If you have access to your checking account information online, you can always go back and review transactions you might have missed. The most "automatic" way to keep track of your check-writing, however, is to use duplicate checks that create a copy of each check you write. These duplicates remain in your checkbook and provide a "paper trail" of all your checking account withdrawals. Duplicate checks often cost a bit more than standard one-part checks, but many people find the convenience worth it.
Here's another strategy, if you do your banking online. You might be able to download banking transactions directly from your checking and savings accounts into personal finance software on your home computer.
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