Why are some automated emails failing even though the address is valid?

This usually happens when the [SigningRequestLink] placeholder has been added to a general email template. That placeholder only works in an email sent from a signing request. Used anywhere else, it breaks the send.

How to fix it

1. Select Automations > Failed first. Automation log - failed jobs shows the error message for each failed email in the State column, so you can see why it didn't send.
2. If the template contains [SigningRequestLink], go to Settings > Communication > Message templates and select the edit button on that template to open Edit template.
3. Remove the placeholder, then select Save. The emails will go through as normal.

Once it's fixed, you can resend a failed email: select it in Automations > Failed, then select Apply.

Where the placeholder belongs

[SigningRequestLink] is "A direct link to the signing request". It's meant for eSigning Request templates such as "Document awaits signing", and the Insert placeholder list only offers it there. It can still be typed or pasted into other templates, though.

Signing requests are sent from the file itself: in the client's Files, open the file's File details, then Signing requests > + request signing.