9 Replies Latest reply on Sep 19, 2018 9:23 AM by drjonesy

    Gmail setup keeps failing

    jennjoe4

      Hi All,

      I want to know how to configure outgoing and incoming mail setting with gmail account for Web Help Desk.  I have version 12.5.2 - Build #12.5.2.84, setup as a virtual appliance.

       

      On incoming mail account, it doesn't matter whether I configure the mail setting using IMAP or POP.  I keep getting the same message of "Email Account was updated successfully.  However, the following error occurred while attempting a connection with the mail server:  Authentication Failed"

       

      I'm not seeing how the authentication can fail, since I'm able to log into Gmail with the email address and password that I'm trying to setup.

        • Re: Gmail setup keeps failing
          justin.gray@weldre4.k12.co.us

          We use the following for incoming:

          And the following for Outgoing:

          • Re: Gmail setup keeps failing
            fluffy midnight

            Hi jennjoe4,

             

            If you still can't get this to work and you have the mail servers with the correct addresses as per justin's screenshots, please can you provide screenshots of your configuration (personal details blanked out).

             

            As this is Virtual Appliance, have you got the appropriate ports open to connect to and from Gmail?

             

            Have you gone into the Gmail settings and enabled 'Allow less secure apps'? You can enable this within the sign-in & security section.

             

            -Midnight

              • Re: Gmail setup keeps failing
                jennjoe4

                I tried the settings per Justin's instructionsOutgoing, but still received "Email Account was updated successfully.  However, the following error occurred while attempting a connection with the mail server:  Authentication Failed".

                 

                I've attached both the incoming and outgoing configurations. 

                 

                Incoming Config

                On Virtual Appliance, do I have to open ports on it?

                Yes, for the email address that I'm using I have enabled less secure apps. 

                  • Re: Gmail setup keeps failing
                    fluffy midnight

                    Hi jennjoe4,

                     

                    For the outgoing mail, can you disable SSL and use port 587? - this is the TLS port.

                     

                    If it is still failing after this, can you check if you have IMAP enabled within gmail.

                     

                    As Gmail is responding with the authentication failed message I would presume the cause wouldn't be the Virtual Appliance, however it's still worth ruling this out by having the port open whilst you are trying to resolve the issue.

                     

                    If all this fails, try resetting your gmail password and trying again.

                     

                    -Midnight

                      • Re: Gmail setup keeps failing
                        jennjoe4

                        That worked.

                         

                        I'm able to send create a ticket via email  But, now I have another issue.  It creates a ticket, but does not send out an email notifying me of the ticket.  I get the following error.

                         

                        Red mark on envelope upon creating a new ticket

                         

                         

                        Error message from previous image

                          • Re: Gmail setup keeps failing
                            fluffy midnight

                            Hi jennjoe4,

                             

                            You don't have STARTTLS enabled, however as we now have the incoming mail working, I'd recommend changing the outgoing back to SSL with port 465 to see if that now works.

                             

                            It's quick and easy to change the port/ssl rather than enabling STARTTLS, however if it doesn't work then the next step would be reverting back to the TLS connection and enabling STARTTLS.

                             

                            Note that STARTTLS can be blocked by antivirus so a rule should be in place to allow this through (or temporarily disable the antivirus whilst testing to confirm that isn't an issue).

                             

                            -Midnight

                    • Re: Gmail setup keeps failing
                      it@cristoreybalt.org

                      Try re-inputting the password before you confirm the settings. I think there's a bug in the interface that does something with the password field between clicking "Save" and "Confirm Settings"

                       

                      I had this issue and did the following:

                      1. Input your password
                      2. Click Save
                      3. Input the password again
                      4. Click "Confirm Settings"

                       

                      That worked for me.

                      • Re: Gmail setup keeps failing
                        drjonesy

                        Not sure if you resolved this -  we use Gmail for business -  its best to generate an 'Application Password'  in Gmail as Google can often block service accounts