Skip to main content

How can we help you?

Search

How to Resolve Common Test Send Failures

If your test email fails to send, ContactMonkey emails you an alert with a specific error message. This article explains what each error means and the steps to resolve it so you can get back to testing your emails.

How do I fix the "404 Not Found: Draft not found" error?

This error means ContactMonkey could not locate the draft it was trying to send a test from. It has two common causes: a draft that is no longer available due to the wrong mailbox being used, and a reliance on Send As Permissions that Send Test does not use.

Cause 1: The wrong mailbox was used

This happens when the Microsoft account you're signed in to doesn't match the email address licensed with ContactMonkey, or when you're sending from a shared mailbox that isn't set up correctly.

  1. Open the ContactMonkey Add-in in Outlook and click the gear icon
  2. Compare the email address shown in the sidebar with the email address on your ContactMonkey license. If they don't match, click Log Out, then sign back in with the correct Microsoft account.
  3. If you're sending from a shared mailbox, confirm you are following the steps in this article
  4. If the issue persists, clear your Outlook cache

If you use Outlook for Mac and the error persists after these steps, contact your IT team and ask them to update the shared mailbox's UPN to match its email address exactly.

Cause 2: You rely on Send As Permissions used for SendGrid

Send Test does not use the Send As Permissions configured for SendGrid. If your organization can only send from a given mailbox because of SendGrid, Send Test will not have access to that mailbox, and you will see the 404 Not Found: Draft not found.

  1. Do not use Send Test from a mailbox that only works through SendGrid
  2. Instead, send a tracked email (Send & Track) to yourself or a small internal group to preview the email
  3. Use that tracked send to confirm formatting and content before sending to your full audience

How do I fix the "Could not authenticate with Outlook" error?

This error means your ContactMonkey connection to Outlook has expired or broken — often after a password change or a period of inactivity. Resetting your Outlook token resolves it in most cases.

Reach out to support@contactmonkey.com to request a manual token refresh. If the issue persists, ask a ContactMonkey Admin to navigate to Settings → Integrations and reconnect to the Graph Utility Account tile by signing out and back in.

How do I fix the "You do not have permission to 'Send As' the selected mailbox" error?

This error means the address in your From field requires Send As permission that your account doesn't have.

  1. Confirm which address is in the From field of your test email
  2. Contact your IT team or Exchange administrator and request Send As permission for that mailbox. ContactMonkey can't grant Microsoft mailbox permissions on your behalf.
  3. To check that the permission works, send a regular (non-ContactMonkey) email from that mailbox using Outlook's native Send button. If it sends successfully, retry your test email in ContactMonkey.

How do I fix the "There was an unhandled error" message?

This error means something unexpected interrupted your send. Retrying after refreshing your connection resolves most cases.

  1. Close and reopen the ContactMonkey Add-in in Outlook, then retry your send
  2. If the error repeats, log out of the sidebar with the gear icon and sign back in
  3. If the error still appears, contact our support team at support@contactmonkey.com with the date and time of the failure and the email template you were testing, so our team can investigate

Related articles