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TaxCaddy simplifies tax time

TaxCaddy is a software solution that makes gathering tax documents and sharing them with your tax professional at Windes a breeze! You can easily and securely respond to the questionnaire, keep track of what documents you already uploaded, and see a list of additional files to upload. You can even use TaxCaddy year-round to save important tax-related information as it occurs, keeping us in the loop of major transactions or events. TaxCaddy prioritizes security and utilizes best-in-class technology, data centers, and infrastructure to meet the strict requirements of the most security-sensitive CPA firms in the world, so you can feel confident that your data is secure.



We’ll send you an email invitation to join TaxCaddy. Only use the personalized link in your email to sign up – do NOT use the “sign up free” option on the TaxCaddy website.
Use this form to request an email invitation from Windes.
Learn more about creating your TaxCaddy account.


Log in to your TaxCaddy account, navigate to the Overview screen, and click the Accept Connection button to establish a connection with Windes.
Learn more about first-time login.
Learn more about connecting your TaxCaddy account with Windes.


Now you are ready. You will see in your account that we have provided a list of requested documents based on last year’s tax return. Once you have uploaded the documents, we can communicate with you on the status and finalize the process.

Request an invitation to TaxCaddy!

Download the mobile app to send documents and messages directly from your mobile phone.

Set up Smart Links with your financial institutions to streamline the process of sending us W-2s, 1099s and 1099s.
Learn more about Smart Links.

Be sure to fill out the Questionnaire to let us know about life events that can affect your taxes.
Learn more about filling out the questionnaire.

Frequently Asked Questions

Q:  Are there any fees associated with TaxCaddy?
A:  TaxCaddy is provided at no additional cost to you.

Q:  Is TaxCaddy secure?
A:  Yes! TaxCaddy has been independently audited, tested and validated by C-Level Security, LLC. TaxCaddy also uses two-factor authentication to help keep your account secure by prompting you to enter a security code each time you log in from a new device.

Q:  Can I add my spouse to my TaxCaddy account?
A:  Yes, your spouse or a financial advisor can be added as an additional user and granted access to your TaxCaddy account at any time. Learn more about adding a user.

Q:  How do I contact TaxCaddy support?
A:  Many of your questions may be answered in the TaxCaddy Help Center. During support hours, you can live chat with TaxCaddy support by clicking “Help” from your account screen. You can also email or call 1-833-TaxDesk (833-829-3375) from 7am – 5pm PST, Mon-Fri.

Q:  Will I still get a paper organizer mailed to me this year?
A:  To help simplify the tax process, Windes will no longer be providing a paper organizer and instead will begin using an interactive questionnaire that will be accessible through TaxCaddy.

Q:  Once I submit all the preliminary documents, is there a way to check on the status of my return using TaxCaddy?
A:  Yes, your TaxCaddy account will reflect your tax return progress with us. You will only need to provide the documents and tax information that are pending.

Q:  What is the benefit of uploading documents to TaxCaddy versus providing the information to Windes via email or postal mail?
A:  There are two main benefits:

  • Increased security of your sensitive information since you are uploading to a secure portal. No need to password protect your files prior to sending.
  • Documents are digitally stored in an organized format. You can track which requested documents have been uploaded and what’s still pending.
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