How to install Vista Upgrade editions in Parallels

Installing MS Win­dows Vista into Par­al­lels is a bit of a chore if you’ve only got an upgrade edi­tions of the soft­ware. This how-to tells you the steps in order to make it work.

First­ly, make an image of your Vista DVD. This will make the install run much faster, and you’ll need to be doing two of those. Insert the vista DVD, then in Disk Util­i­ty, select the DVD UDF Vol­ume and press “New Image”. Call it Vista, save it to the desk­top, and change the image type to “DVD/CD Mas­ter”

Once that fin­ish­es, it’s time to pow­er up Par­al­lels. Make sure you’re run­ning at least Release Can­di­date 1 — down­load it from the Par­al­lels web­site if not. Cre­ate a new VM and select “Cus­tom”. On the next page, make sure the OS ver­sion is set to Win­dows Vista. Leave the mem­o­ry, hard disk set­tings and the net­work set­tings alone. Name the Vir­tu­al Machine (or again just accept the default).

On the next page, where you’re asked to insert the instal­la­tion CD, open up “More Options”, select “ISO Image” and press “Choose” to select the image cre­at­ed ear­li­er — saved to your desk­top. Press “Fin­ish” to begin the Vista instal­la­tion.

Well, actu­al­ly, your first Vista instal­la­tion. Because we’ll be doing two here. The trick is that we don’t enter your licence key the first time around, thus fool­ing Vista into installing. Unlike XP upgrades, which just need­ed a look at a CD or a pre­vi­ous instal­la­tion to pro­ceed, licenced Vista won’t install unless it’s being installed over the top of a pre­vi­ous OS. Luck­i­ly, “pre­vi­ous OS” includes unli­censed Vista!

Start the instal­la­tion going. The first thing it will ask you is your inter­na­tion­al set­tings. Set them as appro­pri­ate. Click onto the next page, then click “Install Now”. On the fol­low­ing page, it will ask for your prod­uct key. Do not type in your prod­uct key — instead, press “Next”, say “No” to the fol­low­ing dia­log box, then on the next page choose the ver­sion of Vista you’re installing.

(I have no idea what the dif­fer­ence between, say, Busi­ness and Busi­nessN is — can some­one enlight­en me? I just chose from the non‑N ones.)

Tick the box on that page, press Next, accept the licence terms, press Next. On the fol­low­ing screen the type of instal­la­tion will be set to “Cus­tom”. That’s fine. Press Next to choose where to install it, the default is fine so press Next again.

At this point the instal­la­tion of Vista will start. The VM will reboot sev­er­al times — just let it do so. Instal­la­tion will run to com­ple­tion just fine, go away for 30 min­utes.

(time pass­es)

Choose a user­name and on the next page, a com­put­er name. These aren’t vital but you’ll need to remem­ber the user­name for the next 30 min­utes. Then, on the secu­ri­ty updates page, select “Ask me lat­er” — one of the cur­rent Vista updates breaks Par­al­lels, and we don’t want that to hap­pen. Final­ly, set your time­zone, then press “Start”.

Vista will then check the VM’s per­for­mance, then start up. Con­grat­u­la­tions, it’s installed. Log in, and

Do not install Par­al­lels Tools right now. It will cause you pain lat­er.

Now we’re going to do all of this over again, this time with a licence key.

From the Start Menu, choose Com­put­er, then dou­ble-click on the DVD dri­ve. Dou­ble-click on Set­up. Allow the pro­gram to run. Click on “Install now”.

On the next screen, don’t get the lat­est updates for instal­la­tion at this time, because it might crash Par­al­lels. On the next screen, enter your prod­uct key. Accept the license, as before.

On the fol­low­ing screen, again click on “Cus­tom” for type of instal­la­tion. Accept the default for the instal­la­tion disk, as before, then click “OK” in the dia­log box.

Instal­la­tion will then start. Anoth­er 30 min­utes here.

(time pass­es, again)

This time, when asked for a user­name and com­put­er name, choose ones you wish to stick with as this is final. Choose “Ask me lat­er” for the secu­ri­ty updates, then set the time­zone as before.

Vista will again check per­for­mance, then start.

That’s it. We’re done. Just tidy-up to do now.

First­ly, install Par­al­lel Tools from the Mac “Action” menu. This will give prop­er inte­gra­tion between your Mac and the Vista VM. It’ll need a reboot. After that, nav­i­gate from “Com­put­er” on the Start Menu to your hard disk, then delete the “windows.old” direc­to­ry. That was the ini­tial install.

Now, from the Mac’s “Action” menu, run the Par­al­lels Disk Com­pres­sor, in order to neat­en up the VM’s hard disk. This takes a while. But once it’s done:

Con­grat­u­la­tions. You have a per­fect­ly fresh work­ing installed copy of Vista, from a Vista Upgrade CD, in a Par­al­lels VM.

Now go and enjoy before Par­al­lels bring out a new ver­sion, forc­ing this to become incor­rect and me to write out a cor­rect­ed ver­sion.