If you are running into an issue where you have to perform a rematch for a control to match in the object explorer, you should perform the following troubleshooting step to see if it resolves your matching issue.
Open the Web Adapter properties and look for a property called EnableMatchInProcess. The default for this property is True. You should set this value to False and retest. The EnableMatchInProcess property determines whether or not the adapter will use in process matching or out of process matching. In Process matching is usually faster but we have commonly experienced issues where some controls do not match (This all has to do with how the control is being loaded i.e. Dynamic content, AJAX, etc).