Invalid Outgoing Email Settings

If you've set Help Scout up to send using your own SMTP server or Google OAuth, your Account Owner or Administrator might receive an "Action Required" email from once in a while informing you that there's been an issue connecting with your server. No need for alarm! These are usually temporary things that will be resolved by the time you read that email. Here we'll share a bit more information on what this email means and share with you some of the errors you may see. 

In this article

Overview

When you set up a custom SMTP connection or use Google OAuth, that means that your emails are handed off to your email provider to send from their servers, rather than Help Scout sending from our servers. From time to time, we may run into blips or issues trying to connect to your server. It might be that there's a credentials or authorization error, or we weren't able to communicate with the server at that moment due to many different possible reasons, or your provider may have had connection issues on their side. 

Never fear -- your emails will still be sent, but we will send them from our servers instead. We will also send you a notification as a heads up that we did this. Each situation is a bit different, and the error that we received when trying to connect will be included in this email notification. Many times there's nothing to worry about at all, sometimes there are just temporary connection issues that are already resolved by the time you're reading that email.

Other errors may require your attention. While we can't predict every error you might ever see, because every email server has their own versions of errors, we can offer some advice with some. If you've received an error in the notification email that isn't listed here, give us a quick shout and we'll take a peek to see if we can offer more guidance! 

Google OAuth Errors

invalid_grant

This error can mean many different things from Google, but typically disconnecting the OAuth connection and reauthorizing it will patch things up! Take a peek at Use Google OAuth to Send From Help Scout for the steps there! 

Office 365 or Exchange errors

Authentication unsuccessful

The email address and password combination that you've set in Help Scout is incorrect. Head into your Outgoing Email Settings for your mailbox and check the email address there and re-enter the password to reset. If the password for that email account used there ever changes, you will need to update that in Help Scout again.

SMTP.office365.com has timed out 
Could not read from outlook.office365.com

These are usually just temporary blips connecting to Office365's servers, and will correct itself after a minute or so. If you only see this one time, or every once in a while, nothing to worry about. If you're seeing these errors every day or very often, you might want to reach out to your email admin, IT team, or Microsoft support to inquire. 

SendAsDeniedException

This means that the Office 365 email address that you've authenticated as when you set up the Custom SMTP connection is not allowed to send email as the address you're trying to send from. This can be because your Users have chosen to forward out of Help Scout using their own address, or you are replying from an alias. You want to make sure the the email account you use to authenticate when you set up SMTP has permissions to Send As any of the addresses you're using in Help Scout. 

Miscellaneous errors

Could not open socket
Connection timed out

Temporary issue trying to connect to your server, and will correct itself. No action needed within Help Scout, but you can triple-check your mail servers just to be sure that things are running smoothly. You can also check out any logs if they are available to you from your email provider to see if there were any disconnections happening on your server's side.

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