I’m on customer scoping call number 102 for Windows 10 and/or Office 365/2016 migration.  The pattern is solidifying as to where the the potholes, pitfalls, wormholes and landmines are typically found.


First off, it’s rarely a Windows 10 issue that causes the biggest challenges.  It’s more often that Windows 10 is the light that shines on hardware shifts and crappy coding practices.  In other cases it’s a matter of the project itself bringing attention to areas of the business that were neglected for a long time.

Landmine No. 5 – Plugins and Extensions

Office add-ins, IE plugins, extensions to Chrome and Firefox, and other parasites that suck the blood from their host applications.  Sometimes it’s more specialized than the wider-known products, for example, extensions to Adobe, Autodesk, and other vendor’s products.  The base product may be fine, but the overlooked extensions can jump up and bite the customer in the ass later on.

Landmine No. 4 – Local Admin Rights

Applications that *expect* users to have local Administrator rights are f-ing stupid.  Stupider than dumb.  Dumber than stupid.  In fact, any vendor that argues that their product “requires” the user to be a local administrator, on a typical desktop or laptop device, should be (get ready….) beaten with a pepper spray can, whipped with a chain made of razor wire, doused in white phosphorus and gasoline, ignited with a blow torch and stomped out by an angry, drunken rugby team wearing ice climbing boots.

And then re-ignited and repeat the whole process again.

If they refuse to comply with common sense development practices, find another vendor.   If no other products exist, hire some developers and make them yourself, the right way.  I’ve actually seen quite a few companies do just that.  When making the shift to “best practices” at the desktop level, this is when some of those shitforbrains applications pop up like wack-a-mole.

All I can suggest is this:  If you’re going to spend the time and money to make a major shift in the area of operating systems, don’t get lazy and drag along a bunch of bad habits as well.  You’ll never truly get the benefits of the upgrade unless you adopt the right habits along with it.

Landmine No. 3 – Office-Dependent Apps

The evilest of evil beasts lives in this dark cave: Microsoft Access Database “Applications” (yes, they call them “applications”).  They shackle you to the Access version, which means your Office migration plans now run into a forest of thorns and landmines.  The more you have, the uglier it gets.  Migrate them to “real” applications: SQL Server and some sort of decoupled UI/UX like VS project or a web app.

If your business depends on this “critical” beast, treat it like it’s really “critical” and put some work into it.  A business-critical application is like a house: build it to live in and live onward.  Toss out the plastic toy hammers, and buy a real hammer.  Access is a well-crafted, mature application, but it’s not a multi-user, business critical application unless you’re high on methanol and pig tranquilizers.

Landmine No. 2 – Hardware / Device Drivers

Applications that involve hardware peripherals or interfaces to hardware, are often the cause of Windows 10 migration hold-ups.  These are often found in specialized industries where the applications are very unique and specific to the business function, and not produced by big-name vendors.

For example, in a food processing business, the app that controls the old, rusty, belt-driven machine that grinds the rotting animal carcass scraps into a thick slurry of liquids with the label that says “high-protein supplement”.  That one.  The driver app or console, was written when Jimmy Carter was apologizing for the Iran mess, on a Commodore 64.

So you get a wet rag and wipe off the machine cover to get the phone number to “Jimmy Tech Inc.”.  You call and Jimmy answers surprised, as if nobody has spoken to him in decades and he thought humans had been wiped out in a nuclear Armageddon.  After he repeatedly asks for your name, you ask about Windows 10 compatibility.  He replies “Windows 10?  (long pause) Is this a prank?  Did Bill put you up to this?”  You try to continue talking, but his cats are stepping on his keyboard and he keeps stopping to talk to them using their individual names.  Then one of them starts eating his cold cup of ramen noodles and he drops the phone to chase her away.

Hang up.  Find a new product, or hire a hungry coder.

Landmine No. 1 – 32 bit to 64 bit

This has been the most common challenge to applications and drivers getting in the way of a smooth Windows 10 migration effort. In most of the cases I’ve seen, it’s really just basic application development issues such as hard-coded file system paths, registry keys, and even hard-coded component references (rather than installation or runtime referencing).  Organizations which migrated to 64-bit on Windows 7 or 8.x almost always skip right past this one, which is a good thing.

Outside of those lucky places that shifted to 64-bit earlier, the biggest portion of application compatibility issues I’ve seen thus far has been 32-bit apps and trying to move to a 64-bit environment.  Of all 5 landmine types described thus far, this one takes about 80% of the pie

Honorable Mentions

Other issues that can jump out in front of a Windows 10 migration like a deer on a late night highway drive:

  • Poorly written and poorly maintained in-house applications
  • Lack of consistent standards for desktop configurations
  • Lack of documentation
  • Lack of public brutal beatings for insubordinate users
  • Lack of political backing from upper management
  • Poor prioritization of IT projects
  • Squirrels fighting outside the window
  • Election campaigns and ensuing office arguments
  • Lack of motivation / low morale
  • Weather turns really nice after a few weeks of being really crappy

I’ll be on travel for the next few days.  If you’re in Boston, I’m sorry. It wasn’t my decision, but I’ll try to not ruin it.


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