Upgrading to Windows 8 rocky road part 2

This article was last updated on April 16, 2022

Canada: Free $30 Oye! Times readers Get FREE $30 to spend on Amazon, Walmart…
USA: Free $30 Oye! Times readers Get FREE $30 to spend on Amazon, Walmart…Things did not go as planned on Windows 8 upgrade despite months of preparation

Windows 8 Pro upgrade

Upgrading to Windows 8 is supposed to easy.

While upgrading may go as smooth as silk for some people, others will spend days working through the issues.

From Windows 7 to Windows 8 should have been a task lasting a few hours.

Instead, it took three days and the work is not over yet. I just ran out of time over the weekend.

After waiting more than 9 hours for the $40 download upgrade, that road seemed like a dead-end.  As I posted in Upgrade to Windows 8 Pro a rocky road, I capitulated on Friday and bought the $70 DVD.

The DVD upgrade installed in 20 minutes but my troubles were just beginning.

Windows 8 Upgrade Assistant would only do a clean install.  That means you lose all programs, settings and data in the upgrade process.

Unlike the promises on the Microsoft website, Windows 8 Upgrade adviser would not upgrade Windows 7 Ultimate without wiping the boot drive of all apps, settings and my data.

Upgrading my main workstation

For the last 8 months I tested Windows 8 Consumer Preview, Release Preview and Release to Manufacturing (RTM). I felt confident installing the general release on my main workstation. What could go wrong?

The computer to be upgraded is a super computer used for video and photo editing. It is amazingly fast with a 6 core/ 12 thread processor with a Windows Experience rating is 7.9 out of a possible 8.2. Although it is 2-years old, the Processor is rated equal to the , one of the high performance chips of today.

  • Intel i7 X980 Extreme Edition Gulftown Processor @ 3.33Gz, 12 GB RAM
  • Windows 7 Ultimate 64 bit
  • Asus P6X58D-E Motherboard
  • Boot Drive Intel SSD 160GB
  • Other Hard drives 2 x 1 TB, 1 x 2 TB Western Digital

Upgrade Assistant

Chose What To Keep

Both the online and DVD upgrade use a program called Windows 8 Upgrade Assistant that makes the process easy, if not frustrating at times.

Ignore what it suggests at your peril.

The first decision point is to upgrade only the operating system and keep Windows settings, personal files and apps. That is the quickest upgrade but only available if you are on Windows 7. which I was but didn’t get that option.

The second choice is keep “Just personal files” which means settings and apps are lost.

Installing programs again is a bit of work but sometimes a good idea to make sure things work properly. I looked at my list of 40 installed programs and realized half of them were unnecessary freeware so they will not get re-installed on the computer.

Microsoft has a sense of humor with the “Chose what to keep – nothing.”

That wasn’t much of a choice.

Losing all the settings is more than an annoyance. You have to  re-entering the login and passwords for programs and websites. It’s handy to have a record of all those passwords stored somewhere not in your main computer.

Some settings would be more catastrophic. I boot on an SSD drive for speed but store my user documents on a separate drive since SSD drives are small. It was not possible to save or restore that setting and it cost me plenty of pain. More on that later.

Backup First

Installing Windows 8 with a clean upgrade removes any incompatibilities with the old one.

It’s always advisable to have a complete backup of any computer before an upgrade. However, a backup cannot restore the settings and programs.

We have a Windows Home Server that automatically does nightly backups. I had tested restoring and it works so I was not worried about the data.

Clean upgrade

Windows 8 downloading

When you buy the $40 download upgrade, this is your next screen.

I saw that one but it hung for hours which is why I bought the DVD for $70.

The download may get faster as the rush to upgrade passes.

In the end it was easier to pay the extra $30 and have the DVD media for any future problems and re-installs. I re-installed Windows 8 once already.

For the rest of the download screens and procedures, see Upgrade to Windows Pro for $39.99

With the DVD, that’s essentially it. If the Upgrade Assistant finds a legal copy of Windows XP, Vista or Windows 7, it starts installing. There are several re-boots and before long the upgrade is done.

Windows 8 first screen, click with the mouse to show the login screen

Windows 8 has a brief tutorial before asking you to personalize the screen colors and login for the first time.

At this point it’s helpful to have a Microsoft, Live or Hotmail account.

You can login without an account but eventually you need one to register the software and access the Microsoft Store and SkyDrive cloud services. A Microsoft account is mandatory like having an iTunes account is mandatory for owning an iPhone or iPad.

What they don’t tell you is that your c:\Users sub-directory is based on the login name. If you want to keep your old login name, use it or lose it at this point. Although the documentation is no clear, it appears to pick a login name and user sub-directory from the email address.

I put in my Hotmail address and it parsed out my first name. Now my files are stored under C:\Users\Stephen.

Since it didn’t retain them, all of documents, videos, music and pictures will have to be copied or restored to the new sub-directory.

Purchase Windows 8 Pro Upgrade and get a $15 Amazon credit (US only)
Purchase Windows 8 Pro Upgrade and get a $15 Amazon credit (US only)
Amazon.ca – Canada    

What went wrong

I was not able to keep the custom setup for the user directory that worked in Windows 7 with the SSD drive for C:\ to speed up the boot process.

In Windows 7, I moved C:Users to G:\Users. The Microsoft Community documented procedure was a little tricky but it worked. It does not work in Windows 8.

Trying the same routine in Windows 8 wiped out my sub-directory which took two days of restoring from the server to fix. More on that later.

Microsoft warned beta users that installing Windows 8 RTM or Release Preview on a separate hard drive volume would allow Windows 7 to be upgraded and save everything. Despite removing all traces or the pre-release software, the upgrade found them. So the upgrade saved nothing.

The only choice was a clean install. That did not worry me since I backup my computers every night to a Windows Home Server. It still meant a lot of work to restore about 900 GB of old files, video projects and photos.

I had to leave that computer without restoring my photos.I ran out of time.

The only program that is re-installed is Office 2013 but nothing else.

Getting help for Windows 8 Upgrade is frustrating since there is so little documented about the nits and picks of Windows 8. The best source of help is the Microsoft Community Forum for Windows 8. Getting a specific answer can take days. The Forum is run by volunteer moderators with some Microsoft staff pitching in.

You can get direct support from Microsoft. I tried and they said it was too busy, call back. Obviously the pain of early adopters is very real.

Would I do it again? Of course, I am going to upgrade a Dell XPS 630i this week. It’s the computer that I used with Windows 8 since February. It should be easy but you never know.

My wife laughed when I showed her Windows 8 running on the computer. “Wow!” she said. “All that work makes me want to run to Staples now and get a copy.”

By Stephen Pate, NJN Network

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  1. Huh, I went from 7 to 8 using the download option, and it just fired the whole thing up (retaining old settings so no reinstalls were necessary) within an hour. It dcomment_IDn’t hurt that I was installing it to an SSD, and running the installer of a USB stick. Wasn’t timing it too carefully since I left my machine, but it was closer to 30 minutes than a full hour too.

    Probably dcomment_IDn’t hurt that I dcomment_IDn’t have any funky configurations for my user folder though.

    Now if only I could find a way to change the destination drive for newly installed apps so they don’t all default to installing on my SSD C:\ drive…

  2. You dcomment_IDn’t even mention that it’s not possible to go from a 32-bit windows (XP, Vista, 7) to 64-bit Windows 8 with the Windows 8 Upgrade adviser. Nowhere in the adviser process is the user asked what # of bits they want. It just chooses the same as you already have in your OS (not what your PC is capable of). You need to order the DVD backups (so MS told me) to upgrade from 32 to 64 bit. And, I think I may have to reinstall XP in order to do it! Right now I’ve got a 32-bit Windows 8 install that looks nice but isn’t what I want. I have to wait till my DVDs arrive and start over, or even further back (with a fresh but temporary XP install) to get what should have been given the 1st time around!

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