As a veteran of many operating system upgrades, I am usually somewhat cautious when it comes to system upgrades, but keeping my data in the cloud has perhaps made living on the wild side a little less dangerous.

I have two desktop computers, an I5 Mac Mini and Lenovo tower also powered with an I5 processor. In addition to OS X, the Mac Mini also runs Xubuntu Linux through VMware Fusion.

During the last ten days of October 2013, I did major upgrades on all three of my operating systems. Over the years I have seen lots strange things happen when doing a single operating system upgrade. I once did a Mac OS X upgrade and it took me a week to get my email to work again. I have done early Linux upgrades and had applications break beyond my ability to fix them. Linux upgrades caused me so many problems that I gave up on the operating system until I discovered Ubuntu.

I don’t have as much experience upgrading Windows systems since I typically have gotten my new operating systems by purchasing a new computer and passing on my old Windows machines to someone else. Still, I lived through the many upgrades to Vista, so I saw networking on my laptop break more than once.

Doing three major upgrades very close together is obviously inviting trouble. However, it is also a good way to measure if we are making any progress in the operating system world.

Enter The Penguin

For years, I lived by the mantra of a “clean install” when upgrading my Macs. This time I decided to go for broke and make the first upgrade on my virtual Linux system, pushing my Xubuntu install up to Saucy Salamander—aka Ubuntu 13.10—the underpinning of Xubuntu Linux.

To be very honest, my Linux upgrade happened behind the scenes with no intervention from me other than typing my administrative password and rebooting Linux. I am sure the Linux folks added a lot to the latest version and I have read the notes, but so far my undiscerning Linux eye hasn’t found anything which looks new. I mostly use the Firefox browser and Thunderbird email client on Linux. They both seem to work the same as they did before. LibreOffice has a few new features, including the ability to embed fonts in documents when sending them to someone else. It is a credit to the Linux folks that upgrading is now so painless. I am happy with my Linux world.

The Race Is On

My experiences upgrading to Windows 8.1 and OS X Mavericks were more interesting.

I had been forewarned that the download for Mavericks could be slow, so I started the download before I went to bed. The next morning when I came upstairs to my office, I found that I had a successful download and OS X Mavericks was ready to be installed. Being a little old school, I used DiskMaker X to make a bootable OS X Mavericks installer on an empty USB drive so I would not have to go through the download again in case there was a need.

Also, to make things more interesting, I queued up the Windows 8.1 download so I could start it at the same time OS X Mavericks started installing. Not that it really matters much, but it turned out Windows 8.1 downloaded and installed quicker than OS X Mavericks finished installing.

Surprisingly, the upgrades went smoothly for both the Lenovo desktop and the Mac Mini. Of course we all know that the fun begins once you start trying to do the same things that were once easily accomplished using your old operating system.

Checking Out Mavericks

One of my least favorite parts of operating system upgrades is having to buy upgraded applications that are broken by the operating system upgrade. Usually there is at least one, and it was not surprising that VMware, my virtual machine client, was the one that broke. Which meant that things were starting not to work well in Linux, though no fault of Xubuntu's.

I checked and found that there was a “new and improved” VMware version that was designed to work with OS X Mavericks. I paid the $49.95 upgrade fee, downloaded and installed the new version of VMware, and my Xubuntu experience was back to normal.

I did the OS X Mavericks upgrade hoping that the new OS would fix a printing problem that developed with Mountain Lion. I have three printers on a network and one of them was showing as available on the Mac, but when I tried to print to it, it would never connect. The same printer worked fine from my Windows computer on the same network. I tried reinstalling it a couple of times but I never could get it to work.

I was pleasantly surprised when I tried to print to the printer under Mavericks and it actually worked. Unfortunately a couple of days later, it quit working so I finally gave up and hooked it to the Mac using USB while having the Windows machines access the printer through Ethernet.

So far I have only had one crash on my Mac running Mavericks. It was the old version of Pages and it has not happened again.

Windows On The World

How did the Windows system upgrade fare? Actually, things seemed to go very well until I tried to upload some photos using the built-in SD slot on my Lenovo tower. The SD slot did not work.

I rebooted and it worked, but the next time I tried it, it would not work again. I plugged in an external SD reader and it seems to work fine. It is actually a little easier to reach that than the slot in the tower so I may just ignore the problem.

I did have another somewhat scary problem after I upgraded to Windows 8.1: when I tried to wake the system from sleep the next day, I got the message that my system was broken and needed to be taken to a dealer. I rebooted, the message went away, and so far the problem has not reappeared. My fingers remain crossed.

So far on Windows, all my applications are working and Windows 8.1 is still the same multi-personality OS that it was before. I use Start8, so I mostly ignore the new Windows 8 interface on my desktop machine. I do use the touch features on my Lenovo Yoga which I have not upgraded to Windows 8.1.

The Biggest Changes

Of all the changes in the three operating systems, the one that tried to change the way I work the most was the new default way that second screens are used on the Mac. My Mac desktop has two screens and after a few days I decided the new setting which gives each screen its own Space just would not work for me. I found the solution buried deep in the Mission Control preferences. There is a check box that lets me change back to the old way where a single Mac window could stretch across two screens.

I haven’t used the new iWork suite extensively, but with no support for linked text boxes, it is definitely not the same Pages. I am most impressed with iWorks in the Cloud. It seems to be a nice balance of speed and functionality. I even got it to work from a browser in Linux. I have tried opening a couple of RTF format documents with Word and iWorks. iWorks looks like it might be speedier. I have been told the formats of the new version of iWorks are not backward compatible with old versions but you can export the new versions to the old format.

All in all, congratulations should go out to the folks who have brought us these modern operating systems. My triple roll of the upgrade dice was definitely made on a hot table.