Invalid Certificate after Security Update 2015-004 in Mavericks

After recently installing Security Update 2015-004, I found that I could no longer browse to any website using the root certificate “VeriSign Class 3 Public Primary Certification Authority – G5” without a security warning (“invalid certificate”). This included sites such as Twitter and Apple, and it also meant that applications such as Software Update would no longer function.

After digging into it (see here, here, here and here) I found the cause was a chain of events that while a bit convoluted, were fairly prevalent among users.

First off, 2015-004 updated the list of trusted root CAs which by itself isn’t an issue. The problem was when I then logged into Amazon S3 using an older version of Cyberduck (< 4.7). That version of Cyberduck was adding the certificate chain retrieved from Amazon to my login keychain which also by itself isn't an issue. The problem was that the intermediate certs Amazon was using were outdated and signed with 1024bits. This caused a mismatch between the certs installed by 2015-004 and the ones being saved to the keychain by Cyberduck. Like I said, convoluted.

Luckily everyone seems to have implemented fixes – Cyberduck no longer writes the intermediate certs to the keychain (as of version 4.7) and Amazon has updated their intermediate certs to 2048bit signatures.

If you run into this issue, you probably still have the invalid certs sitting in your keychain. Simply open up Keychain Access and delete the bogus entries in the login keychain so that the system entries are used instead (select login, then Certificates, you should see them at the bottom of the list – "VeriSign Class 3 Public Primary Certification Authority – G5").