how to bypass windows remote desktop connection for mac certificate or associated chain not valid

If a certificate being used for a connection is expired or invalid, then OS X will notify you of this when attempting to use it, and offer you the choice of continuing with the connection, inspecting the certificate, or canceling the connection.

Such warnings are convenient for detecting an invalid connection, such as one that might be malicious, so if they happen then consider looking into them; however, there may be times when practically every connection you attempt gives you a certificate warning.

To fix this, go to the Date Time system preferences, and ensure the option to Set date and time automatically is checked (click the lock to authenticate if this option is grayed out).

Be sure the time server used is one that is appropriate for your location, and then close the system preferences.

Within a few moments, OS X should adjust your system clock, which should clear the certificate errors.

You can ensure this is always the case by using a dedicated time server for your system.

To do this, open the Keychain Access utility (in the Applications Utilities folder), and select your login keychain.

In here, click the Certificates category, and then locate the certificate for the service you are connecting to.

You can do this by searching for the domain name of the service, or by sorting the certificates by name and scrolling through them.

In these cases, you can right-click the certificate and remove it from your system.

If the connection requires one, then it will be downloaded from the service again the next time you connect and authenticate.

For instance, a certificate may be used for SSL validation, but if this trust setting is not set up properly, then OS X will prompt you to use this certificate every time an SSL connection attempts to use it.

You can try similar options for the other trust settings, but only enable those that the certificate is specifically used for.

While you should not need to clear your entire keychain and set it up from scratch again, you can select and remove the certificates that are mentioned by these errors.

Doing so will have the system re-download new certificates for connections that demand them, potentially overcome configuration errors in the prior certificates.

Note that you should only do this for your accounts login keychain.

There is a special keychain called System Roots that contains a number of certificates.

These are public certificates issued by numerous trusted certification authorities, and are used to validate certificates issued by online services to which you connect.

Removing or modifying these will break your ability to validate connections, so it is best to leave these alone.

How To Bypass Windows Remote Desktop Connection For Mac Certificate Or Associated Chain Not Valid