Mac OS Upgrade Saga: Moving to Yosemite

I recently upgraded my Retina MacBook Pro to Mac OS X Yosemite and had several issues with the upgrade. The OS upgraded fine; the applications I normally use, however, had some issues. Not many, to be sure, but the ones I did have were very interesting in that they dealt entirely with communication. They also had something to do with previous upgrades causing issues with the latest upgrade.

Installing Yosemite was seamless, but dealing with the mail and calendar apps was far from normal. In fact, they would not work without a bit of tweaking.

Calendar App

The calendar app would not pick up my ownCloud calendars. They worked before, but failed to work with the latest calendar app. The fix was to remove the old ownCloud account and re-add the account.

Continuity and Privacy

I would really like to maintain continuity, but it requires two things that are interesting: that devices be on the same network, and that iCloud support be enabled. There is a reason I use ownCloud over iCloud: privacy. I have my own cloud, with my own services for sync and share. I’m not sure I want to use iCloud. However, iCloud needs to be enabled for continuity. It does work between my iPad and iPhone. They both have iCloud enabled so that I can use Find my iDevice, but I do not have it enabled on my MBP yet. I do not want it to sync everything on me before I have a chance to disable all the other syncs that will happen. Also be sure to follow the instructions at

Mail App

This one was painful. Horribly painful to upgrade. The Yosemite upgrade finished, and I opened the Mail app. Immediately, my copy of Letter Opener (to read winmail.dat files) needed to be replaced, but this is normal. The real issue was twofold:

  • Could not log in to my Mail server (yes it was working).
  • Horribly, horribly slow. Unusable slow.

Now, the previous version occasionally missed deletions, but the Mail app was now unusable. The solution was to do the following:

  • Exit the Mail app.
  • Remove the entire Mail config (not just in the Mail directory but in associated plist files as well); for good measure, I also removed an old Thunderbird instance.
  • Copy all Mail folders to the desktop.
  • Start the Mail app.
  • Reconfigure email to read from my server and make sure that it works (it did, with no performance problems).
  • Import all old Apple Mail from the saved Mail folders. Since I layer folders, this required a bit of directory manipulation. The inner folders needed to be moved to a directory.

Once all my email was imported and rearranged the way I like it, the Mail app worked seamlessly.

Upgrades Should Be Painless

Upgrades of operating systems should not impact your crucial communication applications. If they do, there should be sufficient documentation to instigate a fix. Mail app is crucial; if all that was required was a re-index, then it should have happened during the first run after the upgrade. But perhaps there were configuration and index file issues stemming from past upgrades? In either case, this is something Apple should have had an available fix for, and not something requiring a bunch of manual effort. Scripting this would have been tough for me to do, so I spent the time doing it by hand.

Edward Haletky

Edward L. Haletky, aka Texiwill, is an author, analyst, developer, technologist, and business owner. Edward owns AstroArch Consulting, Inc., providing virtualization, security, network consulting and development and TVP Strategy where he is also an Analyst. Edward is the Moderator and Host of the Virtualization Security Podcast as well as a guru and moderator for the VMware Communities Forums, providing answers to security and configuration questions. Edward is working on new books on Virtualization.

2 thoughts on “Mac OS Upgrade Saga: Moving to Yosemite”

  1. I’ve only had my Macbook for about 2.5 years. I’ve gone through the upgrade process to Mavericks and now, Yosemite. Like you said, the OS goes down just fine but I’ve had applications break both times. Going to Mavericks, iMovie and two other apps, I forget which, would not launch. I had to remove and re-install them. I also could no longer connect to my NAS until Apple released an update that fixed it. Ditto my WiFi…

    This time around, a couple of my third party apps no longer work and the vendors suggest moving to their new versions. Boot times are a bit slower now but not too bad. Also been having issues with Java, keep getting prompted that it’s not installed but it is…Aside from issues, I’d love if they offered more valuable features. I don’t have an iPhone, so I don’t really get the benefits of the cloud features. But at least I don’t have to pay for it.

    1. Re: Java

      I run a windows VM to access whatever I need to in Java. Apple no longer installs it for security reasons. That could be why.

      Do you know which third party apps? Every update I have to upgrade LetterOpener (winmail.dat reader) for the Mail app, would be nice to start a list of those apps you need to update.

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