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Email integration failure with Office365


I migrated to web based Helpspot recently and have not been successful in setting up email integration using my office365 smtp server credentials.
During the set up test, it will work only one time, successfully sending out the test mail. But on the second test, error coder 235 will pop up:

"Error: Expected response code 250 but got code “235”, with message "235 2.7.0 Authentication successful target host " Log data: ++ Starting Swift_SmtpTransport << 220

I am currently using a 3rd party smtp server to relay the mail sending. It works well, except that mails often end up in the junk folder of the recipients.

Anyone experiencing the same problem?


I now use gmail smtp to do the email integration. Need to first go into gmail account setting to activate “Allow less secure apps” under “Apps with account access” in “sign-in security” setting.

At the very first time of testing emailing in Helpspot, Gmail server will reject it, followed by sending a warning email to my gmail inbox alerting me that it has blocked a sign-in attempt from an unknown device in Ausburn Virginia (Helpspot). By allowing the sign-in from this location will finally make the email integration work properly


Sorry for the trouble there! In HelpSPot version 5, we’re looking into using Gmail through it’s API rather than direct SMTP connection, which is their (Google’s) preference and generally avoids the extra hoops we have to go through in their security.