Tax Season 2027 Timeline
Tax season preparation should not start in April. Here is the ideal timeline:
| When | What to Do |
|---|---|
| January | Gather W-2s, 1099s, and tax documents as they arrive |
| Early February | Most tax documents arrive by February 15 |
| February-March | Organize documents, identify deductions, choose filing method |
| March-April | File your return (earlier is better for refunds) |
| April 15 | Filing deadline (or file extension) |
Documents You Need
Collect these documents before you start filing:
Income Documents
- W-2: From each employer
- 1099-NEC: Freelance and contract income
- 1099-INT: Bank interest earned
- 1099-DIV: Dividend income
- 1099-B: Investment sales
- 1099-G: Unemployment or state tax refunds
Deduction Documents
- 1098: Mortgage interest paid
- 1098-T: Tuition payments
- 1098-E: Student loan interest
- Charitable receipts: Donations over $250 need written acknowledgment
- Medical receipts: Expenses exceeding 7.5% of AGI are deductible
- Business expenses: If self-employed, categorized expense records
Deductions to Track
Many people miss deductions simply because they do not track expenses during the year. If you use Pocket Clear to categorize your spending, pulling deduction data at tax time is straightforward.
Commonly missed deductions include:
- Home office expenses (if you work from home)
- Vehicle mileage for business, medical, or charitable purposes
- Professional development and education expenses
- Health Savings Account (HSA) contributions
- State and local tax payments (SALT deduction, capped at $10,000)
- Charitable donations (including non-cash donations)
Getting Organized
Create a simple system for tax document organization:
- Physical folder: As paper documents arrive, put them in one folder labeled "2026 Taxes"
- Digital folder: Create a folder on your computer for digital tax documents
- Checklist: Print or save a checklist of expected documents and check them off as they arrive
- Expense export: If you tracked expenses in Pocket Clear, export your 2026 data as CSV for reference
Tools That Help
Throughout the year, tracking expenses by category makes tax preparation dramatically easier. Pocket Clear's export feature lets you pull a complete record of your spending, categorized by type. When your tax preparer asks "how much did you spend on business expenses," you have the answer in seconds instead of hours of receipt-hunting.
Start tracking early in 2027 so your 2027 taxes will be even easier to prepare.
Frequently Asked Questions
What Users Say About Pocket Clear
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