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I cannot send out any email, including notifications from my XG.

I have a sophos XG home instance running 17.0.5 MR-5. Today I tried to set up notification emails using both smtp.gmail.com as a relay, and smtp.office365.gmail.com as a relay. Zero success on both of them. The test email simply says "Failed to connect to the mail server. For more information please check the Log Viewer". Checking the log viewer under "email" reveals nothing. That log is blank. I have gone through the entire log and for the life of me cannot find anything in it at all related to email or port 587 or port 465. Can someone give me an idea of where to look?

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0 Usbkey over 7 years ago

gmail requires app password for API access. You need to create one first in your gmail account. This is not the password you use to login to your gamil account
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0 Justin Rutledge over 7 years ago in reply to Usbkey

Yes I am very aware of the multi-factor authentication system that Gmail uses. I have set up and app password as I done plenty of times for other applications, but that did not help. As a workaround for now I had to set up a free mailjet account which is working just fine.
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0 ShunzeLee over 7 years ago in reply to Justin Rutledge

Since you know the multi-factor authentication system with Google,

try the following setting.

It works with my XG.
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0 Justin Rutledge over 7 years ago in reply to ShunzeLee

I think I have caused confusion. I am no longer using google for email. I have moved to office365 with exchange online. They require using smtp.office365.com with port 587. Inputting all of this information correctly into the XG simply results in "Fail to send mail : Cannot connect to mail server smtp.office365.com : 587".

However, I do know that the XG can at least talk to that smtp server, because changing the Connection Security to "STARTTLS" results in the error message "Fail to send mail : Authentication method LOGIN PLAIN is not supported by the server"

This tells us it is talking to the smtp server, but does not seem to be talking to it correctly. ... Are there any other ideas out there?
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0 Usbkey over 7 years ago in reply to Justin Rutledge

Have you tried adding smtp.office365.com as a trusted domain?
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0 Justin Rutledge over 7 years ago in reply to Usbkey

I have to admit that is NOT something I have tried. And it shows my ignorance frankly. Where do you make that change please?
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0 Usbkey over 7 years ago in reply to Justin Rutledge

Sorry, after another look, it is only applies to Sophos Web gateway so I don't think it is related.

here it is anyway

community.sophos.com/.../122679
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