Laravel sending mail fails on droplet: 535-5.7.8 Username and Password not accepted

Hi guys,

I’ve build a Laravel project, but I’m stuck in sending emails using Gmail in the droplet. Locally it’s working fine. I’m getting this error:

Expected response code 250 but got code "535", with message "535-5.7.8 Username and Password not accepted

I’ve tried to remove 2-way auth, setting “less secure app on on your gmail account”, but nothing helps

I’m using Ubuntu 18.04. Settings in Laravel:

MAIL_PASSWORD=xxx -> App password

As it is working locally, do I have to add some extra setting for Digital Ocean or my setup/firewall (UFW) ? Hope you can help me. Thanks in advance!


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Hey friend,

While I can’t get you through to the end result, I can help you to at least know that there is no DigitalOcean specific configuration required here, and that firewall adjustments will not be relevant. In this case it seems that your droplet is actively reaching out to Google to authenticate, and Google is telling you that what you are sending is incorrect.

Given that information, I think I would focus more heavily on making sure that what you think you’re sending is what you’re actually sending, and that this information is accepted for SMTP authentication on the other side. It sounds overly simplistic, my honest feeling is that it probably is. It’s the simplest things that often escape us, even looking over it I can’t accurately say what exactly it is that is wrong (just what it isn’t).