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When adding another Gmail hosted account, Gmail automatically configures the server settings and there is no means to enter a password, let alone an App Password. -OR- Are you saying if you enable 2FA and create an App Password, configuring Send Mail As will trigger the request for the App Password? ...

We have users who take advantage of the Send Mail As feature in Gmail. When using with another Gmail account, Google requires enabling Less Secure Apps (for the secondary account) or you end up encountering the attached error. Does anyone have a workaround for keeping Send Mail As enabled with LSA disabled? ...