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The ability to Print to File is disabled in the ArcMap Print dialog box.
Print to file is only enabled when the 'Use Printer Paper Settings' option is checked on in the Page and Print Setup dialog box.
At ArcGIS Desktop 9.2, the ability to print to file is enabled whenever the settings result in one page, for example, a tiled print with only one page set to print.
Set the layout page to use the printer paper settings, which locks the layout page to the paper size of the currently selected printer.