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Rob4077Flag for Australia

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Outlook fails to send emails via GMail

I just had to swap my SSD due to a failure and reload all the software. Everything is fine except my GMail via MS Outlook (yahoo mail works fine via Outlook). Attached is a screen print of the setup and the error message I am getting. As can be seen it receives messages but just won't send them. Can anyone spot what I am doing wrong?

BTW I am using the GMail recent keyword because it enables me to receive emails all my emails on all my devicesUser generated image
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Shaun Vermaak
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Hi Shaun, It is set up for POP3 and incoming messages work. It's only outgoing that won't work. I tried less secure apps but can't find it there anymore since I have activated 2 step authorisation
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Tried the troubleshooter and port 587 with TLS but no change
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Running Windows 10 - fresh install with MS Office 2016 - fresh reinstall too. At the time I first did this it was only running Windows Defender. In the last few minutes I reinstalled Trend security but no change. I had some screen prints of what I had in there before I changed disk and it did have TLS with port 587 as well as the recent keyword. It also had just my username, not username@gmail.com so I tried changing it to that but still not working.
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Hi Lisa. You're right in that gmail has needed me to use an app password for some time. Without it gmail will not receive emails. However in my case I have been using an app password all along and it does receive emails but just won't send.
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I tried all four options and here are the results

465 SSL Send test email message: Your outgoing (SMTP) email server has reported an internal error. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).  The server responded: 503 5.5.1 RCPT first. j128sm26345649pfg.73 - gsmtp

465 TLS  Send test email message: The connection to the server was interrupted. If this problem continues, contact your server administrator or Internet service provider (ISP).

587 SSL Send test email message: Your server does not support the connection encryption type you have specified. Try changing the encryption method. Contact your mail server administrator or Internet service provider (ISP) for additional assistance.

587 TLS Send test email message: Your outgoing (SMTP) email server has reported an internal error. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).  The server responded: 503 5.5.1 RCPT first. y184sm26332261pfg.86 - gsmtp

I wonder if Google offer any assistance?
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Hi Lisa, I tried it both ways with the same result. I have now raised a question on the GMail support site as well to see if anyone there can help. I will see what happens. Sounds like I have a bit of a unique issue
Alright, let me know as now I'm curious. The only other thing I can maybe think of (happened to a client today) is only have the beginning of the gmail account in the username box. Weird, but with the whole email it didn't work. Thank god I get paid enough to deal with this cra cra stuff.
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Wow, this is new for me. I will do a test on my Gmail today as I need to learn more about this, might happen to a client!

I don't care about points or winning, I am not here to win only help and learn. Just award yourself! ;)
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Lisa I very much appreciate your help on this one... Rob
Add the solution, mark it as accepted.
Mark Lisa's answer as assisted and move points
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On review it is apparent all of you contributed to helping me take a systematic and logical assessment of the problem that finally led me to seek a solution on the Google Forum so I have tried to share the points among you all for your very kind assistance