Things that break when you change your iCloud password and Tunnelblick problems

Well a bunch of things definitely break when using your Mac in a secure way. I have two problems. First is with Tunnelblick, the open source VPN connection. It keeps hanging Yosemite. I finally uninstalled it and am trying privateinternetaccess.com’s own client.

Also. I’ve been having trouble with iCloud and with so many hacks, decided to change the password.

This causes many issues if you have synced your iCloud Password to be your Mac password. For instance keychain access just breaks completely and it keeps asking for the old iCloud password. Here is what I think is happening:

  • I think what is going on is that there is not really a sync. Instead, when you say use your iCloud password as your local Mac password, it is just taking the current password and validating that it is the true iCloud password and then using it’s own hash to store it. This means that if you change the iCloud password it will not sync with your Mac. So after you change, break the link and reauthenticate.
  • If you don’t do this, then all kinds of strange things happen to the local keychain since it is encrypted with your old iCloud password and not your new one. Most folks recommend just deleting it, but this causes more sync problems. I’m still investigating.

Finally on tunnelblick, I’ve been having more and more problems with it. It seems to hang networking. So I’ve uninstalled it for now. It also doesn’t seem to work well with DNSCrypt.