Beginning in 2009, the Massachusetts Department of Revenue requires all 1099 forms to be submitted in "machine-readable form." What this means, essentially, is that you must submit any 1099 forms your employees received to the DOR electronically, via their website. This requires creating a Web account for your business and uploading the forms to the account. All 1099 forms must be sent to the DOR by the last day of February.
Register to submit 1099 by navigating to the Massachusetts Department of Revenue website (see Resources).
Select "I am registering to file, pay taxes or submit new hire reports for my company only" and click "Next."
Select "My business is registered with the Massachusetts Department of Revenue to file/pay taxes" and click "Next" -- but only if your business is already registered as a business entity with the Massachusetts DOR. If your business is brand new and you haven't yet registered, you can do it online -- select "My business is not registered with the Massachusetts Department of Revenue to file/pay taxes," click "Next," and follow the on-screen instructions. Once you're done registering your business, you can proceed to Step 4 to register for the web service.
Fill out the Registration Form with the official information about your business. You'll also have to create an account for use on the Massachusetts DOR website -- enter a username, password, and password retrieval question and answer. Check the "I Agree" box at the bottom of the page, click "Submit," and follow the on-screen instructions.
Log into the site with your username and password. Move your cursor over "Submit Reports," then click "Financial Reporting." The screen that appears will give you an option to file 1099 forms. Follow the instructions to do so. Once you've filed electronically, you needn't submit a paper copy to the DOR, but remember you'll still have to submit a separate copy to the IRS as part of your federal tax return.