: note that the option to "Use less secure apps" is not available with 2FA enabled It was a pure luck or they managed to trigger reassigning of their backend computer, so they luckily got assigned a non-banned machine. This also explains why some people on the forums claim they solved the issue by enabling 2FA, or doing some captcha woodoo with Less Security Apps setting, orīy removing and re-adding the email account in "Send emails from a different address or alias" settings. until it stops again - because some other backend computer got banned and your gmail web client happened to be using it. so the feature now started working again.Or there is a chance your gmail client starts using a different backend computer, say C1 because of rotation. So it is possible that during next 24h or so, it starts working again. anyways, C0 ban is somehow time-limited.Only partially correct historical pages describing various stages how it worked in the past or confusing pages not related to the issue. You try to google for some explanation and there is no clear answer. And you have no idea what "Less Secure Apps" mean, because you already have 2FA enabled, so this option is nowhere to be found. This leads to a great confusion because your username/password are 100% correct. Please check your username/password and Less Secure Apps.". You will get back "Authentication failed. then you go into gmail settings and try to re-enter your password,.later when you try to send an email via gmail web interface, it uses C0, and you get "535 5.7.8 Username and Password not accepted." response back.later some bad actor using gmail web interface behaves in a way which triggers ban, say it happened to be C0 machine.you are able to setup "Send emails from a different address or alias" with your GSuite login+password, no problem in validating your credentials.your web interface is assigned to work with C0.assume none of them is currently banned by., C9 to implement the "Send emails from a different address or alias" feature assume Gmail web-interface uses 10 backend computers: C0, C1, C2.This would exaplain the random behaviour of the issue: The likely root of the problem is that Google's own computers providing "Send emails from a different address or alias" So might refuse to communicate with a banned IP. Imagine a more strict black list for abusing computers. Recently (probaly around April 2020) Google likely deployed more security hardening of. ( may be used by any 3rd party app to send emails via google). Not related to the "Send emails from a different address or alias" feature of gmail. Note that is another independent service running in the cloud, Gmail immediatelly performs a test of the connection and then has to store the credentials for later use. When you add a new email via "Send emails from a different address or alias" This is probably some google's cloud so it is not one but many Gmail web-interface uses some backend services to send emails. Anyways, I tested both methods and both are subject of this issue. This is causing quite some confusion among users. you must generate a new app-specific password.and you must have enabled "Use less secure apps" under the account security.Generally there are two ways how to use (speaking about the secondary email google account, GSuite in my case): Method 1 First, don't get side-tracked with fiddling with "less secure apps" The Internet is full of complains with messy answers and without proper solution. It suffers from intermittent "535 5.7.8 Username and Password not accepted." issues. Unfortunately this solution is no longer working properly. The feature and send emails via my secondary email without problems. Historically it has been possible to use with my GSuite credentials to enable GMail offers "Send emails from a different address or alias" feature. To send emails using secondary email address which is managed by GSuite. I'm using web-based gmail as my primary email client.
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