I’ve been having problems using an Office 365 account for sending e-mails (using SMTP). I get the following error:

Swift_TransportException: Failed to authenticate on SMTP server with username “webmail@domainhere.com" using 2 possible authenticators. Authenticator LOGIN returned Expected response code 235 but got code "535", with message "535 5.7.3 Authentication unsuccessful

The settings used are:

SMTP address: smtp.office365.com Encryption protocol: TLS Authorization required Username and password of course

My client and I have been trying to fix this for weeks. They’ve been talking to Microsoft who suggested adding an SPF record which hasn’t resolved it, nor have their other suggestions: disabling security defaults in Active Directory and doing some commands in PowerShell to change the SmtpClientAuthenticationDisabled value.

Incidentally, I appreciate it’s more likely related to Swift itself and not October but I’m asking on the off chance anyone here has experienced the same.

Many thanks in advance.

Andrew

I've used SMTP with an account hosted on smtp.office365.com recently with branch 1.1 so I know this works in October... probably a mis configuration in exchange

Thanks - yes, another of my clients uses Office 365 with October without an issue so it was a long shot.