Making it work: a tale of poking down the wrong rabbit holes for fun

It’s 12:18 AM as I write this. First up, some of you are going to want to behead me at some point. Maybe resist the urge, and finish the read.

This began back in March, I think. I’d been using my work Mac (a 2011 model) for almost two months now. So far, fine. I liked the hardware (bit old, but worked for me), and the software let me write my code my way. But, there were some things I wanted to try.

I wanted to try a dual-boot. The OS choices were Arch and Windows 10. Arch for tinkering, and Windows 10 for the fact that it let me do everything, and because I like the new stuff my Windows Insider account gives me, besides the fact that I find Windows to be the most useful desktop OS (I see daggers pointed at me).

** buys insurance**

A little background here. I like to switch my primary OS every few months, because I get bored easily. In the last two years alone, I’ve been through Lubuntu, Ubuntu, Linux Mint, Arch, MacOS Sierra, and Windows 10. I’m considering Fedora, right now.

As fate would have it, Windows 10 is not officially supported in Boot Camp Assistant for the 2011 model. Not a huge problem. You see, Windows 10 installation is not very different from Windows 8, which was supported. Only thing I couldn’t do was use a flash drive to install Windows 10. No problem. I burned a DVD.

The install was a breeze. Booting into Windows, I had to configure the Boot Camp drivers, and I was in business.

3 months went by without incident.

(Around 11:30 PM) But then, one night, I remembered something. Sierra was still there in the shadows on the other partition, occupying half the SSD. I wanted that space. So, I innocently booted into Mac last night, and shrunk the Sierra partition. Still didn’t remove Sierra entirely, just in case.

Then came the restart.

Then, nothing.

I waited while Boot Camp looked for a bootable partition with the name Windows. It didn’t seem to find it. I rebooted several times. No luck.

Then, I rebooted into Sierra (holding the option key). Worked fine. I could see the Windows partition with all the data (praise the lord!) from inside Sierra. But, I still couldn’t boot into Windows.

I was locked out of my work, and it’s still only midweek. The prospect of a wipe, fresh install, and setting up on a weekday didn’t seem too exciting. Of course, there wouldn’t be data loss. Everything is on the cloud.

I turned to Google to help me in getting Microsoft’s OS running on Apple’s hardware. Didn’t find anything helpful, because I’m probably the only one retarded enough to land in this mess.

This wasn’t the first time I had dual-boot issues. I’ve been multi-booting Windows with Linux distros and other Windows versions for 7 years. I’ve had boot issues before. And there has always been a workable solution because Grub is a teddy bear, and MBR can be fixed with well-known tools.

One of the first solutions I hit upon was using the Windows installtion DVD to sort it out (without a wipe). It took me some time, but I was able to boot with it. Then, it took its own time to initialize, and show me the installation options.

Let me state here that I had little hope with this plan. It had solved Windows boot and startup issues with multi-boots before using the Repair Startup option because there used to be MBR/BCD. In this case, Windows was on top of Boot Camp. For me, this was mostly unchartered territory, and given Windows 10 isn’t officially supported, I naturally thought, it probably wouldn’t work.

But I took a shot. I navigated to the Repair Startup option buried in the installation disc, and waited for it to returned with either an error or nothing, as I ranted about my situation to a colleague.

Incredibly, it worked. Almost seamlessly. My Windows partition magically became bootable and visible from Boot Camp just like before.

Here’s to the people who wrote the Windows 10 installation media software!

(Yes, I use Windows for programming. Judge me.)