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Tag: 1099 Filing

  • Are You Filing W-9s Wrong? Find Out

    Are You Filing W-9s Wrong? Find Out

    Introduction

    On the surface, the W-9 form looks harmless, just a tidy one-pager asking for a name, tax ID, and a signature. But here’s the thing: W-9s are like mousetraps in a clean kitchen. You don’t notice the danger until it’s too late.

    I still remember a client, a fast-growing design agency in Austin, who swore they were “on top of their W-9s.” But when January rolled around and it was time to send out 1099s, they discovered that 17 of their contractors had submitted outdated or incomplete forms. The result? Delays, panic, and hours of chasing signatures during the tax season’s busiest week.

    As a CPA, I can’t count how many businesses I’ve seen get blindsided by the hidden consequences of W-9 mistakes. It’s not just about paperwork, it’s about compliance, time, and trust. That’s why we created this guide to help you spot the top 5 mistakes before they cost you.

    Let’s start with the most common slip-upone that nearly everyone makes without even realizing it.

    1. Using an Outdated or Incorrect W-9 Version

    Imagine trying to enter a high-security building with last year’s ID badge. The guard might smile, but you’re not getting through. That’s exactly what happens when you submit an outdated W-9 form to a payer—or worse, to the IRS.

    Every so often, the IRS updates the W-9 form to reflect policy changes, clarification of instructions, or updated definitions for business structures. Yet many businesses print a stack once a year and use them blindly, unaware that the version they’re handing out is out of date.

    Why It Happens:

    • Businesses copy old templates or reuse PDF downloads from years past.
    • Employees don’t know where to check for updates.
    • Some online tools don’t sync with the latest IRS changes.

    What’s the Risk?

    • Compliance issues: An outdated W-9 might not ask for all required data or use obsolete formatting.
    • 1099 rejections: Mismatched forms can delay filing or lead to IRS follow-up.
    • Fines and backup withholding: If you’re missing required info, the IRS can mandate 24% withholding on payments.

    CPA Tip:

    Always fetch the W-9 directly from IRS.gov. Better yet, use a tool like GetW9 that ensures your recipients are filling out only the most current version, and no more guessing.

    One of our GetW9 users, a virtual event company, discovered mid-January that 40% of their vendors had submitted a 2018 W-9 they downloaded from Google search. Using GetW9, they triggered auto-reminders with a fresh form link, and got compliant forms back in 48 hours without lifting a finger.

    2. Missing or Incorrect TIN/EIN Entries

    Think of the Taxpayer Identification Number (TIN) like a fingerprint, it uniquely identifies the contractor to the IRS. Get it wrong, and it’s like trying to unlock a door with the wrong key. Nothing works. Worse, the IRS may step in with penalties or force you to withhold 24% of future payments under backup withholding rules.

    One of my clients, a boutique marketing firm in Chicago, found this out the hard way. They submitted 1099s for five freelance writers, only to have the IRS bounce them back due to mismatched TINs. The writers had typed in their Social Security Numbers incorrectly, and no one had double-checked. The result? Hours of cleanup, amended filings, and frustrated contractors asking why their payments were suddenly being withheld.

    Why It Happens:

    • Contractors don’t always understand the importance of entering their TIN correctly.
    • Businesses collect W-9s by email or PDF and never verify the information.
    • Some rely on memory or autofill tools, which can introduce errors.

    What’s the Risk?

    • IRS penalties for submitting incorrect forms.
    • Backup withholding obligations on future payments.
    • Delays in 1099 filing, which can affect both your business and your contractors.

    3. Wrong Classification of the Payee

    Filling out a W-9 is not just about entering numbers. It’s about checking the right boxes, literally. One of the most misunderstood parts of the form is the payee classification. Choosing the wrong business type might seem like a small error, but it can ripple into serious tax reporting issues.

    I once worked with a client who hired a web developer that marked themselves as an individual. But when tax time came, the developer’s accountant insisted they were an S Corporation. That mismatch caused the 1099 to be flagged, and both sides had to refile documents. It wasn’t malicious, just a misunderstanding of what that little checkbox meant.

    Why It Happens:

    • Contractors don’t understand the difference between being a sole proprietor, LLC, or corporation.
    • Some assume “individual/sole proprietor” covers everything if they don’t have employees.
    • Businesses rarely ask follow-up questions to verify the selection.

    What’s the Risk?

    • Incorrect 1099 filing: Some entities, like S Corporations, may not need a 1099 at all.
    • IRS rejections or mismatches, leading to time-consuming amendments.
    • Audit exposure if classification errors are repeated across multiple contractors.

    CPA Tip:

    Always confirm the contractor’s business structure. If they’re unsure, encourage them to speak with their tax advisor before submitting the form. Tools like GetW9 can help simplify this process by guiding contractors with inline explanations for each classification type.

    4. Failing to Sign and Date the Form

    A W-9 without a signature is like a contract without consent; it’s not valid. And yet, it’s one of the most common mistakes businesses encounter. A contractor might fill in all the right fields, check all the right boxes, but forget that one small line at the bottom. The result? You’re holding a form the IRS treats as if it doesn’t exist.

    This happened with a client in the real estate space who onboarded a dozen new agents during the year. They collected all the W-9s via email but didn’t notice that four of them were unsigned. When it was time to prepare 1099s, their accounting software flagged the missing signatures, and the scramble began. Calls, emails, and follow-ups, it turned into a week-long chase just to get four lines signed.

    Why It Happens:

    • Contractors forget to scroll to the bottom of the form.
    • Digital or scanned copies get cut off.
    • No system in place to review completeness before submission.

    What’s the Risk?

    • Invalid form: The IRS does not accept unsigned W-9s.
    • Delays in processing: You can’t file accurate 1099s without a valid W-9.
    • Time drain: Chasing down signatures after the fact takes time away from year-end tasks.

    CPA Tip:

    Always treat the signature field as non-negotiable. In a manual workflow, use a checklist to verify before storing. Even better, use a tool like GetW9 that doesn’t allow submission unless the form is signed and dated.

    5. Storing W-9s Insecurely (or Not At All)

    You wouldn’t leave tax documents lying around in a coffee shop, but storing W-9s on an unprotected computer or in an inbox isn’t much better. These forms contain sensitive information names, addresses, and Social Security Numbers, and mishandling them can expose your business to serious legal and financial risk.

    One of our clients, a staffing agency based in California, used to keep contractor W-9s in a shared Dropbox folder. It worked fine until an employee left the company and took access with them. Worse, none of the files had been encrypted. When they realized what had happened, they had to notify their entire contractor list and tighten their data policies overnight.

    Why It Happens:

    • Businesses store forms on desktops, in email threads, or unsecured cloud drives.
    • There’s no formal process for organizing or limiting access to W-9s.
    • Teams underestimate how valuable this data is and how often it’s targeted.

    What’s the Risk?

    • Data breaches: Exposing TINs or SSNs could trigger compliance violations and lawsuits.
    • Loss of records: Without proper storage, forms can be misplaced before 1099 filing season.
    • Audit risk: The IRS expects you to retain W-9s for at least four years.

    CPA Tip:

    Treat W-9s like bank records. Store them securely, limit who can access them, and never rely on email or personal drives. With GetW9, all forms are stored in a centralized, encrypted dashboard where access is logged and controlled. You can find, download, or audit any form in seconds.

    Conclusion: So, Are You Filling W-9s Wrong?

    Most businesses don’t realize they’ve made a W-9 mistake until it’s too late. Maybe it’s a missing signature, an incorrect tax ID, or a file lost in someone’s inbox. Individually, these issues might seem small. But come tax time, they snowball, slowing your operations, frustrating your contractors, and putting your compliance at risk.

    If any of the five mistakes we covered felt familiar, you’re not alone. These are the kinds of errors even smart, organized teams make. But the good news is, they’re also completely avoidable.

    What would it feel like to head into January knowing every W-9 is current, complete, and secure? No loose ends. No surprises. No panic.

    That peace of mind is what GetW9 is built to give you.

    You’ve worked hard to grow your business, don’t let paperwork drag you down.
    Let GetW9 handle the forms, the reminders, and the storage, so you can focus on the work that matters.

    Try GetW9 for free. See what a smoother tax season feels like.

  • Why Late W-9 Collection Costs Businesses More Than They Think | GetW9

    Why Late W-9 Collection Costs Businesses More Than They Think | GetW9

    Introduction

    Picture this: It’s January 25th. Your bookkeeper’s face is pale. You’ve got coffee in one hand, a spreadsheet in the other, and one big problem: five contractors you paid last year still haven’t sent in their W-9s. One of them is traveling abroad. Another has changed their email. The rest? Radio silence.

    Now, the IRS deadline is a week away. Your team is chasing signatures instead of closing the books. And worst of all? You paid these people months ago, so they have no incentive to respond quickly.

    If this sounds familiar, you’re not alone.

    Many small businesses treat W-9s as a January chore. But by then, it’s often too late to gather forms without added stress, risk, or cost. In fact, collecting W-9s late is one of the most expensive “minor” oversights you can make not just in terms of IRS penalties, but in lost time, strained vendor relationships, and operational drag.

    At GetW9, we’ve worked with dozens of businesses who swore they had a “system” until that system collapsed under tax season pressure.

    So let’s unpack exactly why collecting W-9s late is such a big deal, and what you can do to fix it (without spreadsheets or stress).

    Why Timing Matters with W-9 Collection

    Let me share a true story. One of our customers, a mid-sized creative agency, hired a dozen contractors for various client projects throughout the year. But no one on the team had time to request W-9s up front. “We’ll deal with it later,” they said.

    When January hit, it was chaos. One videographer had moved, two designers were unreachable, and one contractor outright refused to send the form unless he was paid again for his time.

    Sound extreme? It’s not. We hear stories like this every tax season.

    Why this happens:

    • Once you’ve paid a contractor, your leverage is gone.
    • Contractors are busy and may not prioritize your W-9 request.
    • People move, change emails, or disappear altogether.
    • Your team ends up doing detective work instead of accounting.

    Collecting W-9s early, ideally before the first payment is issued, avoids all of this. It’s the same reason HR departments require W-4s from new employees before issuing paychecks. It’s just good sense.

    Think of it like boarding a plane: you wouldn’t wait until landing to ask for someone’s ID.

    Make W-9 collection part of your onboarding workflow. If you’re using GetW9, you can automate this with a branded request link, secure upload, and automatic reminders. No more email chasing. No more missing forms.

    Late W-9 Collection Wastes Time (and Trust)

    Now let’s talk dollars and consequences.

    Collecting W-9s late or not at all doesn’t just slow you down. It can directly impact your bottom line through IRS penalties and compliance issues. And unfortunately, ignorance isn’t a valid excuse in the eyes of the IRS.

    What’s at stake?

    • Penalty per incorrect 1099: Up to $310 per form
    • Penalty for failure to file on time: Up to $630 per return in cases of intentional disregard
    • Backup withholding: If you don’t have a W-9 on file, you’re required to withhold 24% of all future payments to that contractor and remit it to the IRS

    These aren’t hypothetical numbers. We’ve seen small businesses face thousands of dollars in fines simply because they didn’t have complete W-9s in time.

    Why it gets messy:

    • Incorrect TINs (Taxpayer Identification Numbers) trigger automatic alerts
    • IRS B Notices require you to fix errors and notify vendors
    • Late filings often result in extension requests, which signal disorganization

    And if you’re ever audited? Missing or incorrect forms will be one of the first red flags they look for.

    Don’t gamble with compliance

    When it comes to W-9s, it’s not just about checking a box. It’s about protecting your business from financial and legal consequences. Collecting them early and verifying the data puts you in control and keeps the IRS out of your hair.

    Lost Time = Lost Money

    If you’ve ever watched your team scramble to collect W-9s in January, you know the time cost is real. But it’s not just about filling out forms it’s about the hours (sometimes days) spent chasing, tracking, correcting, and re-filing. That’s time you’re not spending on things that grow your business.

    Here’s what’s really happening:

    • Admins are digging through email threads, Slack messages, and payment apps.
    • Your finance lead is triple-checking TINs instead of closing the books.
    • You miss opportunities to finalize accounts, run projections, or start Q1 strong.

    It adds up fast:

    • Time delay leads to missed deadlines and errors
    • Overtime or extra hours may be needed to clean up the backlog
    • Frustration grows across departments

    Wasted time = wasted trust

    It’s not just your internal team. Contractors can lose trust in your process too. Late requests, multiple follow-ups, and back-and-forths send the message that your operations aren’t tight, which could affect future working relationships.

    With GetW9, you can collect, verify, and securely store W-9s the moment you onboard a new contractor, freeing your team to focus on revenue, not red tape.

    The Right Time for W-9 Collection Is Before Payment

    Here’s the simple truth: if you’re asking for W-9s after paying someone, you’re already behind.

    The ideal moment to request a W-9 is during onboarding, right alongside payment terms, bank details, or NDAs. It should be baked into your vendor or contractor workflow so that no invoice is approved without it.

    Why this works:

    • You have leverage before money changes hands
    • Contractors expect onboarding paperwork it’s not a surprise
    • You ensure IRS compliance from day one

    One GetW9 client embedded a W-9 collection link directly into their onboarding form using our platform. Result? A 95% W-9 collection rate before the first payment was ever issued.

    How to do it right:

    • Add W-9 collection to your vendor setup checklist
    • Communicate early — “We’ll need your W-9 to activate payment.”
    • Use a tool like GetW9 to automate the request and secure upload process

    This one small change saves hours and builds a cleaner, more professional experience for everyone involved.

    When contractors know your payment process includes W-9 collection as a standard step, they respond faster and with fewer questions.

    How to Automate W-9 Collection and Stay Compliant

    Let’s face it: you don’t want your team spending their time chasing paperwork. That’s what automation is for.

    With the right tool, W-9 collection can become a background task, one that runs smoothly without human intervention. No follow-ups. No folders. No last-minute panic.

    What automation does for you:

    • Sends W-9 requests instantly after contractor onboarding
    • Provides a secure place for contractors to upload forms
    • Triggers automated reminders if someone forgets
    • Verifies TINs in real time to prevent IRS flags
    • Stores everything in one organized, searchable dashboard

    Think long-term

    Tax time shouldn’t feel like a fire drill. With automation, you can build a consistent, repeatable process that scales with your business.

    No more hunting for forms. No more rushing deadlines. Just compliance, built-in.

    If your business works with even 5+ contractors per year, automation pays for itself in saved time, reduced errors, and peace of mind.

    Conclusion: Make W-9 Collection Easy with Automation

    Let’s be real, no one wakes up excited to manage tax forms. But that doesn’t mean W-9s have to be a headache.

    The cost of collecting W-9s late goes far beyond penalties. It drains your time, stresses your team, and introduces avoidable risk into your operations. But with a simple shift, requesting forms before payment and automating the follow-up, you can take control of the process and stay compliant without chaos.

    If you’ve ever thought, “There must be a better way to handle this,” you’re not alone. Plenty of growing teams have already traded the stress of spreadsheets for smarter solutions, and they’re not looking back. Maybe it’s time to see what that feels like.