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.

Happy New Year!

Happy New Year to our loyal customers and Happy New Year to those who may be just joining us or thinking about joining us here at LetterStream!

As we reflect back on this past year we can’t help but be so grateful for you, our incredible team and the continued growth of this printing and mailing company that we know and love as LetterStream.

LetterStream started back in 2003 (Woah! How cool) and now as we’re here embracing the new year of 2024, it’s fun to reflect on how far we have come.

A Look Ahead at 2024

We’re also excited about all the plans we have for 2024. We’re in the process of revamping our website and blog and we’re excited to keep implementing new processes that aid in the customer experience. Last year we introduced our new chatbot that enhanced how customers can get answers in real-time, along with new printing and mailing updates that served our customer base. Keep checking back in on our blog to see what new updates we have for you in 2024!

Printing and Mailing Tradeshows and Beyond

This year we plan on attending some tradeshows throughout the nation that pertain to the print industry, mailing industry, printing and mailing industry and the SAAS (Software as a Service) industry, along with shows that focus on HOA’s (Homeowner’s Associations) and law firms. Again, be sure to check back here on the blog to find out which shows we’ll be attending. We’d love to have you come stop our booth and say hi if you’ll be there as well!

We’re Here for You!

We hope this next year is full of abundance both personally and professionally. Remember we’re here for you to send out your First-Class Mail, Certified Mail, postcards, statements and invoices, flat envelope mailings and even FedEx 2Day mailings! Check out our 2024 Postal Holiday Calendar to see when we’re open and mailing even when the USPS (United States Postal Service) is closed! Yes, there are holidays where we can still send out mail!

Wishing you a very Happy New Year!

How to Send Mail on USPS Postal Holidays

Sending mail during the Christmas season can seem a bit hectic. Actually, let’s be honest, the month of December as a whole can be chaotic. Then trying to send out your holiday gifts and mail your Christmas cards and letters on top of it can also be a bit much. On top of that, there’s also the added stress of knowing when the postal holidays are, when the Post Office is closed and when deadlines are to get everything mailed on time for it to get to its destination before Christmas.

So much to think about.

U.S. Postal Holidays 2023 – Christmas and New Year’s Day

We’ll get right to the point on when the USPS is closed during this time of year. The 2023 postal holiday schedule is pretty simple. The Post Office is Closed on Christmas, December 25th and New Year’s Day, January 1st. Many wonder, “Is December 26 a postal holiday?” and it is not. USPS mail runs the day after Christmas each year…at least for now.

Others also wonder “Is Christmas Eve a postal holiday?” It is not, however, what you may not know is that some of the Post Offices do close early on Christmas Eve, December 24th. We recommend calling your local USPS Post Office to see what their hours are. Just something to keep in the back of your mind.

Like the Post Office, we are closed on both Christmas Day and New Year’s Day. However, we are open and mailing on Christmas Eve and New Year’s Eve. We do have limited staff during this time of year and we too deal with USPS backups of mail but our team is working extra hard to always provide fast, perfect mail for our customers.

Our 2023 postal holiday calendar can be found here and the USPS postal holiday schedule 2023 can be found here.

mail truck for the usps postal service in a christmas tree for mailing on postal holidays

Shipping Deadlines for Christmas 2023

The shipping deadlines for Christmas 2023 vary, but here are some general deadlines:

USPS:

  • USPS Ground Advantage — December 16
  • First-Class Mail (including greeting cards) — December 16
  • Priority Mail — December 18
  • Priority Mail Express — December 20

FedEx:

  • FedEx Home Delivery: 1-Day Shipping — December 22
  • 2-Day Shipping — December 21
  • 3-Day Shipping — December 20
  • 4-Day Shipping — December 18
  • 5-Day Shipping – December 15

The USPS gives a more in-depth overview of mailing deadlines, here.

Tips for Getting Mail Out Before the Delay

Christmas tree, Christmas mailbox with a mail truck in front of a merry christmas can

If you’re worried about getting your mail out on time before the Christmas rush, here are some quick tips to avoid any delays with your mail delivery service:

  1. Get your mail out ASAP. Start early if you can
  2. Use Priority or Express Mail services
  3. Double-check addresses
  4. Include return addresses in case there are any issues
  5. Avoid peak shipping days
  6. Send letters, cards and mail online through the LetterStream portal so you never have to set foot in the Post Office
  7. Track your shipments and track your letters

You’re probably not going to be using Certified Mail to send your holiday mail, however, if you use it for other purposes or you just decide to, here is where you can track your USPS Certified Mail on our website.

LetterStream Is Open on Certain Postal Holidays

Ok, now let’s talk a little bit about LetterStream during other postal mail holidays. A fun fact about us is that there are a lot of holidays when the USPS is closed, however, we can still get your mail out for you!

You may be wondering how that is possible. If the Post Office is closed during postal holidays, then how is mail being delivered through LetterStream? Good question!

LetterStream is a printing and mailing company that works with the USPS. Just because the front counters are empty and the doors are closed to the public doesn’t mean that the back-office staff (those behind the scenes of the United States Postal Service aren’t still working hard). Because of that, we can have our dedicated team work on getting your mailings out the door and a driver to pick up the letters that need to be delivered.

Even though the mail may not be delivered on the actual holiday because USPS drivers are off, that doesn’t mean that we can’t get the internal process done beforehand. This allows us to be ahead of the curve for the next day’s mailing schedule. If mail goes out the door during a postal holiday then that means it is ready to be mailed the next day, whereas if we were closed we’d still have to do our internal part the next day. Basically, we’re one step ahead of the Post Office by being open on certain postal holidays.

The USPS accepts and processes our mail on President’s Day (Washington’s birthday), Columbus Day, Veterans’ Day, MLK Day and Juneteenth.

Click here to view our Postal Holidays 2024 Schedule which gives you a complete overview of when the Post Office is closed, when LetterStream is closed and when we are open and mailing even if the Post Office isn’t open.

Happy Holidays and Happy Mailing!

Postal Holidays in 2023 to Keep In Mind

As we embrace the festive spirit, it’s crucial to stay informed about the USPS holiday schedule to ensure your holiday mailings reach their destinations on time. It feels like just yesterday we were talking about the USPS Postal Holidays 2022 and now here we are a year later going over the United States Postal Holidays 2023. Crazy how fast time flies!

Ok, let’s get into it. Here’s a quick rundown of the 2023 USPS Christmas and New Year’s schedule, followed by a sneak peek into the 2024 USPS holiday season.

2023 USPS Christmas and New Year’s Schedule: Plan Your Mailings Accordingly

If you’re wondering what the rest of the 2023 postal holiday schedule looks like for the United States Post Office, look no further!

Both the USPS and LetterStream will observe the following holidays during the rest of the 2023 holiday season.

USPS Postal Holidays 2023

  • Christmas Day – December 25, 2023 (Monday): USPS will be closed and mail delivery will not be taking place.
  • New Year’s Day – January 1, 2024 (Monday): USPS will be closed and mail delivery will not be taking place.

Keep in mind that it’s important to plan your mailings around these dates to avoid any delay. Stay tuned for another blog post where we talk about crucial days to remember during the 2023 holiday season to help avoid any late deliveries.

Oh, and you might also be wondering. “Is December 26 a postal holiday?” or “Is December 31 a postal holiday?”…actually you more specifically might ask, “Is New Year’s Eve a postal holiday?”

Neither one of those is a federal holiday or a U.S. Postal Service holliday and because of that Post Office locations will be open and they are not included in the U.S. Postal Service holiday schedule. To be on the safe side you may want to call and check with your local Post Office to see if they might be closing early on New Year’s Eve but most will be open and doing their normal delivery services which include sending regular mail, also known as First-Class Mail, Certified Mail, Marketing Mail and more.

Looking Ahead to 2024 Postal Holidays: USPS Holiday Schedule & LetterStream’s Holiday Schedule

Part of Christmas tree branch and a Christmas bell located next to a LetterStream lanyard with Certified Mail envelopes and Certified Mail tracking and USPS stamps

As we bid farewell to 2023, (can you believe it is already that time?!), it’s wise to get a glimpse of the upcoming year’s holiday schedule for better long-term planning.

We created a 2024 holiday calendar for you that not only showcases the USPS postal holidays and when the Post Office is closed in 2024 but also which days LetterStream is still open and mailing during that time.

You can find the 2024 USPS holiday schedule here.

Count on LetterStream for Your Holiday Mailings

LetterStream’s committed to providing fast, efficient and perfect mailing services throughout the holiday season and beyond. Our team is here to support you, offering assistance and guidance to make your mailing experience as smooth as possible.

While we have you, we wanted to extend our warmest wishes for a joyous holiday and a prosperous New Year. Thank you for choosing LetterStream as your trusted partner for all of your mailing and printing needs!

The USPS Holiday Season is Here! Let’s Give Thanks!

As we are in the thick of the holiday season with the increase in USPS holiday mail, our hearts are filled with warmth and joy over here at LetterStream. This time of year allows us to reflect on the abundance of blessings that surround us, from the meaningful connections we’ve forged to the challenges we’ve overcome together. As we are navigating our busy season with the increase of USPS holiday mail, we can’t help but reflect on how thankful we are for being able to still produce fast, perfect mail for our customers after all of these years.

In the spirit of gratitude, we invite you to join us in appreciating the moments that make this season so special. Here are a few ways we are truly grateful this holiday season and every day: 

Expressing Thanks for Team Collaborations

LetterStream’s success as a printing and mailing company is a testament to the incredible team that works diligently behind the scenes. This holiday season, we extend our deepest gratitude to each team member who contributes their unique skills and perspectives, fostering an environment of creativity and innovation. Together, we’ve achieved milestones and faced challenges head-on, emerging stronger and more resilient.  

As a team, we just held our Q3 Bonus Party and Thanksgiving Dinner. Our theme this year was, indeed, gratitude. Every quarter we do a bonus party for our staff because we want to let them know how grateful we are for the hard work they do, the mail they help produce and their dedication to not only LetterStream as a company but to our customers that we work with daily. It’s our way to say “thank you” to them each quarter.   

This bonus party felt a little extra special this year. As a company and as individuals we have so much to be grateful for and we not only wanted to showcase that at our dinner but it’s also something we are remembering and practicing for the rest of this quarter (and beyond).   

Appreciating Our Loyal Customers

To our valued customers, we want to express our heartfelt appreciation for the trust you’ve placed in us over the last 20 years. Your unwavering support has been the driving force behind our commitment to excellence.

Our loyalty and commitment has always been about treasuring people. In fact, that is our top core value; “we believe in the tremendous value of people and that all should be treasured.” With that said, we are excited to continue our growth into 2024 while finding new ways to continuously improve our processes to help add value and ease for our customers.

This holiday season, we celebrate the relationships we’ve built and look forward to continuing our journey together in the coming year. 

Reflecting on Community Engagement

Beyond the office walls, our commitment to gratitude extends to the communities we serve. Whether through charitable initiatives or local partnerships, LetterStream is dedicated to making a positive impact.

This year we contributed donations to the different Maui wildfire relief efforts to help individuals and animals affected by the fires. We are also currently participating in the St. Mary’s Food Drive and Toys for Tots program to help those in need.

This holiday season, we encourage everyone to find opportunities to give back to those in need. Not only does it bring joy to those who are less fortunate but it also helps build the collective strength that comes from supporting one another.    

First-class mail on top of Certified Mail envelopes with Christmas decor around it for usps holiday mail

Counting Our Blessings in a Digital World

In a fast-paced, digital age, taking a moment to unplug and appreciate the simple joys can be transformative. Even though we are a SAAS company, we still encourage everyone to embrace the beauty of simplicity through meaningful in-person connections.

Maybe that looks like sitting down with someone for a meal or coffee, bringing in donuts or cookies to team members as a small token of appreciation, writing a handwritten note, or giving a nice card. Maybe it’s as simple as telling someone that you appreciate them or saying “thanks for being such a great help and I’m so thankful we worked on this project together to get the job done.”

Recognizing the power of personal connections in an increasingly virtual landscape is so important to remember.  

All-in-all, let’s come together to celebrate the spirit of gratitude this holiday season! We are so thankful for the relationships we’ve cultivated, the challenges that have shaped us, and the opportunities that lie ahead. As we express our gratitude, may we inspire others to do the same, creating a ripple effect of positivity that extends far beyond the holiday season!

And, just a friendly reminder to check the USPS website or our blog post for the postal holidays schedule so you can plan your USPS holiday mail and printing and mailing needs accordingly.

Remember: There is always something to be GRATEFUL for.   

With so much gratitude and appreciation,   

The LetterStream Team  

PROPOSED 2018 USPS Rate Increases

USPS Price Increase2
On October 6th, 2017, the United States Postal Service (USPS) announced a price increase to take affect January 21st 2018.

The new price schedule increases the retail price of first class postage for letters and postcards by 1 cent each.  Certified Mail with Electronic Return Receipt will see a 15-cent increase.

Keep in mind, the USPS “proposes” their new pricing, but the Postal Regulatory Commission (PRC) must approve the pricing before it can become official.

Historically the PRC has denied or adjusted price increases if the USPS attempts to raise prices too high compared with the current consumer price index (CPI).  In this case the USPS is only raising rates by 1.9% which is believed to be accepted by the PRC.

Below is the primary list of rates that may impact LetterStream customers.  Also keep in mind that LetterStream historically does not raise prices on any item beyond the actual USPS price changes.  If you are working on a First-Class Mail project for the new year, we’d encourage you to schedule it before the new rates are implemented.

2018 UNOFFICIAL Postage Rates:
– First Class Stamps up from $.49 to $.50
– First Class Postcard Rate up from $.34 to $.35
– Extra Ounces staying at $.21
– International Rates staying at $1.15
– Certified Mail up from $3.35 to $3.45
– Return Receipt staying at $2.75
– Electronic Return Receipt up from $1.45 to $1.50
– Registered Mail up from $11.70 to $11.90
– Flats (.0001 – .999 oz) postage up from $.98 to $1.00
– Flats extra ounces staying at $.21

For more information review the USPS press release:

View the Press Release Here

For all the gory details, see the USPS NOTICE OF MARKET DOMINANT PRICE ADJUSTMENT that was filed by the USPS with the PRC

USPS Stamp Prices Going Down in 2016!

USPS Postage Rates 2016

The biggest news in the mailing business, in maybe forever, or since the forever stamp.  The United States Postal Service (USPS) is LOWERING the price of a first-class stamp.  The price DECREASE goes into effect on April 10, 2016, when your cost for a first class stamp will be reduced to 47 cents each.

The last time the USPS decreased the price of a first-class stamp was in 1919, when the price dropped a single cent from 3 cents each to 2 cents each.  Now, the greatest price decrease in the price of a first class mail stamp since 1885; the USPS is cutting the price of a first-class stamp by a whopping 2 cents!  For more information check out the wikipedia page on the History of United States postage rates.

Why are Stamp Prices Going to 47 Cents?

The federal regulatory body that governs USPS pricing is the Postal Regulatory Commission (PRC)(https://www.prc.gov).  This organization decides whether the Postal Service can raise prices and by how much.  A year ago the USPS was given a special waiver by the PRC to increase prices by more than the maximum amount allowed (according to their rules), so now the PRC is making the USPS roll prices back.

It really makes no sense though, as the post office is still operating at a loss.  Follow this link to read the USPS press release on the topic of lowing prices (https://about.usps.com/news/national-releases/2016/pr16_009.htm).

What Other Postage Prices are Changing in April?

In addition to the decreasing price of a first-class stamp, other stamp prices are going down as well.  In fact, nearly every increase that took effect in 2015 is being reversed.  Seems a bit odd that the Postal Regulatory Commission and the USPS couldn’t work out a meet-in-the-middle solution, but their loss turns out to be mailers’ gain. Here’s a sampling of new postage rates:

  • First-Class Postcards will decrease from $.35 to $.34 each (reversing last year’s increase)
  • Additional ounces for First-Class mail will decrease from $.22 to $.21 (reversing last year’s increase)
  • Certified Mail base fees will decrease from $3.45 to $3.30 (reversing last year’s increase)
  • Certified Mail Return Receipt Green Card fees will decrease from $2.80 to $2.70 (reversing last year’s increase)
  • Certified Mail Electronic Return Receipts will decrease from $1.40 to $1.35 (reversing last year’s increase)
  • International First-Class Letters will go down from $1.20 to $1.15 (reversing last year’s increase)
  • One ounce First-Class flats will decrease from $.98 to $.95, and 2 ounce pieces will fall from $1.20 to $1.15 (reversing last year’s increase)
  • Registered Mail letters will decrease from $12.20 to $11.70 (falling more than last year’s increase by another 25 cents)
  • The price of a First-Class Stamp will fall from $.49 to $.47 (there was no increase in the price of a first-class stamp last year)

We encourage everyone to take advantage of the cheaper postage prices in 2016 and send more mail.  If you need some help with that, give us a call, we are what you call experts.

 

USPS First-Class Mail Slowing Down… Or Is It Me?

Stopwatch Man Waiting for First-Class Mail

Does it seem like your First-Class letters don’t travel as quickly as they used to? Well, it’s not just your imagination. The United States Postal Service (USPS) has been intentionally and systematically slowing down First-Class letters in order to reduce costs and create efficiencies in their mail handling operations.

This slowing down process has been rolling out for several months now and will continue to be noticed as postal facilities consolidate and the new plans take shape. The most obvious change occurred in January of this year (2015) when the USPS eliminated next day delivery of First-Class mail. This change has effected almost everyone who receives First-Class mail.

Judging by the number of phone calls we’ve already received about this, it’s not necessarily what any of us expected. If there is an upside, the USPS still quotes a delivery service standard for First-Class mail of 3 days (from and to) anywhere in the first 48 U.S. States. (But don’t quote us on this; we are still a little skeptical).

Here’s a good overview published by the USPS in September of 2011; it’s pretty clear and easy to read, and spells out their elimination of next day First-Class mail: USPS Frequently Asked Questions – Service Standards

If you want to dive into all the glorious details in a far-less user friendly document, you can review the implementation plan in the USPS Final Federal Register 39 CFR Part 121. This document spells out the specifics of the USPS implementation process. Phase one began on July 1, 2012, and phase two began on February 1, 2014.

In January of this year, the USPS posted a revised interactive service level map on their website in order for mailers to graphically see the service standards for various types of mail originating at your nearest post office. Follow the link to do some experimenting of your own based on your location. For LetterStream customers, use 850 PHOENIX AZ as your Originating point.

Keep in mind that the USPS service standards are not service guarantees. You know… “results may vary“.

In summary, your next day delivery of First-Class letters is probably gone for good, and we are likely to see additional days of transit built in as the USPS consolidates facilities. Editor’s note: Just between you and me and Mr. Stopwatch here; I’d caution you to not expect faster service if your letters already take 4 to 5 days for delivery.

Why Do I Get So Much Returned Mail?

Stack of USPS return mail

Gosh, we wonder the same thing. Will it ever stop?

But fortunately for us, we get paid to process returned mail, so maybe it’s not such a bad thing after all (at least, not in our case). 😉

Mail gets returned to the sender for a lot of different reasons, and sometimes, for no reason at all. Almost all returned mail has a yellow sticker on it that has been placed there by the Post Office.

In this blog post we’ve put together a little Troubleshooting Guide to Returned Mail that should help you “sort it out”–sorry, couldn’t resist.

Let’s start with the obvious reasons and work our way down.

1. The address on your letter is incorrect. This could be anything from the wrong zip code, to a misspelled city name, to a street address that doesn’t exist. The yellow sticker may say “No Such Address” or “No Unit” or “No Such City”. To correct this, a) Double check your records and make sure you’ve got the right address and/or b) go to USPS.com, click on the link on the left to “Find a Zip Code” and enter your address. If the USPS website can’t find the address, chances are it isn’t correct. You can also use our online address correction tools to clean up an entire mailing list.

2. The person no longer lives at that address. It could be that your address is fine but the mail piece was returned because the person has moved. The yellow sticker might say “Unable to forward” or “Forwarding Address Expired” or “Not at this address” or “No such person”. With north of 7% of Americans moving each year, you can anticipate that your mailing list will have similar changes. When someone moves, they fill out a change of address card (online or at their local post office) which the Postal Service puts in their computer systems to verify addresses. So, when a letter is addressed to a good address, to a specific person who filled out a change of address card, their mail will be forwarded to their new address. Unfortunately, if the person didn’t fill out a change of address card, but they did move, that mail piece will be returned to you. This is the same as “moved – left no forwarding address”. We have an online tool that lets you see if people have moved (filling out the changed of address card) any time in the last 18 months and provides you with their new address.

3. The person has no mailbox. This isn’t very common, but it can happen. The yellow sticker might say “No receptacle”. This means there is no mailbox for the mail carrier to put the mail in. This could occur because the house is new, isn’t built at that address yet, or the mailbox was blown over in a storm or run over by a car. There could be many other things that take out a mailbox, or it could have been taken down intentionally by the owner. Unfortunately we don’t have any online tools to solve this one.

4. The Post Office didn’t get it right. Sometimes the postal clerk or someone else at the post office gets confused and assumes or incorrectly determines that the mail can’t be delivered. There’s not much we can do to help out on this one, but if you believe everything is correct with the name and address then drop it back in the mail and see what happens. It just might make it where it needs to go the second time around!