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Ever since I have upgraded to OS9 (9.04) I can't get the Print Window command to print all of a folder's content. It works if there are only a few items in the folder, but once it hits a certain amount it stops. In OS8 (any version and lower) if you Print Window it printed the the whole content list inside the selected folder.
I'm doubting it's a bug. Although I've got 9.1 on my home machines, I work often on someone else's B&W G3 with 9.04 installed and use the print window feature regularly to print CD contents, sometimes over 60 items ... 2 pages.
Although the Finder's 'Print Window...' command can sometimes work well in Mac OS 9.0.x (as bluebean pointed out above), it does occasionally fail to print all contained items. This is a known issue which can occur even under Mac OS 8.5.x and 8.6, particularly in large-icon views.