Contract Review

Contract Review

Quick start

Attach a contract file, forward the email containing it, or paste the text directly.

User: "Review this MSA and flag anything I should push back on."
→ Skill reads the document, identifies parties and contract type,
  analyzes 8 risk categories, returns a severity-tiered summary
  with a negotiation playbook, and exports a redlined DOCX.

Workflow

1. Get the contract — Pull from one of three sources, in order of preference:

• Gmail: Search for recent emails with contract attachments (see reference/gmail-fetch.md)
• DocuSign: Fetch the envelope by ID or search recent drafts awaiting signature (see reference/docusign-fetch.md)
• Local file or paste: Read the PDF (chunked via pages parameter for 10+ page files) or DOCX via Read tool. If the user pastes text directly, work with what's provided.

Read the full document before analyzing. Dangerous clauses are frequently in exhibits and schedules at the back.

2. Identify contract type and parties — Determine agreement type (NDA, MSA, SOW, SaaS subscription, consulting, subcontractor, vendor) and which party is the user's company vs. the counterparty. Note if it looks like a counterparty template — these are typically one-sided and the counterparty expects pushback.

3. Analyze across 8 risk categories — Work through the contract from the ops/finance perspective of a small business owner without in-house legal. Categories are ordered by typical risk severity; use judgment for context.

Category 1: Payment terms and cash flow

• Payment timing: Net-30 is standard; Net-60+ is flaggable; Net-90/120 is a hard negotiation point
• Payment triggers: acceptance periods that let the client slow-walk approvals indefinitely
• Late payment penalties: absence is a gap worth noting
• Invoicing requirements: rigid formats or PO numbers that can delay payment on technicalities
• Expense reimbursement: pre-approval requirements and caps
• Rate adjustments: annual increase mechanism for multi-year engagements

Category 2: Liability and indemnification

• Liability caps: uncapped liability is always a red flag
• Mutual vs. one-sided indemnification
• Indemnification scope: "any and all claims arising from the services" is not standard
• Insurance requirements: E&O, cyber, general liability — achievability at the required limits
• Consequential damages waiver: missing = flag prominently

Category 3: Termination and exit

• Termination for convenience: is it mutual? 30-day notice is typical
• Termination for cause: cure period; vague "material breach" without definition
• Wind-down: payment for in-progress work at termination
• Transition assistance: paid vs. unpaid, time-limited vs. open-ended
• Survival clauses: indefinite indemnification survival = flag

Category 4: Intellectual property

• IP assignment vs. license
• Pre-existing IP and background tools carve-out — absence means inadvertent assignment
• Work product definition breadth: drafts, notes, internal tools

Category 5: Scope and change management

• Scope definition clarity
• Change order process: absence = scope creep without compensation
• Acceptance criteria: subjective ("to client's satisfaction") vs. defined
• Timeline asymmetry: user penalized for delays but client is not for slow feedback

Category 6: Non-compete and exclusivity

• Non-compete scope, definition of "competitor," duration
• Exclusivity requirements on the user's company
• Non-solicitation: employee poaching is normal; industry-broad restrictions are not

Category 7: Confidentiality and data

• Confidentiality scope: "all information shared" with no exceptions is overly broad
• Duration: 2–3 years is typical; perpetual is aggressive
• Data handling security requirements vs. company size and data sensitivity
• Return/destruction requirements post-termination

Category 8: Operational concerns

• Governing law and dispute resolution; mandatory arbitration
• Auto-renewal: opt-out window and notice period (missing a 60-day window is a common SMB mistake)
• Assignment rights, especially if the client gets acquired
• Most favored nation: constrains pricing across the entire client book
• Audit rights: scope and frequency

4. Present flagged summary — Organize by severity:

🔴 Red flags (push back before signing) — For each: quote the exact clause, explain the problem in plain language, suggest specific alternative language.

🟡 Yellow flags (negotiate, not deal-breakers) — For each: quote the clause, explain the concern, describe what "better" looks like.

🟢 Key terms to note (awareness only) — Payment schedules, notice periods, renewal dates, insurance requirements, key contacts.

📋 Contract summary — Plain-language summary: who does what, for how much, over what timeframe, under what conditions.

💡 Negotiation playbook — For each red and yellow flag: what to ask for, how to frame the ask, and what a reasonable compromise looks like.

5. Export redline DOCX — After presenting the summary, offer to export a redlined DOCX with the suggested changes marked up. Use the docx skill to generate a Word document that:

• Preserves the original contract structure
• Marks suggested deletions in strikethrough and additions in underline
• Adds a cover page summarizing the changes

Ask: "Want me to export a redlined DOCX you can send back to the counterparty?"

Approval gates

• Never characterize the output as legal advice. Always recommend attorney review for red flags or binding decisions.
• Quote actual clause language, not paraphrases. The user needs the exact text for negotiation calls.
• Flag what's missing, not just what's there. A contract silent on liability caps or change orders is often more dangerous than one with unfavorable terms.
• Do not flag standard boilerplate. If a clause is fair and market-standard, skip it. The user wants signal, not a clause-by-clause restatement.
• Compare to market norms when flagging: "Net-90 is uncommon in professional services — Net-30 is standard."
• Adjust recommendations to the power dynamic. A Fortune 500 procurement MSA is a different negotiation than a small startup agreement.
• Never send the redlined DOCX to the counterparty without explicit user confirmation.

Reference

• reference/gotchas.md — edge cases in contract analysis
• reference/docusign-fetch.md — pulling envelopes from DocuSign
• reference/gmail-fetch.md — finding contract attachments in Gmail
• reference/examples/flagged-summary-saas.md — worked example: SaaS agreement review output

DocuSign: fetching contracts for review

Use the DocuSign MCP connector to pull envelopes awaiting signature.

Fetch pending envelopes

Use getEnvelopes to list envelopes in sent or delivered status (awaiting recipient action):

Tool: getEnvelopes
Params: { status: "sent" }  // or "delivered"

Returns a list of envelopes with: envelopeId, emailSubject, createdDateTime, status, recipients.

Download document from envelope

Use getEnvelope with the envelopeId to get the full envelope details, then download the document for reading.

What NOT to do

• Never call triggerWorkflow or any action that moves the envelope forward in the signing process.
• Never call updateEnvelope to modify the document.
• Never call createEnvelope — this skill is review-only.

Fallback

If DocuSign is not connected or the envelope is not found:

"DocuSign isn't connected — paste the contract text or attach the file directly."

Example: SaaS vendor agreement flagged summary

A worked example of contract-review output. Contract: a SaaS subscription agreement from a mid-size software vendor.

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Input

"Review this SaaS agreement before I sign. We're a 12-person consulting firm."

Contract: 18-page SaaS Subscription Agreement, vendor template, governing law: California.

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Output

📋 Contract summary

12-month SaaS subscription, auto-renewing annually. Vendor provides project management software. You pay $2,400/year billed monthly. Vendor hosts data; you own your data but grant vendor a broad license to use it for "product improvement." You can terminate with 30 days notice but owe fees through end of the contract term.

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🔴 Red flags (push back before signing)

1. Uncapped liability

"IN NO EVENT SHALL VENDOR'S LIABILITY EXCEED THE AMOUNTS ACTUALLY PAID BY CUSTOMER IN THE THREE (3) MONTHS PRECEDING THE CLAIM."

Problem: Three months of fees = $600. If a vendor data breach exposes your client data, your recovery is capped at $600 — regardless of actual damages. For a consulting firm handling client information, this is inadequate.

Ask for: Cap at 12 months of fees paid ($2,400), or at a fixed floor of $50,000 for data security incidents. Suggested language:

"Vendor's total liability shall not exceed the greater of (a) fees paid in the twelve (12) months preceding the claim or (b) $50,000 for claims arising from data security incidents."

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2. Auto-renewal with 60-day opt-out window

"This Agreement shall automatically renew for successive one-year terms unless either party provides written notice of non-renewal no less than sixty (60) days prior to the end of the then-current term."

Problem: You have a 60-day window to opt out. Miss it and you're committed to another year. With a $2,400/year contract, that's easy to overlook.

Ask for: Reduce to 30-day opt-out, or add a reminder obligation from vendor. Alternatively, calendar the opt-out deadline now (2027-04-01 if signing May 1, 2026).

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🟡 Yellow flags (negotiate if possible)

3. Broad data license

"Customer grants Vendor a non-exclusive, worldwide license to use, process, and analyze Customer Data to improve Vendor's products and services."

Concern: Vendor can use your data — including client project data — to train their product. This may conflict with your client confidentiality obligations.

Ask for: Restrict to aggregated, anonymized usage only. Suggested language:

"...limited to aggregated, de-identified data and expressly excluding any Customer Data that identifies Customer's clients or projects."

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4. No termination for cause cure period

"Vendor may terminate this Agreement immediately upon Customer's material breach."

Concern: Vendor can cut off access immediately for any "material breach" with no chance to fix it. No definition of "material." You could lose access to your data mid-project.

Ask for: 15-day cure period. Suggested: "...upon written notice and Customer's failure to cure such breach within fifteen (15) days."

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🟢 Key terms to note

• Payment: Monthly, auto-charged. Keep credit card current or service suspends immediately.
• Data portability: You can export your data at any time and for 30 days post-termination. Plan export before cancellation.
• Governing law: California. Any disputes go to Santa Clara County courts.
• Uptime SLA: 99.5% monthly. Credits issued as account credits, not cash.

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💡 Negotiation playbook

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This is not legal advice. For binding decisions, consult an attorney.

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Redline DOCX

A redlined DOCX with these suggested changes marked in tracked-changes format was exported to: contract-review-redline-2026-05-01.docx

Gmail: finding contract attachments

Use the Gmail MCP connector to find contract attachments in recent email.

Search for contract emails

Use search_threads with a query targeting recent emails with attachments:

Query: "has:attachment (contract OR agreement OR NDA OR MSA OR SOW) newer_than:14d"

What to do with results

1. Present a short list (subject, sender, date) if multiple candidates match. 2. Ask the user to confirm which one before downloading. 3. Use get_thread to fetch the full thread, then locate and read the attachment.

Fallback

If Gmail is not connected or no matching attachment is found:

"I didn't find a recent contract attachment in Gmail — can you forward it or attach the file directly?"

What NOT to do

• Do not read emails unrelated to the contract (no general inbox trawl).
• Do not send any reply or draft email during the review workflow.

Gotchas

Edge cases in contract analysis. Good / Bad pairs.

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Gotcha: Flagging standard boilerplate as a red flag

Why it matters: Over-flagging trains the user to ignore the summary. If everything is a red flag, nothing is.

✗ Bad

Contract has a standard mutual NDA confidentiality clause, 2-year duration.
Claude: "🔴 Red flag: Confidentiality clause imposes obligations on both parties."

Standard mutual NDA is market-norm. Flagging it as a red flag destroys signal-to-noise ratio.

✓ Good

Contract has a standard mutual NDA confidentiality clause, 2-year duration.
Claude: [skips; does not flag]

Reserve red flags for genuinely non-standard terms. If a clause is boilerplate and fair, omit it.

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Gotcha: Missing clauses aren't missing from the analysis

Why it matters: For SMBs, the absence of standard protections (liability cap, change order process, consequential damages waiver) is often more dangerous than an unfavorable clause — the default legal position fills the gap, usually in the counterparty's favor.

✗ Bad

Contract has no liability cap.
Claude: [no mention; only analyzes clauses that are present]

User signs thinking liability is limited. It isn't.

✓ Good

Contract has no liability cap.
Claude: "🔴 Missing: No liability cap. This contract contains no limitation-of-liability
clause. Under default law, your exposure is uncapped. Standard practice is to cap at
fees paid in the prior 12 months. Suggest adding: 'Each party's total liability shall
not exceed the fees paid or payable in the 12 months preceding the claim.'"

Treat absent-but-standard clauses as red flags. Explicitly label them "Missing."

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Gotcha: Large PDFs truncated mid-analysis

Why it matters: Contracts over 20–30 pages often have the most dangerous terms in exhibits, schedules, or "Order Forms" at the back. If the PDF is read only up to page 15, key terms are silently missed.

✗ Bad

Skill reads pages 1–10 of a 40-page MSA. Schedules A–D (starting page 28) contain
the IP assignment and liability cap. Skill produces a "clean" summary.

✓ Good

Read the PDF in chunks: pages 1–10, 11–20, 21–40. Analyze all chunks before
producing the summary. If a section heading mentions "Schedule," "Exhibit," or
"Appendix," flag it explicitly and ensure it was read.

Always read the full document. Use the pages parameter to chunk large PDFs.

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Gotcha: Counterparty template vs. negotiated draft

Why it matters: Recommendations should match the negotiating context. Pushing back hard on a startup's first-draft agreement is different from pushing back on a Fortune 500 procurement template — the latter is often non-negotiable on 80% of its terms.

✗ Bad

Fortune 500 vendor agreement with standard procurement terms.
Claude: "🔴 This Net-60 payment term should be renegotiated to Net-30.
         Their legal team will likely accept the change."

Unrealistic recommendation wastes the user's political capital.

✓ Good

Claude: "🟡 Net-60 payment terms. This is longer than typical (Net-30 is standard),
         but common in large enterprise procurement templates. Worth asking for
         Net-45 as a compromise — they may accept it, especially for recurring work.
         Note: if this is a Fortune 500 template, payment terms are often non-negotiable
         in the first engagement."

Match the recommendation to the power dynamic. Label it yellow, not red. Acknowledge the reality.