Contract Redline

Contract redline

Translates an objection email into a properly-marked tracked-changes redline of a counterparty contract (DOCX), produces margin comments per clause authored as Matteo Tittarelli, and ships the result through three surfaces: local Downloads, Google Drive, and a Gmail draft reply.

Doctrine inherited (Step 7 — 0626 rollout, locked 2026-06-04)

Internal-reference legal skill. Applies [[feedback_execution_doctrine_refinements_step6]] R1 (margin comments cite clause sources inline — auditability), R3 (comment voice operator-direct), R9 (verb-led comment structure). Gmail draft reply inherits R6 (close → signed contract primary). R2/R5/R7/R8 not applicable.

Use this when the counterparty sends a standard supplier-hostile contract template (broad IP assignment to "Group Company", one-way uncapped indemnification, unilateral termination, perpetual confidentiality, sole-discretion offset, perpetual assignment) and the negotiation needs proposed counter-language tracked inline rather than buried in a 1,000-word objection email.

When to use

• Counterparty (e.g., ClientCo, ClientCo, ClientCo, future ClientCo renewal) sends a contract draft with terms that need amendments.
• You already have an objection email or list of issues — this skill is for executing the redline, not for drafting the objections.
• Counterparty has explicitly asked for redlines ("could you put these in as tracked changes?"), or the negotiation is at the stage where redlines beat further email.

Don't use this skill for: the upstream proposal/scoping work (use /client-proposals), the discovery research (use /client-discovery), or post-signing onboarding (use /client-onboarding).

Process — five phases

Phase 1 — Map the issues to clauses

Read the user's objection email (or list of asks). For each issue, locate the exact paragraph in the contract's document.xml by extracting paragraphs and finding the run that contains the load-bearing phrase. Produce a 12-column table (or however many issues) mapping:

| # | Section | Original (deletion) | Proposed (insertion) | Comment rationale |

Most enterprise contracts have ~10–15 redlines. Some are surgical edits (one-word swap); some are wholesale clause rewrites; some are new clause insertions (e.g., a missing liability cap).

Phase 2 — Unpack the DOCX

Use the document-skills:docx skill's redlining workflow. Setup steps:

1. Create a Python venv at /tmp/contract-venv and install defusedxml + lxml. The skill's library requires both.
2. Run python ooxml/scripts/unpack.py <contract.docx> /tmp/contract-work/unpacked. Note the suggested RSID — copy it for the Document(...) constructor.
3. Pre-patch any whitespace violations in the unpacked document.xml (most older legal templates have trailing   non-breaking spaces missing xml:space="preserve"). Search for <w:t>...&#160;</w:t> and add the attribute, or the save step will fail validation.

Phase 3 — Apply redlines in batches

Group redlines into batches of 3–10 per script. Two-batch shape works well for a 12-item contract:

• Batch 1: the dealbreakers (6 items)
• Batch 2: the material risks (6 items)

For each redline, choose the right pattern from document-skills:docx:

For every redline, immediately add a doc.add_comment(start=..., end=..., text=...) with the rationale lifted verbatim from the user's objection email. Comments must be authored as Matteo Tittarelli (set in Document(..., author="Matteo Tittarelli", initials="MT")).

After each batch, doc.save() and verify via Python that the expected redline strings are present in document.xml.

Phase 4 — Pack + verify

1. Run python ooxml/scripts/pack.py /tmp/contract-work/unpacked <output.docx> to produce the final DOCX.
2. Write the output to ~/Downloads/{original-name} - REDLINED MMYY.docx.
3. Verify via Python:
   • Open the.docx as a zip
   • Confirm word/comments.xml, word/commentsExtended.xml, word/people.xml all present
   • Count <w:ins> / <w:del> / <w:commentReference> — should roughly match expected counts
   • Confirm all comment authors are "Matteo Tittarelli"
4. Extract "accept-mode" text for the key clauses to confirm the contract reads cleanly if the counterparty accepts all changes. Catches grammar issues from multi-run replacements.

Phase 5 — Ship through three surfaces

1. Local Downloads — the.docx is already there from Phase 4. Done.
2. Google Drive — node.claude/mcp/gdrive/upload-file.mjs <path> --client <slug>. Use upload-file.mjs (preserves DOCX with tracked changes) NOT create-doc-unified.mjs (which flattens tracked changes during MD→GDoc conversion). The Google Doc preview will render tracked changes natively in Suggesting mode.
3. Gmail draft — search for the counterparty's thread via mcp__gmail__search_threads, then mcp__gmail__create_draft with replyToMessageId set to the latest counterparty message. Include the GDoc URL in the body so they can review either format. Note: Gmail MCP create_draft does not auto-attach the local.docx — the user attaches it manually before sending.

Critical patterns

Author + RSID setup:

doc = Document('/tmp/contract-work/unpacked',
               author="Matteo Tittarelli",
               initials="MT",
               rsid="<copy from unpack output>")

Preserve run properties on every replacement:

rpr = tags[0].toxml() if (tags:= node.getElementsByTagName("w:rPr")) else ""
replacement = f'<w:del><w:r>{rpr}<w:delText xml:space="preserve">{old}</w:delText></w:r></w:del>...'

Special-character entities for Word XML:

• Curly apostrophe ’ → ’
• Curly quotes " " → “ ”
• Em dash — → —
• Non-breaking space →  

Always use xml:space="preserve" on <w:t> and <w:delText> with leading/trailing whitespace. The save validator will block on missing attribute.

Comment ID auto-generation: the Document library auto-generates w:id for new tracked changes and comments. Don't hard-code IDs.

Anti-patterns

• ❌ Using create-doc-unified.mjs to push the redlined doc to Drive — that script converts markdown to a Google Doc and would lose all tracked changes. Use upload-file.mjs to preserve the DOCX intact.
• ❌ Modifying text inside another author's <w:ins> or <w:del> tags — use nested-deletion pattern per document-skills:docx ooxml.md guidance.
• ❌ Drafting wholesale-replacement clauses when surgical edits would suffice — the user's email tells you which edits are dealbreakers (full rewrite OK) vs. nuance tweaks (preserve as much original text as possible for review).
• ❌ Skipping the verification pass — extracting "accept-mode" text catches grammar errors from multi-run replacements that would otherwise reach the counterparty.
• ❌ Attaching the.docx to the Gmail draft via the MCP — create_draft doesn't reliably attach local files. Note in the response that the user attaches manually before sending.
• ❌ Auto-sending the Gmail reply — this is review_gate 3. The user reviews the redlines + the email body before send.

Inputs required

• Original contract.docx — typically in ~/Downloads/ from the counterparty's email.
• User's objection email or asks list — typically inline in the conversation. Contains the per-clause rationale that becomes the comment text.
• Client slug in gdrive-config.json — controls the Drive folder routing. Add if missing (mirror an existing entry, set name, code, domain, folderId, brand).

Quality gate (review_gate 3)

Before claiming done:

• All N redlines from the issues table appear in the verification grep
• All comments authored as "Matteo Tittarelli"
• Accept-mode text reads cleanly for the top 3-5 most-edited clauses (no broken grammar)
• Drive upload succeeded (URL printed)
• Gmail draft created in the correct thread (verify by thread ID match)
• User-facing summary clearly states: open Gmail, attach.docx, send

Composition with other skills

• Upstream: /client-proposals (the deal that brought the contract to the table). The proposal's scope drives some of the redline content (e.g., the agreed Service Period length).
• Downstream: /client-onboarding (post-signature). Once the counterparty agrees, the signed contract becomes the canonical scope reference for the engagement.
• Sibling: /client-discovery (research before proposal). Pre-call research can flag known supplier-hostile patterns by counterparty so the redline pass starts faster.

Final ship gate

Run /premortem --output before ship. See .claude/skills/meta/orchestration/premortem/SKILL.md for the 5 execution domains and output template.