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It's possible you ran Wing as Administrator in the past and are not during the attempted update and there are disk permissions errors. You may be able to see details in the ide.log file in your AppData\Wing Pro 12 directory. You could also replicate the problem and immediately afterward send in a bug report from Wing's Help menu and include the error log. That will hopefully show us the details of the failure.
It's possible you ran Wing as Administrator Adminstrator in the past and are not during the attempted update and there are disk permissions errors. You may be able to see details in the ide.log file in your AppData\Wing Pro 12 directory. You could also replicate the problem and immediately afterward send in a bug report from Wing's Help menu and include the error log. That will hopefully show us the details of the failure.