -- how can I tell?
If the message does not remain in the POP Peeper Outbox then it has probably been sent - you can confirm this by looking in your "Sent" folder for the account in question. If you have the POP Peeper PlusPack then you can use the "Sent Mail Viewer" to confirm - otherwise, as previously mentioned, you can confirm if a message has been sent via the "Sent" Folder of the relevant Email account (by logging into the account on-line).
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
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mjs
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Re: Weird error

Post by mjs »

So sgeneris - you have apparently updated your previous post, removing the questions you posted that I have answered above - to say "Looks like MS fixed it...".

As Jeff mentioned in the link he provided: "It should be fixed by Outlook eventually, but to fix this immediately, you can switch POP Peeper to use the password method instead of Oauth2..." - if in fact you are now able to send messages without any errors then that's good news (perhaps the issue has been "fixed by Outlook").

With that said, if you have more than one email account you might try sending a message from one account to another account to confirm the issue has been resolved by MS (instead of sending to the same account - which is what it appears you have done based on your previous post).
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
sgeneris
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Re: Weird error

Post by sgeneris »

Thanx.

I sent test messages to all my accts and they got thru without the error.
I sent a message to an external acct and it went thru without the error.
That's when I thought MS fixed it.
But then I sent to a 2nd external acct and got the error, then seems to have gotten thru.
So it's not fixed, but the error is intermittent and yet msgs seem to go thru.
Weird.
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mjs
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Re: Weird error

Post by mjs »

Did you confirm whether or not the message(s) did actually get sent by checking out what I previously posted (as referenced in the answer to your second question)?

Or is that what you meant by "...is recorded in the Sent mail AFTER the error" - that is, that you did check the "Sent" folder to confirm (and the sent message(s) are there?)?

If so, I would agree, it is a "weird" problem that MS has produced.... :?
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
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Jeff
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Re: Weird error

Post by Jeff »

I have not had a single test message go through yet. However, I don't typically use Outlook for sending and I've done maybe a dozen tests in the past few days and I always delete the test message from the outbox (ie. I've only done spot checks and not allowed it to continuously retry).

That being said, I don't think this is the first time this has happened with Outlook and I do believe it's been intermittent before.
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mjs
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Re: Weird error

Post by mjs »

For the record I have not had any tests that end up getting sent as well. And in every case when attempting to send a message by way of an MS account messages continue to remain in the POP Peeper Outbox (in a state of error) as one would expect in the event of a "send" error.

To go over what transpires in my case, when attempting to send a message using Outlook.com:
1) The (Oauth2 type) Error occurs each time when attempting to Send a message using MS email for multiple tests.
2) All messages with the "Send" error continue to remain in the POP Peeper Outbox (in a state of error).
3) None of the messages (tested over a period of more than 2 hours) have at any time been sent (to the recipient account) as a result of initially sending the message or (retries) as a result of either a manual "Check Mail" and/or a scheduled (12 minute polling interval) "Mail Check" (ultimately requiring my deletion of the test messages from the Outbox). (hence, as one would expect in the event of an error, the messages [w/ errors] continue remain in the PP Outbox and do not at any time reach the recipient accounts "Sent Folder").

To be clear, result 2 and result 3 (above) are in general what would be the expectation in the event of a "Send" error occurring in POP Peeper. I do not get (what I would call the "weird" outcome) where a message actually leaves the POP Peeper Outbox and ends up getting sent to the recipient account in spite of a POP Peeper "Send" error occurring).
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
sgeneris
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Re: Weird error

Post by sgeneris »

Yes, that's what I called weird.

At the time of my reporting this,

1. I would get the error,
2. the msg would remain stuck in outbox
3. after a few seconds it would disappear.
When I checked the Sent folder, the messages were there.
I also tested this by CCing the messages to me and I received them.

But today they get stuck in the Outbox and DO NOT get sent -- the weirdness went away, but the error
remains.

It's unbelievable that MS has not fixed this in such a long time, but hey -- that's monopolies for you.
sgeneris
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Re: Weird error

Post by sgeneris »

It's been two weeks since I reported the Oauth2 problem with Live.com.
I still experience the error.

In normal circumstances it would be hard to believe that they would
not fix the system for such a long time, but in the monopolistic oligarchic corporate
welfare state is expectable.

Any info on the status?

FP
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Jeff
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Re: Weird error

Post by Jeff »

Thanks for reminding me about this. What I can tell you now, after doing some research, is that this is definitively not specific to POP Peeper. I've found several forum topics, but this is perhaps the best one:
https://learn.microsoft.com/en-us/answe ... n-but-retu

It's fairly technical so I'll summarize:
- The OP reports the same behavior as you see in PP -- IMAP works, but SMTP reports error #535 5.7.3 authentication unsuccessful
- A Microsoft employee (Akshay-MSFT) chimes in and then claims to post the solution
- There are 5 replies to that solution, all saying that it's only a solution for work/school accounts and not for consumer accounts (e.g. free @outlook.com accounts)
- No follow-ups after posting an official "solution"


btw, I had previously stated that I thought I had seen this kind of long outage before, but I was cloudy on remembering it (unfortunately, I don't keep records of this kind of thing), but I did find this comment in my code regarding Outlook's Oauth2:
// tested sep 24, 2021 after long outlook outage -- no fix

The "tested" and "no fix" is referring to my attempts to fix it client-side. I'm confident that Outlook eventually fixed this themselves (as opposed to a PP fix). Looking at the release history for POP Peeper, on Sep 30, 2021, the only relevant change was to change PP's Oauth2 *button* to the dropdown we have now -- as I recall now, this was a direct reaction to Outlook's issue, in order to make it easier to switch between Oauth2 and password. I could be wrong, but I think the 2021 issue affected IMAP.


Other reports:
https://learn.microsoft.com/en-us/answe ... or-consume -- Akshay-MSFT copy/pastes the same solution, again ignoring the responses
https://learn.microsoft.com/en-us/answe ... en-using-o -- topic posted 5 days ago, no replies.
https://stackoverflow.com/questions/753 ... entication -- StackOverflow conversation
sgeneris
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Re: Weird error

Post by sgeneris »

As I said, typical MS/monopolism.

I read this to mean: it does not work yet.

I switched back to pw -- if they fix it, all I have to do is just choose Oauth2 from the dropdown?

The question is how will we know when they fix it -- just keep testing?
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Jeff
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Re: Weird error

Post by Jeff »

sgeneris wrote: Tue Feb 21, 2023 1:23 pm if they fix it, all I have to do is just choose Oauth2 from the dropdown?
I'll be honest, you may just want to stick with password. MS has proven that they are not ready to force Oauth2 onto their users like Gmail and Yahoo have (which means they probably will :roll: ). I've been considering removing Oauth2 for hotmail, or at least not making it the "recommended" method.

sgeneris wrote: Tue Feb 21, 2023 1:23 pm The question is how will we know when they fix it -- just keep testing?
Yup. Outlook used to have a status page that showed problems (although, for email, it was generally only updated for the business-side; see a pattern here...?); ah, here it is, same-old same-old:
https://portal.office.com/servicestatus
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mjs
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Re: Weird error

Post by mjs »

What I've done (FWIW) is to create a new account just for testing this MS issue (that I don't otherwise use). This way I just leave the account set to Oauth2 (saves steps switching from Password to Oauth2 and back to Password each time) and try sending a message with the account every few days or so.... (delete the "Outbox" message - if no change) - works for me. :wink:
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
efremk1
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Re: Weird error

Post by efremk1 »

Just want to post an update with what I'm currently seeing.

A personal outlook.com account still receives the same SMTP error message, but 2 older hotmail.com accounts do not. All 3 accounts use the same SMTP servers.
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Jeff
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Re: Weird error

Post by Jeff »

Thanks for the feedback, efremk1. Have your 2 accounts always been working or did they stop working at any point (since early Feb)?


I decided to take another look at it. One of those conversations I posted above had some new info (not from a MS rep :roll: ). One person says: "It's Googlable... the app registration in the Azure AD may need the "Live SDK compatibility" checkbox checked."
I cannot find a "Live SDK compatibility" checkbox anywhere. And googling it returns exactly one result -- from the same article.
Suspiciously, I originally mentioned that article on Feb 20, and that quote from that article was from Feb 10 -- I do NOT remember seeing that post before now.

Anyway, someone else replied on Mar 15 (2 days ago) -- I tried their suggestion. It didn't work.

And then another follow-up (today) saying nothing works. That's a post I agree with.


Since my previous post (probably the same day), I did what I said and POP Peeper won't recommend Oauth2 for Outlook accounts. PP v5.4.6+
efremk1
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Re: Outlook SMTP Oauth2 error

Post by efremk1 »

Hi, Jeff-

Until I tested those (rarely used) accounts yesterday, I had not tried to send via POP Peeper or any other 3rd party client for a long long time, so I can't answer that question, sorry.

The following info won't help for basic or free outlook maiboxes, but for Exchange mailboxes, there may be a fix in there.
(I can't find a "Live SDK compatibility" checkbox either.) The most relevant settings I can find, in the Exchange Admin Center, are the security checkboxes in

Untitled.png

Also, these 2 articles dated Feb 20 Feb 22, may be of value:
https://learn.microsoft.com/en-us/excha ... -smtp-auth
https://learn.microsoft.com/en-us/excha ... submission

Note: I have not tested any of these changes.
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Jeff
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Re: Outlook SMTP Oauth2 error

Post by Jeff »

Thanks for the links.

The first link refers to old TLS methods that current versions of POP Peeper don't use. The current TLS libraries that PP uses support TLS v1.3. ftr, if you want to see what TLS version PP is using for an account (which has connected at least once to the server since PP started), you can right-click on the account and select "Server Info" -- TLS version is at the very bottom. If you don't see "server info", enable "Advanced options" under main menu: Tools / Options / General.

The second link is for disabling standard SMTP Auth -- this is not Oauth2 (smtp auth is the standard method that most smtp servers use). Free outlook accounts have not disabled standard smtp auth, which is why disabling Oauth2 works.
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