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Windows 7 Upgrade Paths: Tread Carefully

Today's column isn't my review of Microsoft's Windows 7, but it's a necessary precursor. Unless you'll buy a brand-new PC to get Windows Vista's replacement, you first need some idea of how easy it might be to install this on your own PC.


As you can read in the piece, I think most Windows Vista owners should have a relatively smooth upgrade, while a minority of Vista owners -- along with everybody running Windows XP -- will have a much more difficult path to 7. But I'm also afraid that a small minority of users will see their attempts to upgrade to 7 go catastrophically wrong for no good reason at all -- just because Windows can be like that sometimes.

I didn't have room in the column to go into detail about some parts of the Windows 7 upgrade process, but that's what this blog is for ...

* Windows Easy Transfer: Microsoft shipped an earlier version of this program to help people with the move from older editions of Windows to Vista. This update looks considerably more capable -- if only Win 7's backup program offered such a clear list of what types of application-specific files and settings it covered -- but editing its default listings requires navigating a nested array of files and folders that Windows usually hides from view. In other words, this isn't anything remotely comparable to Apple's Migration Assistant and "Archive and Install" option.

(Note that if Easy Transfer misses something, you can look for that file in the "Windows.old" folder that Win 7's installer will leave on the hard drive after a custom install.)

The Windows 7 release-candidate build's installer didn't offer enough help getting to the Easy Transfer tool, either. When I started loading Win 7 on that old Dell laptop, the installer suggested that I run it -- but linked me to a tech-support file on Microsoft's site with instructions on how to navigate to the "migwiz.exe" application on the DVD instead of just opening the program for me.

* Hardware support in a custom install: I knew that a custom install -- the "nuke the site from orbit" option -- would wipe out all the existing applications on the computer. But I didn't realize what kind of trouble it could cause with the machine's hardware, too. To not have sound working on the computer brought me back to the worst days of Windows 3.1. To not have Ethernet, the simplest possible form of network connectivity ... that was absurd. (And yet WiFi worked.)

Yes, this laptop (a Dell Inspiron 600M) was five years old, but it's not like it had any particularly unusual hardware onboard. Had I installed any new version of Linux, I'm sure I would have had more use of the laptop out of the box. And I wouldn't have paid anything for it.

Bear in mind, I don't think staying on XP is that great of an option, either.

* Other upgrade paths: Microsoft shipped four versions of Windows Vista in the United States alone (Home Basic, Home Premium, Business and Ultimate) and it will ship three of 7 here (Home Premium, Professional and Ultimate). Oh, and each version comes in 32- and 64-bit editions, too -- although at least Windows 7, unlike Vista, will include both flavors in every box.

That makes for a lot of possible upgrade scenarios, not all pleasant. Microsoft's attempt to outline them all -- a chart it provided to the Wall Street Journal's Walt Mossberg -- overstates the complexity of this situation by including some improbable upgrade scenarios. For example, ZDNet writer Ed Bott was able to condense that information into a much more compact graphic.

But in both charts, there are too many scenarios that involve a custom destructive install. It says nothing good about Microsoft's operating-system foundation that it's too fragile to permit an in-place upgrade in those situations.

I'm nowhere near done covering Windows 7. What else would you like to know about it? Post your thoughts in the comments ...

By Rob Pegoraro  |  August 14, 2009; 12:11 PM ET
Categories:  Windows  
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It's going to have to release some fixes to smooth the transition from XP, isn't it? Millions of us still use XP.

Posted by: tomtildrum | August 14, 2009 12:53 PM | Report abuse

OS upgrades on operational machines is a foolish thing to do anymore.

XP machines that work quite fine today, may not be as spiffy as the new Windows, but the hassles/pitfalls etc of putting a new OS on doesn't make it worthwhile.

A new machine really doesn't cost that much. The best strategy is to wait. MS can roll out the new Windows, it'll have teething problems (like any software), and within a year or so it'll be smoothed out. THEN buy a new machine.

Until then, I'm riding my XP until it stops working.

Posted by: kolbkl | August 14, 2009 1:44 PM | Report abuse

This is such a non-story that Mossberg and now Pegararo are blowing up into a much bigger issue than it ever will be for most people. The number of people who ever upgrade their computers to a new OS is minuscule. I don't know any "average" computer users among my family and friends who have ever desired to upgrade their OS. Their upgrade path is a new computer.

Microsoft's own numbers suggest that retail boxes are no more than about 5% of Windows sales. And I guarantee that the vast majority of that 5% are computer savvy people like me who have adequate backups and are familiar with doing fresh Windows installs anyway.

I know it's fashionable to bash Microsoft but suggesting that this is going to be a problem for the "average consumers" who you claim your column is aimed at is disingenuous and hyperbolic.

Posted by: scarper86 | August 14, 2009 2:56 PM | Report abuse


I thought I had read that those who upgrade from XP will require a clean install of 7. Does this mean that I can install a new hard drive in my existing XP machine, put a clean install of 7 on this new drive, then be able to dual boot the machine into whichever OS I want? Then I can migrate to 7 at my own pace (and if there are any critical issues, like ethernet not working, it wouldn't stall me from using this machine completely).


Posted by: ssolomo | August 14, 2009 3:35 PM | Report abuse

@ scarper86: I agree wholeheartedly with your comment. VERY few people will do an in place upgrade to Windows 7. Even if someone buys a retail copy, most will use a clean install.

I'm afraid Rob has become a bit more biased in his Windows reviews. Passing strange, that. Gee, it's only used by 90+% of the world tech population. Catering to a vocal minority leads down the road to olivion

Posted by: slummo | August 14, 2009 5:52 PM | Report abuse

Should read oblivion. Typo time.

Posted by: slummo | August 14, 2009 5:54 PM | Report abuse

Scarper and Slummo:
I gotta agree with RobP on this one. It would SURE BE NICE if, given the disaster that is Vista, we COULD do a trouble-free in-place install of Win7, instead of having to back up everything and then reinstall all of our software from scratch. I have better ways to spend a week. Reconfiguring several internet browsers would probably take an hour by itself.

Just because the clean machine is the best technical approach doesn't mean it SHOULD be the best approach.

Given the enterprise's big thumbs down (or perhaps thumb in the eye) to Vista, I would bet you dollars to donuts that most Vista USERS (as opposed to Vista licenses which were then downgraded to XP) are retail and not corporate. We know that Microsoft lies about Vista uptake.

Posted by: 54Stratocaster | August 14, 2009 10:24 PM | Report abuse

Join the Microsoft Boycott Campaign at:

and send Bill Gates a message in the only language he understands... money!

Posted by: Ricardo3 | August 15, 2009 1:20 AM | Report abuse

@kolbk: I predict there are going to be VERY few teething pains with Win 7 because it's basically an advanced service pack to Vista, and as such has been having the kinks worked out for several years. Moreover, the beta testing of Win 7 has been extensive, most drivers are the same as those in Vista, etc. Win 7 should be ready for prime time from day one.

Posted by: jfw9 | August 15, 2009 5:17 AM | Report abuse

Best upgrade path: get a Mac!!

Posted by: sayNo2MS | August 15, 2009 6:32 AM | Report abuse

I have done this upgrade on nearly 30 machines. The REASON to do the upgrade is simple: if the machine with the printers etc is an XP or Vista machine your new machines will have a very hard time accessing the printers etc. (There is a complex work around but the upgrade is easier.)

What does go wrong falls into four patterns:

1) Sound It turns out that many motherboards with built in sound have chips which are inconsistant with the Win 7 AC '97 driver. The solution is to find other drivers.

2) Ethernet. Similar issue.

3) Freezing. If the windows 7 installation freezes midway you need to reformat the hard drive. Other attempts to install will simply freeze later in the process. If you gte Windows 7 installed and then it starts freezing the problem is the power monitor on the motherboard. Switch the power plan setting to performance and the freezing will stop.

4) Programs will not install. If the program is critical to you, this can be a serious issue. The problem usually is one of permissions and compatability. The .exe file or .msi file needs to be run as administrator and the entire folder needs to have "read only" unchecked.

Posted by: lissack | August 15, 2009 7:28 AM | Report abuse

Scarper and Slummom - Strat is right. You two sound like you're straight from Redmond. Sounds like y'all don't realize the economy isn't doing so well and most people won't want to buy a new computer just so version one of Windows 7 can work.

The people who know what they're doing in computing and want to stay with Microsoft taking one very intelligent step - they're going to wait at least a year and the first SP's are released. It's idiocy to buy an initial release on any new OS, although Apple seems to have the better model.

Posted by: Leofwine | August 15, 2009 8:12 AM | Report abuse

Many elderly people became functionally adept with XP and were annoyed with, even angered by Vista. Among the frustrations were Microsoft's virtual decree that at least some, older, still useful printers would no longer work. Personally, having converted to Ubuntu, I feel little sympathy for MS's need to chronically roll out "new" OSs as a way to sustain cash flow in support of a bloated work force that offers virus-prone software in the name of pseudo-innovation.

Posted by: TeresaBinstock | August 15, 2009 8:43 AM | Report abuse

The scoundrel Billion Gates should be hung up by his thumbs for spending our $ 50 billion on Third World nations instead of fixing the software. I would like to whack him with a stick like a piƱata while he's hanging there, and try to get some answers out of him, while playing the Windows XP install music.

Posted by: washpost35 | August 15, 2009 9:10 AM | Report abuse

Next month, Apple will release "Snow Leopard" an upgrade to the current 10.5 OS on the Mac. I have upgraded from 10.4 to 10.5 and will do 10.6. Previous upgrades have taken 45 minutes with no hassles and all software and hardware intact.

All for $29.

What is wrong with this picture?

Posted by: Keenobserver | August 15, 2009 11:35 AM | Report abuse

I've been using Win 7 since the beta came out. I build my own desktops and did a clean install on a good machine. I did it on a separate HD so I could dual boot XP. I hardly ever used the XP. I dl'd the RC a month or so ago and used the easy transfer for backup before again doing a clean install. I've been using XP for years and I still have it on a couple of machines, never went to Vista. I like the speed and feel of 7 and have pre-ordered Pro. I bought a laptop 2 wks ago w/Vista and a free upgrade to 7. I have an Epson printer that still does not have a Vista driver, but it works with 7. The only problem I've had is with anti-virus programs. McAfee had numerous problems and Kaspersky will sometimes kill the computer while doing a auto scan. But everything is still in pre-release mode so I'm not surprised.

Posted by: jimbo1949 | August 15, 2009 11:56 AM | Report abuse

I'm surprised that anyone who knows how to do a clean install would even consider doing an upgrade in place.

I'm going to do a clean install having backed up everything to an external HD. That way any and all traces of Vista ickiness get zapped, right? Why gamble on having vestigial remnants of it running around in the machine just waiting for an opportunity to strike when Windows 7 misses something?

Stratocaster you mentioned "Reconfiguring several internet browsers would probably take an hour by itself."

So? That's what commercial breaks in Redskins games are for. Once 7's installation is done, download Firefox 3.5.whatever, and drop in your backed up settings. Much better that way than having a teen horror movie monster that you thought was dead buried in your computer.

Note: it's best to mute Terry Bradshaw while doing something like this.

Posted by: Georgetwoner | August 15, 2009 12:35 PM | Report abuse

Using Win7 on VMWare on MacBookPro... printers, bluetooth, work fine.

Posted by: kkrimmer | August 15, 2009 1:05 PM | Report abuse

My first PC was a Zenith laptop with a b&w screen. I used PC's, mostly Dells, for decades. Recently got hammered with trojans despite having full Norton antivirus, various pro firewalls, etc.

Bought a Mac. Took me three days to learn how to use it, customize it, and transfer everything over. Won't go back.

Posted by: thranx | August 15, 2009 1:23 PM | Report abuse

I love how people think more firewalls will block viruses...
Anyways, I use Windows and love it, but the windows easy transfer is joke. Not just because it's really poorly coded, but because it is falsely advertised as a easy way to transfer your older files to your new computer, without really telling you what it's doing. The windows easy transfer for the vista upgrade was a joke, and I am thinking it will be the same way for 7.

Posted by: BMACattack | August 15, 2009 2:49 PM | Report abuse

Strat and Leofwine are right. The Windows-philes posting here probably work for MicroSoft. There is no reason in the world for anyone who bought Vista to have to pay for what is essentially a service pack, much less have to do a clean install to make it work. After one year of Vista on a brand new notebook, I went out and got a MacBook. With Office for Mac (a poor substitute for iWorks), I can work seamlessly with my less-fortunate colleagues who are still trapped in MSHell.

Thranx is right. I have used everything from a Radio Shack TRS-80 to several models of Compac, Dell, and HP with versions of Windows ranging from 3.1 to Vista. Nothing works as fast, reliably, and easily as a Mac. And yes, you can transfer and use all your Windows files on it. You can even install Windows and run your Windows apps on it if you want, but once you use OS 10 you won't want to.

Posted by: hisroc | August 15, 2009 3:40 PM | Report abuse

Having used both Windows machines and Macs, there is no question in my mind that Apple provides a far smoother approach to upgrading hardware:

1. Connect old Mac to new Mac with firewire cable.
2. Turn on old Mac while holding down "T".
3. Turn on new Mac.
4. Initiate account transfer.
5. Come back in a couple of hours to start work on the new Mac with all applications, documents, and drivers in place.

I've done this three times between different machines and three versions of MacOS. The latest migration a few weeks ago was from a 2001 iMac to a 2005 eMac for my dad. Each time the process has worked without a hitch, with the exception of an old application that requires me to re-enter a registration number.

Posted by: PaKo7 | August 15, 2009 3:59 PM | Report abuse

Thanks to Rob Pegoraro for helpful advice. We're a Windows-based software company and don't use Vista internally for anything but a test environment. Too many problems and low performance. So we won't plan on trying to upgrade XP Pro on nearly all our machines. If you can't do an automatic upgrade and keep applications running, all the handwork is not financially sound.

After SP2 came out, XP became an effective environment for business and professional users. Machines from the last few years have plenty of capacity for those markets, and they will continue in use for many more years. We hope Win7 does solve the problems with Vista but will now plan on getting it only when we buy new machines.

Posted by: AppDev | August 15, 2009 4:16 PM | Report abuse

One solution would be a dual-boot system, with Windows 7 on one hard drive, and XP on another. Here's a neat little 3.5" bay device that will allow you to select which hard drive to boot up:

Posted by: Ricardo3 | August 15, 2009 4:54 PM | Report abuse

One big issue with a clean install is what to do with installed software on your current XP machine. Older apps either won't work, or you've long since lost the CD.

However, if you have an external drive big enough to backup all your data, you can use Norton Ghost and VMWare Workstation to create a virtual machine copy of your XP machine and bring it back inside Windows 7. I'm working on this now for my PC which I just rebuilt with new hardware and Windows 7.

I realize this isn't for everyone, but a mention of ideas like this would be nice to see in the tech press.

Posted by: john65001 | August 15, 2009 5:58 PM | Report abuse

"I know it's fashionable to bash Microsoft..."

The main trouble with OS debates is that valid technical criticism is automatically seen as "bashing."

Posted by: jamshark70 | August 15, 2009 6:55 PM | Report abuse

Hey Rob, try installing Apple's Leopard OS on a 5 year old Mac laptop - IT WILL NOT INSTALL - this is not a Apple Vs MS issue. You should know that but unfortenately you are too Mac biased rather than reporting facts!!!

Posted by: SammyB1 | August 15, 2009 9:07 PM | Report abuse


you should take this opportunity to tell people it's time to move past 32 bit windows. If they're going to take the trouble to upgrade their computer, go 64 bit Windows 7.

If you're looking for a new computer, insist on Windows 7 64 bit.

You'll do everyone, including Microsoft, a big favor by getting rid of 32 bit versions. They're slower and less capable than the 64 bit versions.

Posted by: Ombudsman1 | August 15, 2009 9:56 PM | Report abuse

I have a lot of old software that runs fine on Windows XP. My next laptop will probably have Windows 7 installed. I'd like to know how my old software will run on the Windows 7 XP compatibility mode, if it does not run on full-blown Windows 7. Doesn't have to run fast. Just has to run.

Also, can just certain software use the XP compatibility mode, or does the whole computer somehow get shifted to that mode for as long as it is running? What, exactly, is it?

Posted by: Bitter_Bill | August 15, 2009 10:04 PM | Report abuse

Curious. I have not been able to glean the answer to this from "the chart"...

Currently running Vista Ultimate. Looking to upgrade to Win7Pro.

As far as I can tell, the only difference will be the lack of BitLocker in Win7Pro, which I do not use in Vista Ult.

Any issues or problems with that upgrade that you know of?

Posted by: aart12 | August 16, 2009 12:07 PM | Report abuse

I don't usually bother with these small web discussions attached to a story from a newspaper off their website. But after being involved on and off with the discussion about Win 7 beta on the techie computer boards (like arstechnica) and having read Mr. Pegararo's article, I've about had enough. As a subscriber and reader of the Post, for better than three decades, they have made numerous changes to save money in these hard time for the newspaper business, I don't like them, but they are understandable. I suggest they can save a bit more by just eliminating the computer/tech reporting in their paper. Mr. Pegararo can fish for a job in Cupertino, CA. where he can receive his payments from Apple directly, instead of behind the scenes.

When will the Post, offer a computer/tech column for the 90% of us who use Windows and Windows based products? Currently, what is offered as computer information and analysis, is nothing more than fan boys service (if not worshipfication) to all things Apple. If you read Rob and Rob only, you'd wonder how websites like macfixit or moab (Month Of Apple Bugs) could possibly exist (not to mention others) it what always seems to be the world's most perfect product from a small mom & pop shop run of a garage in suburban California? There are actually enough users of Apple products who have problems, to warrant those type of websites? If you read the post, you wouldn't think so.

So that's it, IMO Pegararo's column is at best an anachronism and at worst, just one more example of Apple's RDF of which most Mac users fall under the spell. So here's one last thing in the Post I have to take the time to read. And now the clock ticks further on to see what comes first, the Post closing its doors or me ending my subscription for a paper which has more and more has less and less articles for me to take the time to read?

Posted by: member8 | August 16, 2009 1:06 PM | Report abuse

After no unusual problems running the Win7 beta or RC, I reverted to Vista to upgrade to the RTM version. I would have done a clean install except for the OEM edition of Office 2007 that would have been lost.

Quite a few problems surfaced immediately. Random permissions problems across the root drive and other local partitions that prevented programs from accessing or modifying their own configuration files, not limited to Windows components and some desktop gadgets.

After deauthorizing and reauthorizing a new install of iTunes I'm now stuck in an infinite already authorized/not authorized loop that means it wants to delete all my iPhone apps.

Family Tree Maker 2008 just crashes, even run as an admin and in compatibility mode.

Live Messenger refuses to accept any profile images.

Multiple uninstall/reboot/reinstall cycles of these programs has not helped.

Posted by: memew | August 16, 2009 10:48 PM | Report abuse

Comments on your comments...

@kolbkl @scarper86 @slummo Are you all saying that it's OK to have an OS that's difficult to upgrade in place if most people don't bother with in-place upgrades? What if the difficulty of that upgrade path itself discourages people from attempting such a thing? (As evidence to the contrary, I'd like to introduce you to the in-place upgrade experiences of Mac OS X and Ubuntu Linux.)

@TeresaBinstock If old printer drivers don't work, I'd blame the authors of the printer drivers who couldn't be bothered to update their software. An OS developer should be allowed to improve its software at the potential cost of third-party compatibility... otherwise, we'd all still be running Windows 3.1 and Mac System 7.

@PaKo7 I wouldn't say the OS X Migration Assistant is quite that simple--you may have to copy over some files, such as desktop pictures, stored in /Library, and some applications require a reinstall from a disc or download--but it is worlds better than Windows Easy Transfer.

@SammyB1 If you think I don't call out Apple on its compatibility issues, you must be new to my work.

@Ombudsman1: Sorry, can't agree with you on that. I can't remember the last time a reader wrote in to praise the performance improvements made possible by x64 Windows. But I've gotten numerous complaints about x64-specific software and hardware incompatibilities. Microsoft and computer vendors have no business promoting 64-bit Windows releases to home users without much more specific compatibility warnings.

@Bitter_Bill: FYI, Win 7's XP Mode is only available in 7's Professional and Ultimate editions. But if your software's developers did their job, those programs should run in 7 on their own.

@aart12: Sorry, going from Vista Ultimate to Win 7 Pro requires a "custom install."

@member8: You're complaining that I don't focus on Windows in a comment on a blog post that is devoted almost solely to Windows? Funny logic you've got there. BTW, if you're going to critique me for inaccuracy, could you at least spell my name correctly? It's right at the top of this page and everything...

- RP

Posted by: Rob Pegoraro | August 17, 2009 1:29 PM | Report abuse

Dear Rob:

After being in fear of Vista, with all the bad PR it got, I was a solid VP believer!

Recently I bought a new Dell 15.4 inch cheapy notebook for $399. It came with Windows Vista Home Premium. The Dell gave me a Pentium Dual Core and 3GB RAM. Anyway, the Vista has been flawless! I really am enjoying it and have seen no problem. Granted, I do not get carried away with too many heavy programs ... but so far the Vista has been great and the Dell even better!!

Posted by: EZReader1 | August 17, 2009 8:51 PM | Report abuse


The thing is that it's a new OS, and not an 'upgrade'. It's not an increment (from 5.6 to 5.8, or 10.5 to 10.6). Windows 7 is a whole new beast, just like Vista, XP, etc were before that.

The process is more like brain surgery and not a true update. The axiom is "if it ain't broke, don't fix it" most people's machines fall into the "ain't broke" category, and therefore should not go through any OS upgrade process and just get the best OS available when they get a new machine.

You point out the (wonderous) Mac upgrades, but they're incremental upgrades (just new updated versions of linux piled up on each other), similar to security updates or service packs from MS. Those incremental updates from MS are relatively painless and invisible to the average user. If someone was running MAC's OS 9 (Apple's last ground up OS) it would be a PITA to upgrade to OSX, there'd be a lot of hair ripped out and software functionality lost.

My advice is just to never update to a whole new OS, just keep puttering along until you get a new machine. What's wrong with keeping functional machines functional?

Posted by: kolbkl | August 19, 2009 4:17 PM | Report abuse

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