This walkthrough is to help you update to the latest Cloud Connector in case you have a build prior auto update support in 1.4.1, or your 1.4.1 has auto update disabled due to special configuration requirements.

For full details on planning and deploying Cloud Connector, please see Https://aka.ms/CloudConnector.

For troubleshooting upgrade issues, please see Troubleshooting Cloud Connector Edition 1.4.2 Updates and New Deployments

Prepare for Upgrade

Schedule a maintenance window for the work. If you have a single appliance and are updating from a build prior to 1.4.1 (version 1.3.X), you will need to plan for downtime in PSTN calling during the upgrade process which will take between 1.5 and 2 hours. If you have CCE version 1.4.1 the downtime in PSTN calling will only be a few minutes when switching from the previous version to the latest version.

Gather credentials that you will need for the deployment used when running Register-CcAppliance. You will need local Cloud Connector administrator password and Office 365 Tenant administrative password.

Backup your existing Cloud Connector configuration file for reference (see below for details) when creating a new configuration file for the latest version. After installing latest Skype for Business Online Cloud Connector, you will obtain the latest version file by running Export-CcConfigurationSampleFile from administrative PowerShell.

Update from 1.3.4 to 1.4.2

As there were significant changes since 1.3.4, you need to clean up the 1.3.4 deployment before installing the latest version.

Remove 1.3.4

1. Backup the %userprofile%CloudConnectorCloudConnector.ini to another drive so it will be available for reference when creating the new CloudConnector.ini file.
2. Stop all the Cloud Connector VM’s in Hyper-V Manager on the Cloud Connector host appliance.
3. Delete the Cloud Connector VM’s and virtual disks which are in the <Appliance Directory>Instances folder. Run Get-CcApplianceDirectory cmdlet from administrative PowerShell to find the directory if not known.
4. If you want to use the existing external Edge certificate, back it up. Run Get-CcExternalCertificateFilePath to find the current location of the certificate.
5. Delete all content from the following folders
   1. %userprofile%Cloudconnector.
   2. Appliance directory. Run Get-CcApplianceDirectory [BH3] to find the location of the directory.
   3. Site directory. Run Get-CcSiteDirectory to find the location of the directory.

Prepare the Appliance

Gather credentials that you will need for the deployment used when running Register-CcAppliance. You will need local Cloud Connector administrator password and Office 365 Tenant administrative password.

Follow all instructions in Prepare your Cloud Connector appliance including steps to create a new base VHDX for the Cloud Connector virtual machines. Note – be sure that this step completes successfully. If the Base VM needs special network configuration, e.g. Proxy settings, to connect to the Internet for obtaining windows updates, be sure to use the PauseBeforeUpdate setting to allow you to connect to the VM and update network settings to allow connectivity before continuing.

When updating the Cloud Connector configuration file, refer to the backup copy you made in step 3 above. Also, if you manually created a Hybrid PSTN site in your tenant, be sure that the Site name and Edge FQDN defined in the Cloud Connector configuration file matches site settings in your tenant. Run Get-CsHybridPSTNSite in Skype for Business Online PowerShell to see sites defined in your tenant. In the latest version, Register-CcAppliance cmdlet will either create a new site based on name defined in configuration, or update existing site if a site with same name exists in your tenant.

Install the latest version

1. Follow instructions to Deploy the first Skype for Business Cloud Connector Edition appliance in Deploy a single site in Cloud Connector.
2. Confirm Appliance status in Skype for Business Online Admin Center > Voice > on premises PSTN, or by running Get-CsHybridPSTNAppliance using Skype for Business Online PowerShell.
3. Validate the new deployment following Validate your Cloud Connector deployment.

Update from 1.3.8 to 1.4.2

1. Backup the <Appliance Root>CloudConnector.ini for reference when updating CloudConnector.ini file for the latest version. Run Get-CcApplianceDirectory to find location.
2. Uninstall the current appliance. To do this, start a PowerShell console as administrator and run Uninstall-CcAppliance.
3. Follow instructions to Deploy the first Skype for Business Cloud Connector Edition appliance in Deploy a single site in Cloud Connector.
4. Confirm Appliance status in Skype for Business Online Admin Center > Voice > on premises PSTN, or by running Get-CsHybridPSTNAppliance using Skype for Business Online PowerShell.
5. Validate the new deployment following Validate your Cloud Connector deployment.

Update from 1.4.1 to 1.4.2

1. Remove the Forward PAI section in the <Appliance Root>CloudConnector.ini. Run Get-CcApplianceDirectory to find location. Forward PAI has been deprecated in 1.4.2 as it’s no longer required to resolve missing caller ID for outbound calls from Skype for Business Mobile clients which has been resolved with changes in outbound routing logic for Cloud Connector.
2. Follow instructions to Upgrade a single site to a new version Upgrade to a new version of Cloud Connector.
3. Confirm Appliance status in Skype for Business Online Admin Center > Voice > on premises PSTN, or by running Get-CsHybridPSTNAppliance using Skype for Business Online PowerShell.
4. Validate the new deployment following Validate your Cloud Connector deployment.