Troubleshooting Outbound Email Delivery Issues

Outbound email refers to the emails that you send from Help Scout — whether it's a reply to an ongoing conversation, a new conversation you've started, or even email sent via Workflow or Auto Reply. Any email going out to someone else from Help Scout is outbound. 

This article will cover some common issues with outbound email and offer you help troubleshooting! 

My customer reports that they did not receive my email. Can you tell me why?

Most of the time this happens because your customer's email service has stopped the email as spam — they may or may not see the email in their spam or junk folder when this happens, as some spam blockers will quarantine the emails separately and not surface that to the recipient at all. 

There is no way to guarantee any email you send from any source will not get blocked, but there are steps you can take to improve deliverability for the emails that you send from Help Scout. 

Check out Outgoing Email Settings for the options Help Scout offers for sending emails. If you want to use Help Scout servers to send, make sure that you have set up the DNS records so that Help Scout is an approved sender for your domain. Check out Use DKIM to Help With Email Deliverability for more help on how to set those up.

Alternatively, you can set up Help Scout to connect to your email provider to send instead of using our servers.

See Use Google OAuth to Send From Help Scout if your email provider is Google Workspace. Use SMTP to Send From Help Scout has help for any email provider that allows you to send using SMTP.

Did you get a bounce when you tried to email that address? Check out Troubleshooting Conversations in Needs Attention and Bounces for help from there! 

I sent an attachment, but my customer says they did not receive it.

As long as the file is successfully attached in Help Scout, it was sent with your reply. In most cases, the customer likely received the attachment. It's entirely possible they're just overlooking it, or their email client is not displaying the file as it should. If you have any doubts, let us know, and we can take a look at our logs to make sure that the attachment was handed over to their server or your provider's SMTP from Help Scout. 

Note: We are only able to search logs going back 7 days; if the email you sent was more than 7 days ago we will not be able to pull a log for it.

Note that when the combined size of all attached files is over 8MB, we send the files as links in the email instead of attachments to the email. This conversion to links is to make sure your email gets through — some email clients will block emails with large attachments, and spam filters are more suspicious of email with big attachments. If you're sending a large number of attachments, ask your customer to check the links within the email itself. 

There are some spam protection services that will strip attachments from email as well. You may want to have your customer reach out to their own IT team or email administrator to check to make sure they're not stripping the attachment. 

Something else regarding email sent from Help Scout

If you're finding conversations in the Needs Attention folder with a Bounced status, or you're receiving Delivery Notice emails and you're looking for help with those, check out Troubleshooting Conversations in Needs Attention and Bounces.

If you need some help setting up all of your outgoing settings, check out Outgoing Email Settings to get started there. 

For anything else, give our team a shout with as much detail as you can about the issue, and we'll be happy to lend a hand!