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The server certificate on the destination computer (outlook.office365.com:443) has the following errors

dnyandev
over 1 year ago

Hi All,

I am trying to connect Exchange Online and while creating synchronization project I get below error messge.

Do I need to install microsoft certificats on jobserver from where I am trying to connect exchange Online.

If anyone has same issue Could you please tell me what is missing and how to fix.

Thank you in advance.

[System.Management.Automation.RuntimeException] Connecting to remote server outlook.office365.com failed with the following error message : The server certificate on the destination computer (outlook.office365.com:443) has the following errors:
Encountered an internal error in the SSL library. For more information, see the about_Remote_Troubleshooting Help topic.
[System.Management.Automation.Remoting.PSRemotingTransportException] Connecting to remote server outlook.office365.com failed with the following error message : The server certificate on the destination computer (outlook.office365.com:443) has the following errors:
Encountered an internal error in the SSL library. For more information, see the about_Remote_Troubleshooting Help topic.
at VI.UI.Wizards.Wizard._HandlePageFinished(IWizardPage page)
at VI.Projector.UI.Wizards.SystemConnectWizardPage.TestConnection(ISystemConnectorDescriptor descriptor, String connectionString, Boolean throwExceptionOnError)

https://1drv.ms/u/s!At2ViqLAc9HpzBhnHMQvy6A8uHAR?e=5bRKd7 

Kind Regards,

Dnyandev

Parents
  • 1 month ago

    If you're encountering SSL certificate errors when connecting Outlook to an Exchange server, it's essential to address the underlying issues to ensure secure and reliable email communication. Here's a step-by-step troubleshooting guide:

    1. Check Certificate Expiry: Ensure that the SSL certificate used by your Exchange server has not expired. You can check the certificate's expiration date in the server's certificate details. If it has expired, you'll need to renew it.

    2. Verify Certificate Chain: Confirm that the SSL certificate chain is complete and properly configured. This includes the server certificate, intermediate certificates, and root certificate. If any intermediate certificates are missing or incorrectly configured, it can lead to SSL errors in Outlook.

    3. Update Outlook: Ensure that you are using the latest version of Outlook. Older versions may have compatibility issues with newer SSL/TLS protocols or cipher suites. Updating Outlook to the latest version can resolve such compatibility issues.

    4. Enable Root Certificate Authority: If your SSL certificate is issued by an internal Certificate Authority (CA), ensure that the root certificate of the CA is installed and trusted on client machines. Without the root CA certificate, Outlook may not trust the server's SSL certificate, leading to certificate errors.

    5. Check Server Configuration: Review the SSL/TLS configuration on your Exchange server. Ensure that it supports modern encryption protocols and cipher suites, and that it's configured to use a valid SSL certificate for the correct domains.

    6. Verify DNS Settings: Ensure that the DNS settings for your Exchange server are correct. If Outlook is connecting to the server using a hostname, verify that the hostname resolves to the correct IP address.

    7. Check Firewall and Proxy Settings: Confirm that there are no firewall or proxy settings blocking Outlook's connection to the Exchange server. Sometimes, intermediary devices can intercept SSL traffic, leading to certificate errors.

    8. Restart Exchange Services: Occasionally, restarting the Microsoft Exchange services can resolve SSL certificate-related issues. Restarting services like the Exchange Information Store and the Exchange RPC Client Access service may help.

    9. Test with OWA: Try accessing Outlook Web Access (OWA) using a web browser. If you encounter SSL errors in OWA as well, it indicates an issue with the server-side SSL configuration. If OWA works without errors, the problem may be specific to Outlook client settings.

    10. Contact Exchange Administrator: If you're unable to resolve the SSL certificate errors, reach out to your Exchange server administrator or IT support team for further assistance. They can help diagnose and troubleshoot the issue from the server-side.

    By following these steps, you should be able to diagnose and resolve Outlook SSL certificate errors when connecting Outlook to your Exchange server.

Reply
  • 1 month ago

    If you're encountering SSL certificate errors when connecting Outlook to an Exchange server, it's essential to address the underlying issues to ensure secure and reliable email communication. Here's a step-by-step troubleshooting guide:

    1. Check Certificate Expiry: Ensure that the SSL certificate used by your Exchange server has not expired. You can check the certificate's expiration date in the server's certificate details. If it has expired, you'll need to renew it.

    2. Verify Certificate Chain: Confirm that the SSL certificate chain is complete and properly configured. This includes the server certificate, intermediate certificates, and root certificate. If any intermediate certificates are missing or incorrectly configured, it can lead to SSL errors in Outlook.

    3. Update Outlook: Ensure that you are using the latest version of Outlook. Older versions may have compatibility issues with newer SSL/TLS protocols or cipher suites. Updating Outlook to the latest version can resolve such compatibility issues.

    4. Enable Root Certificate Authority: If your SSL certificate is issued by an internal Certificate Authority (CA), ensure that the root certificate of the CA is installed and trusted on client machines. Without the root CA certificate, Outlook may not trust the server's SSL certificate, leading to certificate errors.

    5. Check Server Configuration: Review the SSL/TLS configuration on your Exchange server. Ensure that it supports modern encryption protocols and cipher suites, and that it's configured to use a valid SSL certificate for the correct domains.

    6. Verify DNS Settings: Ensure that the DNS settings for your Exchange server are correct. If Outlook is connecting to the server using a hostname, verify that the hostname resolves to the correct IP address.

    7. Check Firewall and Proxy Settings: Confirm that there are no firewall or proxy settings blocking Outlook's connection to the Exchange server. Sometimes, intermediary devices can intercept SSL traffic, leading to certificate errors.

    8. Restart Exchange Services: Occasionally, restarting the Microsoft Exchange services can resolve SSL certificate-related issues. Restarting services like the Exchange Information Store and the Exchange RPC Client Access service may help.

    9. Test with OWA: Try accessing Outlook Web Access (OWA) using a web browser. If you encounter SSL errors in OWA as well, it indicates an issue with the server-side SSL configuration. If OWA works without errors, the problem may be specific to Outlook client settings.

    10. Contact Exchange Administrator: If you're unable to resolve the SSL certificate errors, reach out to your Exchange server administrator or IT support team for further assistance. They can help diagnose and troubleshoot the issue from the server-side.

    By following these steps, you should be able to diagnose and resolve Outlook SSL certificate errors when connecting Outlook to your Exchange server.

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