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I'm actually kind of excited that you're doing that. I have been hoping to see a .omniplan of Napolean's Winter campaign into Russia or something like that.

Before I get to your issue I'd like to head off a performance problem. Before you start setting task far in the past, I recommend setting your project's start date. If you don't, OmniPlan will want to keep the start date in the Gantt view and in order to draw it, it will have to go back through 1000 years or so and figure out where all the weekends and non-working hours are and performance will be poor. Plans like yours are one reason we specifically don't default new tasks to "now" instead of the project start date.

The date formatter is not as clever as we might like. Though it's obvious to you and I that "1066" is intended to be a year, if your system date format is set to 2 year (System Preferences.app -> International tab -> Formats), that's really all it will be able to parse reliably. We'd like to add some brains to that, but in the meantime, the simple, user accessible solution is to customize your date format in system preferences and use a four year format.

That will change the date system-wide though, and you may prefer only to change it for OmniPlan. If that's the case, you'll want to open up a Terminal.app window and run this command:

defaults write com.omnigroup.OmniPlan AppleICUDateFormatStrings -dict-add 1 "M/d/yyyy"

I've tested that on Tiger (Mac OS 10.4), but Apple may have changed just how date formats are stored in your defaults database under Leopard (10.5), so let me know if you need help figuring that out.

-Tom