Setting a complicated timepiece isn't quite as simple as pulling out the crown on a standard three-hander. If you own an annual calendar, you need to follow a specific sequence to avoid damaging the delicate internal movement.
By the end of this guide, you'll know exactly how to adjust your calendar safely without risking scratches or broken gears.
Before getting hands-on, it helps to know what your watch is actually doing under the dial.
An annual calendar automatically tracks the correct date across the whole year, adjusting perfectly for months with 30 or 31 days. The only time it needs your help is at the end of February. It doesn't calculate leap years, so you will need to manually advance the date to the 1st of March.
A perpetual calendar takes it a step further. It calculates that extra day in February and will often feature a leap year indicator, showing whether you are in the first, second, third, or fourth year of the cycle.

When you buy a watch with recessed pushers, like a Patek Philippe, it normally comes with a setting pin made from white gold or a material matching the case. Leave it in the box.
Using a metal tool on a metal case is risky. Depending on how confident you are when depressing the setting mechanism, a slight slip will leave a permanent scratch.
Instead, use a standard wooden toothpick. Wood cannot scratch a precious metal case, and it naturally prevents you from pushing too hard. If you prefer, you can whittle down a small plastic prying tool to do the same job.

The most critical rule of setting any calendar watch is to avoid the danger zone. Never use the quick-set pushers when the time is between 9:00 PM and 3:00 AM.
During the top half of the dial, the movement's cogs are already engaged, preparing to roll the date over at midnight. Forcing a change while these are engaged will shear the gears and result in a very expensive repair.
To be completely safe, pull out the crown and immediately change the time to 6:00. Check your AM/PM indicator—often a 24-hour subdial—to ensure you are in the morning, well clear of the changeover period.

Take your wooden toothpick and press very gently on the recessed pushers to change the day, date, and month.
The trick here is to stop one day early. You want to set the watch to the day before the actual current date. For example, if today is Monday the 17th of July, you should set your watch to Sunday the 16th of July.
With the calendar set to yesterday, use the crown to advance the time manually.
Always turn the crown clockwise; never wind it anti-clockwise. As the hands sweep past midnight, you will see the cogs engage naturally and the calendar displays will click firmly into place for the current day.

Now that the date is correct, continue winding clockwise until you reach the current time. Look at your AM/PM indicator one last time to confirm you are setting the time for the correct half of the day.
Once everything is aligned, push the crown all the way back in. If your watch has a screw-down crown, make sure it is screwed in tightly. This is vital to keep the case waterproof and protect the movement.
Take your time, use the right soft tools, and enjoy the mechanics of your watch.