Support Centre

Unable to Send Emails – Troubleshooting Guide

Updated on

In this article we will show some common errors that are experienced when trying to send emails from Roomkey

The following are some errors messages that you may encounter when trying to send email confirmations and the steps you must take to troubleshoot the issue.

Common Issues

Issue 1 - When I close out of the Reservation Confirmation, the "Email Confirmation" box does not appear.

  • Ensure the Registry Tab is filled out properly with your email settings (System Configuration > Property > Registry Tab)?
  • Ensure the guest has an email address on their Guest Profile

Issue 2 - Error Message: "There was an error connecting to the email server. Email could not be sent. Authentication Required"

  • An outgoing authentication password is required in order to send email confirmation. Ensure under System Configuration > Property > Registry Tab, that the "Secure Password Authentication" box is checked and the outgoing authentication password entered into the box below is the same as your email password. If you are unsure what password to use, please contact your Email Service Provider

Issue 3 - Error Message: "There was an error connecting to the email server. Email could not be sent. Username & Password not accepted" OR "Access denied"

  • The Email User Account and/or Password entered into System Configuration > Property > Registry Tab could be wrong. Reconfirm information with your Email Service Provider.

Issue 4 - Error Message: "There was an error connecting to the email server. Email could not be sent. Must issue STARTTLS command first"

  • A TLS option must be selected from the drop down box under System Configuration > Property > Registry Tab.

Issue 5 - Error Message: "There was an error connecting to the email server. Email could not be sent. Socket Error #10060. Connection Timed Out."

  • It is possible that the SMTP you are using or the Port # is incorrect. Contact your email service provider to reconfirm your settings. If your settings are correct, try erasing all your settings from the registry tab and re-entering them. Something as simple as a blank space after the SMTP or one incorrect letter can prevent emails from being sent.

Issue 6 -  Error Message: "There was an error connecting to the email server. Email could not be sent. Start SSL negotiation command failed."

  • A TLS option is selected from the drop down box under System Configuration > Property > Registry Tab but it should NOT be. Select the relevant SSL option.

Issue 7 - Error Message: "There was an error connecting to the email server. Email could not be sent. Socket Error #10001. Host not found."

  • The SMTP entered under System Configuration > Property > Registry tab is not a valid SMTP. Contact your Email Service Provider to reconfirm your SMTP. If SMTP is correct, try to erase the SMTP and re-enter as something as simple as a blank space after the SMTP or on incorrect letter can prevent emails from being sent.

Issue 8 - Error Message: "There was an error connecting to the email server. Email could not be sent. Unable to connect to email server."

  • This error indicates a lack of communication with your email server. Contact your Email Service Provider to help troubleshoot the issue.

Issue 9 - I am not being copied on any email confirmations that are being sent.

  • Ensure that the "Copy Confirmation To Hotel" box is checked under System Configuration > Property > Preferences
  • Check your Spam & Junk mail to ensure the email confirmation is not being sent there by accident

Issue 10 - Error Message: Authentication unsuccessful [YQXPR0101CA0008.CANPRD01.PROD.OUTLOOK.COM]*

  • *Your error message within the brackets [ ] may not be exactly as shown above.
  • Office365 does not support some forms of multi-factor authentication and this may affect SMTP access to your email server. This may need to be enabled through your Exchange server settings as shown here .

Issue 11 - Gmail specific error "settings on registry are incorrect" "Password incorrect"

  • For Gmail accounts, you may also need to ensure under your security settings 'less secure app' access is turned on. Please click here for further details.

Issue 12 - Yahoo specific error "There was an error connecting to the email server. Email could not be sent. (#AUTH005) Too many bad auth attempts."

  • For Yahoo accounts, you may need to ensure that less secure app settings are in place. Please click here for for further details.

 IMPORTANT: Below is a diagram to explain how the email process works, RoomkeyPMS is using your account information to send out mail through your SMTP to your Internet Service Provider’s (ISP) Mail Server or Microsoft Exchange Server.

Common Issues
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