LCS 2005 & Messenger for the Mac on Leopard

One of the changes with OS X 10.5 Leopard is the lack of the X509Anchors keychain being installed by default. The problem this creates is that a lot of Microsoft applications for the Mac depend on this keychain for their certificate authentication. They check the X509 keychain for a certificate and when it doesn’t exist, they fail to authenticate. The annoying part here is that the application doesn’t even have appropriate error messages included. Instead of something logical like the "the certificate is not valid or trusted" the user gets an error that their sign-in name or password is incorrect. Fortunately there’s a workaround and you can add this keychain back to make it functional again.

  1. Open Keychain Access (Using Spotlight to search for it is probably easiest)
  2. Click File > Add Keychain
  3. Browse to Machintosh HD | System | Library | Keychains and select the X509Anchors keychain. Press Open.
  4. Now select the X509 keychain in the Keychain Access window and drag all of the certificates you need onto this window. You should be prompted for your admin credentials.
  5. Now you’ll see a window asking which keychain you want to install the certificates to. Choose X509Anchors and press OK.
  6. Once your certificates are installed, try signing in again. This time it should succeed!


Recent content I've written for you—just for you!— to enjoy while you're here.


Quick commentary and links to other sources you'll find interesting. I promise.


Some personal background, links to related projects, and other ways to connect.

Hi there. My name is Tom Pacyk and this is my small home on the web. I love the intersection of design, technology, and communication, which is a combination that led me to a career in sales and marketing roles at places like Zoom and ServiceNow. They're a bit old now, but I also had the opportunity to publish a couple of books along the way.

Portland, Oregon is home for me, my wife Beth, and our three kids, but I'm actually a Midwestern transplant—I grew up in the Chicago suburbs and went to school at Purdue and Illinois. When I find some free time I'm probably going to concerts, rooting for the Portland Timbers, or working on my Sunshine Burn Photography project.