Save hours every week with the Bookkeeper AI Operating System
A command center plus five connected jobs for monthly close, reconciliations, and client comms — drafted into your Gmail, Calendar, and Drive for your approval, with living trackers. Ambient CPA-boundary guard keeps you out of tax-advice territory. Every prompt included — 69 skills in all.
Installs as a Claude Cowork plugin — and every prompt is included as an HTML page you can use in ChatGPT, Gemini, or any AI. How to install → Prices are in USD; Gumroad applies fair local pricing at checkout in eligible countries.
Bookkeepers use Claude to write up the work around the numbers: bank reconciliation reports with the adjusting entries laid out, monthly summaries that tell a business owner what their P&L means, tax-season document checklists, and reminder emails. You supply figures from the ledger and the bank statement; Claude drafts and checks the arithmetic, and you tie every number back to the source before anything is posted or sent.
Below: one bank reconciliation drafted from a month-end's figures, the free Bookkeeper plugin and its four commands, five more month-end and tax-season tasks, and straight answers on reconciliations, tax advice and client data.
Worked example: a bank reconciliation that balances
It's month-end for a landscaping client. In Claude, type /reconciliation-report, pick it from the menu, then paste the figures. The account is identified by its last four digits only:
Business checking (ending 0000), period ending March 31. Client: landscaping LLC.
Bank statement balance: $45,230.00. Book balance: $44,180.00.
Outstanding checks: #1042 $800.00, #1045 $250.00.
Deposit in transit: $1,500.00 (deposited 3/29).
On the statement but not in the books: customer ACH payment $1,525.00; bank service fee $25.00.Claude returns the report (shortened here):
BANK RECONCILIATION
[Client name] | Business Checking (ending 0000) | Period ending: March 31
Balance per bank statement $45,230.00
Add: deposits in transit $1,500.00
Less: outstanding checks ($1,050.00)
Adjusted bank balance $45,680.00
Balance per books $44,180.00
Add: customer ACH not yet recorded $1,525.00
Less: bank service fee ($25.00)
Adjusted book balance $45,680.00
Reconciliation status: Balanced
ADJUSTMENTS TO BOOKS
| Description | Debit | Credit |
| Record customer ACH | Cash 1,525.00 | [Accounts Receivable, confirm] 1,525.00 |
| Record bank service fee | Bank Service Fees 25.00 | Cash 25.00 |What's left for you: tie each figure to the actual statement and ledger, confirm which invoice the ACH payment settles, and post the two entries in your accounting software yourself. If the balances hadn't matched, the report would show the unreconciled difference instead of "Balanced", and finding it would still be your job.
The free Bookkeeper plugin: four commands
The Bookkeeper plugin is free and adds four month-end commands to Claude. Type the command, then select it from the menu; pasting it makes Claude read it as ordinary text.
| Command | What it drafts |
|---|---|
/reconciliation-report |
A monthly bank reconciliation with reconciling items and adjusting entries |
/financial-summary |
A narrative summary of the month that a business owner can follow |
/tax-prep |
Tax-preparation checklists, document lists and client letters by entity type |
/client-email |
Updates, document requests, deadline reminders and onboarding emails |
Two skills switch on by themselves when they're relevant: Financial Reporting and Tax Communication.
To install it in the Claude desktop app: Customize → Plugins → Add → Add marketplace → Add from a repository, paste alexclowe/awesome-claude-cowork-plugins, click Sync, then click Add next to Bookkeeper under Discover. Plugins need a paid Claude plan. In Claude Code: run /plugin marketplace add alexclowe/awesome-claude-cowork-plugins, then /plugin install bookkeeper@awesome-claude-cowork-plugins. Full steps are on the plugin page.
What's paid: You can do everything above with the free plugin. If you'd like monthly close organized for you, the Bookkeeper AI Operating System ($19, paid once) adds a command center with five connected jobs covering monthly close, reconciliations and client messages. Drafts land in your Gmail, Calendar and Drive for your approval, living trackers follow each client, and a built-in guard keeps your wording out of tax-advice territory. It includes 69 skills.
Set up a Claude Project for your bookkeeping practice
Step 1: Create a Bookkeeping Project. In Claude, go to Projects and create one called "Bookkeeping Practice." This gives you a persistent workspace where your context carries across every conversation.
Step 2: Set your custom instructions. In the Project settings, add:
You are my bookkeeping and accounting practice assistant. Here is my context:
<practice-profile>
- Role: [Bookkeeper / CPA / Enrolled Agent] at [Firm name / solo practice]
- State: [Your State] (for tax and compliance references)
- Clients: [Number of clients, typical entity types — sole props, LLCs, S-Corps, etc.]
- Software: [QuickBooks Online, Xero, FreshBooks, Wave, etc.]
- Services: [Monthly bookkeeping, tax prep, payroll, advisory, etc.]
- Reporting style: [Narrative summaries, dashboard-style, detailed with journal entries]
</practice-profile>
<rules>
- Financial summaries should explain what the numbers mean, not just restate them
- Client communications should be professional, clear, and free of jargon
- Tax documentation should reference applicable forms and schedules
- Reconciliation reports should include outstanding items, adjustments, and a client-facing note
- Never include real client financial data in prompts — use generalized or anonymized figures
- Remind me to verify all figures against the actual accounting records
</rules>Step 3: Upload reference documents. Add your preferred financial summary template, reconciliation report format, client letter templates, and any firm-specific formatting guidelines.
Step 4: Always work inside this Project. Your context loads automatically, saving you from re-explaining your practice every session.
Five more month-end and tax-season tasks
1. Client Financial Summaries
The monthly financial summary is the most valuable deliverable you provide to clients, and it is the one most bookkeepers skip or shortchange because of time. Claude turns raw numbers into narratives.
<task>Draft a monthly financial summary for a bookkeeping client.</task>
<context>
- Client: Small marketing agency, LLC, 12 employees
- Period: January 2026
- Revenue: $142,000 (up 8% from December, up 22% YoY)
- Expenses: $118,000 — Payroll $78K, Rent $8K, Software $12K, Marketing $7K, Misc $13K
- Net income: $24,000 (16.9% margin, up from 12.4% last month)
- Notable: New enterprise client contract started ($15K/month recurring), one-time office renovation expense of $5,000, accounts receivable aging has two invoices over 60 days totaling $18,000
- Audience: Business owner (not an accountant)
</context>
<instructions>
- Open with the big picture — is the business doing well, improving, or showing warning signs?
- Explain revenue and expense trends in plain language
- Highlight the notable items and what they mean for the business
- Flag the AR aging issue with a recommendation
- Close with 2-3 actionable recommendations
- Keep it under 500 words
</instructions>
<format>
Professional narrative with section headers. Not a table of numbers — the client already has that in their accounting software.
</format>2. Monthly Reconciliation Reports
Bank reconciliation is the backbone of bookkeeping, and the report you produce needs to be clear enough for clients to understand and detailed enough for audit purposes.
<task>Draft a monthly bank reconciliation report with a client-facing cover note.</task>
<context>
- Client: Consulting firm, S-Corp
- Period: January 2026
- Bank statement ending balance: $67,432.18
- General ledger (book) balance: $65,847.93
- Outstanding checks: Check #2041 $850 (contractor), Check #2043 $1,200 (office supplies), Check #2047 $2,500 (quarterly insurance premium)
- Deposits in transit: Client payment $3,100 deposited 1/31 (clears 2/1)
- Adjustments needed: Bank service charge $35 not recorded, interest income $12.75 not recorded, NSF check from customer $1,100 needs to be reversed
</context>
<instructions>
- Calculate the reconciled balance showing both the bank-to-book and book-to-bank reconciliation
- Organize outstanding items by category with dates and amounts
- Write adjustment journal entries with debit/credit accounts
- Include a 3-4 sentence client cover note explaining the status and any items needing their attention
</instructions>3. Tax Preparation Documentation
Tax season multiplies documentation needs across every client. Claude generates entity-specific checklists, organizes received documents, and drafts the client letter that keeps the process moving.
<task>Generate tax preparation documentation for a client.</task>
<context>
- Client: Small business owner
- Entity: S-Corporation
- Tax year: 2025
- Key items received: W-2 for officer compensation ($85,000), QuickBooks P&L and balance sheet, bank statements, equipment purchase records ($22,000 new computer systems)
- Missing: Final payroll reports from payroll provider, 1099s issued to contractors, vehicle mileage log, health insurance premium documentation, retirement plan contribution records
- Notable: Client took a large distribution in December, new equipment may qualify for Section 179
</context>
<instructions>
- Create an S-Corp-specific preparation checklist organized by category
- Summarize documents received with key figures
- Write a client letter explaining current status, items still needed, and the Section 179 opportunity
- Prioritize the missing items list by urgency with instructions for obtaining each one
</instructions>4. Client Communication Emails
Bookkeepers send dozens of similar emails every month — updates, requests, reminders, and reviews. Claude drafts them in your voice with the specific details each client needs.
<task>Write a document request email for a bookkeeping client during tax season.</task>
<context>
- Client: Restaurant owner, multi-member LLC taxed as a partnership
- Situation: We have most of their 2025 records but are missing several critical items needed to complete their return
- Missing items: Point-of-sale system annual summary, tip reporting records, liquor license renewal documentation, property tax statements, final December bank statement, 1099s for contractors (DJ, cleaning service)
- Deadline: Need everything by March 1 to meet the March 15 filing deadline
</context>
<instructions>
- Open with a positive note about the progress so far
- List the missing items clearly with brief explanations of what each is and where to find it
- Emphasize the March 1 deadline and explain why it matters
- Offer to help if they are unsure where to find anything
- Professional but warm tone — this is a long-term client relationship
</instructions>
<avoid>
- Threatening or urgent language
- Accounting jargon the client will not understand
- Making them feel like they are behind or disorganized
</avoid>5. Year-End Financial Reviews
The year-end review is your best opportunity to demonstrate advisory value, and Claude helps you prepare a comprehensive review that goes beyond just the numbers.
<task>Draft a year-end financial review letter for a bookkeeping client.</task>
<context>
- Client: E-commerce business, LLC taxed as S-Corp
- Revenue: $680,000 (up 28% from prior year)
- Net profit: $112,000 (16.5% margin, up from 14.2%)
- Key trends: Strong Q4 driven by holiday sales, inventory costs up 15%, shipping expenses doubled due to expanded product line
- Tax items: Estimated tax payments made quarterly ($7,500 each), Section 199A QBI deduction eligible, may benefit from retirement plan establishment
- Concerns: Rapid growth straining cash flow, should consider a line of credit, AR aging increasing
</context>
<instructions>
- Summarize the year's financial performance with highlights
- Identify 3-4 key trends or observations with what they mean
- Include tax planning recommendations (retirement plan, QBI, estimated payment adjustment)
- Flag the cash flow concern with a recommendation
- Suggest a meeting to discuss the review and plan for next year
- Keep it professional but congratulatory — the business is growing well
</instructions>Prompting tips for financial write-ups
1. Always specify the entity type. Tax implications, reporting requirements, and document checklists vary significantly between individuals, LLCs, S-Corps, and C-Corps. Always include the entity type in your prompt.
2. Specify the audience for every document. A reconciliation report for your files is different from one going to a business owner who does not know debits from credits. Tell Claude who will read it and adjust the language accordingly.
3. Include comparison data. Financial summaries are most useful when they show trends. Include prior period or prior year numbers so Claude can explain what changed and why it matters.
4. Use actual account names from the chart of accounts. When requesting journal entries or adjustment notes, use the specific account names your client's software uses. Claude will incorporate them and the output will be ready to enter directly.
5. Ask Claude to flag issues. Add "Flag any items that seem unusual or warrant further investigation" to your prompts. Claude will catch patterns you might miss when processing multiple clients.
6. Batch your monthly work. Run all five prompts for each client in a single session. With your Project context loaded, the summary, reconciliation report and client email come out consistent with each other.
Can Claude do bank reconciliations?
It can draft the reconciliation report, the adjusting entries and a short client note from the balances and items you give it, and it will show whether the adjusted balances match. It doesn't post anything: the free plugin works from what you paste or upload and doesn't log in to your accounting software, so you post the entries and tie every figure to the statement yourself.
Can Claude give tax advice to my bookkeeping clients?
Claude can draft tax-prep checklists, missing-document lists and deadline reminders, but tax advice is a separate service: if you aren't a CPA, enrolled agent or tax attorney, route tax questions to the client's preparer instead of answering them in your emails. Tax rules and thresholds change, so check any tax statement in a draft against current IRS guidance before it goes out.
Can Claude explain financial statements to a business owner?
Yes, that's what the financial-summary command is for. Give it the month's revenue, expenses, net income and anything unusual, and it writes a short narrative of what changed and what needs attention, in language for an owner rather than an accountant. You check the figures and the interpretation before sending.
Is it safe to put client financial data into Claude?
Give Claude only what the document needs. Use "Client A" or a business type instead of a name, the last four digits of an account at most, and leave out EINs, Social Security numbers and full account numbers. Your engagement letter and any confidentiality terms with the client still apply.
You can review how your Claude plan handles your chats and files in Anthropic's Privacy Center.
Is Claude or ChatGPT better for bookkeepers?
Either can write a client email or a summary from your numbers. On the Claude side, the Bookkeeper plugin adds fixed commands, so reconciliation reports and monthly summaries come back in the same layout for every client.
We compare the two side by side in ChatGPT vs Claude for bookkeepers.
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Get my free setupBookkeeper AI Operating System
A command center plus five connected jobs for monthly close, reconciliations, and client comms — drafted into your Gmail, Calendar, and Drive for your approval, with living trackers. Ambient CPA-boundary guard keeps you out of tax-advice territory. Every prompt included — 69 skills in all.
Get the Operating System for $19Installs as a Claude Cowork plugin — and every prompt is included as an HTML page you can use in ChatGPT, Gemini, or any AI. How to install → Prices are in USD; Gumroad applies fair local pricing at checkout in eligible countries.