The story of Rip Van Winkle probably saved author Washington Irving from bankruptcy, but it was hardly original. The German folk tale Peter Klaus, Jewish equivalent about Honi M’agel, and Chinese legend of Ranka all hinge on unnaturally long periods of sleep, and the consequences of waking up years into the future.

For those who install the latest OS X updates within a few hours of release, it is a salutary experience upgrading the Macs of others in large leaps: in my case, five years ago I had to take a small network from OS X 10.3.x and Adobe CS up to a mixture of 10.5.8 and 10.6.3 with CS4. The job was simple – a word that so often seems to presage my tales of woe. I had next to no time to replace two working PowerPC iMacs with two new Intel models, and drag one of those old iMacs screaming and kicking up to Leopard, to play nice with the Snow Leopards.

To everyone else’s credit, much of it went seamlessly. Getting the three systems to print duplex to their original Lexmark printer was the unexpected nightmare, though. First the network admin’s claim, that I only had to plug the Macs in for them to work, proved illusory. Checking the old iMacs revealed that neither could find the purported DHCP server, so had self-assigned IP addresses, whilst the printer sat with an address dumbly set to 0.0.0.0. Of course the old systems happily chatted to it using AppleTalk, not an option any more.

I followed my own advice and set the Macs and printer to fixed IP addresses. Now applications started to print, the green light on the printer flashing enticingly, before aborting, paper untouched. The printer needed a Gateway address set, and plugging that in through its menu hierarchy enabled it to spit pages out whenever I instructed. Every application except InDesign CS4 was then happy to dance duplex, and completion seemed tantalisingly close.

Adobe’s peculiar aversion to standard print dialogs has long irritated me, and in the next hours it was to become maddening. Despite having a supported printer with a widely-used duplex option, Adobe’s own efforts at the print dialog did not even offer that option. If I ignored the dire warnings and dared enter the more usual print dialog (via the Printer… button), I could make up a double-sided print preset – which Adobe’s dialog silently ignored.

After a few minutes searching support sites, I stumbled across tirades of disappointed users who had suffered the same problem. My heart sank when some of them were still printing single-sided after trying every suggestion. Indeed, others just gave up and exported to PDF, resorting to Acrobat or Preview to talk more respectfully to their printers. Armed with suggestions, I went back to my little band of iMacs ready for the worst, having to explain to their users how the huge improvements in CS4 did not quite reach the problem of printing prudently.

My final battle with InDesign CS4 opened with a quick tweak in CUPS to make the Lexmark printer default to duplex, but this made no impression on the enemy. It was not until I changed the page size to read “Defined By Driver” that the duplex mechanism burst into action and my campaign was won. I was left struggling to get my head around how setting a page size to be that defined by the driver could possibly be synonymous with ‘duplex’.

My Rip Van Winkles were ready to waken, and to be handed back to their users.

Updated from the original, which was first published in MacUser volume 26 issue 16, 2010.