I have been working in personal finance for 18 years, am a Certified Financial Planner(TM), and hold a Master of Science degree in personal financial planning... Mint.com and Quicken, both products of the company Intuit, are clear leaders in the personal finance application space. Mint.com is for those who don't mind having all their data stored in the "cloud" and want a free product in exchange for seeing advertisements. While Quicken is a paid offline software package. Like Mint, Quicken is fully capable of automatically importing your bank and credit card transactions, and categorizing those transactions based on your rules. It is also far more flexible than Mint for the creation of custom categories. There are certainly other options -- Yodlee, Guide, Balance, to name a few -- but the companies and features are still in early development compared to the offerings of Intuit. I am an active user of each of these software packages and services. If you have any follow up questions, feel free to schedule a call with me.