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Education, IRS, Tips

Rules for When To Issue a 1099 Form to a Vendor – Updated for 2023

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As is the case every year, we’re hearing from lots of folks confused about when to send a 1099 form or other “information returns” to someone.  It is true that over time, these forms have continued to change, and the rules have become more specific… but the basics remain the same. The most important point is that only businesses need to issue 1099s — if you paid someone for personal purposes, you are not (yet) required to send them or the IRS a Form 1099.

WHAT’S NEW (or isn’t) FOR 2023:
 – Beginning in 2022, the 1099-NEC was made so that it’s no longer year-specific; there are no changes to the form for 2023.
– The IRS launched IRIS, a new free online portal, for businesses to file 1099 returns. (Beginning January 2024, you will no longer be able to file using a legacy transmitter code using the old FIRE system.)
– You must file now file 1099 Forms electronically if you have 10 or more information returns (down from 250).
– There are even more complexities regarding whether or not to issue a 1099 based on the payment type, and I expect this area to become even more challenging in future years, as new payment platforms continuously come into being.

Here’s a crash course for each type of form, followed by an FAQ.

1099-NEC
This form was new for 2020 and replaces the old Box 7 of Form 1099-MISC. “NEC” stands for “non-employee compensation”. It is due to recipients and the IRS by January 31st (or the first business day after that, if 1/31 falls on a weekend).

If you paid:
1) a NON-corporation (*see below);
2) for services (not products);
3) via check, cash, ACH, Zelle, or wire transfer — but not merchant services or electronic payments (such as credit & debit cards, PayPal Business, Venmo Business (**see below);
4) $600 or more in a calendar year;
then you need to send them a 1099-NEC.

(*) A lot of folks get confused and think the rule is if you paid an “individual,” but really the rule is a “non-corporation,” which means that partnerships and LLCs are included. Just because they have a business name doesn’t mean they’re incorporated. You cannot depend on the company’s name to determine corporate status, nor can you rely on the state LLC/Corp database, as it only indicates the entity type at the state level — almost any type of entity may elect corporate status with the IRS.

So, keep in mind that a company can be an LLC but be taxed as a corporation. In this case, you would not need to send them a 1099, because in the eyes of the IRS, they are incorporated. Here’s an example of a W-9 showing an LLC that is taxed as an S-Corp:

This is one of many reasons you should collect Form W-9 from all service vendors before giving them their first check, just to be safe. The person filling out the W-9 will indicate their entity type and whether or not they are taxed as a corporation.

There’s also an exception to the incorporation rule for attorneys and law firms. You must issue a 1099 to a lawyer or law firm regardless of whether they are incorporated. (Law firms and attorneys have so many specialized 1099 issues, they get their own blog post.)

(**) There’s a lot of confusion over Venmo and PayPal, because there are personal-use “Friends & Family” versions as well as business versions of both platforms. Legally, no business should be using the non-business versions of these payment types… but in real life, many do. It’s very hard to distinguish which payments were made using which method — in theory, a 1099-NEC would need to be issued to a vendor who was paid via a personal Venmo or PayPal method, but I’m not sure how this would be tracked. My recommendation (for many reasons) is to only use the business versions, and then the 1099-NEC is a non-issue (because Venmo and PayPal will issue a 1099-K instead).

I know, that’s all very confusing. Here’s a nice, simplified decision-tree provided by our friends over at Bookkeepers.com, courtesy of Bookkeeping Buds.

However, it’s easy to end up with issues like “what if I paid with my credit card, but used PayPal Friends & Family,” or “I use a practice management system that is funded with a bank account, so why do they issue a 1099-K,” or any number of confusing situations based on payment type. There’s simply no easy answer to these questions.

It’s so confusing, in fact, that my colleague Jennifer Dymond saw the need, and created an absolutely incredible resource at 1099problems.io which goes into detail about which payment methods are included on a 1099-K versus which ones you must issue 1099-NEC or 1099-MISC for yourself; it’s maintained regularly and updated as the proliferation of non-traditional payment methods continues. The first 1,099 people to subscribe using code DANCING1099 will receive 10% off their first order (offer expires March 31, 2024).

1099-MISC

Items such as rent payments, royalties, attorney settlements (as mentioned above, not payments for legal services), and medical healthcare payments will still be reported on Form 1099-MISC, though the form has been redesigned and the boxes renumbered.

Report prizes and awards of $600 or more that are not for services performed in Box 3. Include the fair market value of merchandise won. And be careful here, as it is easy to accidentally include these on Form 1099-NEC if the recipient also provided unrelated services.

  • Rent paid ($600 or more) (Box 1)
  • Royalties paid of at least $10 or more (Box 2)
  • Prizes and awards and certain other payments ($600 or more, see instructions for Form 1099-MISC, Box 3 for more information)
  • Backup withholding or federal income tax withheld (any amount) (Box 4)
  • Amounts paid specifically to physicians, physicians’ corporations, or other suppliers of health and medical services ($600 or more) (Box 6)
  • Direct sales of at least $5,000 of consumer products to a buyer for resale anywhere other than a permanent retail establishment (Box 7)
  • Gross proceeds paid to an attorney ($600 or more whether or not incorporated) (Box 10) – “made to an attorney in the course of your trade or business in connection with legal services, but not for the attorney’s services”; for example, a settlement agreement.

The deadline for providing this form to recipients is the same as above, January 31st. However, the deadline for filing 1099-MISC with the IRS is February 28 if filing on paper, and March 31 if filing electronically.

1099-K

It’s unlikely that anyone reading this will be in the position of issuing Form 1099-K to vendors — but you should know about this form, for a few reasons:
1) You are likely to receive one.
2) It’s the reason you don’t have to issue 1099-NEC to anyone you pay via credit card/debit card, a business PayPal account, a business Venmo account, or any “merchant service” system.
3) You may need to reconcile this form against the amount of sales income you report on your tax return.

Form 1099-K is for payments made in settlement of “reportable payment transactions”, which is any credit card, payment card or third-party network transaction. So if you receive payments in this way (unless you only accept checks, e-checks, ACH, or zelle/QuickPay, you probably do), then you’ll get a 1099-K for this total.

But because these amounts are reported to the IRS for you, you don’t need to issue 1099-NEC or 1099-MISC forms to vendors whom you paid using one of these methods. In that case, the recipient could end up having the same income reported to the IRS twice.

The rule used to be that this form was issued to anyone who had more than 200 transactions or $20,000 worth of transactions — but starting in 2024, that threshold will drop to only $600. (This implementation has been delayed twice already and AICPA is lobbying for a more reasonable threshold.) The IRS is now planning a phase-in of $5,000 for tax year 2024.

As a bookkeeper, accountant or tax preparer, it’s important to protect your small business clients by making sure all taxable income is being reported on their books/returns. If the 1099-K is for an amount that is lower than what’s on the income section of the Profit & Loss, it’s not likely to be an issue. But if it’s higher, you’ll need to do a reconciliation to show that the difference was due to non-taxable receipts such as sales taxes collected, tips collected, refunded sales, and the like.

1099-INT

This form is issued to anyone who lent your business money, and your business paid them at least $10 of interest in the past calendar year. It includes owners, partners, and shareholders.

Note: do not issue this form for accrued interest; it is only for actual payouts of interest in cash or trade.

The form is due to recipients by January 31 (February 1 in 2021), but isn’t due to the IRS until March 1 if filing on paper and March 31 if e-filing.

If not e-filing, you can use the IRS’s fill-in pdf Copy B for the recipient copy, but for the version that goes to the IRS, you have to order an official form with special scannable ink — they’re free, but they take a while to be mailed, so fill out your request early. Make sure to mark the year you are filing for, not the current year — an easy mistake to make.

Another note: I have had clients reach out confused by the language “You are not required to file Form 1099-INT for interest on an obligation issued by an individual”. This means if the loan were TO an individual rather than FROM one, and the individual paid interest to the company. (This is not usually the case.) In that situation, the individual would not have to issue the company a 1099-INT (although the company would still have to declare the interest income).

1099-DIV

This form is issued to a shareholder of a C-Corporation for dividends or other distributions paid in the past calendar year.

Most folks don’t think this applies to them — but if you own a business that is taxed as a C-Corp, and you took money out that wasn’t W-2 or loan repayments, then you may have issued yourself dividends. (And if it was for a loan repayment, did you pay the required amount of interest? If so, see the “1099-INT” section above.)

The form is due to recipients by January 31 (February 1 in 2021), but isn’t due to the IRS until March 1 if filing on paper and March 31 if e-filing.

If not e-filing, you can use the IRS’s fill-in pdf Copy B for the recipient copy, but for the version that goes to the IRS, you have to order an official form with special scannable ink — they’re free, but they take a while to be mailed, so fill out your request early. Make sure to mark the year you are filing for, not the current year — an easy mistake to make.

1098

This form is to report mortgage interest and real estate taxes. You may not think it applies to you, but if you do the bookkeeping for or are a member of a housing cooperative, you may find that it does. This needs to be issued to housing co-op members for their allocated portion of mortgage interest and real estate taxes paid by the cooperative, so they can deduct them on their personal tax return, Form 1040, Schedule A. If not e-filing, you can use the IRS’s fill-in pdf Copy B for the recipient copy, but for the version that goes to the IRS, you have to order an official form with special scannable ink — they’re free, but they take a while to be mailed, so fill out your request early. Make sure to mark the year you are filing for, not the current year — an easy mistake to make.

Frequently Asked Questions

What do I do if the vendor will not give me their Tax ID Number, which I need to file the 1099?

First off, it’s the business’ responsibility to obtain this number. That’s why I recommend getting the W-9 from the vendor before giving them their first payment. But in the case where it’s 1099-time and you still don’t have that TIN for some reason, respectfully let the vendor know that not having their info will not prevent you from filing the 1099. It just means the IRS will receive it with “REFUSED” written in the field where the number should be (or if you use an e-filing program, you will check the box that the number is unavailable). This will almost always trigger an audit for both the business and the recipient, which no one wants. Presented with this information, I find that most non-compliant vendors are suddenly able to fill out that W-9 form after all.

Do I really have to send one to my landlord? They get angry when I bring it up.

If your landlord is not incorporated, yes, you do. If it makes them mad, then consider why… are they trying to avoid declaring it as taxable income? Is that the type of person you want to rent from?

What if you forgot to issue a 1099 to someone?

It’s never too late! Since the statute of limitations never starts if you don’t file a return, penalties and interest can continue to accrue forever. If you noticed that you forgot to file a 1099, even for a prior year, reach out to the recipient in question and make sure they declared and paid taxes on the income you inadvertently forgot to remind them about — and hopefully they have. In this case, no amended return will be required on their end, and the form’s arrival will not come as an unwelcome surprise. If not, then that’s a bigger concern. It is the responsibility of each recipient of income to declare it on their return, regardless of having received the 1099. Not getting the form does not exempt a taxpayer from declaring the income they earned. So, the business owner needs to evaluate the risk involved to their company in knowingly refusing to comply with tax law, versus the recipient’s desire to evade taxes.

What do you do if you receive a 1099 that is incorrect or unnecessary?

If you receive a 1099 that has incorrect information on it, simply reach out to the issuer to ask for a corrected 1099. Do this as soon as possible, as it will help them to fix it before it is submitted to the IRS.

If they will not correct the total, then declare the full amount on your tax return, but “back out” the incorrect amount as a negative, with an explanation to the IRS for why this amount was inaccurate. If you receive an audit notice, provide the IRS with the documentation showing why your calculation is correct, and the support showing you reached out to the issuer when you realized the form was not right.

If you should not have received a 1099 at all, follow the same advice as above. A good example of this would be if you received a 1099-K for credit card payments, but also received a 1099-NEC from the company that paid you (this is quite common… it is extremely challenging in most bookkeeping software to distinguish how a bill was paid in most reports). In this case, if the customer will not void the 1099 form for some reason, simply declare the full amount on your business’ tax return and “back out” the amount that was double-issued, with the explanation that it was already declared in income via 1099-K or some similar wording.

However, if the reason you should not have received the 1099 was that you are taxed as a corporation, and you’ve already declared this income on your tax return, then you can ignore the form — it will have no effect on anything and was just a waste of time on the part of the issuer.

How do I run the 1099 report in QuickBooks? Won’t it tell me who needs a form from my company?

Most bookkeeping professionals don’t use the 1099 report that QuickBooks generates — it’s too prone to user error when setting up the vendors, accounts, and dollar-thresholds. Instead we use a program like Keeper to help us identify potential 1099 vendors and transactions, or in QuickBooks, we run the detail of the cash accounts and filter by transaction type – Check, Expense, Bill Payment… then sort by Name. The problem may be that there is not a name in there, or it is not a Vendor Name: another great reason to make sure you’re setting up bank rules and being careful about data entry to include vendor information on all transactions.

How does PayPal work?

Oh my goodness, is this ever complicated.

If you pay a business using your personal bank or Paypal account, or pay through “Friends & Family” PayPal you do need to send a 1099 (if over $600), because PayPal thinks this was a personal transaction — because, as I mentioned at the top of this post, personal transactions do not require 1099 forms. If you had used “Business” PayPal, then PayPal would send the 1099-K and there would be no reason to issue a 1099-NEC.

A colleague of mine recently called PayPal support about this and here was their response:
If the transaction detail says “money sent”, those qualify as Friends & Family transactions. However, if the transaction says “invoice paid” or “payment”, then it is a business payment — even if it’s within a personal Paypal account.

What about Venmo?

According to Venmo’s term of service, using it for business is a violation, and they can seize whatever money you have sitting in your Venmo account if they catch you using it for business.

However, we know sometimes this is the best way to collect money from folks, or that customers will send you Venmo funds without thinking about it, or that you’ll do the same with your vendors.

Venmo is considered a “peer-to-peer transfer service”, and not a third-party network. Therefore, treat these like cash payments from a business and send a 1099 form to your vendor.

(Side note: Venmo is starting to accept applications from a number of businesses for a new “Business Venmo”, but it’s brand new and very limited. Be careful with this. The problem with Venmo, PayPal, Bento, and other similar companies like that is that they don’t act like they’re banks — and their staff doesn’t realize that banking is actually the primary function of the company they work for — they don’t get the same kind of intensive training that bankers do. I recommend avoiding Venmo for business payments as much as possible.)

What about the states?

Okay, this gets pretty overwhelming pretty fast, so I am linking to a site that has all the states’ rules in one place — https://www.taxbandits.com/state-filing-requirements/

The short version here is that not all states have the same rules. Some allow the IRS filing of certain information returns to substitute for state filing requirements, and some don’t. Some require e-filing and some allow physical mailings. Many states participate in the Combined Federal/State Filing Program. The IRS will automatically forward 1099 information to participating states, eliminating the need to file separately with these states.

So please, do your homework when it comes to state filings.

Where can I find more info on due dates, penalties, and real-life scenarios?

Check out my colleague Mark Kohler’s excellent blog post. His charts for deadlines and penalties are very handy.

Another colleague, Questian Telka, and I worked together on a video series on what a W-9 is, and how to prepare a W-9 for each type of entity; and she followed it up with another video on whether or not you need to issue a 1099.

And as I mentioned earlier, yet another trusted colleague, Jennifer Dymond saw the need for a resource that details which payment methods are included on a 1099-K versus which ones you must issue 1099-NEC or 1099-MISC for yourself, and created 1099problems.io to help navigate these complexities. It’s updated regularly, as the proliferation of non-traditional payment methods continues. The first 1,099 people to subscribe using code DANCING1099 will receive 10% off their first order (offer expires March 31, 2024).

And there you have it! Simple, see?

**many thanks to The Bookkeeping Buds for editing assistance**

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Illinois, IRS, Tips

What Does A Tax Extension Mean For You?

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It’s that time again… Tax Day is upon us and millions of taxpayers will need to have their returns extended for various reasons. What does this mean? The AICPA has released a “Tax Extension FAQ” for CPA members to share with their clients.

What does filing an “extension” do?

• An extension is a form filed with the IRS to request additional time to file your federal tax return. This extends the due date for submitting your individual return to October 15.
• In some states, filing an extension with the IRS will automatically extend the time to complete a state income tax return. My note: In others, you must file a state extension. In still others, you must make a payment as your extension.
• Filing an extension grants you additional time to submit your complete and accurate return, but you still need to estimate whether you will owe any taxes and pay that estimated balance by the original due date.
• Extending your return allows you and your CPA more time to prepare your tax return to ensure the filing of an accurate tax return. In many cases, you may still be waiting for additional information (e.g., Schedules K-1, corrected Forms 1099, etc.) to complete your return.

Why does my CPA suggest we extend my tax return?

• If your CPA has recommended that you file an extension, it may be due to many reasons, such as:
– The volume of data or complexity of certain transactions (e.g., sale of a rental property) on your return requires additional time.
– The amount of time remaining in filing season is limited for the CPA to complete client returns by the due date* due to late-arriving information.
– My note: Your small business accounting file needs to be tied out to source documents and all adjustments booked before we will finalize a return, and there may be delays in this process due to a variety of issues.
• Many CPAs have a “cutoff” or deadline for clients submitting their tax information so they can plan their workload to ensure all client returns and extensions are completed by the due date.
• Your CPA may suggest filing an extension if there are aspects of your return affected by pending guidance or legislation.

Am I more likely to be audited if I extend?

• Extending will NOT increase your likelihood of being audited by the IRS.
• It is better to file an extension than to file a return that is incomplete or that you have not had time to carefully review before signing.

What are the primary benefits of extending my tax return?

• It provides for additional time to file returns without penalty when you are waiting for missing information or tax documents (such as corrected Forms 1099). Just remember that an extension provides additional time to file, but not additional time to pay. Penalties may be assessed if sufficient payment is not remitted with the extension.
• You may qualify for additional retirement planning opportunities or additional time to fund certain types of retirement plans (e.g., SEP IRA).
• It is often less expensive (and easier) to file an extension rather than rushing and possibly needing to amend your return later.

Should I do anything differently if I am filing an extension or “going on extension?”

• No, you still should give your CPA whatever information you have as early as possible or as soon as it becomes available.
• Expect to pay any anticipated taxes owed by the due date.* You still need to submit all available tax information to your CPA promptly so they can determine if you will have a balance due or if you can expect a refund.
• If you are required to make quarterly estimated tax payments, individual first quarter estimated tax payments are due on the same day as annual taxes. Your CPA may recommend that you pay the balance due for last year and your first quarter estimated tax payment for this year with your extension.
• If you are anticipating a large refund, your CPA will likely try to get your extended return completed as soon as possible once all tax information is available. Your CPA may also want to discuss tax planning opportunities with you so that, in future years, you don’t give the IRS an interest-free loan.

My note: I’d like to add that we take filing extensions for our clients very seriously. We collect as much information as we possibly can about the year’s taxable income and deductions, extrapolate based on information from the prior year, and build a complete tax return — filling in estimates where needed. This way, we get as accurate a picture as we can so as to project how much might be owed to the tax agencies. We do our best, although it’s not perfect, and as a result, much more work is involved in putting together an extension than most folks might think.

More from the IRS on filing extensions here, including a link to file your own for free.

More from the Illinois Department of Revenue here, on making an individual tax extension payment online.

Our blog post step-by-step on how to make quarterly estimated tax payments online.

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Illinois, Tips

How To Make Quarterly Estimated Taxes Online — Illinois IDOR

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Reminder: Due to a new law, Illinois S-Corp and Partnership owners should generally pay quarterly IL state (not federal) taxes through the business. The post below is about how to pay IL taxes personally; click here for how to make IL business tax payments.

There are multiple options for paying personal quarterly estimated taxes. You can: have your tax preparer create vouchers that you then print and mail with a check; prepare your own vouchers for the IRS and IL DoR; or pay online.

Since March 2020, agencies have had so many challenges with paper-mailed checks and vouchers that we are encouraging everyone to make all tax payments online.

The due dates for estimated quarterly taxes are approximately:
1Q: April 15
2Q: June 15
3Q: September 15
4Q: January 15 — however for state taxes, especially for cash-basis filers and those in states with PTE tax, we recommend making the final payment by December 31st.

If you want to know how to make IRS estimated tax payments, see my recent blog post with step-by-step instructions.

For the Illinois Department of Revenue (IDOR), go to the MyTax Illinois site. If you already have an account for sales taxes or another reason — do not log in, unless you are making business tax payments. Then click the “> Make an IL-1040, IL-1040-ES, or IL-505-I payment” link (see screenshot above).

Next, follow the instructions for making a quarterly estimated tax payment; it will make you enter your personal information (SSN, etc.) and ask you what kind of tax payment you wish to make.

It may require you to enter your driver’s license information or your AGI from a past tax return to confirm identity and get your IL-PIN.

Then it will take you to a Payment Information page.

You’ll want to select “IL-1040 Estimated Payment” and enter your tax year. Make sure it’s for the correct year and quarter — this is very important. The example below is for the fourth quarter of 2021.

Then, enter your payment information and click the Submit button.

It will require you to enter and confirm your email address before clicking OK.

Make sure to print the confirmation screen, even though they will send you an email receipt — every once-in-a-while IDOR fails to push the request through, and the amount is not debited or recorded. If you have the print-screen, you can prove you attempted to pay it on-time and that the mistake was theirs.

It will also include a confirmation code, the date/time of the request, the reporting period and amount, and bank withdrawal information. You can click “Printable Confirmation” or just print the webpage to pdf.

Please make sure to note how much you paid to each agency and on which dates — and let your tax preparer know this information as well. Securely uploading copies of the final confirmation screen to your tax preparer or bookkeeper is a great practice, so they can easily store the info in your file.

And if you use QuickBooks or another bookkeeping program, please make sure to enter the quarter, year, and “estimated tax” so that you or your bookkeeper or accountant or tax preparer can make sure it’s applied to the correct year, and for the right type of tax.

For how to make IRS quarterly tax payments online, see my recent blog post on the topic, for step-by-step instructions.

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

IRS, Tips

How To Pay IRS Quarterly Estimated Taxes Online — Don’t Let Your Checks Get Buried or Lost In The Mail

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The IRS “Direct Pay” landing page.

There are multiple options for paying personal quarterly estimated taxes. You can: have your tax preparer create vouchers that you then print and mail with a check; prepare your own vouchers and do the same; or pay online.

Since March 2020, the IRS, USPS, and state revenue agencies have had so many challenges with mailed paper checks and vouchers that we strongly encourage everyone to make all tax payments online.

If you want to pay your federal estimated taxes online, the easiest way is to use IRS Direct Pay. Paying online offers confirmation that the payment made it to the agency, reducing the chance of issues down the road, especially if the check is lost in the mail or routed incorrectly in the processing department. It also allows taxpayers to be very clear about what type of tax and tax period are being submitted, again eliminating confusion on the part of the agency and preventing future problems.

Pro Tip: if you have questions about estimated taxes — what they are, whether or not you need to pay them, and how to calculate them — I recommend this great YouTube primer by my colleague, Hannah Smolinski of Clara CFO. It can easily be as much as 20-30% of each freelance check you take home, so get on top of this now… don’t wait until the money’s already been spent.

The due dates for estimated quarterly taxes are approximately:
1Q: April 15
2Q: June 15
3Q: September 15
4Q: January 15 — however for state taxes, especially for cash-basis filers and those in states with PTE tax, we recommend making the final payment by December 31st.

If you are paying online, I recommend making payments one day before the due dates, as sometimes it takes a day for the agencies’ systems to process payments due to overnight automated workflows. The funds are usually pulled from your bank account the same day or one day later, so there is very little wiggle room. This organization will actually send you reminder emails for each payment!

The great news is that you do not need to have an account with the IRS in order to make payments using Direct Pay.

Internal Revenue Service (IRS)

For the IRS, once you get to the Direct Pay site, select the following options (noted in the screen shot below): 1) the reason for the payment; 2) the form you would be mailing in if you weren’t doing this online; and 3) the year to which the payment should apply. For example, for 1st-quarter 2023 personal estimated taxes, you’d select the following:

IRS “Direct Pay” Step 1 of 5.

Pro Tip: you don’t have to wait until the due date for each quarter to make quarterly estimated tax payments! You can pay as early as you like. And if cash flow is a challenge, a great hack is to take the total tax payments required for the year and make monthly or bi-weekly — or even weekly — payments online. (Another trick is to increase tax withholding from your other sources of income, but not everyone has a W-2 job, and not all retirement companies will do that.)

There are many possible reasons for payment — such as extensions, balances due on a filed return, installment payments, amended returns, and so on. The IRS offers a list in their dropdown. For the purposes of this article, we’re focusing on quarterly estimated tax payments.

IRS “Direct Pay” List of Payment Reasons.

It’s extremely important that you select the correct year for payment. The IRS will levy late penalties and interest if you pick the wrong year, and the amount of time and effort that goes into contacting them and getting payments reapplied to the correct year will often cost more for your tax preparer’s time than filing your return in the first place. So keep in mind that the current year is usually the one you want for estimated tax payments, and a prior year is generally for extensions, balances due, installment payments, amended returns, and most other options. Selecting the correct year and type will ensure that these payments show up properly on your transcript.

Once you click the Continue button, you’ll be prompted to confirm the type of form and the period.

IRS Direct Pay Estimated Tax Payment and year confirmation.

At that point the system will ask you to enter a bunch of info to confirm your identity. The basic idea is to provide them name and address data from a prior-year tax return so that… well, so they know it’s really you. Since IRS Direct Pay works without a login, you will need to verify your identity each time you revisit it. Make sure you enter your name and address exactly as they appear on the tax return you are using for verification. If your name or address have changed, try selecting an earlier year for verification and enter the information from that year. This information does not need to be for the same tax year on which you are making your payment. It can be from as far back as 5 to 6 years ago depending on the time of year.

IRS “Direct Pay” Step 2 of 5, part one.
IRS “Direct Pay” Step 2 of 5, part two.

Once you enter all this information and hit the “Continue” button, it will take you to a screen to enter the payment information — amount, bank account, and email address for confirmation. If you are having issues with the system accepting your information, double-check that you’re entering your name, SSN, date of birth and address exactly as it was on the tax return for the year you selected. The IRS has a Direct Pay troubleshooting page if you have more questions.

IRS “Direct Pay” Step 3 of 5, part one.
IRS “Direct Pay” Step 3 of 5, part two.

Next, you’ll need to agree to the disclosure pop-up.

IRS “Direct Pay” disclosure pop-up.

In the final step, you will need to review all the information you have entered, provide an electronic signature including social security number or ITIN, and check the box to authorize the debit. Click Submit and you are done!

Well… except that you may also have to pay state estimated taxes. See here for my post on how to make personal Illinois estimated tax payments. (But if you have an S-Corp or Partnership, see here instead.)

Please make sure to note how much you paid to each agency and on which dates — and let your tax preparer know this information as well. Securely uploading copies of the final confirmation screen to your tax preparer or bookkeeper is a great practice, so they can easily store the info in your file.

And if you use QuickBooks or another bookkeeping program, please make sure to enter the quarter, year, and “estimated tax” so that you or your bookkeeper or accountant or tax preparer can make sure it’s applied to the correct year, and for the right type of tax.

Many self-employed folks get surprised at tax-time with huge balances due, penalties and interest. Don’t let yourself fall into that trap — make regular payments online and taxes will be a breeze next year.

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Illinois, IRS, Tips

Today’s The Day! 2022 Tax Filing Season Begins

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January 23, 2023 — Per IRS 2023-11, following a successful opening of its systems today, the IRS is now accepting and processing 2022 tax returns; taxpayers have until April 18 to file their taxes this year.

According to Acting Commissioner Doug O’Donnell, taxpayers can count on IRS delivering improved service this filing season. As part of the August passage of the Inflation Reduction Act, the IRS has more than 5,000 new telephone assistors and added more in-person staff to help taxpayers.

Taxpayers who electronically file a tax return with no issues and choose direct deposit should still receive their refund within 21 days of the date they file – similar to previous years. Due to tax law changes such as the expiration of the Advance Child Tax Credit and Recovery Rebate Credit this year to claim pandemic-related stimulus payments, many taxpayers may find their refunds somewhat lower this year.

The State of Illinois also opened its tax season today. In a press release, the IDOR Director, David Harris, highlighted the improved and enhanced MyTax Illinois system.

In addition to being able to file Form IL-1040 for free through MyTax Illinois, individuals may also use the site to make payments, respond to department inquiries, and check the status of their refunds using the Where’s My Refund? link.

MyTaxIllinois also allows taxpayers to look up Illinois-Personal Identification Numbers (IL-PINs), which are eight-digit numbers assigned by the department and used as signatures when e-filing returns. Amounts of any estimated tax payments can also be viewed and (when necessary), amounts reported on Forms 1099-G and 1098-F can also be found on the site.

Back to the IRS… in today’s news release, they also shared their tips for a smooth filing season:

Fastest refunds by e-filing, avoiding paper returns: To avoid refund delays, IRS encourages taxpayers to file their tax return electronically with direct deposit instead of submitting a paper tax return. Taxpayers may use IRS Free File on IRS.gov, other tax software or a trusted tax professional. Members of the armed forces and qualifying veterans can file their federal tax return and up to three state tax returns for free electronically using MilTax, a Department of Defense program.

Avoid delays; file an accurate tax return: Taxpayers should make sure they’re ready to file an accurate and complete tax return. This can help avoid processing delays, extensive refund delays and later IRS notices.

Earned Income Tax Credit or Additional Child Tax Credit refunds: Taxpayers may file their returns beginning Jan. 23, but the IRS cannot issue refunds involving the Earned Income Tax Credit or Additional Child Tax Credit before mid-February. The law provides the extra time to help the IRS prevent fraudulent refunds. “Where’s My Refund?” on IRS.gov should show an updated status by Feb. 18 for most EITC and ACTC filers. The IRS expects most of these refunds to be available in taxpayer bank accounts or debit cards by Feb. 28 if people chose direct deposit and there are no other issues with their tax return.

Avoid phone delays; online resources best option for help: IRS.gov is the quickest and easiest option for help. IRS assisted phone lines continue to receive a high volume of calls. To avoid delays, check IRS.gov first for refund information and answers to tax questions. Setting up an Online Account on IRS.gov can also help taxpayers get information quickly. IRS Online Account was recently expanded to allow more people to gain access. The Interactive Tax Assistant can also help taxpayers get answers to many tax questions online at any time.

Online options for free help; answers to common questions: Use IRS.gov to get answers to tax questions, check a refund status or pay taxes. No wait time or appointment needed — online tools and resources are available 24 hours a day.

Other free options for help: IRS Free File is available to any person or family who earned $73,000 or less in 2022. For taxpayers who are comfortable completing their own tax forms, Free File Fillable Forms may be a good option. MilTax is a free tax resource available to the military community, and it’s offered through the Department of Defense. Qualified taxpayers can also find free one-on-one tax preparation help nationwide through the Volunteer Income Tax Assistance and Tax Counseling for the Elderly programs.

2021 tax returns still being processed: Taxpayers can check Where’s My Amended Return? to find out the status of their tax year 2021 Form 1040-X and can still file their 2022 tax returns even if their 2021 tax returns haven’t been processed. Visit the IRS Operations page for more information on what to expect.

April 18 tax deadline: This year, the filing deadline is April 18 for most taxpayers, but automatic six-month extensions of time to file are available for anyone for free. See Extension of Time to File Your Tax Return for instructions. Taxpayers should be aware that filing Form 4868 only extends the time to file tax returns. Those who owe taxes should still pay by April 18 to avoid late payment penalties.

Let the filings begin!

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Illinois, IRS, Tips

2021 Year-End Priority: Pass-Through Entities Should Pay State Taxes By 12/31

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Slide from December 23, 2021 AICPA Town Hall

In a December 17th IAAI tax update webinar, the Illinois Department of Revenue (IDOR) walked through instructions for claiming a new “SALT” tax benefit signed into law in September, and in today’s AICPA Town Hall, the importance of making these payments before year-end was underscored. This new law is a workaround for individual taxpayers who are otherwise unable to benefit from a full deduction on state tax payments on pass-through income from their businesses.

As a result, we (along with probably thousands of other CPA firms) have made a list of our own pass-through clients (aka S-Corps and Partnerships) who might benefit from this increased deduction, and we’re scrambling to calculate estimates and reach out to them to recommend these payments be made by 12/31.

So, what the heck is SALT? And why have the deduction rules changed?

SALT stands for “state and local taxes”, and they are generally deducted by individual taxpayers on their annual 1040 tax return. Before 2018, taxpayers could deduct these taxes by itemizing them on Schedule A.

However, the Tax Cuts & Jobs Act limited this to $10,000. This cap was likely to be removed with the Build Back Better Act, but it appears that legislation will not be passed before year-end after all.

Many states, including Illinois, have passed legislation allowing these taxes to be paid at the business level, on behalf of the shareholders and partners. Since these companies “pass-through” their income to owners, they are known as Pass-Through Entities (PTEs). The PTE does not have a cap on this type of tax, so it reduces both federal and state income and also allows the full deduction.

My colleague, James Hamilton, wrote up a clear explanation with an example, which I recommend reading if you’d like to get into the details.

Why are we all scrambling to do this before year-end?

Usually, estimated state tax payments are paid by the individual and are due 4/15, 6/15, 9/15 and 1/15, with any balance remaining payable by the following 4/15. The IL state law was not passed until after estimated tax deadlines for the first three quarters were already paid. And a December 20 article in Journal of Accountancy, as well as the aforementioned AICPA Town Hall from earlier today, suggest that the IRS guidance requires the business pay the tax by year-end, not by 1/15.

From The Journal of Accountancy: Crucially, a specified income tax payment is one the PTE “makes … during a taxable year” in computing its taxable income “for the taxable year in which the payment is made” (Notice 2020-75, Section 3.02(2)). Even though Sec. 164(a) provides that the SALT deduction is for the tax year in which taxes are “paid or accrued,” the more restrictive, literal application of the notice to taxes paid is the safer course, advocates say.

To get the largest tax benefit from the new law, businesses would want to pay in the entire state tax liability for the year by 12/31, even if the owners have already paid quarterly estimated taxes. In other words, take the company’s full taxable income for the year (which you won’t know before 12/31, but this is where estimates come in) times 4.95% (IL flat tax rate for individuals). The resulting overpayment would be refunded to the taxpayer upon filing their personal tax return.

Not all businesses will have the cash to do this, but to the extent it can be paid, it is certainly a smart tax-reduction move.

Okay, then how do we make the payments?

The step-by-step instructions I painstakingly wrote up earlier this year for making business replacement income tax estimated and extension payments are now out of date, because IDOR revamped their MyTaxIllinois website in September (grrrrr). So here are the basic instructions (a blog post with screenshots is coming soon, but this will have to do for now):

— Log into the business’s My Tax IL account
— On the ‘Summary’ tab, look for the ‘Business Income Tax’ section
— Click on the link for ‘View more account options’

There are two ways to do it from here; the first is:
— In the ‘Account Options’ section, click the link for ‘Make An Estimated Payment’
— Select the period you want to pay, which is 12/31/2021
— Click the first ‘Add Payment’ hyperlink in the Payment Schedule table for each payment you would like to schedule.
— If your payment information is saved in MyTax Illinois, then in the ‘Choose’ tab you can select the dropdown under ‘Payment Channel’
— Otherwise, select ‘New’ and enter your company bank info.
— In either case, on the right where it says ‘Payment’, you can change the payment’s debit date and enter the amount.
— Click Submit, and re-enter your password for security purposes

Alternatively:
— In the ‘Periods and Submissions’ section, click the link for ‘View Account Periods’
— Click the 12/31/2021 link so that your payment is applied to tax year 2021
— In the upper right corner of this page, click the ‘Make A Payment’ link
— Select the ‘Bank Account Debit’ link
— Click the IL-1120-ST Payment link (ST denotes a “Small Business” payment)
— Enter the amount you want to pay in the Amount and Confirm Amount fields
— Click Submit, and re-enter your password for security purposes

Best of luck, and… Happy New Year!

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Education, IRS, Site News, Tips

What Does A Tax Extension Mean For You?

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It’s that time again… Tax Day (May 17th this year, aka my birthday) is upon us and it’s the end of what is certainly one of — if not the — roughest tax seasons in history. Millions of taxpayers will need to have their returns extended for various reasons. What does this mean? The AICPA has released a “Tax Extension FAQ” for CPA members to share with their clients.

What does filing an “extension” do?

• An extension is a form filed with the IRS to request additional time to file your federal tax return. This extends the due date for submitting your individual return to October 15. In some states, filing an extension with the IRS will automatically extend the time to complete a state income tax return.
• Filing an extension grants you additional time to submit your complete and accurate return, but you still need to estimate whether you will owe any taxes and pay that estimated balance by the original due date.
• Extending your return allows you and your CPA more time to prepare your tax return to ensure the filing of an accurate tax return. In many cases, you may still be waiting for additional information (e.g., Schedules K-1, corrected Forms 1099, etc.) to complete your return.

Why does my CPA suggest we extend my tax return?

• If your CPA has recommended that you file an extension, it may be due to many reasons, such as:
– The volume of data or complexity of certain transactions (e.g., sale of a rental property) on your return requires additional time.
– The amount of time remaining in filing season is limited for the CPA to complete client returns by the due date* due to late-arriving information.
– My note: this year exacerbated the situation by requiring small business CPAs to simultaneously navigate the Restaurant Relief Fund (RRF), PPP1 Forgiveness, and 2020 Employee Retention Credit.
• Many CPAs have a “cutoff” or deadline for clients submitting their tax information so they can plan their workload to ensure all client returns and extensions are completed by the due date.*
• Your CPA may suggest filing an extension if there are aspects of your return affected by pending guidance or legislation.
My note: this is the case for many more clients this year than usual; late-changing tax rules delayed the start of tax season, and waiting for guidance has further stretched it thin.

Am I more likely to be audited if I extend?

• Extending will NOT increase your likelihood of being audited by the IRS.
• It is better to file an extension than to file a return that is incomplete or that you have not had time to carefully review before signing.

What are the primary benefits of extending my tax return?

• It provides for additional time to file returns without penalty when you are waiting for missing information or tax documents (such as corrected Forms 1099). Just remember that an extension provides additional time to file, but no additional time to pay. Penalties may be assessed if sufficient payment is not remitted with the extension.
• You may qualify for additional retirement planning opportunities or additional time to fund certain types of retirement plans (e.g., SEP IRA).
• It is often less expensive (and easier) to file an extension rather than rushing and possibly needing to amend your return later.

Should I do anything differently if I am filing an extension or “going on extension?”

• No, you still should give your CPA whatever information you have as early as possible or as soon as it becomes available.
• Expect to pay any anticipated taxes owed by the due date.* You still need to submit all available tax information to your CPA promptly so they can determine if you will have a balance due or if you can expect a refund.
• If you are required to make quarterly estimated tax payments, individual first quarter estimated tax payments are due April 15. Your CPA may recommend that you pay the balance due for last year and your first quarter estimated tax payment for this year with your extension.
• If you are anticipating a large refund, your CPA will likely try to get your extended return completed as soon as possible once all tax information is available. Your CPA may also want to discuss tax planning opportunities with you so that, in future years, you don’t give the IRS an interest-free loan.

Have there been any changes to the due dates of returns for this year?

• For tax year 2020, the IRS is postponing the deadline for all individual tax returns.
– Individual returns otherwise due April 15 will not have to be filed until May 17, 2021.
– Certain states have also postponed their filing and/or payment due dates.
• Note that victims of natural disasters may be granted extensions, such as victims of the Texas winter storms have until June 15, 2021 to file various individual and business tax returns and to make payments.

My note: I’d like to add that we take filing extensions for our clients very seriously. We collect as much information as we possibly can about the year’s taxable income and deductions, extrapolate based on information from the prior year, and build a complete tax return — filling in estimates where needed. This way, we get as accurate a picture as we can so as to project how much might be owed to the tax agencies. We do our best, although it’s not perfect, and as a result, much more work is involved in putting together an extension than most folks might think.

More from the IRS on filing extensions here, including a link to file your own for free.

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.