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Outlook Cutting Off Basic Authentication on 09/16/2024

I still use the app password setup for Gmail.


Hi Mike, did you ever set PM up with the GMail OAUTH2? Are you ONLY using the app specific PW?


[quote="pid:56814, uid:2546"]I still use the app password setup for Gmail.[/quote] Hi Mike, did you ever set PM up with the GMail OAUTH2? Are you ONLY using the app specific PW?

I've never use the OAUTH2. Did the app password many years ago, and it has worked fine for me.
I run Pegasus under wine, so not sure if the OAUTH2 will work with Linux. Perhaps someone has tested it under linux.
Know the IERender has issues with wine, but not sure if the OAUTH2 does or doesn't.


Would have to create another gmail account to test it.


I've never use the OAUTH2. Did the app password many years ago, and it has worked fine for me. I run Pegasus under wine, so not sure if the OAUTH2 will work with Linux. Perhaps someone has tested it under linux. Know the IERender has issues with wine, but not sure if the OAUTH2 does or doesn't. Would have to create another gmail account to test it.

mikes@guam.net

Craig, I am concerned that you are authenticating with the app password and not OAUTH2. To check this go to Tools > Internet options.


Select the Receiving (POP3) tab and confirm that the name of the host contains (OAUTH2) at the end. An OAUTH2 host configuration will not contain a password so you can check that by selecting host, clicking the Edit button, and looking to see whether the password field is blank.


Do the same in the Sending (SMTP) tab except that you will need to open the Security tab to see the authentication details.


The important thing here is that a host configuration is not OAUTH2 if it contains a password, or in the case of SMTP, is configured to authenticate using a POP3 login whose authentication uses a password.


Craig, I am concerned that you are authenticating with the app password and not OAUTH2. To check this go to Tools > Internet options. Select the Receiving (POP3) tab and confirm that the name of the host contains (OAUTH2) at the end. An OAUTH2 host configuration will not contain a password so you can check that by selecting host, clicking the Edit button, and looking to see whether the password field is blank. Do the same in the Sending (SMTP) tab except that you will need to open the Security tab to see the authentication details. The important thing here is that a host configuration is not OAUTH2 if it contains a password, or in the case of SMTP, is configured to authenticate using a POP3 login whose authentication uses a password.

Just to note: I just created a new gmail account pegasusroot03@gmail.com
Did a test under my linux root account and used the gmail OAUTH2 setup and was able to send and recieve emails.
So, it does seem to work under wine with the OAUTH2 but also with the app password.


Good to Know.


Just to note: I just created a new gmail account pegasusroot03@gmail.com Did a test under my linux root account and used the gmail OAUTH2 setup and was able to send and recieve emails. So, it does seem to work under wine with the OAUTH2 but also with the app password. Good to Know.

mikes@guam.net

I spent some time searching for Microsoft's definition of the term modern authentication methods. I haven't found anything relevant in Microsoft's own very corporate words. If you have a reference, and perhaps also a direct reference for App passwords will no longer be supported by MS mail systems, please post the link or other relevant info here.


It was a frustrating process, trying to tease out from the ever-so-friendly warning email what precisely was supposed to work instead, except of course to use Outlook for all one's emails, calendar, contacts, project planning, fitness training, plumbing services, etc. All right, I made some of those up, but that wasn't answering the question I was trying to ask.


Update: found this. https://learn.microsoft.com/en-us/microsoft-365/enterprise/hybrid-modern-auth-overview?view=o365-worldwide#what-is-modern-authentication


  • Mark

I spent some time searching for Microsoft's definition of the term _modern authentication methods_. I haven't found anything relevant in Microsoft's own very corporate words. If you have a reference, and perhaps also a direct reference for _App passwords will no longer be supported by MS mail systems,_ please post the link or other relevant info here. It was a frustrating process, trying to tease out from the ever-so-friendly warning email what precisely was supposed to work instead, except of course to use Outlook for all one's emails, calendar, contacts, project planning, fitness training, plumbing services, etc. All right, I made some of those up, but that wasn't answering the question I was trying to ask. Update: found this. https://learn.microsoft.com/en-us/microsoft-365/enterprise/hybrid-modern-auth-overview?view=o365-worldwide#what-is-modern-authentication - Mark
edited Jul 4 at 9:41 pm

Thanks to Brian. Got an message that mentioned that he had it working with both app password and OAUTH2 under windows. I just didn't want to risk anything before testing. Wa afraid that maybe one you setup the OAUTH2 it might make app password either invalid or no longer an option at all. Never know with GMAIL and Micro$oft. So at least know that the OAUTH2 does work with wine and Linux.


Seems to just create two PND files that have no mentions of password.
cat *.PND


Pegasus Mail POP3 definition, 5 Jul 2024, 4:02:51


Title : pegasusroot03@gmail.com, POP3/OAUTH2
Type : POP3
Flags1 : 524560
Flags2 : 0
Timeout : 90
Port : 995
Host : pop.gmail.com
Username : pegasusroot03@gmail.com
Mailbox :
Memfile : POPSDEWB.PM3
Threshold : 0
SSLMode : 2
Max_Msgs : 0
Min_Interval : 0
Ruleset :
Top_lines : 0
Def_action : 0


Pegasus Mail SMTP definition, 5 Jul 2024, 4:02:59


Title : pegasusroot03@gmail.com, SMTP/OAUTH2
Type : SMTP
Flags1 : 524544
Flags2 : 0
Timeout : 90
Port : 587
Host : smtp.gmail.com
Username : pegasusroot03@gmail.com
Mailbox :
SSLMode : 1
Max_Msgs : 0


Does create a directory and encoded file
ls -l OAUTH2/*
2206 Jul 5 03:57 OAUTH2/XSMMODLU.OA2


Looked like it might be base64 data, but doesn't decode a is.
Tried without 1st and then 2nd lines removed. The later does decode without error, but is just wierd characters. Assume it has more encoding to create memfile that guess would have password.


Seems to use the standard ports for secure pop3 and smtp.


In my app password setup, I have it use the linux Stunnel to make the pop3 and smtp connection.
Had issues with pre 4.8 not working as well. 4.8x has a much newer openssl.


openssl-3.2.1-2.


Don't know if it would or wouldn't work with stunnel.


Thanks to Brian. Got an message that mentioned that he had it working with both app password and OAUTH2 under windows. I just didn't want to risk anything before testing. Wa afraid that maybe one you setup the OAUTH2 it might make app password either invalid or no longer an option at all. Never know with GMAIL and Micro$oft. So at least know that the OAUTH2 does work with wine and Linux. Seems to just create two PND files that have no mentions of password. cat *.PND # Pegasus Mail POP3 definition, 5 Jul 2024, 4:02:51 Title : pegasusroot03@gmail.com, POP3/OAUTH2 Type : POP3 Flags1 : 524560 Flags2 : 0 Timeout : 90 Port : 995 Host : pop.gmail.com Username : pegasusroot03@gmail.com Mailbox : Memfile : POPSDEWB.PM3 Threshold : 0 SSLMode : 2 Max_Msgs : 0 Min_Interval : 0 Ruleset : Top_lines : 0 Def_action : 0 # Pegasus Mail SMTP definition, 5 Jul 2024, 4:02:59 Title : pegasusroot03@gmail.com, SMTP/OAUTH2 Type : SMTP Flags1 : 524544 Flags2 : 0 Timeout : 90 Port : 587 Host : smtp.gmail.com Username : pegasusroot03@gmail.com Mailbox : SSLMode : 1 Max_Msgs : 0 Does create a directory and encoded file ls -l OAUTH2/* 2206 Jul 5 03:57 OAUTH2/XSMMODLU.OA2 Looked like it might be base64 data, but doesn't decode a is. Tried without 1st and then 2nd lines removed. The later does decode without error, but is just wierd characters. Assume it has more encoding to create memfile that guess would have password. Seems to use the standard ports for secure pop3 and smtp. In my app password setup, I have it use the linux Stunnel to make the pop3 and smtp connection. Had issues with pre 4.8 not working as well. 4.8x has a much newer openssl. openssl-3.2.1-2. Don't know if it would or wouldn't work with stunnel.

mikes@guam.net

I apologize for starting the thread and then bailing for a couple of days... life got busy and September (MS's threatened cut off) still seems far off. LOL


Craig, I am concerned that you are authenticating with the app password and not OAUTH2.


You were right Brian. When my initial attempts at installing the OAUTH2 definition failed, I cleaned up ALL of my old definitions... including the OAUTH2. Then, when I attempted to reinstall it and only chose "refresh", I installed a definition based upon an app specific password... which DID work?!? I have now gone back, deleted my original installation, completely installed OAUTH2 and have a functioning definition for GMail. Thanks.


I spent some time searching for Microsoft's definition of the term modern authentication methods. I haven't found anything relevant in Microsoft's own very corporate words. If you have a reference, and perhaps also a direct reference for App passwords will no longer be supported by MS mail systems, please post the link or other relevant info here.


Hi Mark. I did the exact same thing shortly after starting this thread! And came up totally empty handed. Thanks for the link! Time will tell how they choose to implement it but, if I read it correctly, they are including 2FA?


Thanks to all who have invested time on this.
Craig


I apologize for starting the thread and then bailing for a couple of days... life got busy and September (MS's threatened cut off) still seems far off. LOL [quote="pid:56818, uid:28772"]Craig, I am concerned that you are authenticating with the app password and not OAUTH2.[/quote] You were right Brian. When my initial attempts at installing the OAUTH2 definition failed, I cleaned up ALL of my old definitions... including the OAUTH2. Then, when I attempted to reinstall it and only chose "refresh", I installed a definition based upon an app specific password... which DID work?!? I have now gone back, deleted my original installation, completely installed OAUTH2 and have a functioning definition for GMail. Thanks. [quote="pid:56821, uid:2925"]I spent some time searching for Microsoft's definition of the term modern authentication methods. I haven't found anything relevant in Microsoft's own very corporate words. If you have a reference, and perhaps also a direct reference for App passwords will no longer be supported by MS mail systems, please post the link or other relevant info here.[/quote] Hi Mark. I did the exact same thing shortly after starting this thread! And came up totally empty handed. Thanks for the link! Time will tell how they choose to implement it but, if I read it correctly, they are including 2FA? Thanks to all who have invested time on this. Craig

Time will tell how they choose to implement it but, if I read it correctly, they are including 2FA?


In that article, Microsoft lists "Multifactor authentication" under the umbrella of "Modern Authentication". Creating an app password is dependent on enabling "two-step verification". Is "two-step verification" considered "Multifactor authentication"? A web search of those two phrases leads me to believe that the answer is yes but please don't take that as a definitive answer. I hope other forum members will do this search and post their thoughts based on their interpretation in what they find.


[quote="pid:56839, uid:42003"]Time will tell how they choose to implement it but, if I read it correctly, they are including 2FA?[/quote] In that article, Microsoft lists "Multifactor authentication" under the umbrella of "Modern Authentication". Creating an app password is dependent on enabling "two-step verification". Is "two-step verification" considered "Multifactor authentication"? A web search of those two phrases leads me to believe that the answer is yes but please don't take that as a definitive answer. I hope other forum members will do this search and post their thoughts based on their interpretation in what they find.
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