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My recommendation is NOT to upgrade to Windows 10 at this time if you use OneDrive. There is a crippling bug where OneDrive changes permissions on your directories where you can’t use them. If you fix the permissions, they will just go bad as soon as you reboot. Hint: Do not install Windows 10. If you have already installed Windows 10 and are having this problem, see the workaround I developed at the end of the article. Let me add that while I am generally not having a lot of Windows 10 problems, others on the Internet are reporting all sorts of problems, and a fair number of folks have gone back to Windows 8.1 or Windows 7.

I guess this is a topic I have some expertise on since I’ve migrated 6 systems—two desktops, two laptops and two tablets. Two systems were Windows 7 and the other 4 were Windows 8.1. One Windows 8.1 laptop was originally Windows Vista, migrated to Windows 7, migrated to Windows 8.1 and finally to Windows 10.

My first bit of advice about Windows 10 migration is to watch out for the offer of Express Settings at the end of installation. Selecting the Express Settings may be sharing more information with Microsoft than you are comfortable with sharing. Hint: do not accept Express Setup.

Several of my systems did not work right immediately after upgrading. There were a number of weird symptoms, but all were cured by rebooting. Hint: reboot your computer after installation before you try to use it.

The first annoyance in the migration is that the Windows 8.1 machines, which all had nicely configured start screens, ended up with start menus that were jumbled together or missing things. I had assigned my programs into groups—all of which became jammed into one, and a bunch of new stuff (new Microsoft Apps) was added in the front, like the Groove Music and Mail apps. Each system required time to manually unscramble the apps into meaningful categories again, remove the stuff I had no interest in, and to add things that got left out. Hint: take screen shots of your start screen to make the setup quicker under Windows 10.

There is a major SNAFU in Windows 10 and OneDrive that may put you in a world of hurt. Every time you boot your computer, OneDrive may reset permissions on your Pictures, Documents and other folders so that you don’t have access to them, even if you are signed on as the Administrator for the computer. There is a workaround for this problem at the end of this article. Hint: Don’t install Windows 10 until Microsoft fixes this problem or check if you feel comfortable with the steps in my workaround.

Windows 10 decided to convert my home network into a public network, and then to shut down all the services and features reserved for private networks. That meant that all my machines were no longer discoverable to each other. This problem can appear in several ways depending on what you share. Hint: go to the Network Sharing Center (right click on the network icon in the system tray) and select the appropriate type of network.

All of my systems belonged to a homegroup. After installation, they didn’t. I had to re-join each machine to the homegroup. My old homegroup password was not changed. You can fix this by right-clicking the start menu, selecting Control Panel and searching in it for “homegroup.” Hint: re-join your homegroup.

This brings me to a pet peeve about Windows 10, the search. While it seemed that Windows 8.1 search did a great job of locating programs and settings, Windows 10 does not. One thing to understand about Windows 10 is that there is a good deal of asynchronous processing going on, so that while you might see something displayed in a list, that doesn’t mean that the list won’t get longer if you wait. You could, in the previous example, have typed “homegroup” into the desktop search bar and if you waited long enough, the Control Panel homegroup applet would have appeared. In my limited experience, two machines will respond differently to the same search. For example, “uninstall” will get you different results on different machines, and on one of mine, the “Uninstall a program” control panel applet has yet to appear.

If you had not previously signed on with a Microsoft account (as was the case for my two Windows 7 machines), you may want to change to it. You’ll be fighting an uphill battle unless you do, for example you won’t be able to use the new Cortana digital assistant. Hint: when asked to sign on with a Microsoft Account, let it.

One of my Windows 8.1 tablets has a Micro SD card where I keep my file history, downloads and pictures. I’m not sure whether this happened during the Windows 10 upgrade or before, but somehow the drive letter got changed from S: to D:, resulting in some program errors accessing folders. This change also caused the Camera to stop working. Hint: check all your system folders (Documents, Music, Pictures, Downloads…) and make sure they are assigned where you think they should be. To change, right-click on the folder, select properties, and look under the Location tab. Also check your Libraries in the File Explorer to make sure there are no old entries to the prior drive letter.

Cortana is now generally working on my systems, but for some reason it was enabled on some and not on others. If your system won’t recognize “Hey Cortana” then go to the Search Box and enter “Cortana” and you will be directed to the Cortana settings, where there is a switch to enable “Hey Cortana” recognition and a training button to train it in the way you talk. There is a new search box next to the start button, and it has a microphone icon—click that if “Hey Cortana” isn’t working, and the voice recognition will likely work. As I said before, Cortana requires a Microsoft Account. When you first begin, you won’t see the microphone icon until you click in the box and respond to the “Get started” button on the search panel. Clicking on that is also a pre-requisite for Cortana. My hasty examination of this startup dialog is that you have to agree to share a good deal of information with Microsoft to get it to work (stuff I hadn’t wanted to share in Express Setup).

One small issue for users of Microsoft Office 2013 on the Microsoft Surface hardware, is that the button on the Surface Pen starts the freebie version of OneNote, not the advanced version in Office 2013. There is apparently no way to change this at present. Hint: add OneNote 2013 to the task bar.

I had some issues with File History after migration. Two of the machines being migrated were Windows 7 Home Premium versions. Somewhere along the line, the File History that previously was directed to a shared location on one of my computers got turned off for those machines. Under Windows 10, there are two settings paths: Under the Action Center (click the Action Center Icon on the System Tray or type Windows-A) there appears at the bottom (you may have to wait for it) a list of buttons for immediate actions, one called “All Settings.” Under that you can set up your File History, but you cannot set it to a network location with the Home edition! If you type “File History” in the search box next to the start button, eventually there should appear “File History: Control Panel.” That one will let you save the history to a shared drive. Hint: check that your File History is working as intended.

The Skype “Modern Windows” app cannot be installed under Windows 10, so don’t waste time trying. Something new is supposed to be available later in the year. Hint: Use desktop Skype for now.

OneDrive is another area of concern because it works differently under Windows 10. Before, one could see all the files on the OneDrive, whether they were synchronized or not. Opening a file caused it to be downloaded. Now you select the folders to synchronize, and you will see only the files in those folders. Reports are that there will be a new scheme released later in the year, but until then you’ll have to think through what you will need to see on each machine. Until you set this up, Windows 10 will prompt you periodically to set it up. Finding the setting if not responding to a prompt is not obvious. One might look for a setting in the Control Panel, or perhaps under Properties for the OneDrive folder, or as as a right-click option on the OneDrive folder. Actually, what you have to do is to right-click on one of the folders under the OneDrive, and select  "Choose which OneDrive folders to sync." From that, you can set them all. Hint: develop a plan for what you need to see on each machine and create folders to isolate what is automatically downloaded from what is not.

Workaround for Windows 10 permissions problem with OneDrive

I now have all six of my machines solidly working (rebooted several times) and OneDrive is running.

Here is the procedure:

• Go to each high-level folder with File Explorer where you are having problems (e.g. C:\Users\YourNameHere\Documents) and right-click, select Properties | Security | Advanced. Make sure the the "Enable inheritance" button is not showing. If it is, click it. Click OK.
• Go to the C:\Users folder and right-click. Select Properties | Sharing | Advanced sharing
• Click Permissions
• If you don’t see your own account listed, click Add.
• Type in your sign on account, and click OK.
• Then click the Full Control box and OK to close the dialog
• Go back to your Documents folder with File Explorer and verify that you now have your user account listed under Properties | Security.

I consider this is a workaround, an alternate way of providing the security you need that survives a reboot. Still, it’s not too evil and everything works.