Connecticut 1099 Filing Requirements: Deadlines, Penalties, and CT-1096

Connecticut’s 1099 filing requirements apply any time you issue a federal 1099 to a Connecticut resident or to a nonresident for services performed in the state. You send a state copy to the Department of Revenue Services through the myconneCT portal, along with Form CT-1096 as a transmittal, by January 31 of the year after the payment. Form 1099-K runs on its own clock: 30 days after you file it with the IRS. Miss the deadline and penalties start at $5 per form, with separate penalties on the transmittal itself and interest on any unpaid withholding.

Who Has to File and Which Forms

Connecticut does not set its own dollar threshold. If a federal 1099 is required and the payment has a Connecticut connection, you owe a state copy to DRS. The connection exists in two situations: you paid a Connecticut resident, or you paid a nonresident for services performed wholly or partly in the state. The state filing is required even if you withheld no Connecticut income tax.¹

Because the federal thresholds govern, the practical trigger for most 1099 types is $600 in payments during the calendar year. Pay a Connecticut-based contractor $600 or more and you owe both a federal 1099-NEC and a state copy. An out-of-state business still has a Connecticut filing obligation if it paid someone for work done in the state.

DRS accepts state copies of five federal form types, each with its own Connecticut trigger:

1099-NEC for non-employee compensation paid to Connecticut residents, or to nonresidents for services performed wholly or partly in the state.
1099-MISC for miscellaneous income, following the same residency and service-location rules as the 1099-NEC.
1099-R for distributions from pensions, annuities, and retirement plans paid to Connecticut residents. For nonresident recipients, you file a state copy only if you withheld Connecticut income tax.
1099-K for payments to payees located in Connecticut or with business locations in the state.
W-2G for Connecticut Lottery winnings paid to any individual, plus other gambling winnings paid to Connecticut residents.

Form 1099-S for real estate transactions is not on the DRS required list.¹

For 1099-K specifically, the federal threshold now sits at the pre-2022 level: third-party settlement organizations file only when gross payments to a payee exceed $20,000 and the number of transactions exceeds 200 in a calendar year. Both conditions must be met. Payment card transactions have no minimum and are always reportable.² Those federal rules carry straight through to the Connecticut filing.

Form CT-1096 Transmittal

Every batch of 1099s you send to DRS has to be accompanied by Form CT-1096, the Connecticut Annual Summary and Transmittal of Information Returns. The cover sheet reports aggregate totals across all the individual 1099s in the batch. You will need your Connecticut Tax Registration Number and your federal employer identification number to complete it.³

List the total number of forms submitted and the total Connecticut tax withheld across all of them. Check that each recipient’s name, address, and taxpayer identification number matches what you reported federally. Mismatches between state and federal data are a common audit trigger.

Filing Deadlines

Most Connecticut information returns share one deadline. Forms 1099-NEC, 1099-MISC, 1099-R, W-2G, and the accompanying CT-1096 are due to DRS by January 31 of the year following the payment.¹ Recipient copies of the 1099-NEC are also due to the payee by January 31, so the state and recipient deadlines line up.

Form 1099-K is different. It is due to DRS no later than 30 days after you file it with the IRS.¹ The lag gives payment processors time to compile transaction data, but you need to track two separate calendars.

Connecticut law also makes January 31 a statutory deadline to furnish a written statement to each payee showing the total paid and any Connecticut tax withheld.⁴ The federal 1099 forms you send recipients satisfy this as long as they include Connecticut withholding information.

Requesting an Extension

If you cannot meet January 31, mail Form CT-8809 to DRS on or before that date. Approval grants 30 days from the original due date. If you still need more time, you can submit a second CT-8809 with a copy of your first approval letter before the initial extension expires, which grants another 30 days.⁵ Form CT-8809 cannot be filed electronically; it must be mailed.⁶

An extension gives you more time to file, not more time to pay. Any Connecticut withholding that should have been remitted is still due by the original deadline, and interest keeps accruing on unpaid amounts.

Filing Through myconneCT

DRS requires information returns to be filed electronically through the myconneCT portal. You can log in as a standard single-employer filer or as a third-party bulk filer.⁷ The portal supports manual data entry for small batches and bulk file uploads for larger ones. Bulk uploads must follow DRS’s technical formatting specifications.

There is one exception to the electronic mandate. If you are submitting 24 or fewer information returns in total across all form types, paper filing is allowed, though DRS encourages electronic filing regardless of volume.⁸ At 25 or more, electronic filing is mandatory. If you have a genuine hardship that prevents electronic filing, request a waiver by mailing Form CT-8508 to DRS at least 30 days before the due date.

After uploading, myconneCT prompts you to review the data before final submission. Save the confirmation number. That number is your proof of timely filing if DRS ever asks whether you met the deadline.

Penalties for Late or Missing Filings

Connecticut imposes penalties at two levels: one on the individual 1099 statements, and one on the CT-1096 transmittal.

For each individual information return you fail to file on time, DRS assesses $5 per form. The total for all missed forms in a single calendar year is capped at $2,000. The same $5 per-form penalty applies if you were required to file electronically but submitted paper instead, because DRS treats those paper submissions as failures to file.⁹ Both can be waived if you show the failure was due to reasonable cause rather than willful neglect.

If you fail to file the CT-1096 return itself and no tax is due, DRS can impose a separate $50 penalty. When tax is owed, the penalty for a late or unfiled return rises to 10% of the unpaid tax or $50, whichever is greater.⁹

Unpaid withholding tax accrues interest at 1% per month, or fraction of a month, from the original due date until you pay.¹⁰ On a $10,000 withholding balance, that is $100 a month. Filing for an extension does not stop the interest clock.

Reasonable Cause Relief

Connecticut shares a standard with the IRS: if you can show your failure was due to reasonable cause and not willful neglect, penalties may be waived. The IRS evaluates this case by case, weighing whether you acted responsibly before and after the failure, whether you tried to correct it promptly, and whether significant mitigating factors applied, such as being a first-time filer or facing events beyond your control.¹¹ Not knowing about the requirement generally does not qualify, and neither does relying on a preparer who missed it. You remain responsible for compliance even when you hire someone to handle the filing.

Correcting Returns Already Filed

If you find errors in 1099s DRS has already accepted, file corrections through myconneCT using your business employer or third-party bulk filer login. Submit only the corrected forms, not the entire original file. Each corrected record needs a re-submission indicator so DRS can match it to the original.¹

After uploading corrections, myconneCT displays the CT-1096 as originally submitted. Update the totals to reflect the corrected figures, then review and resubmit. You will get a new confirmation number for the corrected filing. If you omitted a 1099 from the original batch entirely, do not mark it as a correction. Submit it as a new original return under a separate filing.

Record Retention

Keep copies of filed 1099s and the underlying payment documentation for at least three years, matching the general IRS period of limitations. If you underreport income by more than 25% of gross income shown on a return, the retention period extends to six years. Employment tax records, which can overlap with withholding documentation, should be kept at least four years after the tax is due or paid, whichever is later.¹²

Store your myconneCT confirmation numbers alongside the returns. If DRS questions a filing, that confirmation is your first line of defense, and keeping the CT-1096 with the matching 1099s makes it far easier to reconstruct what you reported years later.

1
Connecticut State Department of Revenue Services. Form 1099-R, 1099-MISC, 1099-K, 1099-NEC, and W-2G Electronic Filing Requirements
2
Internal Revenue Service. IRS Issues FAQs on Form 1099-K Threshold Under the One, Big Beautiful Bill
3
Connecticut Department of Revenue Services. Form CT-1096 – Connecticut Annual Summary and Transmittal of Information Returns
4
Justia. Connecticut Code 12-706 – Agreements With Other Jurisdictions, Written Statement Furnished to Employees and Payees, Treatment of Taxes Withheld
5
Connecticut eRegulations. Sec. 12-723-4 Extension of Time to File Informational Returns
6
Connecticut Department of Revenue Services. Form CT-8809 – Request for Extension of Time to File Information Returns
7
Connecticut State Department of Revenue Services. Electronically Filing Form W-2 (Wage) and Non-Wage Forms 1099-R, 1099-MISC, and W-2G
8
Connecticut State Department of Revenue Services. Frequently Asked Questions on Electronic Filing Informational Returns
9
Justia. Connecticut Code 12-735 – Failure to Pay Tax or to File Return or Report
10
Justia. Connecticut Code 12-723 – Extension of Time for Filing Returns and for Payment of Tax
11
Internal Revenue Service. Penalty Relief for Reasonable Cause
12
Internal Revenue Service. How Long Should I Keep Records?