My OS X El Capitan and Windows 10 upgrade woes

What’s the next step after an operating system upgrade on a Mac or PC? To see if you can work with your existing applications. When moving to OS X El Capitan and Windows 10 I got off to a rough start, which left me frustrated.

Let’s address the El Capitan problems first. Did the upgrade install? Yes! Was I able to work? Nope.

I consider Office 2011, specifically Outlook 2011, a basic requirement for my work. Post upgrade to El Capitan, Outlook 2011 is crashing, hard -- no email for me and no ETA on a fix from Microsoft.

What makes me incredulous is this statement in Apple's release notes: "After months of beta testing with developers and with public users we are releasing [...]". So, in months of beta testing no one tried Office 2011?

I’m an MSDN subscriber so my first instinct was to upgrade to Mac Office Pro Plus 2016. With key code in hand and downloading the .pkg file, I’m thinking the end is in sight and I’ll be back in email action shortly.

Wrong. "We know that some users of Office 2016 for Mac are experiencing issues as a result of upgrading to Mac OS X 10.11 El Capitan. We are actively working with Apple towards resolution".

At this point I’ve lowered my expectations of "working". Outlook 2011 was completely non-functional, so I would settle with less broken at this point. Download, install and migrate the existing Outlook 2011 identity DB to 2016 -- that took forever.

But finally, yes. Outlook opens! I see my mail... but wait. "Activate License to go online, you can use Outlook 2016 in offline mode, Word is view only" -- what in all Hades is now going on? What is this fresh new Hell?

Turns out I’m an E1. That’s not a US Military Rank, it's what Enterprise Office 365 Subscription I have. Turns out you need E3 or better to actually have "rights" to a physical install of the software on your machine -- this includes Macs -- despite having a legitimate install code for the software, apparently that has to line up against your "E > 3" subscription.

It would appear you can’t do Office 2016 for Mac without an Office 365 subscription that gives you physical rights to the software install on your machine. Upgraded the subscription and all of a sudden my Office 2016 Pro Plus for Mac was back in business. E3 is $12 a month more than E1.

In the process, I called MS support (transferred across three departments) because I started a free trial and thought I had purchased (accidentally) 25 licenses of E3 -- an increase of several hundred dollars per month in invoicing. I just need one license to get my Outlook 2016 working again. I’m already in trouble for a near $1,000-dollar cell phone bill from being on the road for seven weeks.

I also mentioned upgrading to Windows 10, so here is that story.

I’m like a ferret on crystal meth when it comes to my email. I use my smartphone to read and delete email, but when carefully crafting a potentially career-ending response, it’s important to not misspell words like "Analyst". So, a bigger keyboard is essential.

When I requested a key for Office 2016 Professional Plus I got some sort of error with a reference number and did not want to download something I could not license, so I downloaded Office 2013, got a license key and installed and... wait, what now?

The same requirement to go online and license against an Office 365 subscription, but this time in very small font were found these magical words: "use key code instead". I input the key code and hey, presto, my email on a budget Lenovo Thinkpad is up and running. The Windows 10 Office 2013 experience was less traumatic than the El Capitan upgrade on my current generation Mac Mini.

The moral of this story is to beware of vendors bearing gifts of free operating system upgrades. I didn’t follow my own advice, which is to monitor social media to find about any problems with the upgrade. I'm equally disappointed in Apple for not doing more rigorous testing and Microsoft’s lack of enthusiasm for supplying a quick fix.

Both corporations had months to address these problems. With all the emphasis on "new", "better", and "shiny", I plunged down the latest and greatest hole and am digging myself out.

Ian Trump is security lead at LogicNow. Trump serves as a board member of the Canadian Cyber Defense Challenge and IC2.

Image Credit: Syda Productions/Shutterstock