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    Outlook sign in technology for notifications

    Scheduled Pinned Locked Moved General pfSense Questions
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    • M
      mtk67 @jrey
      last edited by

      @jrey I double checked and I'm set to LOGIN not PLAIN.

      1 Reply Last reply Reply Quote 0
      • M
        mtk67 @jrey
        last edited by

        @jrey I'm not using PLAIN. I'm using LOGIN.

        johnpozJ 1 Reply Last reply Reply Quote 0
        • johnpozJ
          johnpoz LAYER 8 Global Moderator @mtk67
          last edited by

          @mtk67 so its the 16th that they make this go away right.. Guess we will know in a few days.. But for sure don't see them taking away app passwords.

          An intelligent man is sometimes forced to be drunk to spend time with his fools
          If you get confused: Listen to the Music Play
          Please don't Chat/PM me for help, unless mod related
          SG-4860 24.11 | Lab VMs 2.8, 24.11

          M 1 Reply Last reply Reply Quote 1
          • M
            mtk67 @johnpoz
            last edited by

            @johnpoz The best guess on what the 'modern authentication' is that they're referring to is similar to what, I think, Google does. And that is upon entering your creds you have to confirm authentication on another device (like your phone). Microsoft uses their Authenticator app.

            I know that Synology uses this now so it was a change they had to make (don't ask me what, maybe OAUTH/2 as someone mentioned in a reply) to make this work. That's really the only other place I'm setup for notifications to this outlook.com address. Thus, this is why I suspect the notice that I received is due to my attempt to use it for pfSense notifications.

            johnpozJ 1 Reply Last reply Reply Quote 0
            • johnpozJ
              johnpoz LAYER 8 Global Moderator @mtk67
              last edited by johnpoz

              @mtk67 Well I bet you a beer ;) that app passwords don't go away..

              On the 17th I will do a test of sending notification emails with pfsense using a @live.com (microsoft) email address and servers.

              An intelligent man is sometimes forced to be drunk to spend time with his fools
              If you get confused: Listen to the Music Play
              Please don't Chat/PM me for help, unless mod related
              SG-4860 24.11 | Lab VMs 2.8, 24.11

              M 1 Reply Last reply Reply Quote 0
              • M
                mtk67 @johnpoz
                last edited by

                @johnpoz I'm sure you're right about app passwords. It'll be interesting to see what, if anything, changes next week.

                J 1 Reply Last reply Reply Quote 0
                • J
                  jrey @mtk67
                  last edited by

                  @mtk67

                  Other the other hand, your notice may have been because of another device (the coffee maker) and not because of the pfSense settings at all.. (their notice of course does not tell you what device, only that you have "something" that is using Basic on that account) Assuming you use outlook on other devices, maybe one of those caused you to get the notice from MS and there are clear instructions for some of those cases in the article. They are truly only flagging that something using your account is using Basic Auth, nothing more.

                  The app password are not going away, the ability to use Normal/Plain/Basic is.

                  In my case the notice was generated because a legacy system (a script actually not even a mail application installed on this system) but that was still wanting to "talk" to outlook to send mail and it was set to basic, opps. Every thing else was already using what they reference as "modern" connections with regards to outlook - and the account and passwords still apply. You are not being asked to change your account or password.

                  the extended wording throughout the article and examples they provide are pretty clear and consistent. Don't use Basic Auth.

                  "Until September 16th, users signing into Outlook.com through Basic Authentication may experience recurring password prompts in Outlook and other third-party email applications. This is a known issue. After September 16th, users attempting to connect their Microsoft accounts through Basic Authentication will fail to do so."

                  You'll still be able to login with your account and password, again just not using Basic Auth.

                  Even though I don't use outlook on the netgate, my expectation (and interpretation of the message below the selection) is that LOGIN should work and PLAIN for those set that may be set that way will start to fail consistently. (assuming all the other setting are correct). Since you are already set for LOGIN - hit "Test SMTP Settings" on the 17th and you will know.

                  Have fun!

                  M 1 Reply Last reply Reply Quote 0
                  • M
                    mtk67 @jrey
                    last edited by

                    @jrey I guess I'll find out next week. But as I mentioned in an earlier reply I am only using this email account in two places... One is on my Synology and the other is here. Pretty sure it's not the NAS as mentioned, so that just leaves this. Maybe this is much ado about nothing.

                    My coffee maker is not connected to the net. ;)

                    johnpozJ 1 Reply Last reply Reply Quote 0
                    • johnpozJ
                      johnpoz LAYER 8 Global Moderator @mtk67
                      last edited by

                      @mtk67 and so did your notifications stop?

                      I just setup notification in my 2.7.2 vm using outlook.com - didn't even create an app password and working

                      working.jpg

                      An intelligent man is sometimes forced to be drunk to spend time with his fools
                      If you get confused: Listen to the Music Play
                      Please don't Chat/PM me for help, unless mod related
                      SG-4860 24.11 | Lab VMs 2.8, 24.11

                      1 Reply Last reply Reply Quote 1
                      • M
                        mtk67
                        last edited by

                        The emails are still working as of this morning. That tells me that either they:
                        A. Didn’t make any change yet despite the 9/16 advertised deadline. -or-
                        B. Incorrectly identified customers using SMTP with LOGIN and created unnecessary panic.

                        Hoping it’s B. If I end up seeing an impact I will post an update back to this thread. But all seems to be working unchanged as of today (9/18).

                        johnpozJ M 2 Replies Last reply Reply Quote 0
                        • M
                          mtk67
                          last edited by

                          By the way, thanks for all the replies, ideas, and help here. Much appreciated!

                          1 Reply Last reply Reply Quote 0
                          • johnpozJ
                            johnpoz LAYER 8 Global Moderator @mtk67
                            last edited by

                            @mtk67 said in Outlook sign in technology for notifications:

                            created unnecessary panic.

                            No - not MS, don't say it is so ;)

                            An intelligent man is sometimes forced to be drunk to spend time with his fools
                            If you get confused: Listen to the Music Play
                            Please don't Chat/PM me for help, unless mod related
                            SG-4860 24.11 | Lab VMs 2.8, 24.11

                            1 Reply Last reply Reply Quote 1
                            • M
                              mtk67 @mtk67
                              last edited by

                              @mtk67 Wanted to post an update in case others are having the same problem. The emails continued to work until this week. Now I get an authentication error, so it seems MSFT had a grace period after their stated deadline.

                              The auth error is
                              Error: LOGIN authentication failure [SMTP: Invalid response code received from server (code: 535, response: 5.7.139
                              Authentication unsuccessful, basic authentication is disabled. [LV3P220CA0009.NAMP220.PROD.OUTLOOK.COM 2024-10-01 T01:39:18.356Z 08DCE11B520D41E6])]

                              I'll wait patiently until netgate provides an auth fix for this. Still working fine on Synology which uses OAUTH2. Otherwise I'll need to switch to another email provider, though they all seem to be going the same route these days.

                              johnpozJ 1 Reply Last reply Reply Quote 1
                              • johnpozJ
                                johnpoz LAYER 8 Global Moderator @mtk67
                                last edited by johnpoz

                                @mtk67 still working here

                                workingheree.jpg

                                Are you using LOGIN, like in my above example?

                                PLAIN yeah fails

                                dontuseplain.jpg

                                Change it back to LOGIN and works

                                works.jpg

                                what version of pfsense are you using? This is from my 2.7.2 version.

                                An intelligent man is sometimes forced to be drunk to spend time with his fools
                                If you get confused: Listen to the Music Play
                                Please don't Chat/PM me for help, unless mod related
                                SG-4860 24.11 | Lab VMs 2.8, 24.11

                                J 1 Reply Last reply Reply Quote 0
                                • J
                                  jrey @jrey
                                  last edited by

                                  @jrey said in Outlook sign in technology for notifications:

                                  But isn't this a simple as the Poster likely has "PLAIN" and needs to select the other available option "LOGIN" ?

                                  GertjanG M 2 Replies Last reply Reply Quote 1
                                  • GertjanG
                                    Gertjan @jrey
                                    last edited by

                                    @jrey

                                    Yeah,
                                    and this one (@mtk67 :):
                                    Microsoft has not like 'us, the common mortals', just one mail server behind one IP.
                                    They have probably a couple of hundreds or more, and they get updated and upgraded one by one - not "all at ones at midnight". After all, if there was some update/upgrade issue, its always better to hinder just 1 % of you clients instead of "all of them at ones".

                                    So, imho, the upcoming app password is a thing, and will be phased in over time.

                                    No "help me" PM's please. Use the forum, the community will thank you.
                                    Edit : and where are the logs ??

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                                    • M
                                      mtk67 @jrey
                                      last edited by

                                      @jrey no. It’s not that simple. I have LOGIN selected not PLAIN.

                                      1 Reply Last reply Reply Quote 0
                                      • J
                                        jrey @johnpoz
                                        last edited by jrey

                                        @mtk67

                                        @johnpoz said in Outlook sign in technology for notifications:

                                        what version of pfsense are you using?

                                        Same question.

                                        johnpozJ M 2 Replies Last reply Reply Quote 0
                                        • johnpozJ
                                          johnpoz LAYER 8 Global Moderator @jrey
                                          last edited by

                                          @jrey so have you created a app password? You sure you hit save all the way on the bottom for if you changed it login? Your is saying basic, my error says plain.

                                          Once/If I get the failure I can switch it over to app password to see if that corrects it. But @Gertjan could be right they could have it rolling through their servers, and I have just not hit one yet.

                                          An intelligent man is sometimes forced to be drunk to spend time with his fools
                                          If you get confused: Listen to the Music Play
                                          Please don't Chat/PM me for help, unless mod related
                                          SG-4860 24.11 | Lab VMs 2.8, 24.11

                                          M J 2 Replies Last reply Reply Quote 0
                                          • M
                                            mtk67 @johnpoz
                                            last edited by

                                            @johnpoz 100% that I’m using an app password. I needed it because I enabled 2FA on the account. Also certain that I’m not using PLAIN. If I can post screenshots here I’ll post it of my settings tonight when I get home. Then we can compare notes.

                                            I read a tech note on their site last night and even went so far as to try using settings for the old POP format (ewww) just to see if it would make a difference.

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