#tax-filing
Tax filing procedures, deadlines, and best practices
Delaware taxes short-term rental stays at 4.5% of rent for agreements entered on or after January 1, 2025. Who collects depends on the booking channel — platforms remit for platform bookings, but direct-booking hosts need the $25 accommodations intermediary license and must file monthly by the 15th, even for zero-income periods. Cleaning fees, linens, and deposits are excluded from the tax base.
Form 4868 gives a sole proprietor an automatic six-month extension to file Form 1040 and Schedule C — moving the 2025 return deadline from April 15 to October 15, 2026 — but the tax itself was still due in April. How to estimate total liability including self-employment tax, request the extension electronically or through a designated payment, and limit the 5%-per-month failure-to-file penalty.
IR-2025-107 and Fact Sheet 2025-08: One Big Beautiful Bill retroactively reinstates $20,000 and 200-transaction 1099-K threshold, undoing ARPA $600 rule. What sellers must still track.
Form T2125 turns a Canadian sole proprietor's invoices and receipts into taxable net business income on the T1 return. For 2026, gig platforms report earnings directly to the CRA, self-employed CPP totals nearly $9,300 at the earnings ceiling, and the June 15 filing extension still leaves payment due April 30.
Irish sole traders filing Form 11 in 2026 face a mid-year PRSI Class S rise from 4.2% to 4.35% on October 1, a €650 minimum PRSI charge, and the preliminary tax rule requiring 100% of prior-year or 90% of current-year liability by October 31 — with a ROS extension to mid-November for those who file and pay online.
A 2026 TIGTA audit found 1,375 unauthorized entries into restricted taxpayer-document areas and critical vulnerabilities left unpatched an average of 223 days at IRS scanning contractors. Here is what the watchdog found, how the IRS responded, and the concrete steps — IP PIN enrollment, early filing, e-filing — that reduce your exposure.
The National Taxpayer Advocate's 2025 Annual Report to Congress found the IRS took over 13 months on average to process 1.6 million business amended returns, after a 27% workforce cut left the Small Business/Self-Employed division down nearly 38%. Here's what the report says and six concrete steps to shield your cash flow.
On April 6, 2026, the IRS opened its free Business Tax Account portal to partnerships, tax-exempt organizations, and government entities, letting a designated official view balances, download an EIN verification notice, and make payments online instead of mailing paper forms.
Starting April 2026, UK sole traders and landlords with combined gross income over £50,000 must file quarterly digital updates to HMRC instead of one annual Self Assessment return, with penalty-free late filing only in the first year.
IRS Direct File will not return for the 2026 filing season; IRS Free File, FreeTaxUSA, Cash App Taxes, VITA, and MilTax remain free options, but only some fully support Schedule C for freelancers and small business owners.
The IRS now requires e-filing once a business issues 10 or more information returns combined — W-2s, 1099-NECs, 1099-MISCs and more, all counted together. Here's how to count correctly, the $340-per-return penalty for 2026-year returns, when a Form 8508 hardship waiver actually applies, and how to e-file free through IRIS.
Late Schedule K-1s are the norm, not the exception — a Form 7004 extension pushes partnership and S-corp returns, and every K-1 tied to them, to September 15, a full five months past the April 15 personal deadline. The fix is a simple playbook, file Form 4868, pay at least 90% of a good-faith estimate, and amend with Form 1040-X once the real numbers arrive.
