Staff users might experience problems with the delivery of their emails when responding to tickets. For instance, they might encounter some error messages related to the email delivery (e.g. failed TLS connections), have their emails/responses not arrive in the recipients' inboxes, or unexpected data on the emails such as the wrong sender name. This article explains how to correctly troubleshoot those issues.
Review SMTP settings
If one is receiving an error message while replying to a ticket that results in the email not being delivered, it is recommended to check the SMTP settings as mentioned in the "Connection Could Not Be Established With Host..." Error article.
Besides that, it is also suggested to check the SMTP settings for the Email Queue in case those are being used to deliver emails as stated in Error 'Uncaught Exception: Failed to Authenticate on SMTP Server With Username' When Sending Auto-Responses.
Update TLS version in the code
As mentioned in "stream_socket_enable_crypto():" Error While Sending Ticket Updates, this occurs when the TLS version being used for the connection is not valid. This is likely due to the PHP version in the environment not using the required one, and one would need to update the Kayako code to specify a TLS version.
Review Kayako version and email service
As mentioned in "Unable to connect with TLS encryption" Error when Sending Emails, older versions of Kayako (and PHP) might have some issues handling TLS connections so it is recommended to use a recent release.
Along with that, it is also a good idea to check the email provider for any service issues as reported in "Unable to connect with TLS encryption..." error when sending Kayako emails using Microsoft Office 365. In such scenarios, it might be necessary to contact the provider for assistance.
Check email provider configuration
An error related to an invalid license while sending an email suggesting this might be a problem with the email provider as was the case with shared mailboxes in O365 covered in Email Flow not Working in Kayako Classic Instance Using O365
Set up SPF
In most cases, it is likely emails are being marked as spam or quarantined by mail servers due to not having the correct SPF records for your email domain. Refer to Ensuring Your Emails Are Received and Do Not Go Into Your Customer's Spam Folder for further instructions on how to set this up.
Review staff name
By default, the sender name in the email will use the name defined for the staff user. Therefore, it is important to make sure the expected name is set for the staff user in the Admin CP > Staff > Manage Staff area.
Check Email Queue Settings
If the staff’s name is the expected one then it is likely the sender name is coming from the Email queue configuration. Thus, one should follow the instructions in the Email Sender Name Doesn't Match the Staff Name article to update the queue configuration.
Review Kayako version
It is important to ensure one is running a recent version of Kayako Classic as there might be some known problems with older versions affecting the delivery of emails. For example, versions older than 4.93.08 had an issue with blank emails as mentioned in Emails Sent From the Helpdesk Are Showing as Blank Emails on End-Users or Recipients.
Check email size
Kayako Classic OnDemand has certain limitations with the email sizes, and as mentioned in the Staff Replies are not Arriving via Email for OnDemand Instance article, it is important to ensure emails responses/attachments do not exceed this limit.
Check mail server
Download customers manage their own mail servers so it would be necessary for them to check their server logs/settings to look for any possible issues with the delivery of emails.
If the problem persists after following the guidelines above, one can Contact Support with the information below to further troubleshoot the issue.
- Affected recipient email address.
- (if available) A copy of the email.
- Secure Access to the Kayako Classic Instance and the affected ticket ID.
- If this is not possible, provide environment information such as the Kayako version, PHP version, and OS.
- The instance name (e.g., domain.kayako.com)
- (if applicate) Error Logs (Admin CP > Logs > Error Log).
- Other details of the issue such as screenshots of the exception message.
For issues with OnDemand customers, make sure to check the articles below as it is possible for some addresses to be automatically blocked by SendGrid.
- Checking Sendgrid Logs To See if Emails Were Delivered Successfully
- Identifying Bounced & Blocked Emails Sent with SendGrid