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SMTP notifications not working with gmail

Scheduled Pinned Locked Moved General pfSense Questions
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  • O
    OpensourceProtection
    last edited by Feb 13, 2018, 10:20 PM

    Thanks for speedy reply slim2016, unfortunately, I tried the guide and still receive the same error code as posted above. The only difference is that the ending port number is 465 instead of 587.

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    • S
      slim2016
      last edited by Feb 13, 2018, 10:39 PM

      I was using a different email for my notification  but i thought I give this gmail a go and it worked at first try. I did however copy and pasted the password on a text file first just to make sure there wasn't any spaces. Maybe someone with more experience can help you.

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      • O
        OpensourceProtection
        last edited by Feb 14, 2018, 5:03 PM

        I wouldn't call this solved, more of a temporary workaround until it's solved.  I got it to where I can get the emails utilizing an internal SMTP relay server, that then forwards said emails onwards.

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        • J
          johnpoz LAYER 8 Global Moderator
          last edited by Feb 14, 2018, 5:12 PM

          I have been using pfsense and gmail in the notification for like ever.. Never had any issues.  Below is my setup..

          I blacked out the gmail address using… And the password is a app password setup in gmail.

          gmailnotification.png
          gmailnotification.png_thumb

          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

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          • G
            Grimson Banned
            last edited by Feb 14, 2018, 5:21 PM

            @OpensourceProtection:

            SMTP Port of E-Mail server: Tried both 465 and 587
            Secure SMTP Connection: I leave it checked.

            Set the port to 587 and uncheck "Secure SMTP Connection" it will then use StartTLS.

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            • J
              johnpoz LAYER 8 Global Moderator
              last edited by Feb 14, 2018, 5:32 PM Feb 14, 2018, 5:26 PM

              Yup that works too… Just changed settings and still works...

              edit:  Here is the exchange of sending test message.. Which is what I would suggest you do.. So you can actually see what the problem is..

              othersettings.png
              othersettings.png_thumb
              exchangegamailsniff.png_thumb
              exchangegamailsniff.png

              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

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              • O
                OpensourceProtection
                last edited by Feb 20, 2018, 2:51 PM

                Solved!

                Every time you test the connection you have a to reinput the password. Even though you'll see the shortened black dots, the password is not saved from the test before. (I'm assuming it's reverting to what it has saved but can't say for certain.)  I was seeing the shortened black dots and thought PFSense was rolling over the password from the previous try this was not the case. Once I copied the setting of johnpoz (with the appropriately changed email addresses) it worked like a charm the first time, and when tested again it failed like before. That's what clued me in.

                If I entered everything fresh, hit save, THEN hit test I could get it working multiple times in a row.

                Thank you everyone for your help with this!

                C 1 Reply Last reply Dec 28, 2021, 12:31 AM Reply Quote 1
                • J
                  johnpoz LAYER 8 Global Moderator
                  last edited by Feb 20, 2018, 3:58 PM

                  Glad you got it working… But it clearly states on the form that "The last SAVED values will be used, not necessarily the values entered here." ;)

                  saved.png
                  saved.png_thumb

                  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

                  D 1 Reply Last reply Apr 18, 2020, 8:51 PM Reply Quote 0
                  • D
                    discy @johnpoz
                    last edited by discy Apr 18, 2020, 8:53 PM Apr 18, 2020, 8:51 PM

                    Had the same issue. Password wasn't saved and would be gone when I re-opened the interface.
                    Test wouldn't work after re-opening the interface, while it worked after I saved.

                    • Disabled/Enabled SMTP over SSL
                    • Changed port
                    • Hit save a couple of times in between.

                    Now the password is kept saved, back on SSL and port 465.
                    Test also works after reloading the interface.

                    Definitely something funky going on here.

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                    • C
                      CrowFather @OpensourceProtection
                      last edited by Dec 28, 2021, 12:31 AM

                      @opensourceprotection said in SMTP notifications not working with gmail:

                      Solved!

                      Every time you test the connection you have a to reinput the password. Even though you'll see the shortened black dots, the password is not saved from the test before. (I'm assuming it's reverting to what it has saved but can't say for certain.)  I was seeing the shortened black dots and thought PFSense was rolling over the password from the previous try this was not the case. Once I copied the setting of johnpoz (with the appropriately changed email addresses) it worked like a charm the first time, and when tested again it failed like before. That's what clued me in.

                      If I entered everything fresh, hit save, THEN hit test I could get it working multiple times in a row.

                      Thank you everyone for your help with this!

                      This was the solution to the issue I was having! Thanks for your help.

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