Ranking Apple’s New Operating Systems

It has been a busy few weeks for Apple. They released a major update to pretty much every operating system in their arsenal. Not all updates are created equal. Here are my experiences with each, ranked from worst to best.

OS X Server 5

Apple no longer releases a standalone operating system for server, so major upgrades to Server.app are essentially the new Server OS. Server 5 is unusual in that it works on both the old and new version of OS X. Previously the server app had to be upgraded in concert with the base OS, but this version will run on both Yosemite and El Capitan. It also has caused a whole lot of headaches for server admins, myself included.

The biggest issue is with Apache server. Apache is hijacking a whole bunch of ports that other applications rely on, most notably port 8443, used by the Casper Suite. But people are also seeing their web servers messed up as well. A great write up of the troubles with Server 5 can be found here. Apple has released some quick patches to fix some of the more glaring issues, but take a look at the reviews for Server.app in the App Store. Clearly there are still a whole host of problems.

Apple’s willingness to make drastic changes tends to serve them well in the consumer space. But servers are a different beast, and these kind of dramatic updates tend to cause way more problems than they solve, and will likely push even more sysadmins away from using OS X server going forward.

watchOS 2

Of all the upgrades, this was the one I was looking forward to the most. And it was the biggest letdown. After a few days delay, watchOS 2 landed, and it landed hard. Nearly everyone I know with a watch had issues upgrading the OS. Downloads would not complete, upgrades would stall, upgrades would report success but leave the watch on OS 1. There is a long list of troubles.

Even after installing it successfully things did not improves. I had to reload a whole bunch of apps that suddenly were glitchy or non functional. Oddly this affected apps that were written specifically for watchOS 2. Even after reloading the apps, I have still seen them suddenly become glitchy for no apparent reason.

I have also noticed that developers have not exactly jumped at the chance to create watchOS 2 apps. On any other platform there would have been a slew of updates right on day one. But this time it has been more a trickle. Given the continued bugs that my watch is seeing, that is probably not a bad thing though.

OS X 10.11 El Capitan

El Capitan does not have a whole lot of new user facing features. And that is a good thing. Ask longtime OS X users what their favorite OS was and you are likely to hear a whole lot of “Snow Leopard”. Snow Leopard was the famous “No New Features” release, and it was $30 for no new features. It of course did have new features, but most of the changes were under the hood. The same is true here. El Capitan, like Snow Leopard is a release that tightens up some of the more dramatic changes we have seen in recent releases. Leopard was a messy release, just as Yosemite was. We need these smaller upgrades from time to time to keep everything running smoothly.

The biggest change in El Capitan is one most users will never notice. System Integrity Protection (SIP, aka rootless) is on by default and difficult to turn off (difficult in a sense that it can only be done from the recovery partition). Apple has made a big deal about security in recent years, and locking down the core parts of the OS from any interference is a great way to continue this trend. I know a lot of power users may lament having more of the system locked down, but given the vast majority of users run as administrators (and it is doubtful that will ever change) these kind of steps are pretty much required.

I have upgraded every computer I own to El Capitan and have yet to see any major bugs. Apple deserves a thumbs up on this one.

iOS 9

I love you iOS 9. It is cleaner, faster, and more reliable than iOS 8. As a person who handles Mobile Device Management (MDM) at work, iOS 9 is a thousand times more reliable than previous versions. If you manage iOS devices at work, iOS 9 will be your friend, especially once your MDM system is updated to take advantage of the new features.

iOS 9 also finally gives the iPad some love after years of playing second fiddle to the iPhone. For the first time in the history of iOS, the iPad gets the biggest new features. I did not realize how useful slide over multitasking (sliding one app on top of another without leaving the first) would be. It brings the tablet much closer to a true productivity device.


I hear a lot of people complain at the smaller operating system upgrades that they don’t see anything different. I understand this from regular users, but when my tech savvy friends say it I am always confused. Drastic visual overhauls should not come yearly. That would be far too disruptive for everyone. Smaller incremental changes are much more valuable in my opinion. They move us ever forward without breaking everything in their path.

Server and watchOS show that bigger changes come with a lot more baggage. El Capitan and iOS 9, by contrast, don’t change the game. They make it much more enjoyable to play.

Ranking Apple’s New Operating Systems was last updated October 4th, 2015 by Michael Truskowski