Community Discussions and Support
Outlook Cutting Off Basic Authentication on 09/16/2024

I checked the TCPIP log for my failed attempts.
These are the lines:
14:52:43.817: --- 27 Sep 2024, 14:52:43.817 ---
14:52:43.819: Connect to 'pop3.live.com', timeout 30 seconds.
14:52:44.894: [] SSL/TLS session established
14:52:44.894: [
] ECDHE-RSA-AES256-GCM-SHA384, TLSv1.2, Kx=ECDH, Au=RSA, Enc=AESGCM(256), Mac=AEAD<lf>
14:52:44.895: [*] Peer's certificate name is '/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com'.
14:52:44.956: >> +OK The Microsoft Exchange POP3 service is ready. [RABVADcAUAAxADkAMABDAEEAMAAwADIAMgAuAEUAVQBSAFAAMQA5ADAALgBQAFIATwBEAC4ATwBVAFQATABPAE8ASwAuAEMATwBNAA==]<cr><lf>
14:52:44.956: << USER xxxxxx<cr><lf>
14:52:44.970: >> +OK<cr><lf>
14:52:44.970: << PASS yyyyyyy<cr><lf>
14:52:45.499: >> -ERR Logon failure: unknown user name or bad password.<cr><lf>
14:52:51.980: << RSET<cr><lf>
14:52:52.008: >> -ERR Command is not valid in this state.<cr><lf>
14:52:52.034: [!] Warning [Benign]: SSL connection improperly closed by remote host.
14:52:52.035: --- Connection closed at 27 Sep 2024, 14:52:52.035. ---
14:52:52.035:


I can confirm that the password is the app password, not the original on-line password.


So it rejects my attempt with:
-ERR Logon failure: unknown user name or bad password.


I have set a new app password and tried that.
Same outcome - no access.


I also tried reverting to my on-line password; same outcome.


This is a very bad development.


I have programs written to enhance Pegasus, eg one to convert copies of emails sent directly from the web to the Pegasaus folder listing format of To: <destination> instead of From <me> and another to convert forwarded emails to show the original sender instead, as well as nearly a thousand folders. Yet I cannot see how I can continue with Pegasus if I cannot access Outlook.


BTW, I can of course log on to outlook.com via browser and to repeat Samsung Android Email still works.


I checked the TCPIP log for my failed attempts. These are the lines: 14:52:43.817: --- 27 Sep 2024, 14:52:43.817 --- 14:52:43.819: Connect to &#039;pop3.live.com&#039;, timeout 30 seconds. 14:52:44.894: [*] SSL/TLS session established 14:52:44.894: [*] ECDHE-RSA-AES256-GCM-SHA384, TLSv1.2, Kx=ECDH, Au=RSA, Enc=AESGCM(256), Mac=AEAD&lt;lf&gt; 14:52:44.895: [*] Peer&#039;s certificate name is &#039;/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com&#039;. 14:52:44.956: &gt;&gt; +OK The Microsoft Exchange POP3 service is ready. [RABVADcAUAAxADkAMABDAEEAMAAwADIAMgAuAEUAVQBSAFAAMQA5ADAALgBQAFIATwBEAC4ATwBVAFQATABPAE8ASwAuAEMATwBNAA==]&lt;cr&gt;&lt;lf&gt; 14:52:44.956: &lt;&lt; USER xxxxxx&lt;cr&gt;&lt;lf&gt; 14:52:44.970: &gt;&gt; +OK&lt;cr&gt;&lt;lf&gt; 14:52:44.970: &lt;&lt; PASS yyyyyyy&lt;cr&gt;&lt;lf&gt; 14:52:45.499: &gt;&gt; -ERR Logon failure: unknown user name or bad password.&lt;cr&gt;&lt;lf&gt; 14:52:51.980: &lt;&lt; RSET&lt;cr&gt;&lt;lf&gt; 14:52:52.008: &gt;&gt; -ERR Command is not valid in this state.&lt;cr&gt;&lt;lf&gt; 14:52:52.034: [!] Warning [Benign]: SSL connection improperly closed by remote host. 14:52:52.035: --- Connection closed at 27 Sep 2024, 14:52:52.035. --- 14:52:52.035: I can confirm that the password is the app password, not the original on-line password. So it rejects my attempt with: -ERR Logon failure: unknown user name or bad password. I have set a new app password and tried that. Same outcome - no access. I also tried reverting to my on-line password; same outcome. This is a very bad development. I have programs written to enhance Pegasus, eg one to convert copies of emails sent directly from the web to the Pegasaus folder listing format of To: &lt;destination&gt; instead of From &lt;me&gt; and another to convert forwarded emails to show the original sender instead, as well as nearly a thousand folders. Yet I cannot see how I can continue with Pegasus if I cannot access Outlook. BTW, I can of course log on to outlook.com via browser and to repeat Samsung Android Email still works.

I can still connect to my outlook.com account. The host server I am connecting to is outlook.office365.com on port 995 via direct SSL. I do not use nor have I ever installed Office365, nor have I ever used the cloud version. I don't have a clue what the difference is between outlook.office365.com and pop3.live.com.


I can still connect to my outlook.com account. The host server I am connecting to is outlook.office365.com on port 995 via direct SSL. I do not use nor have I ever installed Office365, nor have I ever used the cloud version. I don&#039;t have a clue what the difference is between outlook.office365.com and pop3.live.com.

I am using port 995 on direct SSL.
pop3.live.com was (is?) the original POP3 host published by Microsoft.
I have tried accessing outlook.office365.com.
Exactly the same outcome.


I do not use Office365 either.


I think all Pegasus access will be cut off over the next while.


I admire David Harris and his management of a completely free and excellent email. However maybe he could consider developing a version with OAUTH2 capability and CHARGING for it. I would pay a reasonable fee.


I am using port 995 on direct SSL. pop3.live.com was (is?) the original POP3 host published by Microsoft. I have tried accessing outlook.office365.com. Exactly the same outcome. I do not use Office365 either. I think all Pegasus access will be cut off over the next while. I admire David Harris and his management of a completely free and excellent email. However maybe he could consider developing a version with OAUTH2 capability and CHARGING for it. I would pay a reasonable fee.

I just tested pop3.live.com and it is working for me, at least for now. Only time will tell whether app password authentication failure starts affecting the rest of us.


I just tested pop3.live.com and it is working for me, at least for now. Only time will tell whether app password authentication failure starts affecting the rest of us.

Still locked out of POP3 (and IMAP) access from Pegasus to outlook.com


I note from djarvie:
"Returning from holiday yesterday I found that Pegasus no longer connects to Outlook. I get this message: 'Authentication unsuccessful, basic authentication is disabled'. "


I also was locked out on return from holidays.
However my rejection message, as above, is the more conventional "unknown user name or bad password."
(Would I have brought my laptop on holidays if I had feared this? LOL!)


I am also suprised that there is very little mention of this disaster (yes from a software point of view it is that) on the Pmail home page.


Still locked out of POP3 (and IMAP) access from Pegasus to outlook.com I note from djarvie: &quot;Returning from holiday yesterday I found that Pegasus no longer connects to Outlook. I get this message: &#039;Authentication unsuccessful, basic authentication is disabled&#039;. &quot; I also was locked out on return from holidays. However my rejection message, as above, is the more conventional &quot;unknown user name or bad password.&quot; (Would I have brought my laptop on holidays if I had feared this? LOL!) I am also suprised that there is very little mention of this disaster (yes from a software point of view it is that) on the Pmail home page.

I am also suprised that there is very little mention of this disaster (yes from a software point of view it is that) on the Pmail home page.


I don't consider it a disaster, yet. There are only two reports of a problem. One reports "Authentication unsuccessful, basic authentication is disabled", while the other reports "unknown user name or bad password". I wish I knew which one is the expected one if the app password no longer works considering each could indicate a different configuration error. The fact that both were reported after not connecting for awhile is the only consistency so I think we need more, and consistent, reports of the problem before claiming that a Microsoft app password no longer works with Pegasus Mail.


[quote=&quot;pid:57061, uid:27623&quot;]I am also suprised that there is very little mention of this disaster (yes from a software point of view it is that) on the Pmail home page.[/quote] I don&#039;t consider it a disaster, yet. There are only two reports of a problem. One reports &quot;Authentication unsuccessful, basic authentication is disabled&quot;, while the other reports &quot;unknown user name or bad password&quot;. I wish I knew which one is the expected one if the app password no longer works considering each could indicate a different configuration error. The fact that both were reported after not connecting for awhile is the only consistency so I think we need more, and consistent, reports of the problem before claiming that a Microsoft app password no longer works with Pegasus Mail.

The different rejection messages are difficult to understand. I would expect the message received by djarvie:
"Authentication unsuccessful, basic authentication is disabled".
This directly refers to the new Microsoft setup.


The message I get is more routine, suggesting just an invalid username/password combination - which it cannot be since nothing has changed.


I should add that my Samsung Adroid Email has continued to work.
Of course it was never shut down.


The different rejection messages are difficult to understand. I would expect the message received by djarvie: &quot;Authentication unsuccessful, basic authentication is disabled&quot;. This directly refers to the new Microsoft setup. The message I get is more routine, suggesting just an invalid username/password combination - which it cannot be since nothing has changed. I should add that my Samsung Adroid Email has continued to work. Of course it was never shut down.

I think we need more, and consistent, reports


Just an update: Still working here on ASP. I haven't gone longer than 3-4 days in between retrieving mail.
I tend to agree with @BrianFluet, more data is required to try to figure out what MS is doing.

I tend to think that if MS was applying this change incrementally (perhaps to mediate the volume of backlash) they MIGHT have said something like "will start implementing beginning..." instead of giving out a hard date of 09/16. But who can tell what MS is thinking or planning?


Best of luck to all.
Craig


[quote=&quot;pid:57062, uid:28772&quot;]I think we need more, and consistent, reports[/quote] Just an update: Still working here on ASP. I haven&#039;t gone longer than 3-4 days in between retrieving mail. I tend to agree with @BrianFluet, more data is required to try to figure out what MS is doing. I tend to think that if MS was applying this change incrementally (perhaps to mediate the volume of backlash) they MIGHT have said something like &quot;will start implementing beginning...&quot; instead of giving out a hard date of 09/16. But who can tell what MS is thinking or planning? Best of luck to all. Craig

I have in fact received both the messages referred to by Kilmolin. One when trying to retrieve mail and the other when trying to send mail. Can't remember which is which as I am away from my computer for the weekend. Sorry I don't know how to do quotes on my phone. I'll respond more fully when I get home.
David


I have in fact received both the messages referred to by Kilmolin. One when trying to retrieve mail and the other when trying to send mail. Can&#039;t remember which is which as I am away from my computer for the weekend. Sorry I don&#039;t know how to do quotes on my phone. I&#039;ll respond more fully when I get home. David

I did try re-using my normal interactive password, using copy/paste into Pegasus from the successful interactive session. I still get the "unknown user name or bad password" message when I would expect either success or "Authentication unsuccessful, basic authentication is disabled".


OK. I get the error message:
334 535 5.7.139 Authentication unsuccessful, basic authentication is
disabled. [DUZPR01CA0296.eurprd01.prod.exchangelabs.com 2024-
when I try to send via SMTP
So the same as djarvie
The POP3 message is quite off the point but still a rejection.
We seem to have been targetted because of a few days inactivity but I expect all users to hit this problem.


I did try re-using my normal interactive password, using copy/paste into Pegasus from the successful interactive session. I still get the &quot;unknown user name or bad password&quot; message when I would expect either success or &quot;Authentication unsuccessful, basic authentication is disabled&quot;. OK. I get the error message: 334 535 5.7.139 Authentication unsuccessful, basic authentication is disabled. [DUZPR01CA0296.eurprd01.prod.exchangelabs.com 2024- when I try to send via SMTP So the same as djarvie The POP3 message is quite off the point but still a rejection. We seem to have been targetted because of a few days inactivity but I expect all users to hit this problem.

@BrianFluet

and so it begins.... smile
attempted to retrieve mail from Outlook this AM:


07:24:00.701: --- 30 Sep 2024, 7:24:00.701 ---
07:24:00.701: Connect to 'outlook.office365.com', timeout 30 seconds, flags 16842753.
07:24:01.746: [] Setting SNI hostname to 'outlook.office365.com'
07:24:01.867: [
] SSL/TLS session established
07:24:01.867: [] ECDHE-RSA-AES256-GCM-SHA384, TLSv1.2, Kx=ECDH, Au=RSA, Enc=AESGCM(256), Mac=AEAD
07:24:01.867: [
] Peer's certificate name is '/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com'.
07:24:01.922: >> +OK The Microsoft Exchange POP3 service is ready. [QgBZAEEAUABSADAAMQBDAEEAMAAwADYAOAAuAHAAcgBvAGQALgBlAHgAYwBoAGEAbgBnAGUAbABhAGIAcwAuAGMAbwBtAA==]
07:24:01.922: << USER Craig@hotmail.com
07:24:01.959: >> +OK
<< 0023 PASS XXXXXXXXXXXXXXXX
07:24:02.797: >> -ERR Logon failure: unknown user name or bad password.


@BrianFluet and so it begins.... (doh) attempted to retrieve mail from Outlook this AM: 07:24:00.701: --- 30 Sep 2024, 7:24:00.701 --- 07:24:00.701: Connect to &#039;outlook.office365.com&#039;, timeout 30 seconds, flags 16842753. 07:24:01.746: [*] Setting SNI hostname to &#039;outlook.office365.com&#039; 07:24:01.867: [*] SSL/TLS session established 07:24:01.867: [*] ECDHE-RSA-AES256-GCM-SHA384, TLSv1.2, Kx=ECDH, Au=RSA, Enc=AESGCM(256), Mac=AEAD 07:24:01.867: [*] Peer&#039;s certificate name is &#039;/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com&#039;. 07:24:01.922: &gt;&gt; +OK The Microsoft Exchange POP3 service is ready. [QgBZAEEAUABSADAAMQBDAEEAMAAwADYAOAAuAHAAcgBvAGQALgBlAHgAYwBoAGEAbgBnAGUAbABhAGIAcwAuAGMAbwBtAA==] 07:24:01.922: &lt;&lt; USER Craig@hotmail.com 07:24:01.959: &gt;&gt; +OK &lt;&lt; 0023 PASS XXXXXXXXXXXXXXXX 07:24:02.797: &gt;&gt; -ERR Logon failure: unknown user name or bad password.

and so it begins

This is bad news Craig. I had thought that it only affected Kilmolin and me because we had a break from Pegasus when the change took place. Now it looks like we are all eventually going to lose our Pegasus connection to Outlook.


I too tried creating another app password, also creating a new identity in which to use the app password, but neither approach worked.
Looking at the TCP logs, I get the message ‘unknown user name or bad password’ when trying to retrieve mail (POP); I get the message 'Authentication unsuccessful, basic authentication is disabled’ when trying to send mail (SMPT).


Regarding the recent discussion, I connect to 'outlook.office365.com' (POP) or 'smtp.office365.com' (SMPT).
David


[quote=&quot;pid:57067, uid:42003&quot;]and so it begins[/quote] This is bad news Craig. I had thought that it only affected Kilmolin and me because we had a break from Pegasus when the change took place. Now it looks like we are all eventually going to lose our Pegasus connection to Outlook. I too tried creating another app password, also creating a new identity in which to use the app password, but neither approach worked. Looking at the TCP logs, I get the message &lsquo;unknown user name or bad password&rsquo; when trying to retrieve mail (POP); I get the message &#039;Authentication unsuccessful, basic authentication is disabled&rsquo; when trying to send mail (SMPT). Regarding the recent discussion, I connect to &#039;outlook.office365.com&#039; (POP) or &#039;smtp.office365.com&#039; (SMPT). David

Well, as I commented earlier, I had expected this development.
I can still use the Samsung Android Email with an app password but that may go too. However I can switch to Android Outlook.


Dropping Pegasus is an entirely different and much larger problem.
I have attached rules and programs and nearly 1000 folders.
I do not want to have two local email systems.
I have started looking at Thunderbird.


Microsoft have of course adopted the same attitude with Windows 11.
Instead of just warning users that updating to Windows 11 from an old PC or laptop will reduce security, they have denied these users the ability to upgrade at all, with security updates for Windows 10 finishing in 1 year.


It seems at least 2 million PCs and laptops have to be dumped.
What about the green agenda here?


Governments should insist that Microsoft cease these forced upgrades on pain of being excluded from all state tenders.
Let the users decide on thier own level of security.


Well, as I commented earlier, I had expected this development. I can still use the Samsung Android Email with an app password but that may go too. However I can switch to Android Outlook. Dropping Pegasus is an entirely different and much larger problem. I have attached rules and programs and nearly 1000 folders. I do not want to have two local email systems. I have started looking at Thunderbird. Microsoft have of course adopted the same attitude with Windows 11. Instead of just warning users that updating to Windows 11 from an old PC or laptop will reduce security, they have denied these users the ability to upgrade at all, with security updates for Windows 10 finishing in 1 year. It seems at least 2 million PCs and laptops have to be dumped. What about the green agenda here? Governments should insist that Microsoft cease these forced upgrades on pain of being excluded from all state tenders. Let the users decide on thier own level of security.

and so it begins....


Indeed! It has now affected me with "-ERR Logon failure: unknown user name or bad password."


[quote=&quot;pid:57067, uid:42003&quot;]and so it begins....[/quote] Indeed! It has now affected me with &quot;-ERR Logon failure: unknown user name or bad password.&quot;

Well my friends... it was D-Day over here...


What a day as I work at shutting down my Outlook account... should have known better than to trust MS with my email enniwaze. LOL!


A year or so ago I switched ISPs to COX who had dropped their POP3/SMTP/IMAP so I went with MS Outlook... and really did like it... until I couldn't get my mail anymore. Been with Pmail for more years than I can remember... changes are difficult for us old guys.


Now I'm wondering about the future direction. Kinda searching for a POP3 service provider, maybe with a web interface. Gotten really spoiled to glance through mail prior to retrieving and deleting 90% of it.


My friends, I wish us all the best of luck as we navigate this mess.... sigh....


Well my friends... it was D-Day over here... What a day as I work at shutting down my Outlook account... should have known better than to trust MS with my email enniwaze. LOL! A year or so ago I switched ISPs to COX who had dropped their POP3/SMTP/IMAP so I went with MS Outlook... and really did like it... until I couldn&#039;t get my mail anymore. Been with Pmail for more years than I can remember... changes are difficult for us old guys. Now I&#039;m wondering about the future direction. Kinda searching for a POP3 service provider, maybe with a web interface. Gotten really spoiled to glance through mail prior to retrieving and deleting 90% of it. My friends, I wish us all the best of luck as we navigate this mess.... sigh....

Both Gamil and Yahoo provide POP3 via app paswords still accessible by Pegasus and have web interfaces. Yahoo is still folder oriented. It has a lot of ads on the web but that would not matter using Pegasus/POP3. There are other limitations to the free version as well but again not such an issue with POP3.


There is in interesting set of choices for Pegasus/Outlook.com users:


  1. Switch from Pegasus to a mailer supporting OAUTH2 (eg Thunderbird)
  2. Change from Outlook.com to Gmail/Yahoo etc, forwarding from Outlook
  3. Access Outlook.com on the web and Android only

Of course new email addresses might be needed on the new platforms if switching, and "good" ones might not be available.
I don't really like the format <name>1234@ etc


Both Gamil and Yahoo provide POP3 via app paswords still accessible by Pegasus and have web interfaces. Yahoo is still folder oriented. It has a lot of ads on the web but that would not matter using Pegasus/POP3. There are other limitations to the free version as well but again not such an issue with POP3. There is in interesting set of choices for Pegasus/Outlook.com users: 1. Switch from Pegasus to a mailer supporting OAUTH2 (eg Thunderbird) 2. Change from Outlook.com to Gmail/Yahoo etc, forwarding from Outlook 3. Access Outlook.com on the web and Android only Of course new email addresses might be needed on the new platforms if switching, and &quot;good&quot; ones might not be available. I don&#039;t really like the format &lt;name&gt;1234@ etc

and yet... just another busy day in paradise... smile


I thought I'd been covering my bases by sending all my mail to BOTH Gmail and Outlook (I use a mail forwarding service)... BUT... I had overlooked all the mail in my "Temp" folders on Outlook... how to get those emails?


I set up a Yahoo account and tried to connect it to my Outlook, figuring I'd move the mail from the folders to the inbox. No Joy.... Yahoo would not connect with Outlook.


Went back to Gmail and tried to connect it to Outlook. Looked like it worked but couldn't get any transfers accomplished. Tried Gmail again but selected their mirroring app to connect the accounts. SUCCESS. Set up duplicates of Outlook folders on Gmail... where I could access them with Pmail. Immediately severed the Gmail/Outlook connection (for now... but keeping that in the back of mind after I get things squared away... hmmmm) and started cleanup on Pmail, Outlook, and Gmail.


For now, I'm using Gmail and it's crappy "labels" but fully intend on experimenting with Outlook, mirroring to Gmail for the few downloads I want to save with PMail. For me, and my lack of knowledge in POP3/SMTP/IMAP, there will be a learning curve.


Again, wishing all the best.
Craig


and yet... just another busy day in paradise... :D I thought I&#039;d been covering my bases by sending all my mail to BOTH Gmail and Outlook (I use a mail forwarding service)... BUT... I had overlooked all the mail in my &quot;Temp&quot; folders on Outlook... how to get those emails? I set up a Yahoo account and tried to connect it to my Outlook, figuring I&#039;d move the mail from the folders to the inbox. No Joy.... Yahoo would not connect with Outlook. Went back to Gmail and tried to connect it to Outlook. Looked like it worked but couldn&#039;t get any transfers accomplished. Tried Gmail again but selected their mirroring app to connect the accounts. SUCCESS. Set up duplicates of Outlook folders on Gmail... where I could access them with Pmail. Immediately severed the Gmail/Outlook connection (for now... but keeping that in the back of mind after I get things squared away... hmmmm) and started cleanup on Pmail, Outlook, and Gmail. For now, I&#039;m using Gmail and it&#039;s crappy &quot;labels&quot; but fully intend on experimenting with Outlook, mirroring to Gmail for the few downloads I want to save with PMail. For me, and my lack of knowledge in POP3/SMTP/IMAP, there will be a learning curve. Again, wishing all the best. Craig

I just did a web search for 'Outlook "app password"' as was surprised to not find any current info. My Microsoft account Security page still states that an app password will work for an email client. I am fortunate that my Outlook account ended up being an account that I used solely for testing purposes. I won't miss it but the address is out there so I guess I'll need to use its web interface to check it occasionally.


I just did a web search for &#039;Outlook &quot;app password&quot;&#039; as was surprised to not find any current info. My Microsoft account Security page still states that an app password will work for an email client. I am fortunate that my Outlook account ended up being an account that I used solely for testing purposes. I won&#039;t miss it but the address is out there so I guess I&#039;ll need to use its web interface to check it occasionally.

I just tried, and got nowhere with outlook. Had gotten a windows 11 machine a few months ago, and it had me create and outlook.com account as part of setup. Just had 25 junk emails and 2 ads in it. Finally got to point were it gave a string for an app password, but only showed options for limited programs to use it on? So total waste.
Deleted the 25 junk emails, and doesn't seem to be a way to delete ads?? Left a very negative feed back message.


I just tried, and got nowhere with outlook. Had gotten a windows 11 machine a few months ago, and it had me create and outlook.com account as part of setup. Just had 25 junk emails and 2 ads in it. Finally got to point were it gave a string for an app password, but only showed options for limited programs to use it on? So total waste. Deleted the 25 junk emails, and doesn&#039;t seem to be a way to delete ads?? Left a very negative feed back message.

mikes@guam.net

To BrianFluet:


You can certainly log in periodically to check your Outlook email.
However you could also set up a forward from your Outlook account to your active account. You will get your Outlook emails immediately and without any web login. You can chose to keep a copy on Outlook.


To BrianFluet: You can certainly log in periodically to check your Outlook email. However you could also set up a forward from your Outlook account to your active account. You will get your Outlook emails immediately and without any web login. You can chose to keep a copy on Outlook.
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