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Boomer’s Blueprint: Artificial intelligence in the 2025 tax season

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As CPA firms prepare for the 2025 tax season, artificial intelligence is transforming how they manage tax returns, communicate with clients and handle administrative tasks.

AI can improve efficiency, accuracy and client experience, helping firms streamline processes and reduce manual work. By utilizing AI-powered tools like SafeSend, TaxCaddy, and Aiwyn, firms can optimize tax workflows, improve financial management and deliver the advisory services clients increasingly demand.

Whether you prepare returns internally or outsource them, AI drives innovation across the board.

Automating data aggregation

The process of gathering tax-related documents from clients has long been a bottleneck. AI tools like SafeSend and TaxCaddy are designed to automate and streamline this process.

  • SafeSend Returns: SafeSend Returns helps automate the assembly, delivery and approval of tax returns. Automating the collection of signatures (such as Form 8879) and securely delivering returns to clients removes the need for repetitive manual follow-up. The platform integrates e-signature capabilities, ensuring tax returns can be reviewed, signed and submitted electronically, reducing delays and human error.
  • TaxCaddy. TaxCaddy makes the document collection process smoother by providing clients with a secure platform to upload their tax forms (W-2s, 1099s, K-1s, etc.). Its AI-driven data extraction capabilities automatically capture relevant information from uploaded documents, eliminating the need for manual data entry. AI also helps TaxCaddy send reminders to clients, ensuring they submit all necessary documents on time and reminding them to make estimated tax payments.

Both SafeSend and TaxCaddy are equally effective for internally prepared and outsourced returns. They provide consistent, efficient workflows, reducing time spent on administrative tasks and allowing firms to handle a higher volume of returns with greater ease — in other words, they increase capacity.

Streamlining delivery and e-filing

Once the firm prepares returns, AI-driven solutions play a critical role in automating the review, delivery and filing processes:

  • AI-powered review. AI algorithms can quickly review tax returns, flagging missing forms, potential errors or discrepancies. This step ensures tax returns are complete and accurate before they’re sent to clients, reducing the risk of IRS notices or audits.
  • Smart delivery systems. AI tools like SafeSend automate the delivery of tax returns to clients. These platforms can securely send the completed returns for client review, allowing for real-time updates and approval status tracking. Clients can sign electronically, accelerating the process and filing returns promptly.
  • Automated e-filing. After client approval, AI systems can automatically trigger electronically filing returns with the IRS. Integrating AI into the e-filing process reduces the manual steps, ensuring faster, error-free submissions. It also reduces the administrative burden on staff so they can focus on more complex tasks.
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Automating extensions and 7216 compliance 

Filing tax extensions can be a time-consuming process when it requires manually tracking deadlines and client readiness. AI simplifies this process by automating extensions and compliance with legal requirements:

  • Automating extensions. AI systems can automatically identify clients who are likely to need an extension based on incomplete documentation or prior filing patterns. The system can automatically generate the necessary forms, such as Form 4868 for individual returns or Form 7004 for businesses. Then, it can submit those forms electronically to reduce the risk of missed deadlines.
  • Compliance with IRS Code 7216. IRS Code 7216 requires firms to obtain client consent before sharing taxpayer information when outsourcing tax return preparation to third-party providers. AI can streamline this compliance process by generating and managing the necessary consent forms. It can also automate engagement letter creation, ensuring the firm obtains all legal disclosures and client consents, reducing the risk of penalties for non-compliance.

By automating critical compliance steps, AI helps firms mitigate risks and maintain legal standards while outsourcing work.

Enhancing billing and financial management

AI isn’t only revolutionizing tax preparation; it’s also transforming how CPA firms manage billing, collections and overall cash flow. Tools like Aiwyn use AI to automate and optimize these processes:

  • Packaging and pricing services. Aiwyn’s AI-powered platform helps CPA firms bundle services and develop dynamic pricing strategies. By analyzing historical data, AI can suggest optimal pricing for tax services, ensuring that firms maximize profitability while staying competitive.
  • Automated billing and invoicing. Aiwyn automates the billing process, reducing the time between service delivery and invoice generation. AI can monitor work in process and generate invoices based on completed tasks, helping firms reduce the time it takes to send invoices and collect payments.
  • Improving cash flow. AI also assists in the collections process by sending automated reminders for outstanding invoices and following up with clients. By reducing accounts receivable and minimizing overdue payments, firms can improve their cash flow and reduce the administrative burden on staff.

Elevating client experience 

As firms automate routine tasks through AI, they can focus more on delivering what clients genuinely value — advisory and consulting services. Clients today expect more than tax preparation; they want personalized advice and strategic planning. By freeing up time through automation, firms can provide higher-level services that help clients achieve their financial goals.

AI also enhances the client experience by improving communication and transparency. Tools like SafeSend and TaxCaddy offer real-time updates, automated reminders and secure communication channels, giving clients a more seamless, efficient interaction with their advisors. This elevated client experience builds trust and long-term relationships, which are essential for firm growth.

AI is reshaping the tax practices of CPA firms, providing powerful tools like SafeSend, TaxCaddy and Aiwyn to automate data collection, return preparation, delivery, compliance and billing. These technologies help firms streamline their workflows, reduce errors and improve cash flow, while allowing team members to focus on higher-value services like advisory and consulting. By adopting AI-driven processes, CPA firms can handle tax season with greater efficiency, enhance the client experience, and deliver the strategic guidance clients expect in today’s fast-evolving business landscape.

Firms integrating AI now will be well-positioned for success in the 2025 filing season and beyond. The AI train has left the station. It is time to embrace AI, as it will only accelerate. The transformation triangle requires change management, process management and project management. All of which are driven by leadership and the firm’s vision. 

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Accountants on IRS and PwC layoffs, accounting students and more

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Complimentary Access Pill

Enjoy complimentary access to top ideas and insights — selected by our editors.

This week’s stats focus in part on the job titles seeing the greatest losses at the IRS during layoffs; as well as the states that have proposed or passed alternatives to the 150-hour rule; the percentage of master’s in accounting program applicants since 2020; the number of PwC employees laid off in May; the projected size of Deloitte’s new New York City headquarters; and the amount of 2026 HSA annual contribution limits, depending on coverage.

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CrowdStrike says DOJ, SEC sent inquiries on firm accounting

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CrowdStrike Holdings Inc. said U.S. officials have asked for information related to the accounting of deals it’s made with some customers and said the cybersecurity firm is cooperating with the inquiry.

The Austin, Texas-based company said in a filing Wednesday that it has gotten “requests for information” from the U.S. Department of Justice and the Securities and Exchange Commission “relating to the company’s recognition of revenue and reporting of ARR for transactions with certain customers.” ARR refers to annual recurring revenue, a measure of earnings from subscriptions.

The company said the federal officials have also sought information related to a CrowdStrike update last year that crashed Windows operating systems around the world.

“The company is cooperating and providing information in response to these requests,” the filing states.

U.S. prosecutors and regulators have been investigating a $32 million deal between CrowdStrike and a technology distributor, Carahsoft Technology Corp., to provide cybersecurity tools to the Internal Revenue Service, Bloomberg News first reported in February. The IRS never purchased or received the products, Bloomberg News earlier reported.

The investigators are probing what senior CrowdStrike executives may have known about the $32 million deal and are examining other transactions made by the cybersecurity firm, Bloomberg News reported in May.

Asked for comment about the filing, CrowdStrike spokesperson Brian Merrill said, “As we have told Bloomberg repeatedly, this is old news and we stand by the accounting of the transaction.” 

A lawyer for Carahsoft previously declined to comment on the federal investigations, and representatives didn’t respond to subsequent requests for comment about them.

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Elon Musk urges Americans take action to ‘kill’ Trump tax cut bill

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Tech titan Elon Musk ratcheted up his offensive against Donald Trump’s signature tax bill on Wednesday, urging that Americans contact their lawmakers to “KILL” the legislation.

“Call your Senator, Call your Congressman,” Musk wrote in a social media post. “Bankrupting America is NOT ok!”

The post came one day after Musk lashed out at the tax bill, describing it as a budget-busting “disgusting abomination” as Republican fiscal hawks stepped up criticism of the massive fiscal package. 

Trump hasn’t publicly responded to Musk’s comments, but the White House put out a statement Wednesday saying the legislation “unleashes an era of unprecedented economic growth.” 

And House Speaker Mike Johnson told reporters that Musk is “dead wrong” about the bill and that the tax cuts will pay for themselves through economic growth.

Musk’s public condemnation pits him against the president at a critical time as Trump is personally lobbying holdouts on the bill. His campaign against the legislation threatens to stiffen resistance and delay enactment of the tax cuts and debt ceiling increase. 

Musk has attacked the legislation days after leaving a temporary assignment leading the administration’s Department of Government Efficiency initiative to cut federal spending. The Tesla Inc. chief executive officer’s high-profile role in the Trump administration eroded his business brand and sales of his company’s electric vehicles plunged. 

The House-passed version of the tax and spending bill would add $2.4 trillion to U.S. budget deficits over the next decade, according to an estimate released Wednesday from the nonpartisan Congressional Budget Office.

The CBO’s calculation reflects a $3.67 trillion decrease in expected revenues and a $1.25 trillion decline in spending over the decade through 2034, relative to baseline projections. The score doesn’t account for any potential boost to the economy from the bill, which Johnson and Trump argue would offset the revenue losses. 

Musk, the world’s richest man with a net worth of about $377 billion according to the Bloomberg Billionaires Index, has become a crucial financial backer of the Republican party. After making modest donations most years, Musk became the biggest U.S. political donor in 2024, giving more than $290 million.

Johnson said Musk had promised to help reelect Republicans just a day before savaging Trump’s bill. Musk did not respond to a request for comment. 

Most of Musk’s giving was aimed at electing Trump but he also supported congressional candidates. America PAC, the super political action committee that Musk largely funded, spent $18.5 million in 17 separate House races. Though that total pales in comparison to the roughly $255 million he spent backing Trump, the spending means a lot in a congressional election, where challengers on average raise less than $1 million.

Control of the House will likely be decided by the outcome of fewer than two dozen close races in the 2026 midterm elections. The GOP’s chances of holding their majority would suffer a major blow if Musk were to withdraw his financial support.

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