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This has been an ongoing issue for me. No matter what I use to email from LRC (gmail, yahoo, apple, etc.), I cannot get it to send. I checked the outgoing email server - looks fine. SMTP port looks fine. What am I doing wrong? I also get 'Failure to establish connection with the outgoing email server' messages when trying to use my gmail. I updated them per my Google gmail settings and they match. Thanks.
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If you haven't created an application specific password in Google for your email it will not work: https://support.google.com/accounts/answer/185833?hl=en
Not sure why you are encountering email probles with yahoo or apple email. I did just test my gmail again and it does work although I rarely email from within LrC. When I first ran into the password problem I set one up per google instructions and deleted and readded my gmail account and it worked straight away. It was annoying to have to do that although with all of the hacking and vulnerabilities through email it seemed like the right thing to do if I want to be able to use gmail.