I want to a buy a new drive for my laptop (eMachines eME725-4520, Pentium Dual Core Processor T4400 & Windows 7 Home Premium - I bought it 8 years ago). I've filled the original (250 GB). It came with Windoze, which I kept because it was necessary to use the warranty (long expired). Unfortunately I have to use it still when I connect wirelessly from UNM (I can connect with a wire, but that's available in few spots).

If I clone the drive with dd will it be Windoze-bootable?

As long as you don't try to boot with both connected at the same after the cloning is completed, and the new has at least as many accessible sectors on it as the original, it should be bootable no matter what was installed on it. With DD, every partition and filesystem on the clone gets the same UUID, and same volume label, if any, as it had on the original.

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Be careful there also tends to be an issue with the type partition table in use. Windows uses the msdos partition table. These partition carry over the 'bootable' flag. If you're going to do it like this then it's best to use an identical drive which effectively means cloning. In any case if you get a bigger drive you'll then want to resize the NTFS partition after dd which I'm not sure NTFS supports. This can all fairly easily be done under LVM however.

You may want to simply backup your data and reinstall Windoze fresh onto the new drive.

I can't believe you want to use Windows just to connect wirelessly... It has to be a Linux driver that works for a 8 years laptop model, no?

What he said. Fix the problem, not the symptom.
For this laptop when I did similar, I used the Win7 backup tool to create a system image and simply re-installed using that onto bigger partitions. The linux side was simple - and a damn sight quicker.
No problems, no angst.

If it all goes down the toilet, simply reinstall the old disk and figure out what went wrong.

I connect wirelessly all sorts of places. To connect at UNM I have to accept UNM's conditions. I get the opportunity on my first attempt to connect when I use a browser that supports Javascript. In Windoze this works. In Linux both Firefox & Opera report that they can't resolve the address (in lynx I get sent to UNM's 'your browser doesn't support Javascript' page - but the address is resolved). After I connect in Windoze, I can reboot then connect in Linux (as long as I don't change my MAC). I submitted a query on these fora years ago but never resolved it.

You say I can't use dd? That's what I expected; I hoped to get off easy. I made a backup when I bought it - good thing as the burner no longer works.

You CAN use dd which will make an exact copy of the disk(space allowing). The problem is then that if you leave both disks in the machine, Windows will likely get confused as to which to use and cause problems.

I do exactly this and just remove the second disk and keep it as a backup. I work in a very dirty environment- both physically and electronically and it is handy to be able to just do a quick disk swap when the first one gets corrupted - the disks are seldom physically damaged. I do a backup overnight so at most a day's work gets lost.

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Curious, what sort of application is this?

Hands! My laptop has two bootable dive bays

Good. I have only 1 drive bay. Thanks.