Thursday, November 21, 2013

Mavericks OSX 10.9, HTTPS proxy, infinite loop of authentication boxes

If you are behind an obnoxious and thick-as-a-brick proxy, you will quickly find that an upgrade to 10.9 from 10.8 (or any earlier versions) will break your Safari, OSX software update, iTunes etc...

This is largely because of a semi-known bug with HTTPS proxy in KeyChain.   This blog post serves as a summary of what you can do in order to fix the problem (at least, let you get a decent OSX software update from App Store and see what happens there)

I have sorted the potential fixes in the order of likelihood to fix the problem.  For every fix, please open up Safari and see if the fix works(go to any of your favourite *internet* websites).  If yes, stop and go to Software Update.  If no, proceed with the next fix or leave me comments.

Fix #0

Before we proceed, you must make sure that you are comfortable with configuring proxy connections in OSX.  [System Preferences > Network > Network Interface > Advanced > Proxies]
Make sure, where necessary, you have your information input correctly in one or all of the followings:

  • Automatic Proxy Configuration
  • Web Proxy (HTTP)
  • Secure Proxy (HTTPS)
  • other proxies if applicable

Fix #1

As mentioned earlier, if you are like me that likes to dig in, search and look for the one thing that I want to see, you can actually go to [ Utilities > Console ] and you shall see the error messages that Mavericks complains every time it tries to look for the HTTPS key in the Key Chain

1) Open Utilities > KeyChain
2) In [login], you should see your proxy entries

3) Right click and select copy
4) In [system], if you see something similar, i suggest you remove those entries first (we will add them again in the next step)
5) In [system], right click and click paste (if it asks for your credentials, just enter your credentials and click ok)
6) Make sure one entry is for HTTP and one entry is for HTTPS and make sure the Account Name and Password are correct (you can check this by double clicking the entry)
7) For every one of the entries you just pasted, double click (enter credential if necessary) and go to Access Control
8) Select Allow all applications to access this item, click save changes and restart computer
9) Some applications might still ask you for permission to use the key in KeyChain, just say yes and enter the necessary credential

Fix #2

1) Open Utilities > > Type the following 2 commands.
sudo launchctl unload -w /System/Library/LaunchDaemons/
sudo launchctl load - w /System/Library/LaunchDaemons/
2) Restart computer

Fix #3
1) Open Utilities >
2) sudo vi /etc/hosts
3) make sure the ip address to your proxy is set there (ie. and press shift+: and type wq.
4) Restart computer

Just poke google with keywords like mavericks 10.9 https secure proxy safari app store


  1. Worked a treat thanks

  2. Hi Gary,
    I tried FIX1. Didn't work.
    I tried Fix2. Since then VPN doesn't connect anymore.The VPN-logo tries to connect but shuts down immediately without any error notification.
    This was my last terminal reply when trying to apply Fix2 command 1 again:
    launchctl: Error unloading:
    Command 2 reply:
    launchctl: Couldn't stat("-"): No such file or Directory
    launchctl: Couldn't stat("-"): No such file or Directory
    nothing found to load

    Pretty desperately yours


    1. There's an extra space in the "-w" switch for the second command, perhaps you've copied that error into both lines?

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