A Guide to 1099 Deadlines and How to Mail 1099s

As tax season approaches, businesses and freelancers are gearing up to fulfill their annual responsibility of issuing 1099 forms to recipients. Let’s explore the crucial deadlines for mailing out 1099s and we’ll provide some insights on the best practices for a smooth and timely distribution process.

Understanding 1099 Forms

Before delving into the deadlines, let’s briefly review what 1099 forms are. The 1099 series includes various forms that report income, other than wages, salaries, and tips. Businesses use different types of 1099s to report various types of income, such as interest, dividends, or nonemployee compensation.

Filing Deadlines to Send 1099

1. January 31: Deadline for Providing Recipients with 1099s

The clock starts ticking on January 1, and businesses have until January 31 to furnish 1099 forms to recipients. This deadline is non-negotiable and applies to all types of 1099s, including 1099-NEC for nonemployee compensation. Failure to meet this deadline or if a company fails to file it may result in penalties, so it’s crucial to ensure timely distribution.

2. February 28 (March 31 if filing electronically): IRS Filing Deadline

After providing recipients with their copies, businesses must submit the 1099 information to the IRS. The deadline for filing paper forms with the IRS is February 28, while electronic filers get an extended deadline until March 31. Keep in mind that this deadline is distinct from the recipient distribution deadline.

Mailing Out 1099s: Best Practices

If you’re wondering how to send a 1099 to someone, here it is. Let’s discuss the best practices for mailing out 1099 forms efficiently:

1. Gather Accurate Information

Before embarking on the mailing process of sending 1099 to contractor, ensure that you have accurate and up-to-date information for each recipient. This includes their legal name, address, and taxpayer identification number TIN. Mistakes in recipient information can lead to complications and delays.

2. Choose the Right Delivery Method

When it comes to mailing out 1099s, businesses have two primary options: traditional mail and electronic delivery. Traditional mail involves sending physical copies via postal services, while electronic delivery allows recipients to access their forms digitally. Carefully consider the preferences of your recipients and the security measures associated with each method.

3. Use Secure Mailing Practices

If opting for traditional mail, prioritize secure mailing practices. Use envelopes that conceal the contents and consider using Certified Mail or Registered Mail for added security. This ensures that the forms reach their destination safely and confidentially. you can load these into your LetterStream portal, which is a secure account, and then we handle the rest.

4. Communicate Clearly with Recipients

In addition to providing the required forms, consider including a cover letter or accompanying documentation that outlines the purpose of the 1099 and any additional information recipients may need. Clear communication helps recipients understand the importance of the document and how to use it when filing their taxes.

5. Stay Informed About Changes

Tax regulations can change, affecting the requirements for 1099 reporting. Stay informed about any updates or changes in tax laws to ensure compliance. This proactive approach helps businesses adapt their processes accordingly and avoid last-minute complications.

On a side note, some way wonder, “Do I send a 1099 to an LLC?” If it falls under partnership tax or single-member LLC then yes, you send the LLC a 1099 form.

Navigating the intricacies of tax season and meeting 1099 deadlines is essential. By understanding the key dates and implementing best practices for mailing out 1099s, businesses can streamline the process, mitigate risks, and contribute to a successful tax season for both themselves and their recipients. Remember, timely and accurate 1099 distribution is not only a legal obligation but also a demonstration of professionalism and reliability in the eyes of your clients and contractors.

The USPS postage rate increase just took place. Learn more about it here.

LetterStream’s New Chatbot Help Box

Let’s face it, we all need a little help sometimes. Even the LetterStream team needs help getting fast and convenient answers to customers 24/7/365 to include all days of the year, including holidays where we’re closed. That’s where our new chatbot friend comes in. We’ve implemented a new online help chat tool designed to help us, help you, with finding the most up-to-date answers as well as tips and tricks to make your utilization of our website and mail-building tools even more powerful.

Ever-Present Chatbot Help Center

Floating in the lower right corner of every page of our website is a help icon. When clicked it summons a powerful chatbot tool, that through the use of AI, can quickly return answers to your most pressing questions. Make note that the floating button never goes away, however, it can be scrolled out of the way by using your side scroll button in the event that it covers something you are trying to read. To minimize the dialog window after getting your answer, simply hit the icon once more and all is hidden from view. Not to worry; your prior conversations are kept so you can refer back to them whenever you open the chat tool again.

Not Like Other Chatbots

Our chatbot is not like the others. No, other chats can get kind of annoying. You know what I mean? You ask a question and feel like you are waiting for a highly distracted person to get back to you. I often imagine one person with a circle of computers around them. Each one with a person in chat. The operator spins their rolling chair from one computer to the next answering 10 people at a time and never really understanding what anyone asks. Anyway, our chat tool isn’t like that. It is blazingly fast and provides extremely accurate information.

But, I Need a Human, Not a Chatbot

Not to worry. We have plenty of humans behind-the-scenes ready to give you even more personalized assistance. As some of you already know, our team of humans do super-human things and can answer any question you may have. They can even propose changes and fixes to our always-ready-to-help development staff. To reach a human, simply send an email to support@letterstream.com. But, while our humans don’t spin around in office chairs (well, sometimes they do for fun), keep in mind that they might be on break, in a meeting, on vacation or working on the next cool feature, so for the fastest answers, be sure to ask your questions in the chat tool first.

I Have an Urgent Need

Believe it or not, this is the main reason we introduced the chatbot in the first place. People sometimes run into snags and need a solution right now, not in 20 hours or after someone returns from a meeting. This makes our decision to employ a chatbot all the more relevant. It’s not just you that has an urgent need, many customers do, and we want to help them all.

Disaster Averted Thanks to Chatbot

Using the chatbot to find answers quickly takes the urgency and the drama out of your day. Another major thing that we do is provide you the tools, within your account portal, to stop, pause or cancel a job at any point up until it is time to mail. To take advantage of this process, simply log into your LetterStream account, find the job in question, and click the word EDIT appearing in the Options column. From here you can choose what you need to do, stop and shred, pause, delete, etc. Some options come and go as the job moves through our production process. For more information see our help article “Changing a Job.”

Help Pages Still Present

Which reminds me! We still have all our help pages, videos and content. Simply navigate to the bottom of any page and select HELP from the list of options in the footer. These resources are still very beneficial and is one more method you can use to get all the help you need.

FedEx 2Day Now Available at LetterStream to Send Letters

For those of you who see us promoting FedEx letters on our website but can’t quite find the button to make it happen; we have great news! Most of you will now be able to send FedEx 2Day letters, with ease on our website.

What is FedEx 2Day?

FedEx 2Day is just one of the many FedEx fast delivery products that is offered. FedEx 2Day offers the speed, security, tracking and confidence that all FedEx products offer. It’s like an overnight letter that takes one extra day to get there.

LetterStream offers the standard FedEx 2Day letter option, which will get your letters or documents delivered by 5 P.M. the second business day from when you mail it. FedEx does offer a 2Day A.M. product, which we do not currently offer.

How Fast is FedEx 2Day?

FedEx 2Day is pretty quick. Like the name implies, it will take two (2) business days for your letter to arrive and will arrive by 5 P.M. to most destinations. Let’s break this down. If you combine the speed that LetterStream offers along with this FedEx product, then your letter will get there in no time.

If you were to load the documents to our website on Monday, then they will arrive at your intended destination by Wednesday. Keep in mind; no trips to the FedEx store, or post office, no scheduling pickup for your letter, no hassle of buying a FedEx envelope. Just the ease of sitting at your computer, uploading your document and easily sending it on its way.

FedEx envelope with FedEx letter to represent FedEx 2Day shipping.

Why Would I Choose FedEx 2Day?

FedEx 2Day is a great solution for sending a lot of different documents, since it’s not that much more expensive than Certified Mail, especially when you need to send a lot of documents to a specific location. Around 50, 8.5 in. x 11 in. documents, can be placed in a single FedEx 2Day envelope and be delivered for around $18.

FedEx gives you tracking information so you can see where your letter is at any moment. It provides you with proof of mailing and proof of delivery. Unlike other items with tracking, FedEx is dedicated to ensuring your letter reaches its destination. This allows them to achieve a much higher delivery rate than maybe some of their competitors, in our humble opinion.

What’s more, FedEx is a known and trusted brand for delivering on time, nearly every time. When a FedEx package arrives, you know it is something special, that it’s something important that you should embrace and open.

Some competing products that offer tracking don’t quite capture that same vibe. Think about it; have you ever received a letter with a green bar across the top and put it off because you might not want to know what is inside? FedEx generally doesn’t give people that same feeling. Wouldn’t you agree?

How Do I Send FedEx 2Day?

Oh yes, I nearly forgot. You are probably wondering, “how do you actually send a FedEx 2Day letter?”

Sending FedEx 2Day letters is an easy selection when you start to create your mailing on the LetterStream website. You simply click “To Send a Letter,” and you can choose from multiple options like First-Class, Certified Mail, and now FedEx 2Day.

Step-by-Step Process for FedEx 2Day

Backend of LetterStream portal where you create a job and choose send letters

Head to the homepage for www.LetterStream.com.
Log into your LetterStream account.
On the main dashboard page, select the button to “Send Letter(s).”
Name your job, select the address source and then, on the same page, choose the delivery method on the right hand side. There should be an option for FedEx 2Day to select.

LetterStream online portable that shows where you upload your job and how to choose the FedEx 2Day option

If by some chance you’re not seeing that seeing that option:

For security reasons the FedEx product is not available to users who have not been a customer for less than 90 days. It gets complicated but let’s just say we don’t want to block any users from finding this product, so if you have a legitimate need for the FedEx2Day option and you can’t seem to find it, reach out to our support team and we’ll get you taken care of.

When Will Overnight Options be Available?

The FedEx overnight option is currently available to a few select customers who meet our criteria. However, if you have the need to send more than 100 overnight letters per year, reach out to us and we may be able to qualify you for this added service.

To learn more about FedEx 2Day, click here.

Innovations In Printing And Mailing

popular_science_cover

I was flying out of town the other day and picked up a Popular Science magazine to read on the flight. I was happy to see the title was “100 Best Innovations of the Year” and wondered if any of our mailing innovations had made the list. There are a few different mailing innovations that we rolled out this year and I thought I might find one or two discussed in the magazine.

For instance, we have our innovative Return Mail Processing service where we can process our clients’ return mail. This is a good way to keep undeliverable mail from being returned to our customers. Instead, we get it. Then we flag all the addresses in our customer’s account that have been returned, showing the return date and the return reason from the USPS yellow sticker. In addition, reports can be run by user, date range, mail type and many other filters for the letters that were returned.

Another innovation is our USPS Registered Mail solution, which allows users to create and send Registered Mail on our website. If you send Registered Mail, you know that it is one of the most time-consuming and confusing types of mail that you could possibly send. True to LetterStream’s form, we make the process so easy you can create the registered letter–or hundreds of them–in around 2 minutes on our website. We keep track of the USPS tracking information and the signature cards in an orderly fashion on our website.

Some may say that our online Certified Mail process is the most innovative Certified Mail solution they’ve ever seen. We’d like to agree… but we’ve been processing Certified Mail this way for nearly 10 years, so it might not be an innovation of this year.

We’ll, I’ve skimmed the 100 Best Innovations article, and unfortunately I could not find the name LetterStream. But that’s ok, our customers repeatedly give us the honor of being great innovators in the mailing business, and they are the ones we want to please.

If you want to learn more about our mail innovations, check out our website, explore our blog or pick up the phone and call us.

Are We Social or What?

We’ve put it off as long as we can, but we can’t seem to go anywhere without someone asking why we don’t have a Facebook page.

Ok, so here goes, once and for all… We now have a Facebook page!

Hopefully it will be instrumental in communicating constructive information to those needing a little help with their printing and mailing projects.

In addition, we’ve added ways for you to connect with us on Google+, Twitter, and LinkedIn, or you can simply follow us on this blog.

Soon you’ll be able to subscribe to our new-and-improved e-newsletter as well.

Now that we’re Social, we’ll keep you posted!

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* Here are the links to our social media sites… we look forward to connecting with you!