Much of this is probably obvious, but I'm writing this mainly for other Win/OS X file transfer newbies and my future self.

I got a new hard disk drive (500 GB) yesterday, to use as external FireWire/USB drive with my MacBook.

I transferred about 100 GBs of data from my old NTFS-formatted external HDD to a computer running Windows, because that computer had loads of free space. Then I put the new HDD in the enclosure.

All that remained was a simple matter of transferring the data from Windows to my new HDD – or so I thought.

MacDrive

OS X can read but not write NTFS. Both OS X and Windows can read and write FAT32, but it limits file sizes to a maximum of 4 GB. OS X prefers HFS+, but Windows cannot read or write that without e.g. MacDrive.

I formatted the drive with HFS+ and installed the MacDrive trial under Windows. Things went well initially, but after a while I got a Blue Screen of Death (IRQL_NOT_LESS_THAN_OR_EQUAL). This fouled up the file system, so the disk had to be reformatted. Good thing I didn't have anything else on the new drive.

I tried again, after uninstalling Daemon Tools and the SPTD driver since they are apparently in conflict with MacDrive. Still got a BSOD and had to reformat.

At this point, I considered FAT32, but it seemed silly to use an ancient file system just for one transfer from Windows, and more importantly because backup archives could go way above 4 GB.

SMB

Instead, I set up a FireWire network between the Windows computer and my MacBook, connected the HDD to the MacBook through USB, shared the folder in question on the network and mounted it in OS X.

Then I tried to drag-and-drop files from the mounted folder to the HDD. This turned the Finder very sluggish, when it did not stall completely. When I finally got the transfer started, the estimated time until completion was something like 27 days for my 40 MBs of test data.

FTP to the rescue

I activated the OS X FTP server (in the Sharing prefpane), connected from a Windows FTP client (I like FileZilla) using the Mac's IP address and my OS X account name and password, and proceeded to transfer the files to /Volumes/Axolotl – the name of the HDD.

One gotcha I encountered was that Windows and OS X aren't quite agreed on what constitutes an acceptable filename, so FileZilla failed with some files, and I had to rename them in batch and transfer anew.

Using Renamer, I replaced occurrences of :åäöÅÄÖ and various other umlauted or accented characters with something more acceptable (e.g. --, aa, …). Not that OS X minds diacritics, but FileZilla had problems transferring them – perhaps something to do with encodings. For some directories with too many weird characters to replace even in batch (e.g. early Björk albums), I created RAR archives and transferred those.

At one point, FileZilla crashed, and the error log made mention of Norton Antivirus, so I uninstalled the latter – an application that does not offer a "Quit" option deserves no better.

Aside from those issues, FTP transfer seems like the way to go. It's reasonably fast, though not insanely so. I average something like 4 MB/s. Speeds would perhaps be higher if the computers networked through Ethernet and if the HDD were connected through FireWire (as opposed to USB), but I didn't have the cables for it.