Less than 24 hours before I attended Microsoft’s Windows Server 8 Reviewers Workshop, in which Microsoft allowed several journalists to be some of the first non-Microsoft employees to see what Windows 8 server and desktop will deliver, I gave some serious thought to how the new Windows OSs could be a success—before I was influenced by seeing what Microsoft has actually done. Here, in no particular order, is my pre-preview wish list:

1. Help us with passwords. As a security guy, I help IT staffs struggle with what is probably the biggest security problem in the computer world: the passwords that users choose. No user enjoys being preached at by the local IT geek, so I’ve always liked systems that offer an opinion on the effectiveness of your password whenever you create or change one. For example, Google’s password evaluator is terrific—but whatever Microsoft might offer needn’t be anywhere near that good and it could still be of great benefit. A simple check against the 400,000-ish words in the English language would take any modern computer no more than a second. Add a length check, perhaps with some simple comment such as, “Hey, that’s a six-character password, and a PC like me could try every six-letter combination in X seconds; maybe add another character or two.” Toss in the 100 most common passwords (e.g., 1234, Fred, sex, secret, ncc1701,nascar, letmein, jesus) and instantantly we have A Safer Windows. (In case you’re wondering, my approach to finding a hard-to-crack, easy-to-remember password involves the notion known as “passphrases,” stringing together two or three words that have nothing to do with each other, such as “walnuthole.” Works great. Throw in a capital letter or a number and it’s even better, if slower to type.)

2. And speaking of passwords, I offer this second suggestion with tongue only partially in cheek. Now that I’m using longer passwords, it’s getting harder to type the blasted things, because I can’t see what I’m typing, so it. It would be great if all standard Windows logon dialog boxes had a “trust me, Windows, there’s nobody else in the room, please show me what I’m typing” check box. Of course, a network’s admins should be able to block that feature via Group Policy.

3. Tempt me into the cloud. One thing that could really equalize the dew point and atmospheric temperature for cloudnostics like me would be good, cheap, reliable, amazingly-easily-accessed cloud storage. Over the years, DOS, Windows, and now the Windows NT family have quietly expanded the meaning of letter/colon combinations, such as T:, from its original meaning—a floppy disk drive, in DOS 1.0—to a broader meaning (floppy disk or hard disk, in DOS 2.0)—and so on to its current state, where T: might refer to a floppy disk, a Blu-ray drive, an attached virtual hard drive (VHD) file, an iSCSI LUN, a network share, and probably one or two things I’ve forgotten. Give me an interface to cloud storage that uses Windows Explorer, not Internet Explorer. Remember that I don’t live in the Seattle area, and that I therefore sometimes spend as much as an hour at a time not connected to the Internet (honest, Microsoft, such things do happen)—so give me a smart caching system that I don’t notice working and that doesn’t annoy me, which means that it can’t contain any code from Offline Files. (Sorry about that, Offline Files folks. I really want to like it, but it drives me crazy.)

4. Put DiG into the OS. DiG, the Domain Internet Groper, is a DNS troubleshooting tool that beats the pants off Nslookup, the DNS troubleshooting tool that Windows has included since it started supporting TCP/IP back in the Windows for Workgroups 3.11 “Wolverine” days. And heck, as long as we’re talking about raising the quality of the built-in tools, you guys bought Russinovich and Cogswell 5 years ago—isn’t it time to replace Task Manager with Sysinternals’ far-superior Process Explorer?

5. Take off the speed limiters and training wheels, and let boot-from-VHD fly. Windows 7 and R2’s ability to let you package a Windows image as a single VHD file and then boot a physical machine from that file is way cool—and trust me, Microsoft, I’m the guy who’d know, because I’ve done a lot of work with it. But you won’t support the one-VHD-PC scenario or the boot-Windows-from-VHD-on-a-USB-stick scenario, requiring users to use boot-from-VHD only as a second copy of the OS, which is sort of an uncommon situation. Oh, and while you’re at it, could you tweak the code that enables differencing disks? (Differencing disks—which I’ve discussed at length in my regular “Windows Power Tools” column—provides a neat way to bring the convenience of virtual machine “snapshots” to a physical Windows system, and enabled the Steadier State tool that I give away.) When doing a boot-from-VHD scenario from a child VHD, the current Windows code wastes a lot of time every boot cycle by blowing the child VHD up to its maximum size—which also inflates the physical hard disk requirements. Windows 7/R2’s VHD support was a great first step. Let Windows 8’s be even better.

6. Let me configure how Network Awareness works. The idea is a good one: Set things up so that your PC knows where you are, which lets you tell Windows to automatically reconfigure it in different locations. For example, I spend much of my time in one of two locations—my office in Virginia or my office in North Carolina. If my PC were better able to discern which network it was connected to at the moment, I’d like (to offer a simple example) my wired NIC to have one static IP address when in Virginia and a different static address in North Carolina, and I’d like the PC’s default printer to change depending on whether the PC is in Virginia or NC. Some of that capability currently exists in Windows 7, but it’s not really reliable, nor is it well-documented enough for me to get much traction in troubleshooting it. If I could tell Network Awareness, “Just pay attention to the MAC address of your default gateway—if it’s X, you’re in Virginia, and if it’s Y, you’re in NC.” Or, in other cases, I might say, “If your current DNS suffix is X, you’re in Virginia,” and so on. Again, Network Awareness is a great idea, but make it more configurable, and extend what I can do with it.

7. Reduce my reboots. I recently needed to create a clean, freshly-built Windows 7 image. I started from the Windows 7 DVD Setup disk that already includes Service Pack 1 and thought, “Hey, I’m about done”—but nothing could have been further from the truth. It took six reboots’ worth of patches before Windows Update finally shut up. In other words, in late August 2011, I installed a new-in-February-2011 OS, and I still needed about one reboot a month to get current— which certainly isn’t a recipe for four nines of reliability. You’ve been promising us a “more modularized” Windows for quite a while, so please finish the job so we can patch without reboots. (And you’ll notice that I haven’t mentioned that Linux has been doing this for the past 15 years or so. Haven’t mentioned it at all.)

8. Astonish me, Microsoft. At least once. C’mon, you can do it. When you folks lifted the veil on Windows Vista, we saw a lot of amazing stuff. A new TCP stack that understands how to get the most out of big pipes and big, slow pipes. Well thought-out, secure volume encryption. Transaction-based NTFS and registry operations. A new kind of anti-rootkit file permissions, Windows Integrity Levels. (OK, so not all of the amazing stuff turned out to be useful or a good idea, but it was still amazing nonetheless.) Sure, Vista was a marketing disaster, but it introduced the vast majority of the “new features” that supposedly appeared in Windows 7 and R2. Think of it this way: On October 25, 2011, XP will turn 10—and I’d be willing to bet that XP still sits on the majority of Windows desktops. But why? Because buyers don’t see any gotta-have-it-ness. They didn’t see it in Vista (I only did because I’m an OS geek), they didn’t see it in Windows Server 2008 for quite some time, and many still don’t see it in Windows 7. Why on earth, then, release yet another version of Windows for people to ignore? Hence: Astonish us.

Now that I’ve actually seen Windows 8 in action, I definitely have some feedback for Microsoft. Stay tuned to see what I thought of the newest Windows OSs.