Open questions

What ALFA hasn't solved yet.

These came up on the calls and the group didn't reach a working answer. We publish them anyway. Every one is a future session, a tool, or a question we're taking to counsel. It's our roadmap, in the open.

Back to all answers

Open questionAutomation & MCP
When building an AI chat assistant that searches across all client transcripts/data, how do you handle the assistant taking in too much information when queried broadly instead of per-client?
Ben indicated that vector layers had to be added on top of the transcripts because there was too much text for the system to search effectively otherwise.
Jul 8 call
Open questionBookkeeping
When automating bank statement recreation from transaction data (e.g., via QuickBooks or Plaid), is it possible to also pull actual check images?
A member asked whether an automated bank statement/transaction pull could also retrieve check images rather than just recreating the transaction list.
Jul 8 call
Open questionBookkeeping
Can bank statement-style output (with beginning/ending balances) be generated from data pulled through Plaid or QuickBooks rather than obtaining actual client bank statements?
One approach discussed was building a system where a client logs in once through Plaid to grant token access, after which Plaid pulls the exact transaction…
Jul 8 call
Open questionAutomation & MCP
Where does a custom-built practice management/client portal tool actually get hosted, and what's involved in maintaining it long-term?
The custom client portal tool currently runs on Supabase and Vercel, with the underlying hosting managed by the contractor building it; the firm owner wasn't…
Jul 8 call
Open questionAutomation & MCP
Can a fully offline/local AI workflow that maps financials to Drake tax lines be integrated directly with Drake's import process?
A member described a workflow that runs fully offline with local models on local folders (no cloud) to take financials and annotate next to each line where…
59:00Jul 1 call
Open questionSecurity & compliance
Which AI tax prep tool should I use, and does it require 7216 disclosure to clients?
There are many different tools available for tax prep, including Cowork if you have Claude Enterprise (which now offers Cowork with data protection features,…
17:09Jul 1 call
Open questionSecurity & compliance
Is there a resource showing exactly what security settings to turn on when getting started with AI tools?
Yes — the group indicated there is something on the site covering this, and suggested it's a good topic to dig into further as its own conversation.
46:27Jul 1 call
Open questionGetting started
When should I use a plain chat versus setting up a Claude Project?
Projects are useful when you want to silo a specific initiative with its own context so it doesn't bleed into other conversations — for example, creating a…
37:27Jul 1 call
Open questionAutomation & MCP
What does it mean to run AI 'locally' or 'offline,' and is anyone using this to annotate financials and map them to Drake tax software?
A distinction was drawn between two different meanings of 'local': (1) working with files stored on your local machine while still using Claude in the cloud…
57:01Jul 1 call
Open questionBookkeeping
Can you pull bank statements or commercial loan data automatically through Plaid or QBO?
No — most banks do not push commercial loan data through Plaid, and Plaid also does not provide bank statements or check images.
35:01Jun 25 call
Open questionSecurity & compliance
What practical steps can be taken to avoid exposing sensitive financial/PII data when using LLMs for tasks like loan modeling?
Two main strategies were described.
44:13Jun 25 call
Open questionSecurity & compliance
What does the recent guidance on AI use in practice say about which AI models are considered safe, and does it address Section 7216?
The guidance did not spell out a specific list of approved models, but it did state that practitioners should use 'secure enterprise approved AI.' This…
19:00Jun 24 call
Open questionSecurity & compliance
How could a redaction tool let firms use client data with AI while staying compliant?
The idea discussed: build a redaction tool so client data can be anonymized before being used with AI, but it has to be 100% solid, since even sending data…
1:00:57Jun 24 call
Open questionSecurity & compliance
If a client voluntarily uploads their own tax documents into a client-facing AI tool (like Stanford Tax), does that count as the firm's 7216 disclosure, or does the firm still need separate consent?
A member raised this as an open question: when clients are invited to upload documents into a portal/binder tool that uses AI (using Stanford Tax as an…
46:09Jun 24 call
Open questionSecurity & compliance
Does the new OPR guidance say which AI models/tools are safe for practitioners to use?
The guidance didn't explicitly define a 'safe' model, but it did specify that practitioners should use secure, enterpriseapproved AI.
19:12Jun 24 call
Open questionSecurity & compliance
What's blocking members from moving forward with AI adoption in their firms?
A member said the recurring blocker is unresolved clarity on security and IRC §7216 disclosure/consent requirements.
1:00:16Jun 24 call
Open questionSecurity & compliance
Should firms talk to their insurance providers about AI use and 7216, and does this affect cyber coverage?
It was raised as an open question whether anyone had spoken with an insurance provider about how AI use and 7216 consent interacts with their coverage…
56:52Jun 24 call
Open questionSecurity & compliance
What framework can be used to decide whether a given AI use case requires 7216 client consent?
One member shared a flowchart approach for thinking through this.
37:27Jun 24 call
Open questionSecurity & compliance
Do we still need a separate Section 7216 consent/engagement letter when using AI tools like Claude for tax work?
Views differed.
23:29Jun 24 call
Open questionPractice mgmt
Will increased AI efficiency push firms away from hourly billing toward fixed-fee pricing?
Multiple members expect this shift to accelerate.
25:08Jun 24 call
Open questionSecurity & compliance
Is a 7216 consent required for AI tools like Claude or ChatGPT the same way it's not required for practice management software?
The group had no settled answer.
34:16Jun 24 call
Open questionSecurity & compliance
Is there a meaningful difference between using a generic AI tool (Claude, ChatGPT) versus a tax-specific AI tool (like Blue J) in terms of client data risk?
The question of generic vs.
58:16Jun 24 call
Open questionSecurity & compliance
Is it worth the hassle of getting clients to sign a separate 7216 AI consent, or is the pushback just about avoiding client friction?
One view raised is that firms resist doing this mainly because it's a hassle and they fear it will generate a flood of client questions and calls, not because…
50:49Jun 24 call
Open questionAutomation & MCP
Can Blue J be used to upload full source documents and tax returns for an AI-driven review, not just tax research?
One member reported doing a demo with Blue J where the vendor stated that, despite the company's publicfacing focus on tax research, the tool can also accept…
58:53Jun 24 call
Open questionSecurity & compliance
Does using AI to help make tax determinations for a client (e.g., whether something is deductible or taxable) trigger IRC 7216 consent requirements, versus just using AI as a supporting tool?
One member's view is that it largely depends on how AI is being used.
39:00Jun 24 call
Open questionTax
Can an AI tool review a completed tax return PDF against source documents to catch missed items or errors, like an AI reviewer?
One member described a tool (primarily marketed for tax research) that, when asked directly, confirmed it can accept an uploaded source document and an…
59:01Jun 24 call
Open questionPractice mgmt
At what point does a tool like Ramp's Stack replace QuickBooks or Xero as the actual ledger, rather than just automating on top of it?
One participant raised the recurring question of when these automation layers on top of the ledger actually become the ledger itself, noting the presenter had…
58:53Jun 18 call
Open questionAutomation & MCP
How is Stack (Ramp's AI accounting platform) priced, and is it a per-token or per-client-seat cost?
Pricing is not yet finalized.
25:47Jun 18 call
Open questionAutomation & MCP
Can the Stack chat agent take direct actions in the platform, like changing the status of a to-do list item or writing to the database, or does it only produce outputs like files and drafts?
Not today.
27:32Jun 18 call
Open questionAutomation & MCP
Could this client-communication dashboard be built without Airtable, e.g. using Google Drive or OneDrive for client documents?
The response was that it's probably possible, but Airtable is preferred because it functions as a true relational database, and the app builder used for the…
52:36Jun 17 call
Open questionBookkeeping
How can I get a live bank data feed for a client without using QuickBooks Online, since waiting for monthly statements isn't practical?
One option found using Claude for research is a service called SimpleFin, which costs about $1.50 a month.
31:43Jun 17 call
Open questionAutomation & MCP
Should firms wait for their practice management software to release built-in AI features, or build their own AI solutions in the meantime?
Several members are frustrated that inapp AI features from practice management platforms are moving much slower than their appetite for AI adoption.
23:28Jun 17 call
Open questionAutomation & MCP
What is 'Grove' and is anyone trying to replicate its interactive voice questionnaire feature?
One member mentioned a tool called Grove that has a voicebased interactive client questionnaire feature.
1:16:47Jun 17 call
Open questionGetting started
How do you decide which AI model to use for a given task (e.g., Claude Opus vs. other models)?
One approach is to follow the general guidance that you should pick the model that matches the difficulty of the task, using lighter models for simple work and…
20:37Jun 17 call
Open questionGetting started
How do I know when I need to use a higher model like Opus instead of Sonnet in Claude?
A member raised this as an open question they were running into — not knowing when a task requires Opus versus Sonnet.
16:27Jun 17 call
Open questionPractice mgmt
Can I upgrade to a ChatGPT Team plan with fewer than the stated 5-seat minimum?
One member discovered that it was possible to upgrade from ChatGPT Pro to Team with only 2 member seats instead of the advertised 5seat minimum.
19:00Jun 17 call
Open questionAutomation & MCP
Has anyone set up AI voice agents to handle client communication end-to-end, from phone calls through scheduling and record-keeping?
One member described setting up a voice AI agent to answer the phone (after hours or when busy), integrated via Zapier through cal.com to Google Calendar and…
1:11:39Jun 17 call
Open questionGetting started
What's the difference between a 'skill' in Claude for Chrome versus a skill in Claude Desktop?
One member's understanding is that Claude for Chrome has more ability to take actions in the browser (described as more ability to 'do bad things') compared to…
13:59Jun 17 call
Open questionClient comms
How are firms using Gamma to create client-facing tax return presentations, and could tools like Perplexity or AI-generated video improve on this?
One member's process: after the AI review of the tax return, a prompt summarizing the major items in the return is generated and fed into Gamma, which produces…
1:12:39Jun 17 call
Open questionAutomation & MCP
How difficult is it to pull text messages (e.g. from WhatsApp) into Airtable for client communication tracking?
It was described as easy when using a phone system with a good API (the speaker uses Quo, formerly known as Open Phone).
55:09Jun 17 call
Open questionSecurity & compliance
Should I wait for IRS guidance on whether AI tools count as an 'auxiliary service' under 7216 before choosing tax software?
One participant noted that a Google search on 'Blue J 7216' returned information suggesting Blue J runs on dedicated tenant infrastructure and doesn't use…
48:07Jun 16 call
Open questionSecurity & compliance
Is there a 7216 difference between building your own workflow in Claude versus using a purpose-built vendor tool like Blue J or Black Ore?
The view expressed was that using a vetted thirdparty tool (Blue J, Black Ore, TaxGPT) is preferable to building something yourself in Claude, partly because…
43:19Jun 16 call
Open questionSecurity & compliance
If AI is used to review client source documents and build workpapers, does that trigger IRC 7216 disclosure/consent requirements?
The IRS has not updated Section 7216 to address AI directly, so there's no clear ruling on whether AI counts as an 'auxiliary service' (which wouldn't require…
5:00Jun 16 call
Open questionBookkeeping
Can AI automatically organize incoming client tax documents (PDFs from email and TaxCaddy) into workpapers by client, year, and category?
This was raised as a major desired use case: taking PDFs from email and TaxCaddy and organizing them into a firm's share drive by client, year, and category,…
3:49Jun 16 call
Open questionPractice mgmt
Is it better to build custom AI workflows in Claude or rely on AI features being built into the software we already use (like Outlook)?
There's a tradeoff between two approaches: building something highly customized and nuanced to your exact firm situation by working directly with Claude,…
11:36Jun 16 call
Open questionAutomation & MCP
Is there a way to scrub PII from client documents before feeding them to AI tools, without needing coding skills?
One approach discussed: a member with no coding background built a local, noncloud tool by simply asking Claude to create software that scrubs PII from…
6:13Jun 16 call
Open questionSecurity & compliance
Without clear IRS guidance, what practical steps can a firm take to reduce risk when using AI tools on client tax data (e.g., regarding IRC 7216 consent)?
One practical approach discussed: use a trusted, established program (rather than a selfbuilt tool), disclose the use of the tool somewhere in the engagement…
49:01Jun 16 call
Open questionTax
Should I use Claude or a dedicated tax-specific tool to prep returns for review each morning?
The idea floated was having Claude process everything overnight so that a batch of returns is sitting ready for review each morning.
46:45Jun 16 call
Open questionPractice mgmt
Is there a risk of a surprise bill when using Claude Enterprise or Max due to usage-based pricing, especially with heavy multi-user or repetitive tasks?
The risk of unexpectedly high bills applies mainly to Enterprise, which bills based on usage rather than a fixed fee.
28:29Jun 16 call
Open questionPractice mgmt
Is it necessary to require staff to build a separate workpaper (e.g., Excel spreadsheet) when reviewing tax returns, especially for simple 1040s?
One member questioned the value of an extra workpaper step for relatively simple 1040s, arguing that tying source documents directly to the software should be…
25:52Jun 12 call
Open questionTax
Why might a firm choose Blue J over a general AI tool like Claude for tax return review, and what would that workflow look like?
One member said they'd rather use Blue J than Claude because Blue J is taxfocused and taxaware, pulling from the correct authoritative sources, and…
45:17Jun 12 call
Open questionSecurity & compliance
Do I need special client disclosures or consent under IRC 7216 to use AI tools on client tax data?
The group discussed uncertainty around 7216 and AI use.
5:41Jun 12 call
Open questionPractice mgmt
Could AI tools like Blue J and Juno eventually replace the data-entry and review roles in a tax practice?
One member speculated that if Blue J's review capability proves strong enough, it could replace the staff role that currently just checks dataentry accuracy…
47:36Jun 12 call
Open questionAutomation & MCP
Could AI generate the review workpaper automatically instead of having staff manually re-enter data into a spreadsheet?
The group briefly discussed whether documents could be uploaded and AI could generate the worksheet/spreadsheet used for review, eliminating a manual second…
29:02Jun 12 call
Open questionPractice mgmt
How can firms help junior staff develop professional judgment if AI is doing the research and thinking for them?
The group raised a concern: previously, staff were forced to research thoroughly before asking a senior a question, which built judgment over time.
43:09Jun 12 call
Open questionAutomation & MCP
How do I avoid hitting usage limits in Claude when working with large multi-page documents or images?
The issue comes up when feeding a chat too many attachments or a document with many pages (e.g., a 50page document), since each page can count as an image and…
29:01Jun 11 call
Open questionGetting started
Why does Claude Code seem to have lighter/less restrictive usage limits than using Claude's chat interface?
One member's theory (unconfirmed) is that Claude Code has lighter usage limits because it doesn't need to load the context/tools that the chat interface does,…
18:10Jun 11 call
Open questionSecurity & compliance
Is it safe to strip PII from a tax return PDF with Python and send the scrubbed data to Claude via API to analyze or create a checklist, and can this be done for every tax return once the AI confirms sensitive data isn't retained?
One member described a workflow built with a colleague: using Python to import a tax return PDF, redact PII (replacing it with bracketed placeholders), and…
7:03Jun 11 call
Open questionSecurity & compliance
Is it actually risky or against the rules to put client tax returns into AI tools, as some critics on social media claim?
The group discussed a recurring pattern on platforms like X where some accountants publicly criticize others for putting tax returns into AI tools, implying…
54:02Jun 11 call
Open questionTax
How can I automate identifying and filing penalty abatement claims for clients affected by IRS penalty/interest issues (e.g., the 'Kwang' situation), including clients who received notices but weren't in my original calculated batch?
One member described using Claude to build a full playbook after feeding it an article on the topic, then exporting from tax software a list of clients for…
3:27Jun 11 call
Open questionGetting started
What's going on with Claude's new model release ('Fable') hitting usage limits so quickly?
Multiple members reported that a newly released Claude model (referred to as "Fable") burns through usage/session limits extremely fast — one member said it…
16:16Jun 11 call
Open questionBookkeeping
Should bookkeepers focus on building custom AI workflows in Claude, or just rely on AI features already built into their bookkeeping software (e.g., Double)?
One member raised the idea that a bookkeeping platform called Double is adding many AI tools directly into the product, raising the question of whether…
33:39Jun 11 call
Open questionSecurity & compliance
Can data retention/memory be turned off on Claude's team/enterprise plans?
One member noted that memory can reportedly be turned off on Claude's team plans, giving something close to zero data retention (ZDR).
16:57Jun 11 call
Open questionAutomation & MCP
What's an effective method for building an AI skill (e.g., for preparing engagement letters) from scratch?
One effective approach described: walk Claude through the manual process step by step first — talking through what you look for, what you change, and why —…
54:32Jun 10 call
Open questionPractice mgmt
Does anyone have a contact at Anthropic to help set up an enterprise license?
One participant reported trying to reach Anthropic by phone and email to get an enterprise license, with no response, and asked the group if anyone had a rep…
57:39Jun 10 call
Open questionTax
How can I build a better client-facing tool for delivering quarterly estimated tax payments (similar to SafeSend)?
A member described starting work on a tool to better deliver quarterly estimated tax payments to clients, inspired by prior session demos.
9:25Jun 10 call
Open questionGetting started
After downloading a Claude skill file to my desktop, how do I actually use it in Claude?
A member who built skills the prior week was able to open the downloaded skill file from their desktop but didn't know how to load it into Claude so it could…
1:08:47Jun 10 call
Open questionAutomation & MCP
Why is it so hard to get an AI-built skill or workflow fully working, and what should I do differently?
The group's take was that this mirrors normal software development — prototyping is easy, but making something fully reliable is the real work, and…
55:30Jun 10 call
Open questionAutomation & MCP
How easy is it to deploy changes to a custom-built client app -- does it require running command-line/terminal commands each time?
A member asked whether making updates to the custom dashboard requires running command prompts in a terminal every time.
19:36Jun 10 call
Open questionSecurity & compliance
Where does client-provided data (like tax documents) actually reside within this multi-tool setup (Air Table, Assembly, vibe-coding app)?
The question was raised about where client tax forms and provided documents physically reside within the overall system architecture.
59:44Jun 3 call
Open questionAutomation & MCP
When is TaxDome expected to release its MCP integration?
TaxDome has said an MCP is coming, but timing is vague possibly a month, possibly summer.
1:11:14Jun 3 call
Open questionAutomation & MCP
Has anyone tried the MCP that QuickBooks recently released?
It was noted that QuickBooks released an MCP about two to three weeks (maybe a month) prior to this discussion.
1:12:16Jun 3 call
Open questionPractice mgmt
Has anyone demoed or used the tool called Filed?
No one on the call had actually used Filed.
1:12:50Jun 3 call
Open questionSecurity & compliance
Is it safe to drop client tax return data (like a Schedule C) directly into Airtable for this workflow?
The member explained that Airtable functions as their project management/CRMlike tool, and before using it this way they checked its security certifications,…
49:24Jun 3 call
Open questionAutomation & MCP
Can Claude be used to automatically build out or populate workflow templates/sections inside Double via MCP, rather than configuring them manually?
One member asked whether Claude could take a document or conversation and use it to build out sections or templates directly in Double through its MCP…
14:20Jun 3 call
Open questionAutomation & MCP
Why does Claude sometimes suggest steps or features in a software platform (like Canopy) that don't actually exist or aren't possible?
A member noted that Claude doesn't fully know the actual functionality of certain platforms, calling it 'hit or miss.' It will sometimes direct you to perform…
18:35Jun 3 call
Open questionPractice mgmt
What is the biggest bottleneck accounting firms face right now in scaling with AI, and what would 'leaning in' to AI actually require?
Multiple firm owners said their real bottleneck isn't software but people: there aren't enough good accountants, older practitioners are retiring without…
19:40Jun 2 call
Open questionSecurity & compliance
Is offshoring bookkeeping work to overseas virtual assistants a bigger security/control risk than using AI for the same tasks?
One participant argued offshore virtual assistants are probably less secure than AI for nontaxadjacent tasks, calling it a bigger security risk than doing…
22:00Jun 2 call
Open questionTax
Is there an AI tool (like Juno) that can reliably prepare a full tax return?
One participant asked about Juno as an AI tax preparation tool.
46:25Jun 2 call
Open questionSecurity & compliance
What's happening on the US side regarding IRS/regulatory guidance on AI use in tax practice, and how should firms handle data security in the meantime?
One participant noted that the IRS is supposedly going to give guidance on AI use at some point, but that could be up to 10 years out, and there's concern that…
33:49Jun 2 call
Open questionAutomation & MCP
Will the price per AI token/compute increase significantly in the next 6-12 months, and how should firms think about that risk?
The group's view was that AI is currently underpriced relative to the value it delivers — one participant argued that if an AI company is saving a firm…
26:44Jun 2 call
Open questionSecurity & compliance
How should firms think about AI security and privacy risk (e.g., the IRC 7216 concern) when using tools like Claude with client financial data?
The discussion acknowledged that reactions to AI privacy split into two camps: those who feel it's already too late to worry (client data is already flowing…
13:56Jun 2 call
Open questionPractice mgmt
Should firms/builders focus on AI-native tools or use AI as a means to build traditional software, given the risk that AI/token costs could rise sharply?
One builder described deliberately building their first product version with no AI in it at all, out of concern that token costs could rise dramatically and…
25:03Jun 2 call
Open questionSecurity & compliance
Can you limit which files/folders Claude's co-work feature can access, or does it see everything?
You're supposed to be able to point cowork to exactly which folders it should access.
38:07Jun 2 call
Open questionTax
Can Claude realistically generate tax planning reports (e.g., presenting strategies to a client) without a lot of manual review and correction?
One member said they'd love to use AI as a tax planning report generator — feeding in a set of strategies (e.g., 'here's the seven strategies I want to present…
4:56Jun 2 call
Open questionSecurity & compliance
Is it safe to install Claude Desktop on a machine that has access to client files, and how do you get IT/compliance on board?
One member said their IT group has not gotten comfortable with installing Claude Desktop on machines connected to client files, so they've been limited to a…
16:49Jun 2 call
Open questionSecurity & compliance
Does using AI tools like Claude with client tax return data raise IRC 7216 concerns, even if the data is scrubbed or masked?
One member referenced a comment from Brandon Hall on a social media post, noting there is fine print suggesting that even if you scrub or mask sensitive client…
18:09Jun 2 call
Open questionGetting started
How does Claude's built-in microphone/dictation feature compare to Whisper Flow?
Claude has a microphone button directly on the prompt page that lets you dictate instead of typing, similar in concept to Whisper Flow — you can still edit the…
51:21Jun 2 call
Open questionAutomation & MCP
Can a Gmail connector let Claude analyze all past emails with a client without manually printing/uploading them?
The question was raised about whether, with a Gmail connector, you could point Claude at a specific client and have it analyze every email ever exchanged with…
44:29Jun 2 call
Open questionAutomation & MCP
What happens when an AI tool fails or gets stuck on a complex automation task?
A member described spending about five hours with Perplexity trying to build an automation using Power Automate.
48:25Jun 2 call
Open questionAutomation & MCP
How do I migrate from using Claude only inside the Excel add-in to using the full browser/web version of Claude?
A member described using Claude almost exclusively through the Excel addin (on a Claude Max plan, $200/month, purchased as part of a client's corporate…
6:41Jun 2 call
Open questionGetting started
What's the difference between using Claude's desktop app versus the website version?
The only real difference noted is that the cowork feature is only available on desktop, not on the website or phone.
35:31Jun 2 call
Open questionSecurity & compliance
How can I safely delegate a full tax return workflow (checklist, work papers, first-pass review, client summary) to an AI tool like Claude?
One member described wanting to hand a client's full engagement to Claude: generate a checklist of what's needed for the year, turn incoming client documents…
19:01Jun 2 call
Open questionSecurity & compliance
Is it safe to use Claude for Chrome to work directly inside QuickBooks or web-based tax prep software for client work?
One member asked if anyone had used Claude for Chrome to poke around in QuickBooks or webbased tax prep software.
1:02:36May 27 call
Open questionSecurity & compliance
Should firms update their engagement letters to disclose that AI may be used to process client work?
One member relayed advice from another group: consider adding a short paragraph to engagement letters or terms disclosing that the firm may use AI to process…
1:04:43May 27 call
Open questionTax
Can AI tools like Perplexity help research when the IRS changed the RMD life expectancy tables for calculating missed required minimum distributions?
One member described using Perplexity for a client prospect who had inherited an IRA and failed to take RMDs for about 15 years.
4:23May 20 call
Open questionGetting started
What is the 'brand voice' option shown at the bottom of Claude's co-work interface?
The speaker was not fully certain about this feature, noting they'd never actually used it, but believed brand voice lets you create a brand package for your…
59:12May 20 call
Open questionSecurity & compliance
Is there a security/compliance concern with using custom AI models (like open-source models from Hugging Face) to review tax returns, given US regulatory requirements like WISP plans and SOC 2 compliance?
One participant raised concern that in the US, tax preparation firms are regulated entities that must have a WISP (Written Information Security Plan) and use…
29:01May 20 call
Open questionTax
How might AI-driven review of client investment statements and collaborative skill-building evolve for CPAs reviewing tax returns?
One member described their experience building a skill to carefully review complex investment statements (e.g., from a major brokerage) for a tax return tying…
21:52May 20 call
Open questionGetting started
What is the 'brand voice' feature shown at the bottom of the Claude co-work interface, and where should firms manage brand assets like logos and colors?
The feature seen in the cowork interface relates to brand voice/brand packages, but the speaker noted it's likely better handled now in Claude Design rather…
59:17May 20 call
Open questionSecurity & compliance
Is it safe to put client PII into Claude Chat, Claude Team, or similar AI tools?
This was raised as an open concern rather than resolved.
32:35May 13 call
Open questionSecurity & compliance
How can a firm build a system to automatically identify and redact PII from tax documents before sending data to an LLM?
One firm described building an internal system, trained on roughly 60,000 tax documents, that identifies what is and is not PII within a tax return and…
18:14May 13 call
Open questionSecurity & compliance
What are the security differences between ChatGPT Enterprise, Teams, and personal/free plans for handling client PII?
A participant reported that their firm recently invested in ChatGPT Enterprise and partnered with a security consultant, and found there are vastly different…
39:21May 13 call
Open questionGetting started
When should I use Claude chat/Projects ('co-work') versus Claude Code for building tools like spreadsheets or apps?
No firm rule was given.
36:36May 13 call
Open questionTax
Are there similar scripting-over-LLM approaches that could apply to tax work involving sensitive documents like PDFs?
One approach discussed is locally redacting sensitive information (e.g., Social Security numbers) out of PDFs before doing anything with them, so that once…
12:09May 13 call
Open questionSecurity & compliance
Is it safe to put sensitive client information like Social Security numbers into AI tools like Claude or ChatGPT?
The group flagged this as a key open question for the working group to address, since being able to safely use sensitive data would allow much more automation…
8:08May 13 call
Open questionAutomation & MCP
How hard is it to integrate custom workpaper tools directly with tax prep software (like CCH or UltraTax), and has anyone solved the data import problem?
One member said their team did solve direct integration from their workpaper tool into their tax software so no one had to manually touch the data, but called…
59:23May 13 call
Open questionSecurity & compliance
Do you need clients to sign a 7216 consent form (like the one used when a return is prepared overseas) specifically because you're using AI tools?
The view expressed was that 7216 is a much broader category and that people are somewhat 'shoehorning' the AI issue into it.
44:09May 13 call

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When building an AI chat assistant that searches across all client transcripts/data, how do you handle the assistant taking in too much information when queried broadly instead of per-client?

When automating bank statement recreation from transaction data (e.g., via QuickBooks or Plaid), is it possible to also pull actual check images?

Can bank statement-style output (with beginning/ending balances) be generated from data pulled through Plaid or QuickBooks rather than obtaining actual client bank statements?

Where does a custom-built practice management/client portal tool actually get hosted, and what's involved in maintaining it long-term?

Can a fully offline/local AI workflow that maps financials to Drake tax lines be integrated directly with Drake's import process?

Which AI tax prep tool should I use, and does it require 7216 disclosure to clients?

Is there a resource showing exactly what security settings to turn on when getting started with AI tools?

When should I use a plain chat versus setting up a Claude Project?

What does it mean to run AI 'locally' or 'offline,' and is anyone using this to annotate financials and map them to Drake tax software?

Can you pull bank statements or commercial loan data automatically through Plaid or QBO?

What practical steps can be taken to avoid exposing sensitive financial/PII data when using LLMs for tasks like loan modeling?

What does the recent guidance on AI use in practice say about which AI models are considered safe, and does it address Section 7216?

How could a redaction tool let firms use client data with AI while staying compliant?

If a client voluntarily uploads their own tax documents into a client-facing AI tool (like Stanford Tax), does that count as the firm's 7216 disclosure, or does the firm still need separate consent?

Does the new OPR guidance say which AI models/tools are safe for practitioners to use?

What's blocking members from moving forward with AI adoption in their firms?

Should firms talk to their insurance providers about AI use and 7216, and does this affect cyber coverage?

What framework can be used to decide whether a given AI use case requires 7216 client consent?

Do we still need a separate Section 7216 consent/engagement letter when using AI tools like Claude for tax work?

Will increased AI efficiency push firms away from hourly billing toward fixed-fee pricing?

Is a 7216 consent required for AI tools like Claude or ChatGPT the same way it's not required for practice management software?

Is there a meaningful difference between using a generic AI tool (Claude, ChatGPT) versus a tax-specific AI tool (like Blue J) in terms of client data risk?

Is it worth the hassle of getting clients to sign a separate 7216 AI consent, or is the pushback just about avoiding client friction?

Can Blue J be used to upload full source documents and tax returns for an AI-driven review, not just tax research?

Does using AI to help make tax determinations for a client (e.g., whether something is deductible or taxable) trigger IRC 7216 consent requirements, versus just using AI as a supporting tool?

Can an AI tool review a completed tax return PDF against source documents to catch missed items or errors, like an AI reviewer?

At what point does a tool like Ramp's Stack replace QuickBooks or Xero as the actual ledger, rather than just automating on top of it?

How is Stack (Ramp's AI accounting platform) priced, and is it a per-token or per-client-seat cost?

Can the Stack chat agent take direct actions in the platform, like changing the status of a to-do list item or writing to the database, or does it only produce outputs like files and drafts?

Could this client-communication dashboard be built without Airtable, e.g. using Google Drive or OneDrive for client documents?

How can I get a live bank data feed for a client without using QuickBooks Online, since waiting for monthly statements isn't practical?

Should firms wait for their practice management software to release built-in AI features, or build their own AI solutions in the meantime?

What is 'Grove' and is anyone trying to replicate its interactive voice questionnaire feature?

How do you decide which AI model to use for a given task (e.g., Claude Opus vs. other models)?

How do I know when I need to use a higher model like Opus instead of Sonnet in Claude?

Can I upgrade to a ChatGPT Team plan with fewer than the stated 5-seat minimum?

Has anyone set up AI voice agents to handle client communication end-to-end, from phone calls through scheduling and record-keeping?

What's the difference between a 'skill' in Claude for Chrome versus a skill in Claude Desktop?

How are firms using Gamma to create client-facing tax return presentations, and could tools like Perplexity or AI-generated video improve on this?

How difficult is it to pull text messages (e.g. from WhatsApp) into Airtable for client communication tracking?

Should I wait for IRS guidance on whether AI tools count as an 'auxiliary service' under 7216 before choosing tax software?

Is there a 7216 difference between building your own workflow in Claude versus using a purpose-built vendor tool like Blue J or Black Ore?

If AI is used to review client source documents and build workpapers, does that trigger IRC 7216 disclosure/consent requirements?

Can AI automatically organize incoming client tax documents (PDFs from email and TaxCaddy) into workpapers by client, year, and category?

Is it better to build custom AI workflows in Claude or rely on AI features being built into the software we already use (like Outlook)?

Is there a way to scrub PII from client documents before feeding them to AI tools, without needing coding skills?

Without clear IRS guidance, what practical steps can a firm take to reduce risk when using AI tools on client tax data (e.g., regarding IRC 7216 consent)?

Should I use Claude or a dedicated tax-specific tool to prep returns for review each morning?

Is there a risk of a surprise bill when using Claude Enterprise or Max due to usage-based pricing, especially with heavy multi-user or repetitive tasks?

Is it necessary to require staff to build a separate workpaper (e.g., Excel spreadsheet) when reviewing tax returns, especially for simple 1040s?

Why might a firm choose Blue J over a general AI tool like Claude for tax return review, and what would that workflow look like?

Do I need special client disclosures or consent under IRC 7216 to use AI tools on client tax data?

Could AI tools like Blue J and Juno eventually replace the data-entry and review roles in a tax practice?

Could AI generate the review workpaper automatically instead of having staff manually re-enter data into a spreadsheet?

How can firms help junior staff develop professional judgment if AI is doing the research and thinking for them?

How do I avoid hitting usage limits in Claude when working with large multi-page documents or images?

Why does Claude Code seem to have lighter/less restrictive usage limits than using Claude's chat interface?

Is it safe to strip PII from a tax return PDF with Python and send the scrubbed data to Claude via API to analyze or create a checklist, and can this be done for every tax return once the AI confirms sensitive data isn't retained?

Is it actually risky or against the rules to put client tax returns into AI tools, as some critics on social media claim?

How can I automate identifying and filing penalty abatement claims for clients affected by IRS penalty/interest issues (e.g., the 'Kwang' situation), including clients who received notices but weren't in my original calculated batch?

What's going on with Claude's new model release ('Fable') hitting usage limits so quickly?

Should bookkeepers focus on building custom AI workflows in Claude, or just rely on AI features already built into their bookkeeping software (e.g., Double)?

Can data retention/memory be turned off on Claude's team/enterprise plans?

What's an effective method for building an AI skill (e.g., for preparing engagement letters) from scratch?

Does anyone have a contact at Anthropic to help set up an enterprise license?

How can I build a better client-facing tool for delivering quarterly estimated tax payments (similar to SafeSend)?

After downloading a Claude skill file to my desktop, how do I actually use it in Claude?

Why is it so hard to get an AI-built skill or workflow fully working, and what should I do differently?

How easy is it to deploy changes to a custom-built client app -- does it require running command-line/terminal commands each time?

Where does client-provided data (like tax documents) actually reside within this multi-tool setup (Air Table, Assembly, vibe-coding app)?

When is TaxDome expected to release its MCP integration?

Has anyone tried the MCP that QuickBooks recently released?

Has anyone demoed or used the tool called Filed?

Is it safe to drop client tax return data (like a Schedule C) directly into Airtable for this workflow?

Can Claude be used to automatically build out or populate workflow templates/sections inside Double via MCP, rather than configuring them manually?

Why does Claude sometimes suggest steps or features in a software platform (like Canopy) that don't actually exist or aren't possible?

What is the biggest bottleneck accounting firms face right now in scaling with AI, and what would 'leaning in' to AI actually require?

Is offshoring bookkeeping work to overseas virtual assistants a bigger security/control risk than using AI for the same tasks?

Is there an AI tool (like Juno) that can reliably prepare a full tax return?

What's happening on the US side regarding IRS/regulatory guidance on AI use in tax practice, and how should firms handle data security in the meantime?