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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.

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.

Welcome Ashlee, our New Customer Service Manager

Ashlee

Hold on, hold on, before you panic at this headline, Mike hasn’t left the LetterStream team. He is now our Director of Customer Experience. We figured that Mike could get a promotion if he could find someone just as awesome in customer service as he is. That said, we didn’t think Mike would ever get a promotion. Enter Ashlee. We aren’t sure how Mike did it, but he actually found someone who can bring help and joy to customers as well as he can. Ashlee has been with us a few months now, so some of you have already experienced her good nature, knowledge of our systems and overwhelming desire to help people out.

Ashlee has some 5-star training from Marriott hotels and resorts and has supported many different clients in an earlier payroll processing career. These experiences are quite helpful to her on the job, but nothing can compare to the enthusiasm that she has to be a part of our team and her tremendous desire to support all of our customers.

Next time you call in, be sure and say “Hello and Welcome” to Ashlee.

Should You Consider Outsourcing Mailing Projects?

I was working on a proposal this morning for a potential client and found myself pondering the benefits of outsourcing mail room operations and letter shop activities.

For those of you who would like a better printing and mailing solution but are hesitant to enter the world of outsourcing, consider the idea that you are already outsourcing many of your mission critical activities. Yes, that’s right. You are already outsourcing a tremendous amount of your business operations.

You are outsourcing the activities of keeping your money safe to your local bank. You are outsourcing all of your phone conversations to cell and telecom providers. You are outsourcing your electricity to the power company. Once you start thinking about it, the only things you don’t outsource are your core competencies… those things that provide uniqueness to your product and a competitive edge to your organization.

Still skeptical? Check out what other experts say… here’s a good article in Inc Magazine that supports our logic and might shed some additional light.

The question then becomes: Is printing and mailing your competitive advantage? Is folding and inserting what makes your company unique?

If you’d like to see what it might look like to outsource your printing and mailing activities to an organization as reliable as the local power company and probably more helpful than your banking institution please give us a call and let us show you how our unique and competitive solutions can help you focus more on yours.

Mailing W-2s, 1099s, and/or Charitable Giving Statements?

Tax Forms with Glasses

It’s January, which means it’s time to send out 1099‘s, W-2‘s, Charitable Giving/Contribution Statements and other tax related documents for the current tax year.

If you are still trying to figure out how to get your documents mailed without mandatory all-night stuffing parties, we might be the right people to call.

With our hi-tech production facility and knowledgeable staff (friendly staff, too), we can take the burden out of printing, folding, stuffing, licking, stamping and mailing your critical documents.

Call us today and get some expert assistance no matter how many (or how few) documents you have.

Now where did I put that green card?

If you send Certified Mail, you know what sort of pain it is when the attorney asks for the green card (PS Form 3811) and it can’t be found.

green card - certified mail receipt

I know, I know….we all like to put our highest paid employees on the task of filing the green cards so they are always where they need to be. Well, ok…..that’s not exactly true. In reality, they stack up on the receptionist’s desk, then they get moved to the mail room, then they may make it back to the collections department, with each department attempting to file a few whenever they get an idle moment.

Sound familiar?

Wish there was a better way?

Wouldn’t it be great if we didn’t need to worry about hanging on to those pesky green cards? Instead, what if the green cards were electronically delivered to us with the name and address of the recipient and the signature of the person who received the certified letter. Then, what if the signature was instantly and accurately filed, just the way we like.

While we are dreaming, let’s make it one better. What if, when the green card is needed — even if it’s years down the road — all we need to do is type in the name or the address of the person who was sent the letter and we’d immediately see the certified letter, the tracking information and the signature, all available to be printed and handed over to the person who needs it. Now that would be ideal!

And it would also be an explanation of how our Certified Mail process works.

Don’t file green cards, use LetterStream.