I'm trying to keep Mac OS X updated behind an ancient Websense (pre-Cisco websense.com) and corporate IT won't play along. To anything other than Windows, Websense appears as a man-in-the-middle.

So, (rightly) all bogus certificates are refused, and I can't update (an SSH tunnel is impractical for any transfer > 1MB.)


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    We use web sense and have no issues whatsoever with Apple updates. Are you sure it's just not a configuration issue the IT team needs to address? They should white list in my opinion and experience. – bmike May 1 '17 at 21:28
  • @bmike I believe you identify here the exact problem: a configuration issue readily addressed through the white list, not a technical problem but organizational dysfunction. IT won't or can't (decision makers are unclear on the concept, maybe). It is a relief to read your words verifying what I've struggled to piece together (when I described it to my management, they were incredulous: "'white list'? No such thing. That's crazy talk!"). Thank you! – user236122 May 5 '17 at 12:01

If IT is being intractable even when you tell them that you are prevented from updating your OS (which in itself is a security issue), you have three options:

  1. Download macOS updates directly from Apple at https://support.apple.com/en_US/downloads/macos. You can download these off site (if necessary) and copy them to USB external storage.

  2. Use a mobile hotspot

  3. Physically take the Mac to another network without this restriction (like you home for example)

It still surprises me that they are completely unwilling to assist - they could literally bypass the rules or put it on the DMZ for the duration of the update and return the machine back to the being protected after the update.

  • Thank you! 2 and 3 are not options (no cell reception in the office, and the iMac doesn't leave the office), but I will try 1 (what I'm already doing with non-Apple updates). Application triggering and handling its own updates I see as major improvement. Sadly, it requires intelligent configuration and management of IT infrastructure. ("We don't care. We don't have to.") Seems that prime directive guiding policy is to protect the company from disclosures and liability for employee misbehavior online: legal, not technical, concerns. Reassured that it surprises you -- reason for hope! – user236122 May 5 '17 at 12:23
  • Yes, it definitely surprises me. I run my IT departments like customer service organizations with my customers being the employees. Our polices are based around security and directives from management. That said, we still ask what the end user is trying to accomplish and see how we can solve the problem. – Allan May 5 '17 at 12:35

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