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Certified Mail Is the ‘Read Receipt’ That Actually Means Something

Here’s a fun little game: go search your inbox or text messages for “read receipt.” Now, try to remember the last time that actually meant something.

Can’t think of one? Same.

Because while email and text read receipts might give you a tiny dopamine hit, “Ooh! They saw it!”—they don’t hold up in a courtroom, a compliance audit, or even in a conversation where someone swears they never got your message.

But you know what does?

Certified Mail. And yes, it’s still alive, well, and wildly underrated in 2025.

Email Is a Great Tool—Until It’s Not

Look, we’re not anti-email. It’s fast, free, and fine for 90% of your communication. But the moment you need real accountability, something legally trackable, something your future self won’t regret. Just know: email isn’t it.

That’s when Certified Mail steps in like the responsible older sibling who keeps receipts.

Here are some examples:

Need proof a client actually got that legal notice?
Need to confirm a resident received the HOA violation letter you sent last week?
Need to settle a dispute without playing “he said, she said?”

Cue Certified Mail.

Certified Mail is your “We did our job” card. It comes with tracking, timestamped delivery and delivery attempts, and a return receipt if you want it. It’s not just a message—it’s your lifeline for your business.

What Certified Mail Does That Email and First-Class Mail Can’t

Let’s break it down. Because not all mail—and definitely not all “read receipts”—are created equal.

Sure, First-Class Mail is already a big step up from email—it’s physical, it gets business-critical mail where it needs to go, and shows that you took the time to send something real. And for most business mailings, it’s plenty and good enough.

But when you’re dealing with business-critical communication, where the stakes are high, timelines matter, or legal protection is a must, Certified Mail adds to the paper trail. The timestamps, the proof of sending, the receipts and the signature make all the difference when it comes to these types of mailings.

That’s the difference between “We sent it” and “We can prove it.”

There’s something powerful about receiving Certified Mail. It doesn’t just say “we sent this”—it says “this matters.”

Certified Mail Isn’t Just for Lawyers Anymore

To this day, Certified Mail is essential for lawyers. A lot of our customers are lawyers, and for good reason. But it’s expanding and becoming more common in other industries as well. Here’s where we see it the most (and keep in mind, it’s suitable for any and all industries in the end).

HOAs: sending annual meeting notices, fines, and certified compliance letters
Law firms: protecting themselves (and their clients) with documented delivery
Construction companies: mailing lien notices, pay apps, and change orders
Financial services: delivering statements and disclosures with proof

These are make-or-break communications, and no one wants to “hope the email went through” when dollars, deadlines, or disputes are involved.

You Don’t Have to Wait in Line to Send Certified Mail

Now here’s where it gets good: Certified Mail doesn’t have to be annoying anymore.

No more filling out paperwork. No more green cards. No more standing in line behind someone shipping a ton of documents at the Post Office, making your wait time even longer. No more typing in long tracking numbers to see where your Certified letter is.

You can send Certified Mail online in just a couple of minutes with LetterStream. You upload your documents, and we print it, stuff the Certified envelope, apply postage, mail it, and track it. You get the confirmation, and you can track it all from within your account. The recipient gets the message. No drama. No guessing. No “maybe they saw it.” Just the real kind of “read receipt.”

If It’s Important, Send It Certified Mail

If your future self needs proof, send it as Certified. If your company wants peace of mind, send Certified. If you’re tired of wondering whether something got there or not…you get the idea. Just send it as Certified Mail, plain and simple.

Why?

Because “I never got it” stops working the second you’ve got tracking, delivery confirmation, and a return receipt in hand or in our case an Electronic Return Receipt online.

And that folks, is something email just can’t do.

Need to send Certified Mail without the Post Office hassle?
We’ve got you. Learn more about how to send Certified Mail online here.

LetterStream offers bulk printing and mailing services, allowing companies to send physical mail online. Whether it’s online USPS 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.

Small Businesses Can Easily Save Time by Sending Mail Online

Running a Small Business? Here’s the Truth: You Don’t Have Time to Send Mail

I don’t know who needs to hear this; small business owners may be superheroes but they can’t do everything all the time. No matter how much they may want to.

Trust me, I’ve been there.

Every week, I talk to people juggling sales calls, fixing printers, answering customer emails, reviewing budgets, mailing invoices, basically just trying to run their business, sometimes all before lunch. The hustle is real, but the exhaustion is even more real.

And somewhere in the middle of all that, you’re also supposed to figure out how to scale?

It’s a lot! But there are some solutions that can help you manage, at least some of your tasks.

That’s where online platforms come in—not as some shiny tech trend, but as a legit way to give you your actual time back.

Let’s talk about that for a second.

You Don’t Have a Time Problem. You Have a “Too Much Stuff” Problem

The thing that eats up time isn’t usually one big project—it’s 37 tiny ones. Like printing and mailing letters one by one (I beg you, please stop doing this) or waiting to send out statements until “there are enough to make it worth the trip.”

I hear that one a lot.

But guess what? Waiting for mail to pile up can just get you behind. Not to mention the time, energy, and money it takes for supplies, postage, and gas to get your mail out.

This is one of those places where a good online platform changes the game. Especially if you use LetterStream (see what I did there?) You don’t need to wait. You don’t need a minimum. You just upload the file and poof—it’s mailed. Certified Mail with tracking, First-Class, FedEx 2Day, pretty much whatever you need mailed, we can make it happen.

There are no Post Office trips, no printer jams, and no awkward conversations with Cheryl in the office about whose turn it was to buy stamps.

You Don’t Need a Bigger Team—You Need Better Tools

If you’ve ever thought, “We’re just too small to outsource that,” I get it, and I hear you.

But it’s not about being “big enough.” It’s about being smart enough to say, “I shouldn’t be doing this by hand anymore.”

Mail is one of those sneaky things that seems manageable—until it’s not. Until you’re up late stuffing envelopes for a compliance deadline. Until the return address stamp runs dry or the postage meter isn’t working right. Until you realize you’ve spent a quarter of your week doing something that could’ve been automated.

That’s why we built our platform to feel like you’ve hired someone without actually hiring anyone. Literally, all you have to do is upload your documents, and we’ll handle the printing, stuffing, postage, and mailing. Like magic, but USPS-approved.

You Started This Business for a Reason. It Probably Wasn’t to Buy Envelopes

There are so many great platforms out there that save small businesses time when it comes to email marketing, accounting, scheduling…you name it.

But mail is still this weird gap no one talks about. It’s like the boring admin task that somehow still runs a huge part of your operations. And when it’s not done right—or not done at all—it can cause real problems.

We’re not here to fix everything. But if we can make mail one less thing you have to think about, that’s a win. And it’s a big win.

Because your best energy should go into growing your business, not folding paper and hunting down stamps.

You Deserve to Run a Business That Doesn’t Burn You Out

If you’re still mailing everything manually, ask yourself why.

Is it saving you money? Probably not.
Is it helping you scale? Definitely not.
Is it just what you’ve always done? Yeah… that’s usually it.

Let the old way go.

You don’t need to do it all. You just need to stop doing the parts that can be done for you.

And if mail is one of those parts? We’re here. No minimums. No stress. It’s that simple. Remember, small businesses don’t have to do it all and it usually doesn’t help them save money in the end either.

Curious what it looks like to never visit the Post Office again?
Start here: LetterStream.com

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.

Meet Aaron Harris, Our New Head of Sales at LetterStream

When Aaron Harris joined LetterStream as our new Head of Sales, we knew we were bringing on someone special. From day one, he showed up ready to dive in, connect with our customers, and help move the needle in all the right ways for those looking for smarter business mail solutions.

His first big debut? The 2025 CAI National Conference in Orlando—and let’s just say, he made an impression.

Making a Strong First Impression at CAI National

Whether you caught him mid-conversation at the booth, answering tough questions about HOA mail, or just sharing a laugh with a board member juggling too many community deadlines, Aaron brought a level of energy and authenticity that turned heads (in the best way).

We’re now a couple of weeks out from the event and we’re still hearing from folks who said, “Wait—who was that guy? He was great.” That’s Aaron. He listens, he leads, and he shows up with real solutions—something that fits right into how we serve reliable print and mail services every day, for all customers in all industries.

Helping HOA Managers and Organizations Get Ahead.

Here’s the thing: Aaron gets it.

He understands the real-life challenges our customers face—the last-minute mailings, the compliance pressure, the scramble to get things out the door. He’s already bringing fresh ideas to the table, the kind of ideas that help our clients get ahead of their mailing strategy instead of constantly playing catch-up.

Whether it’s optimizing communication for community associations, helping clients streamline Certified Mail, or improving how new users navigate our platform, Aaron’s already adding value to how we help businesses send important mail online—easily, securely, and on time.

Collaboration, Curiosity, and Customer Focus

More than anything, Aaron fits in here in the best way. He cares about people. He’s curious, he’s collaborative, and he’s not afraid to roll up his sleeves. That’s the kind of leadership that makes a difference, not just in sales—but across the entire customer experience.

And at LetterStream, that’s exactly what we’re about: making mail easier for our clients, from HOA notices to statement printing, from Certified letters for lawyers to bulk mail projects for 3rd Party Administrators and everything else in between.

What Aaron Brings to the Future of LetterStream

We’re excited for what’s ahead. Aaron’s helping us think bigger about how we serve the HOA space, legal professionals, small businesses, large businesses, those in construction and anyone looking for a more reliable way to send mail.

He’s already finding ways to make it even easier for new clients to get started, feel supported, and know they’ve got a real partner in their corner.

Welcome to the LetterStream family, Aaron. We’re lucky to have you!

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.

LetterStream’s 2025 Q1 Bonus Party at Snakes & Lattes!

Woohoo! It’s bonus party time again at LetterStream!

On Wednesday, May 21st, the LetterStream team headed to Snakes & Lattes in Tempe for our quarterly bonus celebration. The theme? Olympic Board Game Night. The vibe? Energized, connected, and a little competitive (in the fun way).

Let me tell you how it went.

A Night of Teamwork

We split into teams, grabbed some game boards, ate some food, sipped on yummy lattes, and dove in. No printers, no tracking numbers—just great people, games, and a lot of laughter.

Some teams came to win. Others just came to eat delicious food and roll dice. Either way we got to be together as a work family.

The board game “Olympics” wasn’t just a clever name—it turned into an actual team showdown, with rounds of strategy, bluffing, guessing, and cheering each other on.

We didn’t crown a champion, but let’s just say some teams walked away feeling very accomplished.

Food, Lattes, and That Off-the-Clock Magic

Snakes & Lattes was the perfect setting. Chill atmosphere, excellent menu, and enough coffee to keep us wide awake even after the longest round of Monopoly.

More importantly, it gave us the chance to catch our breath and catch up. These quarterly parties aren’t just about having a good time—they’re also about being together. Getting to talk about something other than mail job or turnaround times. It’s about saying thank you for the hard work that each team member puts in day after day, quarter after quarter, year after year. And a little bit about finding out who’s really good at trivia. Or who’s been quietly training for this moment their entire board-game-loving life. We’re here for it all.

Celebrating Accountability, LetterStream-Style

Each quarter, we highlight a core value, and this time, it was Accountability.

Just like every other bonus party we had a great slideshow to represent the last quarter and showcase our progress and even ways we can continue to improve. We also take the time to recognize new team members, highlights, promotions and new changes. We love to recognize that our team shows up for each other, owns their part of the process, and keeps things moving when it matters most. Q1 demanded that and our team delivered.

Like we mentioned above, this party was our way of saying thanks— in real time, with real connection and of course, with lots of really fun times!

Until Next Time…

To everyone who helped make the night happen—thank you. For showing up, playing along, and being the kind of team people are proud to be part of.

Q1’s in the books. Q2, we’re coming for you—with a little caffeine and a lot of momentum!

Stop Holding Onto Your Mail. Send It Out ASAP.

You know that stack of letters sitting on your desk? The ones you’re “waiting to send” until there are a few more to make it “worth it”? Yeah. That stack is not doing you—or anyone else—any favors.

Let’s talk about the myth that mailing more at once is better. Because honestly… It’s not, at least at LetterStream.

More Pieces Don’t Equal More Value

Somewhere along the way, a lot of folks got the idea that you should wait until you’ve got a big pile of letters before sending them out. Like it’s bulk trash day and you want to make it count.

We get the logic: maybe you’re hoping for a discount, or maybe batching just feels more efficient. But when it comes to important business mail—statements, notices, compliance letters, time-sensitive anything—that delay? It costs more than you think.

There’s no secret reward for holding onto mail like it’s fine wine. It doesn’t get better with age. There’s no “bulk magic” happening behind the scenes. The truth is: with the right system in place, sending one letter or 100 should feel exactly the same—easy, fast, handled.

And if you’re using a platform like ours, that’s exactly how it works.

Late Mail = Bigger Headaches

Here’s the part no one likes to admit: waiting to send mail can quietly wreck your timeline. Especially if you’re managing compliance deadlines, homeowner notices, invoices, or legal documents.

We’ve seen it too many times. A team waits to bundle everything up. They finally hit send. And by the time the mail lands, it’s already too close to the deadline—or worse, too late.

Then comes the damage control. The “we swear we sent it” emails. The callbacks. The fines. The escalations. And all because someone thought they’d get a gold star for waiting until they had a full stack.

You’re Not Saving Money by Waiting

Let’s be really clear: there’s no magical price break coming for your batch of 27 envelopes versus the 5 you had yesterday.

First-Class Mail rates are what they are. Certified Mail? Same deal. Whether you’re sending one or sending now, the cost per piece doesn’t drop just because you waited. And if you’re using a system that charges fairly for exactly what you send—no hidden minimums or batch penalties—you’re not getting some hidden bonus for holding back.

You’re just making your life harder.

Not Waiting Helps LetterStream, Too.

Here’s something else to consider—not just for you, but for the whole ecosystem.

When you wait and then drop a giant job all at once, it takes up one of our production machines for longer than necessary. That can slow down other jobs in the queue—yours included. When mail flows in more evenly, we’re able to keep things moving fast, clean, and on time for everyone.

It’s kind of like a highway: if everyone merges calmly, we’re all cruising. But when 500 cars try to get on the freeway at once, well… you’ve seen what happens.

So if your job is ready, go ahead and send it. It helps your own timeline—and makes the whole process smoother across the board.

Send It When You Have It

That’s our advice. Simple, but solid.

If you’ve got mail ready to go—send it. Don’t let it hang around your office. Don’t wait for a mystical “right time.” Don’t risk missing your deadline because you wanted to be more “efficient.”

We built our mailing platform to be ridiculously fast, no matter how many pieces you’re sending. Upload a PDF, click send, and it’s out the door. Whether it’s one notice or a thousand.

So go ahead—knock that letter off your list. The future you (and your clients, your board, your auditor, your accountant, and your sleep schedule) will thank you.

Why Easily Sending Mail Online is the Future

Let’s be honest—“print and mail” doesn’t exactly scream cutting edge.

Most people still picture someone hunched over a clunky office printer, feeding in paper one page at a time while envelopes pile up like snowdrifts. It’s slow. It’s manual. It’s been “next on the list” for about two weeks now.

But here’s the truth: online printing and mailing isn’t just the future of business communications—it’s the present. And if you’re still doing it the old way, you’re missing out on speed, control, and a whole lot of sanity.

Let’s talk about why more businesses (the smart ones) are switching—and why the future looks a lot less like a jammed printer and a lot more like clicking “send.”

The Old Way Isn’t Working Anymore

There was a time when hand-stuffing envelopes made sense. Maybe you had one mailing a month. Maybe you liked the meditative hum of the folding machine. But now?

You’re juggling statement runs, compliance letters, customer notices, invoices cycles—and that’s just this week.

Manual mailing isn’t scalable, and it’s sure not built for teams trying to move fast. Not to mention: mistakes are easy, and nobody wants to resend 500 letters because of one column in a spreadsheet.

Online Printing Means You Don’t Need a Mailroom

When you move to an online platform, something magical happens: the mail still goes out, but you don’t have to touch it. Or buy stamps. Or stand in line at the post office wondering how your life got here.

Instead, you upload your file, choose your options, and hit send. Done.
Print. Insert. Mail. Track. It all happens behind the scenes while you do literally anything else.

And yes, it still counts as “real mail.” USPS delivers it. Your customers, vendors, or homeowners get a letter in the mailbox—on time and professional-looking.

You Get Speed and Accuracy

Let’s say you’re sending time-sensitive statements or legal notices. You need them to:

Go out fast
Be delivered to the right address
Have proof they were sent

With online mailing platforms, you get all three. Your job’s processed fast (sometimes same day), tracking is baked in, and you can access your full mailing history whenever someone says, “Hey, did we ever send that?”

Spoiler: Yes. Yes, you did.

Your Team Doesn’t Need to Be in the Same Place Anymore

Here’s a big one: remote teams.
It’s 2025. Not everyone works in the same office anymore. So why is your print-and-mail process stuck in 2012?

With an online platform, anyone on your team—remote, hybrid, in-office—can send mail from wherever they are. No printer? No problem. No one to sign off on postage? Still fine. Everything happens online, with visibility and control from wherever you’re working.

The Future Is Already Here

This isn’t some “someday” tech. It’s already how thousands of businesses are handling their most important mail. And once you switch, you’ll never go back.

Seriously—ask anyone who’s made the leap. They’re not hunched over a printer anymore. They’re sipping coffee while the compliance letters are sent for them. That’s the future we’re talking about.

If your mail process still involves toner cartridges, folding paper by hand, or someone saying, “I’ll run these to the post office after lunch,”—well, you already know the answer.

You’re ready.

Start here:
Online Printing & Mail Services – Send Your Letters The Easy Way

Compliance Notices: How to Not Mess Them Up When Mailing

You know those moments when you’re walking out the door and someone says, “Hey—did that compliance notice ever go out?”

And your stomach drops because… maybe?

Sending compliance notices is one of those things that sound simple—until you realize how many ways they can go sideways. And if they do, they don’t just vanish quietly. They boomerang back with consequences: fines, missed deadlines, legal drama, angry homeowners… you name it.

So let’s talk about how to actually get them right. Not perfectly. Not ideally. Just reliably, repeatably, and without the panic attack.

Stop Printing Compliance Notices by Hand

First off: stop printing them in-house if you don’t have to.
Unless your team really loves late nights with paper cuts and jammed printers, it’s just not worth it. We’ve seen too many “oops, we forgot the second page” situations. Not a great look when you’re trying to hold someone accountable for a violation or notify them of a deadline.

Automating compliance mailings is your best friend here. When the system is doing the heavy lifting—printing, stuffing, mailing, tracking—it means fewer fires to put out. That’s not lazy. That’s smart.

Use Certified Mail for Compliance Tracking

Next: use Certified Mail when it counts.
If your notice could ever be questioned—“We never got it!”—Certified Mail gives you that neat little paper (or digital) trail that says, “Yeah, you did.” And you can pull that proof up anytime without rifling through a file drawer from 2019.

It’s the kind of backup that keeps arguments short and lawyers bored.

Write Compliance Notices Clearly

And please, don’t write compliance notices like you’re auditioning for legal drama.
You don’t need five paragraphs of preamble or vague “pursuant to Section 47-B” language unless it’s required. Say what the issue is. Say what they need to do. Say when it’s due.

Simple compliance language is always better:

Use headings or bullet points
Be clear about timelines
Avoid unnecessary jargon

Save the fluff for your next holiday card.

Don’t Wait Until the Last Minute

Timing is everything. If the notice needs to land by a certain date, send your compliance letters early.

If the deadline is Friday, don’t mail it Wednesday and cross your fingers. USPS does a good job, but they can’t time travel (yet). Give it a few days’ buffer, or pick a faster delivery option if the timeline’s tight.

Have a bunch to send? Even better. Batch early, schedule often, and stop cutting it close.

Keep a Record of Every Notice You Send

Whether it’s for legal reasons, your records, or just peace of mind, proof of mailing matters.

The best way to do that? Use a system that keeps a timestamped record of every compliance notice you send. You can pull it up later without digging through piles of paper or wondering who handled it last.

Compliance Mail Doesn’t Have to Be Complicated

Look, we know these notices aren’t exciting. They’re not supposed to be. But they are important, and they deserve better than being last on your to-do list.

When done right, they protect your business. They back up your policies. They show you’re buttoned up and paying attention.

When done wrong… well, let’s just not go there.

If you’re still folding notices in your office kitchen with last year’s envelopes? It might be time for a new game plan. Start here: Free Signup – LetterStream

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.

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.