You Need a Budget
Part budgeting tutorial and part money management guide, the intuitive You Need a Budget program for Windows walks you through setup and fund allocation, helping you add accounts and project spending in dozens of categories. YNAB then maintains a running tab of your spending, with graphs that illustrate how much you've spent over the months and how your net worth has progressed. Security-conscious users will appreciate that YNAB can’t automatically download activity from your bank account. You can import OFX, QFX, and QIF files into the ledger, but YNAB encourages self-reporting because that approach forces you to think more concretely about your spending habits.
You can try out You Need A Budget for free, but it costs $60 to keep. The price of admission also buys you entry into YNAB forums and financial-planning classes, where you can glean advice from experts. Mac and iPhone versions are available as well.
Note: The Download link takes you to the vendor's website, where you can obtain a trial of the software.