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This article provides details about the various scenarios for an email delivery failure in Freshdesk and the steps to resolve them.

Sometimes, outgoing emails, such as agent replies, forwarded emails, and outbound tickets, occasionally fail to reach one or more recipients due to an incorrect domain, invalid email address, or problems with mail server connectivity.


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Identify email delivery failures in Freshdesk

When an email delivery fails, Freshdesk generates notification messages including details about the recipients affected and the reasons for the failure. You can view these notifications on the ticket details page. The list of notifications triggered are:

  • Delivery pending: Indicates that the initial email delivery attempt failed, but Freshdesk is actively retrying to send the email. Common reasons for this include the recipient's inbox being full, temporary service outages, incorrect login credentials, or more. To view the exact reason, open the ticket and click the Review icon in the notification.
  • Undelivered: Indicates that all retry attempts have failed, and the email could not be delivered. Click the Review icon to see detailed information about the reasons for the delivery failure.

Filter and view undelivered and pending messages

To easily view and filter all undelivered and pending messages in your inbox:    

  1. Go to the Ticket Inbox, click on the Ticket Views filter, and select All Undelivered Messages.
  2. You can view all the undelivered and pending messages. You can refine the search using the Delivery Status filter from the right pane. Select the desired status and click Apply.
  3. Click on the ticket to view the detailed notification and the reason. To view the failure reason, click on the review icon.

Set up automation rules to automate actions on email delivery failures

To track email delivery failures, Freshdesk sends notifications to the relevant agents, prompting them to take corrective action when replies or forwards don’t reach the recipients. 

To ensure timely actions from your team, you can set up automation rules to trigger follow-up actions. For example, you can use the pre-configured "Get notified of email delivery failures" automation template to automatically change the ticket status to open, send an email to the agent, and add a tag to easily identify all such tickets. 

  1. Log in as an Administrator and go to Admin > Workflows > Automations.

  2. Click Templates and search for the "Get notified of email delivery failures" template. You can also find this under the Support Efficiency category.

  3. Click Preview and then click Use Template. The events and actions of this automation rule are:

    • Event: mail sent to requester address failed or mail sent to cc or forward address failed

    • Action 1: Set status as open

    • Action 2: Send email to agent

    • Action 3: Add tag (for example, email_delivery_failed)

  4. You can use the template with the same event and actions or modify them as required. 


Note: In some cases, you may receive non-delivered reports from your Email Service Provider (ESP) like Microsoft or Postmaster. In such cases, contact your ESP.

Common causes of email delivery failures

A few common reasons for email delivery failures are:

  • DKIM verification and authentication:
    If your email setup is done using the Freshworks mail server, ensure that email authentication is done with DKIM and SPF configurations. DKIM verification and SPF enhance email security, establish the sender's legitimacy, and ensure better email deliverability. This reduces the chances of emails being marked as spam or phishing emails.
    Note: DKIM setup is not applicable when using a custom mailbox.

  • Invalid recipient email address:
    Ensure that the recipient’s email address is correct and not misspelled.

  • IP Blacklisting:
    Use tools like MXToolbox or Spamhaus to verify the blacklist status. IP blacklisting can impact the email delivery and online reputation. Check out the troubleshooting section below to see how you can resolve this.

  • Spam Filtering:
    Verify if the recipient’s email server is operational and if the email is not landing in the spam folder. Avoid spam-triggering content like suspicious attachments or excessive punctuation. To view the Spam folder, click on the Spam view from the Ticket View filters.
  • Automations or Triggers in Freshdesk:
    Ensure that automation rules are not filtering out emails.

Troubleshooting steps to resolve IP blacklisting

If your IP is blacklisted:

  • Identify the reason for blacklisting. Possible reasons could include unsolicited emails, malware, or being part of a compromised shared hosting network.
  • Take actions to solve the issues:
    • Run security scans to identify and resolve any compromised systems or malware infections.

    • Follow best practices to avoid spam. Avoid sending unsolicited emails and make sure your recipients have opted in to receive your messages.

    • Implement security measures such as strong passwords, firewalls, and up-to-date software to prevent unauthorized access and reduce the risk of being compromised.

    • Implement email authentication mechanisms like SPF, DKIM, and DMARC to verify your email's authenticity and reduce the chances of being flagged as spam.

    • Remove malicious content to prevent further issues.

    • Follow the delisting process of the respective blacklist, providing the required evidence. Each blacklist will have its own delisting process, which typically involves submitting a request through their website or following their instructions. Provide all the necessary information and evidence to support your request for removal.

    • Regularly monitor and maintain good practices to ensure you stay off blacklists.