Switching tax software is the highest-stakes operational decision a solo or small-firm preparer makes. Get it wrong and you risk failed e-files, IRS rejections, lost client data, and a ruined filing season. Get it right and you save thousands of dollars per year and reclaim hours of your time.
This guide walks you through migrating from Drake Tax to TaxOwl Pro — written for the preparer who has decided to switch but wants to avoid every avoidable mistake. We’ll cover the timeline, data conversion, EFIN/ERO transition, bank-product setup, learning curve, parallel-run mitigation, and the common pitfalls.
This is the operational guide. If you’re still deciding whether to switch, read Drake Tax Software Alternative for Growing Firms first.
Who this guide is for
You’re the right reader if:
- You file 30 to 300 returns per year as a solo preparer or in a small (1-5 preparer) practice
- You currently use Drake Tax (any tier — Pay-Per-Return, Drake Power Bundle, Drake Software unlimited) and you’re either at renewal time or have decided to switch
- You hold a PTIN, an EFIN if you self-e-file, and either an AFSP credential, EA, or are a CPA in a small practice without firm-tier software
- You want a step-by-step migration plan, not a marketing pitch
If you file fewer than 30 returns/year, the math on switching may not justify the migration effort regardless of price savings — read the linked alternative-comparison piece for that calculation. If you file more than 500 returns/year and use Drake Network, you’re closer to firm-tier software territory; this guide still applies but you may want to talk to us directly for migration support.
When to switch (the timing matters more than people realize)
The single biggest mistake we see in tax-software migrations is timing. Never switch tax software in January, February, or March. Filing-season migrations fail catastrophically because:
- You don’t have time to learn a new UI while preparing live returns under deadline pressure
- Data conversion errors compound under volume — by the time you find a problem, you’ve made the same mistake on 30 returns
- EFIN registration changes can take 4-6 weeks to process at the IRS — if you switch software in February, you may not be able to e-file until April
- Bank-product setup with new software requires re-application, re-approval, and re-training, all of which take weeks
The optimal switching window is May through August. You’re past the April rush, you have months to learn the new software in a low-stakes environment, and you can complete EFIN/ERO transitions before extension season heats up in September.
Acceptable secondary window: September through October. Tighter but workable. You’ve completed extension returns on the old software; you can install the new software and learn it before December’s prior-year-cleanup work and January’s season ramp.
Decision deadline if you want to be ready for the next filing season: October 31. Any switch initiated after that is a season-2027-or-later migration in practice.
The 90-day migration timeline
Plan for ninety days from “I’m switching” to “I’m filing on TaxOwl Pro.” Some preparers move faster, but ninety days lets you handle the long-tail dependencies (IRS processing windows, bank approvals, real-world software learning) without panic.
Days 1-14: setup + dual access
- Sign up for TaxOwl Pro and complete software activation
- Do not cancel Drake yet. You want both available during the transition
- Watch the TaxOwl Pro getting-started videos and complete the practice-return walkthrough — file at least three sample returns to feel the UI flow
- Identify your three most complex returning clients and pull their prior-year Drake files; these will be your conversion test cases
Days 15-30: data export + conversion testing
- Export your full client list from Drake in CSV format (Reports → Client List → Export)
- Export prior-year tax data files for every active client (Drake’s .DT extension or backup files)
- Use TaxOwl Pro’s prior-year import tool to convert the three test cases identified above
- Spot-check the converted returns against the original Drake-prepared returns. Verify carry-forward items: net operating losses, capital loss carryovers, depreciation schedules, basis tracking, prior-year state credits
- If conversion errors appear, document them and contact TaxOwl Pro support before importing the rest of your client base
Days 31-45: EFIN + ERO + bank-product transitions
- EFIN does NOT need to change. Your EFIN is yours, not Drake’s. Update your TaxOwl Pro account with your existing EFIN — same number you’ve used for years
- ERO information transfers directly. Your ERO PIN, name, address are the same on TaxOwl Pro as they were on Drake
- Bank product enrollment is the long-tail dependency. If you offer Refund Transfer (RT) or refund advances, you’ll re-enroll with the bank-product partner through TaxOwl Pro’s program. Allow 3-4 weeks for approval. Republic Bank, EPS, TPG, Refundo, and SBTPG are the standard partners
- If you used Drake’s bank-product program with revenue sharing or per-return cuts, note that TaxOwl Pro takes no cut — your full bank-product rebate goes to you
Days 46-60: full client-list import + prior-year carry-forward
- Import your complete client list to TaxOwl Pro
- Run prior-year carry-forward import for every active client (last year’s filed return data)
- Spot-check at least 10% of imports — verify name, SSN, dependent count, prior-year AGI, refund/balance-due, carryforwards
- Flag any clients with conversion issues for manual re-entry
Days 61-75: practice + workflow setup
- Set up your firm letterhead, invoicing templates, engagement letters, and client questionnaires inside TaxOwl Pro
- Configure your e-signature workflow (TaxOwl Pro uses Remote Signature; transition any saved templates)
- If you use a client portal, set up document upload folders and notification settings
- Run a final end-to-end test: prepare a sample return, e-file it to the practice environment, verify acceptance, generate the client copy PDF, and send for signature
Days 76-90: parallel-run period
- This is the most-skipped step and the one that prevents the most disasters. For your first two real returns, prepare them on BOTH Drake and TaxOwl Pro
- Compare the calculated tax due, refund, AGI, and any state-return numbers. They should match exactly
- If they don’t match, do NOT file until you understand why
- Once you’ve parallel-run two returns successfully, you can confidently file on TaxOwl Pro alone
- Cancel Drake at the end of your current paid period
Data conversion deep-dive
The single highest-risk part of migration is data conversion. Get this right and the rest is straightforward; get it wrong and you’ll spend hundreds of hours rebuilding client files mid-season.
What converts cleanly
- Client demographic data: name, address, SSN, dependents, contact information
- Prior-year AGI, refund/balance-due, federal withholding
- W-2 carry-forward (employer name and EIN can be used to pre-populate current-year W-2)
- State-return location and filing status
- Direct deposit information (verify after conversion — never assume)
What requires manual review
- Depreciation schedules. Section 179 carryforwards, MACRS class lives, and prior-year accumulated depreciation must match exactly. A misconverted depreciation schedule produces wrong current-year depreciation expense and wrong basis for future sales
- Net operating loss (NOL) carryforwards. Federal NOL post-2017 carryforward indefinitely but with 80% income limitation. State NOLs vary by state. Review every NOL carryforward against the prior-year filed Form 1045 or Schedule A
- Capital loss carryovers. Short-term and long-term, federal and state separately
- Passive activity loss (PAL) carryovers. Form 8582 attachments — PAL by activity, not just total
- Basis tracking for partnerships (Form 1065 K-1 outside basis), S-corps (stock and debt basis), and IRAs (Form 8606 for non-deductible contribution basis)
- State-specific credits and carryovers. Each state’s credits convert separately. Verify against prior-year filed state return
What does NOT convert
- Custom client notes or internal memos in Drake’s free-form fields
- Custom invoicing templates and firm-specific client letters
- Drake’s internal billing records (export to CSV separately for your books)
- Any third-party plugin data (Drake Documents, Drake Portals integrations)
The learning-curve reality
Honest accounting: TaxOwl Pro and Drake have different UIs. There’s no way around this. You will be slower on TaxOwl Pro for your first 5-10 returns. After that, you’ll match your Drake speed. After 30 returns, most preparers report being faster on TaxOwl Pro because the data-entry flow has fewer screens.
What’s similar:
- Both use form-based entry mirroring the actual IRS forms
- Both support both interview-mode and direct-form entry
- Both calculate identically — the underlying tax engine produces the same numbers
- Both e-file through IRS-authorized channels with the same acceptance/rejection workflow
What’s different:
- TaxOwl Pro’s data-entry shortcuts use different keystrokes than Drake. Print the cheat sheet from your account dashboard for the first season
- Multi-state allocation is configured differently — TaxOwl Pro uses a unified state-allocation worksheet vs. Drake’s per-state forms
- Prior-year carry-forward review is presented in a single screen on TaxOwl Pro vs. Drake’s per-form approach
- E-signature flow goes through Remote Signature directly from the return; Drake users typically used DrakePortals or a third-party tool
Common pitfalls and how to avoid them
Pitfall #1: Switching mid-season
If you find yourself wanting to switch in February or March because of a Drake renewal price you can’t stomach, the answer is to swallow the renewal cost and switch in May. Mid-season migrations fail. Period.
Pitfall #2: Skipping the parallel-run period
The temptation to file your first TaxOwl Pro return without parallel-checking against Drake is strong. Resist it. The cost of a failed first return — IRS rejection, client confusion, time lost diagnosing — is dramatically higher than the time spent parallel-running two returns.
Pitfall #3: Forgetting state-credit carry-forwards
State-specific credits (CA renters credit, NY child credit, IL property tax credit, etc.) carry forward differently in each state. The auto-import will get the federal data right but state credits often need manual verification. For every multi-state client, pull last year’s filed state return and verify the carry-forward in TaxOwl Pro matches.
Pitfall #4: Bank-product re-enrollment delays
Bank-product enrollment with TaxOwl Pro’s partner banks takes 3-4 weeks. If you file your first return that has a Refund Transfer attached but bank-product enrollment isn’t complete, the e-file will still go through but the RT won’t fund. Start bank-product enrollment before the official switch date.
Pitfall #5: Underestimating the depreciation conversion
Depreciation schedules are the highest-risk auto-conversion. For any client with rental property, business assets, or vehicles, manually verify the prior-year accumulated depreciation, current-year basis, and depreciation method against the prior-year Form 4562. We’ve seen converted depreciation schedules that were off by hundreds of dollars in current-year expense.
Pitfall #6: Forgetting to update your professional liability insurance
Some E&O insurance policies specify the tax software you use. Notify your carrier of the switch. Most won’t care — coverage is on the preparer, not the software — but the disclosure protects you if a claim arises.
What you’ll save
Real-world numbers from preparers who’ve switched to TaxOwl Pro from Drake:
- Drake Tax Pay-Per-Return + add-ons: typically $1,200-$1,800 per season including state add-ons and bank-product fees. TaxOwl Pro flat $649. Savings: $550-$1,150/season.
- Drake Power Bundle (unlimited): approximately $1,995 plus state add-ons depending on tier. TaxOwl Pro flat $649. Savings: $1,300+/season.
- Drake plus Drake Documents and DrakePortals: add $400-$800/year on top of the above. TaxOwl Pro includes secure document collection and e-signature in the base price. Additional savings: $400-$800/season.
- Drake’s bank-product revenue cuts: some Drake partner programs take a percentage of your bank-product rebate. TaxOwl Pro takes zero. If you file 100 returns with 60% RT attach at average $25 SB Fee, you keep an additional $1,500/year that Drake’s program partners would have shared in
Total all-in savings for a typical 100-return preparer switching from Drake Power Bundle: roughly $2,500-$4,000 in year one.
The founding-cohort offer
If you’re switching from Drake before October 31, 2026, you may qualify for our founding-cohort program. The first ten preparers to commit to season 2027 on TaxOwl Pro get the season free in exchange for:
- A short interview and case study after the season closes (April 2027)
- Permission to publish the case study on our site, with your name and photo
- One referral to a peer preparer if a candidate fit comes up during the season
The math is straightforward: a $649 license value in exchange for a few hours of your time and a public testimonial. We need ten honest, in-the-field reviews from real preparers who switched and made it work — and we’re willing to give the software away to get them.
Apply to the founding cohort →
If you’re ready to switch
Three concrete next steps:
- Apply at /apply/. We’ll set up your TaxOwl Pro account and confirm EFIN/ERO transfer requirements within 48 hours
- Schedule a 30-minute migration consultation with our onboarding team. We’ll walk through your client list size, complexity, and bank-product setup, and confirm a timeline that fits your practice
- Start the 90-day clock. If you commit by October 31, 2026, you’ll be ready for season 2027 with a clean migration and zero in-season risk
The Drake-to-TaxOwl-Pro migration is well-trodden ground at this point. Done in summer, with a parallel-run period, and with the right preparation, the switch is uneventful — which is exactly what you want a software migration to be.