When you choose to file your taxes on your own you can select at-home tax preparation software such as TurboTax to facilitate the preparation and filing process. Depending on the complexity of your taxes you will need to purchase a different level of software to accommodate your needs. If you have bought or sold stocks in the year you are filing for, you will need to purchase TurboTax Premier as the software for at-home filing.
Four levels of TurboTax software are available. Basic provides the tools for simple tax preparation while Deluxe includes more features to walk users through the filing process. Premier is billed as for "Investment and Rental Property" and builds upon the lower two levels with the addition of tools for income based on these sources. The fourth available level is the Home and Business version which adds tools for self-employed filers. You can choose either Premiere or Home and Business for filings that include stocks.
According to the TurboTax website, the Premiere edition of TurboTax includes tools for reporting your investment sales and cost basis. In addition, you can explore employee stock plans as well as tools to manage your 401(k) plan. And while income you make from the sale of stocks must be reported as another source of income, taxes paid on those sales differ depending on how many of your shares are sold and if they are sold at gains or losses. According to Smart Money, selling higher-cost shares of stock can reduce the tax burden. TurboTax premiere will calculate your owed taxes regardless of how you have chosen to sell your stock options.
When preparing to file taxes with TurboTax Premiere, start by gathering together all of the documents that track your investments. Your should have Form 1099-INT for income from interest, Form 1099-B for stock sales and 1099-DIV for any income from dividends. According to TurboTax's preparation checklist, you should also obtain any confirmation slips or brokers' statements for all stocks that you sold. The more information you have, the easier it will be to input the necessary data into the software for an accurate filing.
TurboTax offers free support with the software as well as the option of tax advice for $29.95 for 20 minutes. You can use these options if you are confused about your filing or any of the questions being asked of you. However, you are responsible for any information entered into the TurboTax software and while it is set up to reduce the risk of an audit, knowingly entering false information can still cause trouble between you and the IRS. If you are not comfortable filing with software, consider hiring an accountant or tax preparation service, as adding stocks to your filing can make it more complex than a standard return.