Simple :-) The insurance goes from policy date to policy date so whatever your company's "start" date is is the start for that coming year. So, for example, if your company signed up with the agency that handles its insurance in July of last year, your deductible would be for July 2006 to July 2007. So, when July comes around again and you get a new card and they re-evaluate experience and raise how much it costs, etc. then you'll be on the "next" year, July 2007 to July 2008 which will be called the 2008 year. Or, it just might be from your hire date (December) to the next December, etc., ask your company HR person what the "year" months are.

That's how my company works (the July thing) and we had that exact same confusing questions, don't feel bad.

I don't know that meds have a separate deductible; meds can be confusing as heck :-) I'd ask your HR person where you work, she "should" be able to explain it all but it's extremely "local" to your company and the agency you get your health benefits from, etc. There's often an agency/"middleman" in there, not just whatever your health insurance is provided by (e.g., Blue Cross, Prudential, Aetna, etc.).