printing and mailing | LetterStream Blog

How to Add a Return Envelope When Creating a Job

Look, not every mail-related question is a high-stakes compliance issue. Sometimes it’s just: “Hey… how do I add a return envelope to this thing?”

And, we get it. If you haven’t done it before, this stuff can feel weirdly tricky. But here’s the good news: it’s incredibly easy—and we made a video to walk you through it, just in case clicking buttons under pressure isn’t your thing.

Watch below to see a walk-through of how to add a return envelope or keep reading to get the quick breakdown:

So, if you’re sending out statements, invoices, ballots, or anything else where you actually want a response (like, in the mail, with a stamp and everything), you’ll want to include a return envelope.

Let’s break it down.

What’s a Return Envelope and Why Does It Matter?

A return envelope is exactly what it sounds like: a second envelope, tucked inside your mailing, that your recipient can use to mail something back to you.

They open your letter
They see the return envelope
They use it
Everyone wins

This is especially common for:

Payments (yep, checks are still a thing)
Forms and ballots
Surveys and reply cards

If you don’t include one, your return rate drops. People are busy, and no one wants to hunt down an envelope like it’s 1997, you know? In fact, you can’t find just one and no one wants to buy a whole pack of envelopes either. So, best case scenario is to include one yourself for your customers.

How to Add a Return Envelope to Your Mailing

Ready? It’s literally one step. (Told you it was easy.)

When setting up your job online, when you get to the inserts page, simply click on the blue “Add An Envelope” button and select with #9 you want to choose.

Boom. Done.

The return envelope will be inserted automatically along with your letter or statement. No extra work. No extra clicks. It’s already built into the workflow.

Still unsure? Don’t forget we made a YouTube video that shows you how to add a #9 return envelope.
Because sometimes it’s just easier to see it than read about it.

🎥 Watch: How to Add a Return Envelope: https://www.letterstream.com/redir?utm_source=video&utm_medium=emailvideo&utm_campaign=emailvideo&utm_id=email&link=https://www.youtube.com/@LetterStream

A Few Bonus Tips

Want it pre-addressed? No problem.
Need a windowed return envelope? That’s an option.
Need a #8 ballot or even a 6 3/4 return envelope? Both are options too.

We’ve thought through the logistics so you don’t have to.

Make It Easy for Them to Respond

If you want a reply, make replying easy. It’s that simple.

Adding a return envelope removes friction, increases response rates, and gives your mail that “oh wow, they actually thought this through” energy.

We’re not saying it’ll make your recipients love you more—but… actually, yeah, it might.

If you’re not already a customer, you can create a free account here and if you’ve used us before simply log in here to get your mailing our quickly and easily with or without a return envelope included.

LetterStream offers bulk printing and mailing services allowing companies to send physical mail online. Whether it’s online Certified Mail, First-Class Mail, FedEx 2Day, or 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.

How to Avoid Common Online Mailing Mistakes

Avoiding common mistakes when mailing online isn’t just about saving face—it’s about saving time, money, and possibly your sanity. Whether you’re sending one letter or a thousand, the truth is: mailing online sounds foolproof… until you hit send and realize you just mailed 200 letters to a zip code that doesn’t exist. Oops!

We’ve seen it all. So we figured we’d save you from the usual slip-ups and help you mail smarter, not harder.

The Classic: “Wait, That’s Not the Right Address”

This one tops the list every single time. The address looked right… until it was sent back faster than your coffee hit this morning’s inbox.

Here’s the thing: mailing platforms aren’t mind readers. If the address is off, the mail won’t get there. (And no, USPS can’t deliver based on “well it’s close enough.”)

LetterStream tip: Always double-check your spreadsheet before uploading. Clean columns. No extra commas. Full zip codes. You’d be surprised how many people forget apartment numbers—like the mail is supposed to guess the unit.

Thinking “Online Mail” Means Instant Delivery

Let’s just clear this one up: you’re not sending email. You’re sending real, physical mail—paper, envelope, postage stamp, the whole deal. It still has to go through printers, folders, inserters, and a quick ride with USPS or FedEx.

This means that clicking “send” is just step one. Give it a little breathing room.

LetterStream tip: Build in a day or two for processing—especially for time-sensitive stuff like legal notices or HOA violations. Need tracking or signatures? Certified Mail or FedEx 2Day might be the better route.

Uploading a Glitchy File and Hoping for the Best

Let’s talk about your letter file. Is it clean? Do the addresses line up in the window? Did you accidentally attach last month’s version? These are things to keep in mind and that can be a make or break for your business-critical mail.

LetterStream tip: Before uploading, preview the proof. That little preview button? It’s your best friend. Use it. We promise, future-you will thank you when you don’t accidentally send a test letter to your boss.

Picking the Wrong Postage

This one’s sneaky. You’re in a rush, and without thinking, you pick First-Class Mail when you really needed Certified Mail with an Electronic Return Receipt signature. Or you go all-in with Marketing Mail for your billing statements (spoiler: not a good idea).

Quick breakdown:

First-Class: Fast and reliable for statements, notices, invoices.
Certified Mail: Great when you need a paper trail.
FedEx 2Day: Ideal when timing is critical.
Marketing Mail: For big batches that aren’t urgent.

Formatting Your Data Like a Puzzle

Merged cells, hidden columns, emoji in the address field—oh my. The more “creative” your spreadsheet is, the more likely something will go sideways.

LetterStream tip: Stick to the basics. Name, street, city, state, zip. No formulas. No filters. No random unicorn emojis (no matter how cute they may be). 🦄

And definitely no mixing home and work addresses in the same field. Yes, we’ve seen it.

Skipping the Proof (Again)

We get it—you’re busy. But you know what’s really time-consuming? Fixing a batch of mail after it’s been sent.

LetterStream tip: Pause. Breathe. Preview. Even if you’ve sent the same letter a dozen times before, it takes just a second to catch that typo in the footer or the page that broke in the middle of your sentence.

Waiting Until the Last Possible Minute

We hate to be the bearer of bad news, but if your “urgent” letter gets submitted at 4:59 PM expecting same-day miracles… you’re cutting it close. Plan ahead, always.

LetterStream tip: Get it in early. And if it’s truly an emergency, check out expedited options. We’re fast—but we’re not magic (well, not every time).

Wrap-Up: Mail Online Like a Legend

Mailing online should feel easy—because it is, once you dodge the common traps. Check your addresses, preview your work, choose the right postage, and keep your data clean. (Honestly, most of these are just good life advice, too.)

And if you’re looking for a mailing partner that actually helps you avoid these issues—not one that leaves you staring at a support portal at midnight—LetterStream is here for it.

We make mailing online simple, reliable, and just a little more fun than you’d expect.

How to Send Your First Letter With LetterStream

If you’re new to LetterStream, welcome! You’re about to discover just how easy it is to send mail online, even high-volume mailings—without the hassle of printers, envelopes, or Post Office visits. Whether you’re sending HOA violation notices, legal documents, invoices, or customer statements, LetterStream makes mailing fast, efficient, and stress-free.

📌 Watch the Video Tutorial Below!
Sending Your First Letter with LetterStream

And keep reading if you want the breakdown of how to send your first letter through your LetterStream account, from start to finish.

Step 1: Log Into Your LetterStream Account

First things first—log into your LetterStream account. If you don’t have an account yet, signing up is quick and simple. Once inside, you’ll see your dashboard, where you can manage your mailings, view job history, and track sent letters.

Step 2: Start a New Mailing Job

To send your first letter, click “Create a New Job.” This is where you’ll set up the details for your mailing.

Choose the type of mail you’re sending (First-Class Mail, Certified Mail, or FedEx 2Day®).
Select single or multiple recipients—you can send one letter or a bulk mailing in the same job.
Upload your PDF file containing the letter(s) you want to send or your CSV file of contacts.

Pro Tip: Your document should be properly formatted with the recipient’s address visible in the correct windowed-envelope position. Try our PDF PreFlight tool to make sure your document is formatted correctly.

Step 3: Review Your Document & Addressing

Once your PDF or CSV file is uploaded, LetterStream’s online mailing service will automatically check for proper formatting. You’ll be able to preview your letter and make sure everything looks good before sending.

Step 4: Choose Printing & Mailing Options

Now, it’s time to customize your mailing:

Paper Type: Standard white or specialty paper
Envelope Style: Single-window, double-window, or custom envelopes

Step 5: Final Review & Checkout

Before submitting, review the details:

Preview your letter one last time
Confirm addresses and recipients
Verify your mailing preferences

Once everything looks good, proceed to checkout, where you can select your payment method and submit your mailing job.

Step 6: Tracking & Confirmation

If you choose Certified Mail, after sending, you can track the status of your mailing in your LetterStream dashboard. You’ll receive updates on when it’s printed, mailed, and delivered—giving you peace of mind that your letter is on its way.

Need to send multiple notices? LetterStream also specializes in bulk mailing solutions for HOAs, law firms, and businesses.

And That’s It! 🎉

You’ve successfully sent your first letter through LetterStream’s online mailing service—without ever stepping foot in a Post Office. Whether you’re managing HOA mailings, legal notices, invoices, or critical business mail, LetterStream takes care of the heavy lifting so you can focus on what matters most.

Ready to send your next letter? Log in and get started today! And if you have any questions check out our Chat Help located in the right-hand corner of our website, which provides help 24/7.

LetterStream offers bulk printing and mailing services allowing companies to send physical mail online. Whether it’s online Certified Mail, First-Class Mail, FedEx 2Day, or 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.

Now That You Use LetterStream, You Can Actually Take a Real Break (Yes, Really!)

Now that you use LetterStream, you can actually take a break…like a real break. We’re talking no envelopes, no stamps, no printer meltdowns. Just you, a moment of peace, and maybe even a latte you didn’t have to reheat three times.

Because when someone else takes the mailing chaos off your plate—like a reliable partner offering online printing and mailing services—guess what you get back? Time. Sanity. And maybe a full lunch hour…for once.

Goodbye Mailroom. Hello Midday Me-Time.

Let’s be honest: manually managing business-critical mail is not the glamorous part of your job. (Unless your dream was always to master the art of paper jams.) Between printing, folding, stuffing, labeling, and trying to find that one missing address, and taking a tip to the Post Office to drop it all off, your to-do list can start to look like a scavenger hunt.

But now that you’re using LetterStream’s business mailing solutions, you’re not in the mailroom anymore. You’re in control. You upload your PDF files and hit send. We handle everything else. It’s basically magic—without the wand.

**Let’s Talk About All the Things You’re Not Doing Anymore**

Since you’ve passed off your mailing tasks to an outsourced mail service you can trust, here’s a short list of things you no longer have to stress about:

Running out of toner (again)
Fighting with the folding machine (you know the one)
Spending your lunch hour at the Post Office (fun!)
Stamping envelopes until your wrist gives out
Wondering if your mailing actually got there

All of that? Gone. Poof. Out of your hands. Thanks to LetterStream’s bulk mail services, it’s not just a time-saver—it’s a mood boost.

So, What Do You Do With All This Free Time?

Ah, the possibilities.

There are so many things you can do with your free time now. You could actually take a full lunch break. You could go for a walk that’s not just to cry behind the building. You could sip coffee while it’s still hot. Or hey—maybe you use that time to think big, plan a new project, or simply not think at all.

And here’s a fun fact from the productivity gurus: real breaks help your brain recharge, improve focus, and make you better at your job. So technically, you’re still being productive… just enjoying it a lot more from your new view.

If you’re still stuck manually sending mail, it’s time to rethink the strategy. When you send mail online through a professional service like LetterStream, you’re not just improving efficiency—you’re reclaiming your day.

Everyone’s Winning (Especially You)

Your mail is going out on time. Your boss is impressed. Your customers are getting their statements, invoices, or notices like clockwork. And you? You’re no longer buried under a pile of paper cuts and postage questions.

We’d call that a win.

Take Five, Take Ten—Take the Break You Deserve

Now that you use LetterStream, the only thing you should be folding is a napkin at lunch. The busywork? It’s ours now. Your time? It’s yours again.

Join LetterStream at the 2025 CAI National Show in Orlando

LetterStream is off to CAI’s Annual Conference in Orlando to talk all things HOA mail, and we can’t wait to see you there!

LetterStream is packing up our favorite mail samples and heading to CAI’s Annual Conference & Exposition: CommunityNOW, happening May 7–10, 2025. If you’re planning to be there, come find us at Booth 333. We’d love to say hi—and show you how easy sending HOA mail can actually be with the right online mail platform.

Yes, we said easy and HOA mail in the same sentence. Stick with us.

Why We’re Showing Up

If you’re in community management, you already know that mailing things—violation notices, annual meeting packets, financial disclosures—isn’t always your favorite part of the job. It’s time-consuming. It’s manual. It’s repetitive. And let’s be honest, it’s easy to mess up.

That’s where we come in.

We built LetterStream to take that entire task off your plate. No more printing. No more envelope stuffing. No more rushing to the post office before it closes. Just upload your files and we’ll handle the rest—like, really handle it.

CAI’s Annual Conference is one of our favorite events of the year because it gives us a chance to connect in person with the people who are doing the hard work of keeping communities running. Whether you’re a board member, a community manager, or the go-to person for “who’s mailing what,” we’d love to show you how our HOA mailing services and automated mailing solutions can make your job way less stressful.

What You’ll Find at Booth #333 (Besides a Bunch of Friendly Humans)

We’re not just showing up with brochures and a handshake. We’re bringing real solutions—and a chance to see how they actually work in the wild.

Swing by and we’ll walk you through how easy it is to:

Send Certified Mail without ever leaving your desk
Upload your files and let us handle the printing, stuffing, and mailing
Improve your mailing process without adding more work to your plate

You’ll get to see real mail samples (yes, the actual stuff we print), ask us anything about timelines, compliance, integrations—you name it—and pick our brains about how to make your next big HOA mailing way less painful.

Whether you’re a seasoned community manager or just figuring out what “annual disclosures” even are, we’ve got tools (and stories) to share.

Also, we might actually have snacks. But no promises.

What Makes Mailing with LetterStream Different?

We’re not just another platform. We’re a team of real people who actually get what HOA teams deal with day-to-day. So we built tools that actually solve the problems—not just talk about them.

Here’s what that looks like in practice:

✅ You log in, upload your files, and we handle the rest
No supplies, no equipment, no guessing. Whether you’re sending first-class mail for HOAs, certified letters, or even FedEx, it’s all done from your computer.

✅ You get tracking on certified mail and FedEx
Need to prove it was delivered? You’ll have the receipts (digitally speaking).

✅ You avoid the common mailing mishaps
We’ve built in checks so you’re not losing sleep over missed pages or mismatched envelopes.

✅ You get hours back in your week
Because let’s face it—your to-do list is long enough without “go to the post office” on it. With our print and mail service, you can send hundreds of letters in just minutes.

Come Say Hello

Whether you’ve used LetterStream before or are just hearing about us for the first time, we’d love to meet you. Booth #333. Orlando. May 7–10. Mark your calendar, circle it in red, set an alarm—whatever works.

Let’s talk about the mail you send, the problems you’re trying to solve, or even just which session had the best coffee. We’re all ears (and envelopes).

How to Make Sending HOA Mail Easier

Managing an HOA means juggling homeowners association dues, violation notices, community updates, and board elections—all requiring reliable communication. But sending mail the traditional way can be time-consuming and costly. That’s where online mailing platforms like LetterStream come in.

When using LetterStream, HOAs can easily send mail online, whether it’s a homeowners association annual meeting agenda, proxy ballots, or Certified Mail for violation letters. Our online platform automates the entire process, eliminating the need for printing, stuffing, and mailing letters yourself. Plus, we have an API option that seamlessly integrates with HOA management software companies like CINC, making it even easier.

The Struggles of Traditional HOA Mail

Handling HOA mail manually presents major challenges including:

High costs – Postage, paper, and labor expenses add up.
Time-consuming – Printing and mailing homeowners association dues notices and other documents takes valuable time.
Compliance concerns – Late or lost mail can create legal and financial issues.
Lack of tracking – HOAs need proof that critical letters were sent and received.

A mailing service like LetterStream solves these problems with automation, tracking, and seamless integration.

How LetterStream Streamlines HOA Mail

Simplify Sending Mail

Instead of dealing with printers and envelopes, HOAs can send physical mail online in minutes. Upload your documents, choose recipients, and we handle the rest.

HOA Software Integration for Seamless Mailings

Our API connects with HOA management software like CINC, allowing for automated mailings of homeowners association dues reminders, violation notices, and community updates—all from the same system you already use.

Proxy & Ballot Mailings for HOA Elections

For board elections and annual meetings, HOAs must distribute proxy forms, ballots, and the homeowners association annual meeting agenda. LetterStream ensures:

Accurate mailing of ballots and voting instructions.
Real-time tracking for compliance.
Address verification to reduce return mail.

Send Certified Mail Online for Legal Compliance

Some HOA communications—like delinquency notices and violation warnings—require Certified Mail tracking. Our platform allows you to send Certified Mail online with tracking and the option of an electronic proof of delivery (Electronic Return Receipt). And, you can even track it all right from inside your LetterStream account.

Cost Savings & Bulk Mailing Discounts

HOAs can send mail more affordably when sending bulk mail. When you take into account the time spent to physically send mail yourself including supplies, postage and the time it takes to the Post Office—it adds up. The ability to have it all done for you without literally having to leave your desk, the price to send online is actually priceless.

The Future of HOA Mail is Automated

When HOAs use LetterStream to send snail mail online, they can automate and streamline sending a letter—from financial statements to election ballots. Whether you need to send a letter, send Certified Mail, postcards, proxy and ballet mail or integrate mailings with your HOA software, we’ve got you covered.

Ready to Upgrade Your HOA Mailing Process?

Join HOAs nationwide that trust LetterStream for their mailing needs. Send mail the easy way today at LetterStream.com.

Certified Mail for Tax Time: Why Young Adults and Families Need to Get Serious About Sending Important Documents

Avoid Tax Time Trouble with Reliable Mailing Solutions from LetterStream

As tax season is upon us, young adults—and the parents who may still be helping them—are being urged to get ahead of filing deadlines and financial recordkeeping. A recent Wall Street Journal article emphasizes that many Gen Z taxpayers aren’t fully prepared for what it means to file taxes independently. Whether it’s mailing tax documents, keeping up with deadlines, or dealing with the IRS, the stakes are high—and missing paperwork could mean delays or penalties.

That’s where LetterStream comes in.

We specialize in printing and mailing services, including Certified Mail—a critical tool for anyone sending tax documents, legal notices, or time-sensitive communications. Our platform makes it simple, and everything is handled online, without a trip to the Post Office.

Why Certified Mail Still Matters—Especially for Taxes

Sending documents by Certified Mail is often recommended when dealing with government agencies like the IRS, as it provides a record of mailing and proof of delivery. Unfortunately, traditional green cards (Form 3811) are easy to lose, hard to track, and cumbersome to manage.

LetterStream eliminates that hassle with:

✅ Electronic Certified Mail receipts — Instantly available in your online account

✅ Long-term access — Our digital records outlast USPS retention windows

✅ No more green cards — Everything is tracked digitally with an Electronic Return Receipt (ERR) – add-on option

✅ Peace of mind — You’ll know exactly when your tax documents were sent and received

Whether you’re a parent helping your college-aged child file taxes for the first time, or a young professional navigating self-employment income, using Certified Mail online through LetterStream can help keep record of your filings.

Tax-Time Tips from the WSJ Article (and How LetterStream Helps)

The WSJ article offers smart guidance for young adults and families during tax season. Here are a few key takeaways—and how LetterStream supports them:

🧾 Tip 1: Keep Paperwork Organized

Save W-2s, 1099s, and proof of deductions.

How LetterStream Helps: Digitally send and archive documents via Certified Mail, knowing you’ll have easy access to mailing receipts and documents—even next year.

🧒 Tip 2: File for Dependents (Carefully)

Parents often mistakenly claim children who’ve already filed on their own.

How LetterStream Helps: Use Certified Mail to send statements or communications with legal or financial advisors—and have an electronic receipt so you know if a family member has already sent theirs.

💰 Tip 3: Report Side Income

Young adults with Venmo gigs, tutoring, or Etsy shops may need to report income they didn’t expect.

How LetterStream Helps: Submit forms or tax paperwork to your accountant or IRS with confidence—Certified Mail ensures it’s not “lost in the mail.”

When to Use Certified Mail for Taxes

You have different options when sending mail through the USPS, including First-Class Mail and Certified Mail, however, when it comes to taxes you may want to use Certified Mail for:

• Sending your tax return (if not e-filing)

• Notifying the IRS about an address change

• Responding to IRS letters or requests

• Mailing tax documents to accountants or attorneys

• Confirming delivery of supporting paperwork

Any time the date and sending of your documents matters, Certified Mail is a great option for tracking when it gets sent out and when it arrives—and LetterStream makes it effortless.

Why LetterStream Is the Smarter Way to Send Certified Mail

Instead of standing in line at the Post Office, fiddling with green cards, or losing track of receipts, you can handle it all with LetterStream.com, here’s how:

Sending Certified Mail with Electronic Return Receipt online with LetterStream

• Upload your PDF

• Choose Certified Mail (with or without Electronic Return Receipt)

• Check your proof

• Click send—we print, fold, insert, and mail it for you

• Easily track the status of your Certified Mail letter in your LetterStream account

Track Certified Mail online in your LetterStream account.

Your receipt and tracking are stored securely online. That’s one less thing to stress about this tax season.

Ready to Simplify Your Mailing Process?

Whether you’re a tax professional, parent, or first-time filer, LetterStream offers a fast and reliable way to handle Certified Mail—no printer, envelopes, or stamps required.

👉 Visit LetterStream.com to create your free account and start mailing smarter.

And if you want to dig into the tax tips for young adults, check out the full WSJ article here.

* Note: Check the website for actual delivery/send dates. This blog article is not meant as tax advice, but simply observation.

LetterStream offers bulk printing and mailing services allowing companies to send physical mail online. Whether it’s online Certified Mail, First-Class Mail, FedEx 2Day, or postcards, we give both small businesses and large corporations the 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.

Healthcare Mailing: Why Letterstream Is the Best Choice

Healthcare Mailing Made Simple, Secure, and Reliable

LetterStream understands the unique challenges that healthcare professionals face when it comes to mailing important documents. From ensuring HIPAA compliance to handling high volumes of time-sensitive patient statements, we’ve designed our mailing services to meet the specific needs of medical organizations. Accuracy, security, and efficiency drive everything we do, making us the preferred choice for healthcare providers across the country.

What Sets LetterStream Apart for Healthcare Mailing?

Seamless Online Mailing: With LetterStream’s SAAS platform, healthcare professionals can send patient statements, insurance updates, and compliance notices entirely online. Simply upload documents, choose mailing preferences, and let our system handle the printing, inserting, and sending—all from your computer, with no manual processing needed.

Unmatched Security & HIPAA Compliance: Healthcare mail requires the highest level of confidentiality. LetterStream’s secure mailing services are designed to safeguard patient data while ensuring compliance with HIPAA and other regulatory standards. We handle sensitive documents with precision so that you never have to worry about security risks.

Speed and Accuracy You Can Rely On: LetterStream prioritizes getting your mail out the door as quickly as possible. Our streamlined processing system ensures that patient statements, insurance notices, and compliance mailings are printed, inserted, and sent with minimal turnaround time. Our automated workflows and optimized mailing solutions help healthcare providers avoid delays, keeping operations running smoothly and efficiently.

Making Medical Billing Effortless

Managing patient billing can be overwhelming, but LetterStream streamlines the process with:

Quick uploads of invoice and statement mailings: easily send patient invoices and statements with minimal effort, reducing administrative workload
Real-time tracking: Confirm delivery with Certified Mail tracking and opt-in for an Electronic Return Receipt (proof of signature)
Bulk mailing capabilities: handles large volumes effortlessly

Through your LetterStream account, your office can send billing statements with complete visibility, eliminating bottlenecks in patient communication.

Trusted for Insurance & Compliance Notices

Healthcare providers and insurance companies trust LetterStream’s mailing solutions for:

HIPAA-compliant insurance notifications
Policy updates and regulatory mailings
Appointment reminders and compliance notices
Medical bill statements

With being able to upload jobs in under two minutes or less and with compliance-focused features, we make sure critical documents arrive securely and on time.

Experience Hassle-Free Healthcare Mailing with LetterStream

Our goal is to make healthcare mailing faster, safer, and easier. Whether you’re sending medical statements, compliance letters, or insurance notices, LetterStream handles it all with precision and reliability.

Start simplifying your healthcare mail today with LetterStream’s Online Printing & Mail Services!

LetterStream offers bulk printing and mailing services allowing companies to send physical mail online. Whether it’s online Certified Mail, First-Class Mail, FedEx 2Day, or postcards, we give both small businesses and large corporations the 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.

How to Take the Stress Out of Tax Season with Letterstream

Using LetterStream to send out tax documents makes tax season a breeze.

Tax season can be a logistical nightmare, especially when it comes to sending out time-sensitive documents like 1099s, W-2s, and IRS correspondence. Ensuring your tax forms are mailed accurately and on time is crucial to avoid penalties and keep everything running smoothly. That’s where LetterStream comes in—making tax season easier with secure, efficient mailing solutions.

Meeting Tax Deadlines with Ease

One of the biggest challenges of tax season is meeting strict IRS deadlines. Missing deadlines can lead to fines and compliance issues, but with LetterStream’s quick turnaround, you can easily upload tax documents for immediate processing, ensure on-time mailing with First-Class Mail and Certified Mail tracking options to confirm delivery. LetterStream also offers a way to expedite your mailing to get your tax documents out the door same-day or within one business day, in the event that you’re behind on getting them mailed.

Reducing Manual Work with Automated Mailing

Printing, folding, and stuffing tax documents manually can be a hassle—especially in bulk. LetterStream automates the process, handling everything from printing and envelope stuffing to applying postage and ensuring your mail is secure and sent out quickly. Simply upload your tax forms, and LetterStream takes care of the rest!

Ensuring Security & Compliance

Security is critical when mailing tax documents, as they contain sensitive information. LetterStream prioritizes data protection with secure handling that meets compliance standards, certified mail options for proof of delivery, and processing methods that align with IRS mailing requirements.

Flexible Mailing Options for Businesses & Individuals

Businesses and accountants handling bulk tax documents need adaptable solutions. LetterStream offers options for bulk mailing high-volume tax documents, Certified Mail for IRS correspondence, and priority mailing for urgent send outs, ensuring every tax-related mailing is managed efficiently.

Tracking Your Tax Mailings in Real Time

Concerned about lost tax forms? LetterStream provides Certified Mail with tracking, so you always know when your tax documents are mailed and delivered. With confirmation for each piece of mail, reduced risks of missing important tax documents, and timely updates for clients and employees, you gain complete peace of mind.

Simplify Tax Season Today

Tax season doesn’t have to be stressful. LetterStream is a hassle-free way to send tax documents securely, efficiently, and on time. Save time, reduce errors, and meet every IRS deadline with ease.

Get started with LetterStream’s Online Printing & Mail Services today!

How to Expedite Your Mailing on LetterStream

Get Your Mail Out Faster—Because Time is Money (And Sanity!)

Speed matters, and when you need important documents sent out quickly, every second counts. Whether you’re sending out HOA notices, legal documents, open enrollment letters, or those important business statements, you want them out the door yesterday. The good news? Expediting your mailing with LetterStream is easier than you think. Let’s break down how to get your mail moving at warp speed.

Pick The Right Mailing Option

First, let’s talk about delivery. Now we can’t guarantee when the mail will actually be delivered. However, we can guarantee that we can get it out fast, but once it leaves our facilities and in the hands of the United States Postal Service (USPS) then it’s out of our hands. However, we do offer different mailing options that can help to hopefully get your mail there quicker. Let’s break it down:

FedEx 2Day: The Fastest and most secure way to get your mail delivered. FedEx 2Day does guarantee that your mail will get there within two business days. You can also opt-in to track it and get a signature.
First-Class Mail: Considered the best bet for speed and affordability—typically delivered in 1-5 business days.
Certified Mail: This is good option for tracking and proof of mailing. However, if we’re being honest, Certified Mail can sometimes take a long time to be delivered, but you can track it right from inside of your LetterStream account for when it gets sent off and delivered. You can also choose an Electronic Return Receipt if you’d like to have proof of signature as an option.

Expedite Your Mailing

We’re fast when it comes to getting your mail out the door. How fast you ask? Well, we’re proud to say that 95% of all mail goes out by next business day. So we’d say pretty fast. But, if you have a really critical piece of mail or last-minute mailing that you need to be sure gets out the door within one business day or same-day, then the Expedite mail option is your new best friend. Selecting expedite guarantees your letters go out the same day or guaranteed the next day.

Expedite Options:

Expedite Processing: Your mail will be mailed within 1 business day.

Rush Processing: Your mail will be mailed the same business day if submitted before the cutoff time, which is typically 3 PM Arizona time.

Here’s how to expedite your mailing:

Log in to your free LetterStream account.
Name your mailing and upload your pre-addressed PDF or CSV address list and choose your mailing type.
Choose your return address and then proceed to upload any documents, inserts or return envelopes that may be needed.
Review your recipient’s list.
Review the Job Confirmation page and then continue to payment.
On the My Account – Billing Information page you will see an option for “Expedite.” It is automatically set to choose “normal processing (included).

Click on the dropdown and choose “expedited processing (additional fee)” or “rush processing (additional fee)” for same-day. Take note that it may say “Same Day Available Before 3:00 PM MST” if after the same-day cut-off time.

You can then continue on to pay for your job with the expedited processing fee included.

Upload Like a Pro in 2 Minutes or Less

Want to make sure your bulk mailing can be uploaded quickly and without any issues arising? Here are some tips and helpful resources to make your mailings a breeze:

PreFlight your PDFs with our PDF PreFlight Tool: Use this tool to make sure your PDFs are formatted correctly for easy upload without any mistakes to mailing addresses, perf lines or document discrepancies. Click here to learn more.

Address Check: Check to make sure addresses are properly formatted so there are no delays. LetterStream offers an Address Cleanup service to be extra sure your addresses are correct and up-to-date.

Bulk Upload: Uploading multiple docs? Group them together for a smoother, faster experience.

Using LetterStream to Send Mail Online Is a Breeze

Using LetterStream to send your business-critical mail online is super easy. But if you feel like you need some questions answered or resources to help make your mailing that much easier, we’ve got you!

We have our awesome Chat Help that is available 24/7 located in the bottom right-hand corner of our website.
Our Help Docs are available online to view at any time.
Our YouTube is growing and gives you step-by-step instructions on how to accomplish sending mail through us, along with other tutorials and tips & tricks for how to be successful using LetterStream.

Bottom line, we’re here to make sure your mail gets out where it needs to go—fast.

Expediting Your Mail

Expediting your mail with LetterStream is as easy as clicking “Send.” Whether you need a quick turnaround or full-on lightning speed, we’ve got the tools and expertise to make it happen.

So, ready to skip the mailing stress? Join the LetterStream family and see just how easy it really is!