Troubleshooting Cloud Connector Edition 1.4.2 Updates and New Deployments

This post is to share troubleshooting tips for some common problems when updating or deploying Skype for Business Cloud Connector Edition 1.4.2.

For details on planning and deploying Cloud Connector, please see our documentation posted at

Cloud Connector Download Failed

Cloud Connector Software is download failing with:
Failed to download installation files with exception: Exception calling "DownloadFile" with "2" argument(s): "Unable to connect to the remote server".


Confirm that one Host Appliance physical adapter is configured with a gateway that provides a route to the Internet

  1. On Host Appliance, open a command prompt and run:
    Ipconfig /All

Confirm that a gateway is set on one of the network adapters.

Confirm that the Host Appliance server has Internet connectivity and DNS resolution of external resources

  1. Open command prompt on the host and run and confirm reply:

If you use a Proxy in the DMZ for Internet access, confirm that the Proxy settings are per-machine rather than by user. Otherwise Cloud Connector downloads will fail. Set either with registry change or Group Policy setting:

  1. Registry: HKEY_LOCAL_MACHINE\SOFTWARE\Policies\Microsoft\Windows\CurrentVersion\Internet Settings] ProxySettingsPerUser dword:00000000
  2. Group Policy: Computer>Administrative Templates>Windows Components> Internet Explorer: Make Proxy settings per-machine (rather than per user

Confirm firewall rules allow traffic to the following:

  1. TCP Port 443:
  2. TCP Port 80:

Install of 1.4.2 Fails with Access Denied Connecting to Remote Server

The following error displayed during update to version 1.4.2 of the Cloud Connector appliance:

Connecting to remote server failed with the following error message: Access is denied.

This is because the Domain Admin and VM Admin credentials for the Cloud Connector servers expired. To resolve:

  1. Log in to the CCE AD machine with the CCE Domain Admin password. Open the AD Users and Computers console from Administrative tools, and reset both the Administrator and CCEService account passwords to the original password and set the passwords as non-expiring.
  2. Log in to each of the other CCE machines with the CCE Domain Admin password. Open Computer Management, and reset both the Administrator and CCEService accounts to the original passwords and set to non-expiring passwords.

Note that in 1.4.2 and later all Cloud Connector account credentials are non-expiring and this error would be unexpected unless someone changed credentials to be different that configured in Cloud Connector cached passwords set with Register-CcAppliance.

Install of 1.4.2 Fails with WinRM Error Connecting to Remote Server

The following error displayed during installation of the new Cloud Connector appliance:

Connecting to remote server failed with the following error message: WinRM cannot complete the operation. Verify that the specified computer name is valid, that the computer is accessible over the network, and that a firewall exception for the WinRM service is enabled and allows access from this computer.

If you use a Proxy in the DMZ for Internet access, set WinHTTP Proxy settings on the Host appliance with your proxy server and a Bypass-list including the "192.168.213.*” network used by your Cloud Connector Managements services to bypass the proxy. Otherwise management connectivity will fail and prevent the deployment of Cloud Connector Edition. Note: Match the bypass list to the management subnet that defined in your CloudConnector.ini file. Sample winhttp configuration command:
netsh winhttp set proxy "" bypass-list="*.local;1.*;172.20.*;192.168.218.*'<local>"

Missing CCE Management Service: Install Fails After Uninstalling Current Version of Skype for Business Cloud Connector Edition

The update to 1.4.2 fails after the CCE Management Service stops and the current version of Skype for Business Cloud Connector Edition uninstalls, and use see the following error displayed:

Uninstallation failed with exception System.Management.Automation.MethodInvocationException:

Exception calling "Uninstall" : "Illegal operation attempted on a registry key that has been marked for deletion.

The Group Policy to prevent removal of registry on logoff was either not created or removed in the case of a domain joined Host appliance. To resolve:

  1. Make the Group Policy entry described in Prepare Cloud Connector Appliance
  2. Follow Steps 2-7 here if not in Bits Update time window and want to manually update,, or, steps 2-4 if you are.

Install Fails Connecting to Machine After Waiting 600 Seconds

Installation fails during deployment of the first Cloud Connector VM with:

Can’t connect to machine after waiting 600 seconds

A network issue is preventing the Host appliance from making a PowerShell session to the Cloud Connector Virtual Machine over the management switch.


Confirm no VLAN’s configured on the Host appliance.

If using a Proxy server, confirm WinHTTP proxy settings bypass list includes management switch network as described above.

Check if the switches on the Cloud Connector VM have Automatic Private IP Addresses of 169.x. It they have 169.x addresses, the Convert-CcIsoToVhdx did not complete correctly. To resolve:

  1. Run:
    Convert-CcIsoToVhdx -IsoFilePath <Windows ISO File Path, including file name> -PauseBeforeUpdate
  2. When prompted, connect to the Base VM using credentials provided in the PowerShell output.
  3. Make any necessary adjustments to allow the computer to connect to Windows Update Service.
  4. Complete all Windows Updates and restart the VM.
  5. Return to PowerShell and answer prompt complete the process.
Comments (4)

  1. Oleksandr Semenyuk says:

    On my fresh deployment of the Cloud Connector 1.4.2 I can observe that every 15 seconds Management Adapters are briefly disconnected and reconnected to the Management Virtual Switch. What this mean? Is this by design or I have errors in my CCE deployment?

    1. Hi Oleksandr,

      Yes this is by design. I’ve added this to our Understanding Cloud Connector Edition Auto Recovery article to assist others with this question: During detection the management switch will connect to the cloud connector virtual machines to run PowerShell session to get the status of the services.

      Thanks for the question.

      1. Afkar Maliki says:

        I experienced same issue which the SFB CCE Management switch unplugged intermittently on the 4 CCE components VM. But on the host it is fine. Not sure if this an error or issue?

        1. Hi Afar,

          No this is fine. The CCE management service initializes connection to CCE VM’s over management switch to establish PowerShell session and confirm CCE services are running.


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