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Oct 4, 2016 8:57 AM in response to freelinby SnickZ.,Hey, freelin.
Thanks for posting the screenshot of the dialogue box with empty information when you try to update your MacBook Pro on OS X 10.8.5. I also applaud your patience with this problem but it definitely needs to be corrected. I'll be glad to help.
Try safe mode if your Mac doesn‘t finish starting up -- Safe mode will show if the issue is related to a startup item or plugins. If the dialogue works in safe mode but not in your user account, please check the section titled "If an issue doesn't happen in safe mode" for further troubleshooting steps.
How to test an issue in another user account on your Mac -- If the dialogue box is blank in safe mode, test in a new administrator account. If the dialogue box is blank here as well, I recommend that you reinstall OS X using OS X recovery. To start up from OS X Recovery, hold down Command (⌘)-R immediately after turning on or restarting your Mac. Release when you see the Apple logo. Next, choose Reinstall macOS (or Reinstall OS X) from the utilities window, then follow the onscreen instructions.Take care and thanks for using Apple Support Communities!

