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To install IIS and Microsoft SMTP service, follow these steps: Click Start, point to Settings, and then click Control Panel. Double-click Add/Remove Programs. Click Add/Remove Windows Components. In the Windows Components Wizard, click Internet Information Services (IIS), and then click Details. smtp_sasl_security_options = noanonymous. What this does, however, is remove the noplaintext option (currently the default is noplaintext, noanonymous. Sep 09, 2021 · MAIL_FROM=(email/username) and i got error= Failed to authenticate on SMTP server with username "(email)" using 2 possible authenticators. Swift_TransportException: Failed to authenticate on SMTP server with username "apikey" using 2 possible authenticators. Authenticator LOGIN returned Expected response code 250 but got code "535", with message "535 Authentication failed ... with message "535 Authentication >failed</b>.