DeductIt Tax Helper: Automated Donation Entry for TurboTax Desktop

Updated April 2, 2026 · Foothill AI · v1.3.2

If you've ever typed dozens of donations into TurboTax one by one, you know the pain. Charity name, address, date, amount, donation type, valuation method—screen after screen, for every charity you donated to.

DeductIt Tax Helper automates all of that. It's a free companion app that reads your donation data from DeductIt and enters it directly into TurboTax Desktop—every field, every screen, every charity. You just watch it work.

How It Works

The Tax Helper sits beside TurboTax on your screen. It uses your operating system's accessibility APIs to read what's on the TurboTax screen, type into fields, check boxes, select dropdown options, and click buttons—exactly as you would, but without the tedium.

What Gets Entered

The Tax Helper fills in everything that TurboTax asks for:

• Cash donations — charity name, amount, date
• Non-cash items — item descriptions, fair market value, date, condition, valuation method
• Stock donations — symbol, shares, cost basis, acquisition date, Form 8283 details
• Mileage — trip description, miles driven, vehicle expenses
• Charity addresses — street, city, state, ZIP

This is a significant improvement over TXF import, which only handles cash and basic item amounts and requires manual cleanup afterwards.

Setup Guide

macOS

1. Download the Tax Helper from the Transfer to TurboTax screen in DeductIt (or from deductit.io/download/tax-helper)
2. Open the app. On first launch, it will ask for Accessibility permission—this is required so it can read and interact with TurboTax. The app walks you through granting it.
3. Load your automation guide (exported from DeductIt) via file or clipboard
4. Open TurboTax Desktop and navigate to Charitable Donations > Let's enter your charities one at a time
5. Click Start Automation

Windows

1. Download the Tax Helper from the Transfer to TurboTax screen in DeductIt (or from deductit.io/download/tax-helper)
2. Unzip and run the installer. Windows SmartScreen may show a “Windows protected your PC” warning—this is normal for new apps. Click “More info”, then click “Run anyway” to proceed.
3. Open the app—no special permissions are needed on Windows
4. Load your automation guide and start automation (same steps as macOS)

Tips for Best Results

• Don't touch the mouse or keyboard while automation is running. The Tax Helper controls the cursor and keyboard to interact with TurboTax.
• Position the Tax Helper window so it doesn't overlap TurboTax. Side-by-side works well.
• Start from a clean slate—navigate to "Let's enter your charities one at a time" with no existing entries before starting.
• Restart TurboTax on Windows if it's been open a while. TurboTax for Windows can get sluggish after long sessions, which causes the Tax Helper to wait on screens that are slow to load. Closing and reopening TurboTax gives noticeably better results.

After Automation: Review Your Item Donations

Important: review your item donations after automation. TurboTax asks extra questions for item donations—especially those over $500—that DeductIt can't prefill. For every item donation, the Tax Helper fills in these defaults on your behalf:

• "We need more details for donations over $500" (Form 8283): acquisition method = Purchase, owned more than one year = Yes, acquired on multiple dates = Yes. Cost basis is left blank unless you set an original purchase price in DeductIt.
• "Tell us how [Charity] will use your donated item": No (assumes the charity resells the item).
• "Uncommon situations for your donation": None of these.

These answers flow onto IRS Form 8283. When the Tax Helper finishes, open each item donation in TurboTax and confirm the answers match your situation before filing—especially for donations over $500 and any items the charity used directly. TurboTax may also ask additional questions (like item condition for large donations) that require manual answers.

Troubleshooting

"TurboTax Desktop not detected"

Make sure TurboTax is open and you're on a tax return. The Tax Helper looks for the TurboTax process by name.

"Expected screen X but found screen Y"

TurboTax shows different screens depending on your donation amounts and types. The Tax Helper handles most variations automatically (skipping screens that don't appear), but if it gets stuck, go back to the charity list in TurboTax and try again.

macOS: Accessibility permission not detected

Open System Settings > Privacy & Security > Accessibility and make sure DeductIt Tax Helper is listed and toggled ON. If it's not in the list, click the + button to add it. You may need to quit and reopen the Tax Helper after granting permission.