Easily mail 1099s online with LetterStream.
It’s that time of year again—1099 season! For some, it’s a minor blip on the calendar; for others, it’s a full-on circus. If the thought of organizing, printing, and mailing these forms has you breaking out in a cold sweat, relax. We’re here to help you get through it all without a single printer jam or late-night envelope-stuffing meltdown so you can enjoy your morning coffee break.
Sounds good?
A Quick Refresher: What Are 1099s?
Think of 1099 forms as your way of keeping everyone—contractors, freelancers, and the IRS—in the loop. These forms are used to report payments made to non-employees for their work throughout the year. It’s all about transparency and ensuring that the tax process runs smoothly for everyone involved. While it may feel like just another chore, sending out 1099s is a key step in wrapping up your business’s financial year on the right note.
Mark Your Calendar: Key Deadlines for 2025
Missing a 1099 deadline isn’t just a headache; it’s an invitation for penalties to crash your party. Here’s what you need to know:
- When do 1099s have to be mailed? January 31, 2025: The deadline for mailing 1099s to recipients is January 31st and that means forms must be in your recipients’ hands (or mailboxes) by this date. There’s no wiggle room here.
- When do 1099s have to be filed electronically? March 31, 2025 : The IRS deadline for filing electronically is slightly more forgiving—but only slightly. If you’re still filing paper forms, you’ll need to send them by February 28.
Why Use LetterStream to Send 1099s?
You’ve got enough to do already—wrangling 1099s shouldn’t be another stressor. Raise your hand if you agree. (Just like we thought, lots of hands went up). On that note, enter LetterStream. Here to save the day…or more so your time and sanity.
Let’s quickly go over how we make mailing your 1099s a breeze by easily sending 1099s online:
1. Hassle-Free Uploading. Check.
Forget fiddling with templates or fighting with formatting. Literally, just upload your data to our secure platform, and we’ll handle the rest—printing, stuffing, postage, and mailing. It’s like magic, but better because it’s real. We even offer an easy-to-use PDF preflight tool that lets you check your documents before uploading.
2. Security and Compliance. Handled.
When it comes to sensitive tax forms, security and compliance are non-negotiable. Our processes are designed to safeguard your data and ensure every mailing meets strict IRS requirements. From secure data handling to precise delivery, you can trust us to keep your information protected while staying fully compliant with the latest regulations.
3. Speed and Precision. Yep.
Time is of the essence, especially when January 31 is quickly approaching. We’ll get your forms printed and in the mail quickly and accurately, so you can rest easy knowing your business-critical mail is in good hands.
Pro Tips for Smoother Mailing
Even with LetterStream helping you out, a little prep can go a long way. Here are our top tips to make the 1099 mailing season a breeze:
- Start Early: Avoid the last-minute rush and give yourself time to double-check everything.
- Verify Information: Mistakes happen. Make sure recipient names, addresses, and taxpayer IDs are correct before uploading.
- Secure Your Mail: If mailing physical copies, we’ve got you covered using First-Class Mail with secure envelopes and USPS tracking options with sending Certified Mail online and through FedEx 2Day.
Let’s Talk Results
By the time you finalize your 1099 mailing, you’ll feel a sense of relief knowing everything is handled with accuracy and professionalism. Your contractors, vendors, and even the IRS will appreciate the attention to detail and timely delivery.
There’s no need for added stress this season—streamlining the process ensures your January runs smoothly. Focus on what matters most while your 1099s are managed efficiently and securely.
Ready to take the next step? Create a free account here and start mailing those 1099s ASAP!
Easily send mail online. LetterStream offers bulk printing and mailing services allowing companies to send physical mail online. Whether it’s online Certified Mail and First-Class Mail or FedEx 2Day and postcards we give both small businesses and large corporations that time and freedom back to work on tasks that better serve the company. If you’re interested in creating a free account you can do so, here.
