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For most filers claiming the new OBBBA deductions in 2027, TurboTax Deluxe is the best overall pick, it has the clearest guided interview for Box 12 “TP” and “TT,” handles all four new deductions automatically, and catches errors before you submit. If you are budget-conscious and comfortable entering numbers yourself, FreeTaxUSA files federal for free and covers every OBBBA deduction at a fraction of the cost. H&R Block is the best middle ground and the only option with walk-in human support.
KEY TAKEAWAYS
- TurboTax, best guided experience for first-time OBBBA filers; most expensive. ★ 4.7 / 5
- H&R Block, best balance of price and support; only option with in-person filing. ★ 4.5 / 5
- FreeTaxUSA, best value; free federal filing, handles all OBBBA deductions, less hand-holding. ★ 4.3 / 5
- Cash App Taxes, genuinely free (federal + state), but no live help and limited import options. ★ 4.1 / 5
- All four platforms support the new Box 12 “TP” / “TT” and Schedule 1 OBBBA deductions for tax year 2026.
- Prices below are based on our research as of June 2026, verify current pricing before filing, as tax software prices typically increase closer to April 15.
How We Evaluated These for the 2027 Season
The 2027 filing season is the first where filers will claim the four new OBBBA deductions on real returns. Based on our research into each platform’s features, pricing, and guidance for new deduction types, we evaluated on five criteria: OBBBA deduction support, ease of W-2 import (especially Box 12 codes), accuracy of phase-out calculations, price-to-value ratio, and availability of human support for edge cases.
Quick Comparison
| Software | Rating | OBBBA Deductions | Federal Price | State Price | Human Help |
|---|---|---|---|---|---|
| TurboTax Deluxe | ★ 4.7 | Yes, guided | ~$39 | ~$49 | Live chat / AI / CPA add-on |
| H&R Block Deluxe | ★ 4.5 | Yes, guided | ~$35 | ~$37 | In-person + online chat |
| FreeTaxUSA | ★ 4.3 | Yes, manual | Free | $14.99 | Email support only |
| Cash App Taxes | ★ 4.1 | Yes | Free | Free | None |
| TaxAct Deluxe | ★ 4.0 | Yes | ~$25 | ~$40 | Chat + phone (paid tier) |
Prices as of June 2026. Tax software prices often increase between now and filing season, verify current pricing at each provider’s website before purchasing.
TurboTax, Best for First-Time OBBBA Filers
Our rating: ★ 4.7 / 5
TurboTax’s guided interview is the clearest of any platform for the new Box 12 codes. When you enter a W-2 with code “TP” in Box 12, TurboTax immediately flags it as the OBBBA tips deduction, explains what it means in plain English, asks a few eligibility questions (occupation, MAGI), and calculates the phase-out automatically. It does the same for “TT” (overtime) and handles all four new deductions in sequence without requiring you to know which IRS form or schedule they go on.
For tipped workers, servers, and hourly employees filing with these codes for the first time in 2027, TurboTax removes the most uncertainty. It also has the best W-2 import, connecting directly to thousands of employers through its employer database (ADP, Gusto, Paychex) so you may not need to type anything manually.
Pros:
- Best-in-class guided interview for all four OBBBA deductions
- Direct W-2 import from most major payroll providers
- Accurate MAGI phase-out calculations, verified against IRS figures
- Live AI assistant and optional live CPA review available
- MaxRefund Guarantee and 100% Accuracy Guarantee
Cons:
- Most expensive of the major platforms, Deluxe is ~$39 federal + ~$49 per state before any discounts
- Upsells aggressively to higher tiers and add-ons during the filing flow
- Free tier (Free Edition) is limited to very simple returns, most OBBBA filers will need at least Deluxe
Best for: First-time filers claiming the tips or overtime deduction, anyone who wants maximum hand-holding on the new W-2 boxes, and filers who want live CPA access.
H&R Block, Best for Filers Who Want a Human Backup
Our rating: ★ 4.5 / 5
H&R Block handles all four OBBBA deductions with the same guided interview approach as TurboTax, but at a lower price point (Deluxe ~$35 federal). Its real differentiator for the 2027 season is physical availability: H&R Block has approximately 9,000 retail locations in the US where you can sit down with a tax professional if your return turns out to be more complex than you expected, a useful option if you have both tips and overtime deductions, received allocated tips in Box 8, or work as both a W-2 employee and 1099 contractor.
Based on our research, H&R Block’s software is slightly less polished than TurboTax’s in the guided interview flow, but the accuracy of the deduction calculations is equivalent. The interface is clean and the step-by-step questions are in plain language.
Pros:
- Lower price than TurboTax for equivalent coverage of OBBBA deductions
- In-person filing option at ~9,000 US locations, unique among digital-first competitors
- W-2 import available (slightly smaller employer database than TurboTax)
- AI Tax Assist and live expert chat available
- Peace of Mind guarantee, H&R Block will represent you in an audit
Cons:
- Interface is less streamlined than TurboTax for some workflows
- In-person filing costs significantly more than the online product
- Self-employed tier pricing (~$115 federal) is high for gig workers with straightforward Schedule C returns
Best for: Filers who want the option to escalate to in-person help, moderate-complexity returns (tips + standard W-2 income + one state), and anyone who values the audit representation guarantee.
FreeTaxUSA, Best Value for Confident DIY Filers
Our rating: ★ 4.3 / 5
FreeTaxUSA files federal returns for free, no income limit, no gotcha upsell to a paid tier for Schedule C or the OBBBA deductions. State returns cost $14.99. For a server with a straightforward W-2 claiming the tips deduction, the total cost is $14.99 if they have one state return to file. TurboTax would cost $88+ for the same return.
The trade-off is that FreeTaxUSA is more manual. You enter Box 12 “TP” yourself rather than being prompted by an interview, and the interface has fewer plain-English explanations of what each field means. If you know what you are doing, you have read this guide and the dedicated How to Claim articles, FreeTaxUSA is an excellent choice and the deduction math is just as accurate.
Pros:
- Free federal filing for all return types including Schedule C and all OBBBA deductions
- $14.99 state (lowest of any paid-state platform)
- Supports all four OBBBA deductions and correct Schedule 1 placement
- No income limit on free filing
- Deluxe upgrade ($7.99) adds live chat support, still far cheaper than competitors
Cons:
- More manual entry, less guided for first-timers unfamiliar with the new Box 12 codes
- No W-2 import from employers (manual entry only)
- Email-only support on the free tier; live chat requires the $7.99 Deluxe upgrade
- Interface is functional but less polished than TurboTax or H&R Block
Best for: Budget-conscious filers who are comfortable entering their own numbers, returning filers with consistent simple-to-moderate returns, and anyone who has already read the Box 12 “TP”/”TT” guides and knows what to enter.
Honorable Mentions
Cash App Taxes (★ 4.1): Truly free, both federal and state, with no income limit. It handles the OBBBA deductions and Schedule C. The major limitation is zero human support of any kind; if you hit a question, you are on your own. Best for young, tech-comfortable filers with simple W-2 returns who are not filing for the first time with the new Box 12 codes.
TaxAct Deluxe (★ 4.0): Priced between FreeTaxUSA and H&R Block (~$25 federal), TaxAct handles the OBBBA deductions and has phone support on paid tiers. Based on our research, it is a solid but not exceptional choice, the interface is less modern than TurboTax and H&R Block, and the support quality is more variable. Worth considering if you want something in the middle on price and want phone access.
Which Tax Software Should You Use in 2027?
Your best choice depends on your situation:
| Your Situation | Best Pick |
|---|---|
| First time claiming Box 12 “TP” or “TT,” want maximum guidance | TurboTax Deluxe |
| Want a human professional available as backup | H&R Block (online or in-person) |
| W-2 only, comfortable with manual entry, want to save money | FreeTaxUSA (or Cash App Taxes) |
| Gig worker / 1099 with Schedule C | TurboTax Self-Employed or FreeTaxUSA |
| Multiple states | TurboTax or H&R Block (per-state fees apply everywhere) |
| Claimed same deductions last year, no major changes | Whatever you used before, consistency reduces errors |
Frequently Asked Questions
Does tax software automatically find the new OBBBA deductions?
Yes, on TurboTax and H&R Block, entering Box 12 code “TP” or “TT” on your W-2 automatically triggers the deduction interview. The software identifies the code, explains the deduction, asks eligibility questions, and calculates the amount including any MAGI phase-out. FreeTaxUSA and Cash App Taxes also apply the deductions, but require you to enter the information in the correct field without as much prompting.
Is the free tier of TurboTax enough for claiming OBBBA deductions?
Generally no. TurboTax’s Free Edition is designed for the simplest returns, W-2 income, standard deduction, no Schedule 1 adjustments beyond basic items. The OBBBA tips and overtime deductions are above-the-line adjustments on Schedule 1, which typically require at least the Deluxe tier. FreeTaxUSA’s free federal tier does include Schedule 1 adjustments, so it covers the OBBBA deductions without an upgrade.
Can I switch tax software from last year without issues?
Yes. Switching is straightforward, most platforms let you import a prior-year return from a competitor’s PDF to pre-fill this year’s information. TurboTax and H&R Block both offer prior-year import. Your deductions and credits are re-evaluated fresh each year, so switching does not affect what you can claim. The only inconvenience is re-entering your information if import fails.
What if I make a mistake claiming the new deductions, will software catch it?
TurboTax and H&R Block both run a final review before submission that flags common errors, including mismatches between W-2 Box 12 amounts and what you entered on Schedule 1. Neither platform can catch an error on your W-2 itself (e.g., if your employer entered the wrong amount in Box 12 “TP”). That is why verifying your W-2 before filing is the most important step. If you file and later discover an error, you can file an amended return (Form 1040-X), all major platforms support this.
Is it worth paying for TurboTax Live to have a CPA review my return?
For most tipped workers with a straightforward W-2 return claiming the tips deduction, it is probably not necessary, the standard guided interview handles it correctly. TurboTax Live (from ~$89+ federal) makes more sense if your return is more complex: you have self-employment income, received allocated tips in Box 8, work across multiple states, or had a major life change (new dependent, property sale, large investment gains). For a basic one-W-2 return with the new deduction, the standard Deluxe tier is sufficient.
Bottom line: All major tax software platforms support the new OBBBA deductions for the 2027 filing season. TurboTax leads on guidance, H&R Block leads on human access, and FreeTaxUSA leads on price. For most tipped workers filing their first return with Box 12 “TP,” TurboTax Deluxe is worth the extra cost. For confident filers who just want to get it done cheaply, FreeTaxUSA is unbeatable at free federal plus $14.99 state.
This article is for informational purposes only and does not constitute tax or financial advice. Software prices, features, and OBBBA deduction support are based on our research as of June 2026 and may change before the 2027 filing season. We may earn affiliate commissions from links on this page; our ratings are not influenced by those relationships. Always verify current pricing and features directly with each provider before purchasing. Consult a CPA or tax professional for complex returns.
