Apple

Fix: The Certificate or Associated Chain is not Valid

Several users are reporting that they are unable to connect to a different machine using Remote Desktop Connection. Affected users report that they get the following warning: “The certificate or associated chain is not valid”. In most cases, the issue is reported to occur if the user tries to use the Remote Desktop Connection as a Guest from a Mac OS computer.

The certificate or associated chain is not valid

Update: In all cases that we’ve managed to identify, the issue is occurring when the user tries to use the MAC version of Remote Control in order to connect to a Windows 10 PC. Most users are reporting that the issue only started occurring after they upgraded to Sierra.

What is causing the ‘The certificate or associated chain is not valid’ error?

We investigated this particular issue by looking at various user reports and the repair strategies that are commonly used to resolve this particular problem. From our investigations, it seems like there are multiple potential culprits that might end up triggering this error message:

  • Guest’s Remote computer authentication is not set to Always connect – This is the most popular culprit when it comes to this particular error message. Remote Desktop Connection is will refuse to connect if a single security factor fails during the authentication stage. In this case, you can circumvent the issue by modifying the guest’s security preferences to connect even if the authentication stage fails.
  • Microsoft Remote Desktop version is outdated – As a couple of users have reported, the connection might fail with this particular error message if the Mac that is trying to connect uses an outdated version of RDC. If this scenario is applicable, updating to the latest version from the Mac App Store will resolve the issue automatically.
  • Remote connections are restricted on the Host computer– If the PC that you’re trying to connect to is not configured to allow remote connections, you will also receive this error. In this case, you’ll need to access the System Properties menu on the host computer and enable Remote Connections.

If you’re struggling to resolve this particular error message, this article will provide you with several troubleshooting strategies that other users in a similar situation have successfully used to either circumvent or resolve the “The certificate or associated chain is not valid”.

Method 1: Modifying the Guest’s Preference Remote Authentication method

This is by far the most effective solution out of the bunch. The vast majority of affected users have reported that the “The certificate or associated chain is not valid” error was resolved after they updated a Remote Desktop Connection preference from the guest computer to ‘Always connect, even if authentication fails’.

Here’s a quick guide on how to do this:

  1. Open RDC (Remote Desktop Connection) from the computer that is displaying the error.
  2. Go to the Preferences menu and access the Security tab.
  3. Once you get there, set the Remote Computer authentication to Always connect, even if authentication fails.
    Changing the Remote computer authentication method
  4. Save the changes, then restart the RDC client and see if the issue has been resolved.

If you’re still seeing the ‘The certificate or associated chain is not valid’ error when you try to connect, move down to the next method below.

Method 2:  Installing the latest version of Microsoft Remote Desktop Connection

As it turns out, this particular issue can also occur if the Microsoft Remote Desktop version that you’re using is severely outdated. Several affected users have reported that the ‘The certificate or associated chain is not valid’ error was no longer occurring after they upgraded to the latest RDC version.

Upgrading to the latest Remote Desktop Connection version is extremely easy – just visit this link (here) and download the latest version. Your MAC system will automatically override your current installation and replace it with the latest one.

Updating your RDC client to the latest

If this method is not applicable or you already have the latest Remote Desktop Connection version, move down to the next method below.

Method 3: Allowing Remote connections on the Host computer

Another potential scenario in which the ‘The certificate or associated chain is not valid’ error will occur is if the host computer (the one that you’re trying to connect to) doesn’t allow a remote connection. Several users struggling to resolve the same issue have reported that the issue was fixed as soon as they enabled remote connections from the System Properties menu.

Here’s a quick guide on how to do this:

  1. Press Windows key + R to open up a Run dialog box. Then, type ” sysdm.cpl” and press Enter to open up the System Properties menu.
  2. Inside the System Properties menu, go to the Remote tab and make sure that the box associated with Allow Remote Assistance connections to this computer is checked.
  3. Then, click on the Advanced button below and make sure that the box associated with Allow this computer to be controlled remotely is also checked.
  4. Click Apply to save the current configuration, then restart your computer to make the changes permanent.
Enabling Remote Control on a Windows computer

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Expert Tip

Fix: The Certificate or Associated Chain is not Valid

If the issue is with your Computer or a Laptop you should try using Reimage Plus which can scan the repositories and replace corrupt and missing files. This works in most cases, where the issue is originated due to a system corruption. You can download Reimage by clicking the Download button below.

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