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The file transfer utilities (PSCP and PSFTP) ought to handle really really big (>2Gb) files. There have been reports that they don't do so properly. (Apparently, on Windows, this will only be meaningful under an NT-series OS; the 95 series inherently can't handle more than 2Gb in any case.)
2004-04-27: One symptom we've had reported a lot recently is the error message "Assertion failed: actuallen <= len, file scp.c, line 1435" for files >2GB. As of the 2004-04-28 snapshot, there should be a fix which will make this go away (thanks to Krzysztof Kowalczyk), but we've not been able to test that; also note that the same error can still occur if files change in size. In any case files over 4GB are still not supported (and this would require some upheaval to fix).
2006-08-13: I (OSD) have checked in a pile of stuff which should allow large file support where possible. On Windows, this basically means NT and above.
Audit trail for this semi-bug.