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Gmail SMTP authentication

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  • artwawA artwaw

    @JonB Apparently "less secure apps" is enabled for personal accounts by default.
    Short path:

    • open myaccount.google.com (assuming you are logging in with the account in question).
    • on the left hand side you'll have "security" menu option. Click.
    • follow the help page https://support.google.com/accounts/answer/185833?hl=en-GB

    And for non-managed google account that should be all.

    If the account is managed by the Google Workspace type of organisation (former GSuite) admin of that needs to:

    • login to admin.google.com
    • security -> access and data control -> less secure apps
    • enable feature for user in question.

    As for "what changes" on May 30th I have no idea but quick search found this: https://h30434.www3.hp.com/t5/Scanning-Faxing-Copying/After-May-30th-2022-what-will-be-the-way-to-scan-to-gmail/td-p/8320453

    Which means that for the account in question google will phase out plain login without OAuth challenge. The right way to proceed is to create "less secure apps" credentials and continue as before.

    JonBJ Offline
    JonBJ Offline
    JonB
    wrote on last edited by
    #11

    @artwaw said in Gmail SMTP authentication:

    follow the help page https://support.google.com/accounts/answer/185833?hl=en-GB

    Under "Signing in to Google," select App Passwords. You may need to sign in. If you don’t have this option, it might be because:

    2-Step Verification is not set up for your account.

    For my own Gmail I do not see any "App Passwords". That may be because I personally do not have 2-step active, and don't wish to do so/try it out....

    At the bottom, choose Select app and choose the app you using and then Select device and choose the device you’re using and then Generate.

    If I (the end user) got this far, I don't know how "our app" would appear as one to be selected. Sounds more like a list of apps registered with Google?

    Let's say this does all work. Now that means 2-step verification with mobile is enabled. An end user does something in our desktop app which causes it to want to send SMTP email. That might mean Google wants to send a code to mobile and have user enter it? Would that authentication appear on the desktop OK when run from a non-web desktop Python Qt program?

    artwawA 1 Reply Last reply
    0
    • JonBJ JonB

      @artwaw said in Gmail SMTP authentication:

      follow the help page https://support.google.com/accounts/answer/185833?hl=en-GB

      Under "Signing in to Google," select App Passwords. You may need to sign in. If you don’t have this option, it might be because:

      2-Step Verification is not set up for your account.

      For my own Gmail I do not see any "App Passwords". That may be because I personally do not have 2-step active, and don't wish to do so/try it out....

      At the bottom, choose Select app and choose the app you using and then Select device and choose the device you’re using and then Generate.

      If I (the end user) got this far, I don't know how "our app" would appear as one to be selected. Sounds more like a list of apps registered with Google?

      Let's say this does all work. Now that means 2-step verification with mobile is enabled. An end user does something in our desktop app which causes it to want to send SMTP email. That might mean Google wants to send a code to mobile and have user enter it? Would that authentication appear on the desktop OK when run from a non-web desktop Python Qt program?

      artwawA Offline
      artwawA Offline
      artwaw
      wrote on last edited by
      #12

      @JonB said in Gmail SMTP authentication:

      , I don't know how "our app" would appear as one to be selected

      it does not matter. Select "custom", provide recognisable name:
      cce05cd9-d316-4163-b82e-e5d2861c7bc4-image.png

      After providing the name you'll see something like this:
      795419af-e3d5-467a-8c34-89bd6c1365b3-image.png

      The yellow is the password (no spaces). Make a copy as this disappears forever as you hit "done". Then just use the users full email and that password to login to smtp.

      This circumvents 2FA, so nothing will be sent anywhere in that regard. As this hampers the security aspect of the account take special care not to share those credentials.

      For more information please re-read.

      Kind Regards,
      Artur

      JonBJ 1 Reply Last reply
      1
      • artwawA artwaw

        @JonB said in Gmail SMTP authentication:

        , I don't know how "our app" would appear as one to be selected

        it does not matter. Select "custom", provide recognisable name:
        cce05cd9-d316-4163-b82e-e5d2861c7bc4-image.png

        After providing the name you'll see something like this:
        795419af-e3d5-467a-8c34-89bd6c1365b3-image.png

        The yellow is the password (no spaces). Make a copy as this disappears forever as you hit "done". Then just use the users full email and that password to login to smtp.

        This circumvents 2FA, so nothing will be sent anywhere in that regard. As this hampers the security aspect of the account take special care not to share those credentials.

        JonBJ Offline
        JonBJ Offline
        JonB
        wrote on last edited by
        #13

        @artwaw
        Thanks, this looks great!

        I note it says "from Apps on devices that don't support 2-step". As I said earlier, I never get to see what you show

        For my own Gmail I do not see any "App Passwords". That may be because I personally do not have 2-step active, and don't wish to do so/try it out....

        so still not sure how I'm supposed to get to the screenshot you show, unfortunately....

        artwawA 1 Reply Last reply
        0
        • JonBJ JonB

          @artwaw
          Thanks, this looks great!

          I note it says "from Apps on devices that don't support 2-step". As I said earlier, I never get to see what you show

          For my own Gmail I do not see any "App Passwords". That may be because I personally do not have 2-step active, and don't wish to do so/try it out....

          so still not sure how I'm supposed to get to the screenshot you show, unfortunately....

          artwawA Offline
          artwawA Offline
          artwaw
          wrote on last edited by
          #14

          @JonB I am afraid that rolling 2FA is unavoidable for this.
          (A side note outside of the topic is that 2FA should be mandatory wherever possible for obvious security reasons, but that's just my sysadmin persona speaking).

          For more information please re-read.

          Kind Regards,
          Artur

          JonBJ 1 Reply Last reply
          0
          • artwawA artwaw

            @JonB I am afraid that rolling 2FA is unavoidable for this.
            (A side note outside of the topic is that 2FA should be mandatory wherever possible for obvious security reasons, but that's just my sysadmin persona speaking).

            JonBJ Offline
            JonBJ Offline
            JonB
            wrote on last edited by
            #15

            @artwaw said in Gmail SMTP authentication:

            @JonB I am afraid that rolling 2FA is unavoidable for this.

            OK, but the text says "for devices which do not support 2FA"! That's pretty confusing! Does it mean "You will need to use 2FA enabled on your account in order to set this up for your app, but then an end user will not need 2FA to use this way of connecting to Gmail SMTP once you have set it up"?

            artwawA 2 Replies Last reply
            0
            • JonBJ JonB

              @artwaw said in Gmail SMTP authentication:

              @JonB I am afraid that rolling 2FA is unavoidable for this.

              OK, but the text says "for devices which do not support 2FA"! That's pretty confusing! Does it mean "You will need to use 2FA enabled on your account in order to set this up for your app, but then an end user will not need 2FA to use this way of connecting to Gmail SMTP once you have set it up"?

              artwawA Offline
              artwawA Offline
              artwaw
              wrote on last edited by
              #16

              @JonB said in Gmail SMTP authentication:

              You will need to use 2FA enabled on your account in order to set this up for your app, but then an end user will not need 2FA to use this way of connecting to Gmail SMTP once you have set it up"?

              That is my understanding of the situation, yes. (Please bear in mind that I did not work outside 2FA Google environment for quite some years now)

              For more information please re-read.

              Kind Regards,
              Artur

              1 Reply Last reply
              0
              • JonBJ JonB

                @artwaw said in Gmail SMTP authentication:

                @JonB I am afraid that rolling 2FA is unavoidable for this.

                OK, but the text says "for devices which do not support 2FA"! That's pretty confusing! Does it mean "You will need to use 2FA enabled on your account in order to set this up for your app, but then an end user will not need 2FA to use this way of connecting to Gmail SMTP once you have set it up"?

                artwawA Offline
                artwawA Offline
                artwaw
                wrote on last edited by artwaw
                #17

                @JonB
                Take a look at the original message you've got from google:

                "On May 30, you may lose access to apps that are using less secure sign-in technology. To help keep your account secure, Google will no longer support the use of third-party apps or devices which ask you to sign in to your Google Account using only your username and password. Instead, you’ll need to sign in using Sign in with Google or other more secure technologies, like OAuth 2.0."
                

                That implies that logging in with google functionality will cease to work without 2FA challenge enabled. But in order to keep the functionality you have now, you need to enable 2FA and generate the "less secure app" credentials. That's the scope of the changes you face, if I read the situation correctly.

                For more information please re-read.

                Kind Regards,
                Artur

                JonBJ 1 Reply Last reply
                0
                • artwawA artwaw

                  @JonB
                  Take a look at the original message you've got from google:

                  "On May 30, you may lose access to apps that are using less secure sign-in technology. To help keep your account secure, Google will no longer support the use of third-party apps or devices which ask you to sign in to your Google Account using only your username and password. Instead, you’ll need to sign in using Sign in with Google or other more secure technologies, like OAuth 2.0."
                  

                  That implies that logging in with google functionality will cease to work without 2FA challenge enabled. But in order to keep the functionality you have now, you need to enable 2FA and generate the "less secure app" credentials. That's the scope of the changes you face, if I read the situation correctly.

                  JonBJ Offline
                  JonBJ Offline
                  JonB
                  wrote on last edited by
                  #18

                  @artwaw
                  All good, thank you very much for your time. I will have to try this out --- or rather, get others to try it out.

                  I cannot be sure but am marking this topic as solved.

                  1 Reply Last reply
                  1
                  • M Offline
                    M Offline
                    mchinand
                    wrote on last edited by
                    #19

                    I'm not sure how it works in the background for initiating this request for access, but for my Synology NAS I recently set up email notifications. In the process of configuring it, it went to a Google page asking to authorize access to send emails on my behalf. Going to the Security page of my Google account and viewing the 'Third-Party Apps with Account Access', I now have Synology listed; perhaps your app will have to obtain the same authorization.
                    95fc2491-2823-4868-baf9-aa3ce33a9051-image.png

                    JonBJ artwawA 2 Replies Last reply
                    0
                    • M mchinand

                      I'm not sure how it works in the background for initiating this request for access, but for my Synology NAS I recently set up email notifications. In the process of configuring it, it went to a Google page asking to authorize access to send emails on my behalf. Going to the Security page of my Google account and viewing the 'Third-Party Apps with Account Access', I now have Synology listed; perhaps your app will have to obtain the same authorization.
                      95fc2491-2823-4868-baf9-aa3ce33a9051-image.png

                      JonBJ Offline
                      JonBJ Offline
                      JonB
                      wrote on last edited by JonB
                      #20

                      @mchinand
                      Yeah, that (the need to "register" anything about the app with Google) is precsiely what I am hoping to avoid, which I believe/hope @artwaw's suggestions will allow me to do. The app is not released, not for sale, not for general consumption, so we don't need such hassles!

                      1 Reply Last reply
                      1
                      • M Offline
                        M Offline
                        mchinand
                        wrote on last edited by
                        #21

                        I'm not entirely sure just ensuring 2FA is enabled will work. In Google's message, they mention using either Sign In With Google or OAuth2. 'Sign In With Google' is one of their APIs, I don't think they are using it in the generic sense, sign-in with Google. https://developers.google.com/identity/gsi/web

                        1 Reply Last reply
                        1
                        • M mchinand

                          I'm not sure how it works in the background for initiating this request for access, but for my Synology NAS I recently set up email notifications. In the process of configuring it, it went to a Google page asking to authorize access to send emails on my behalf. Going to the Security page of my Google account and viewing the 'Third-Party Apps with Account Access', I now have Synology listed; perhaps your app will have to obtain the same authorization.
                          95fc2491-2823-4868-baf9-aa3ce33a9051-image.png

                          artwawA Offline
                          artwawA Offline
                          artwaw
                          wrote on last edited by
                          #22

                          @mchinand But this is SAML/OAuth authentication. It is a different mechanism than the one we try to workout here.

                          For more information please re-read.

                          Kind Regards,
                          Artur

                          1 Reply Last reply
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                          • JonBJ JonB referenced this topic on

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