Long-Thread Compression
When this applies
Activate when any of the following conditions are true:
- The conversation has exceeded approximately 50 turns (a "turn" being one user message + one assistant response).
- The estimated context window utilization is at or above 80% (based on estimated token count or explicit signal from the runtime environment).
- A major matter milestone has been reached: a document has been finalized, a negotiation round has concluded, or a filing has been submitted.
- The user explicitly requests: "summarize this thread", "compress the context", "give me a summary of where we are", or similar.
- Before exporting or sharing the thread (e.g., sending a matter summary to a client or colleague).
This skill does not apply to short, fresh conversations or to single-turn queries with no ongoing matter context.
Behavior
Compress older conversation turns into a single, structured matter-summary block. Replace compressed turns with the block in place. Keep the most recent 5–10 turns full and uncompressed — they contain the live working context that must not be flattened.
What to preserve — no exceptions
Every piece of information in the following categories must survive compression, even if it requires multiple sentences:
- Matter context: parties (full names, roles), document type, purpose of the matter, deadline.
- Jurisdiction and governing law: confirmed or tentative.
- Key decisions made: any clause, position, or agreement that was reached — include the turn number where confirmed, the precise term agreed, and by whom.
- Open issues: explicitly list every unresolved item, every pending question, and every "I'll check this" noted during the thread.
- User preferences expressed: drafting style, tone, formatting preferences (e.g., "user prefers IRAC for analysis", "client wants bilingual AR-EN final draft", "use numbered clauses not lettered").
- Skill IDs invoked: which skills have already been run (prevents re-running intake already completed).
- Client instructions and constraints: deadlines, redline instructions, negotiating positions, budget constraints.
What to drop — no exceptions
- Verbose back-and-forth on questions that have already been resolved.
- Confirmations and simple acknowledgments ("Got it, I'll add that", "OK, proceeding").
- Pleasantries and social exchange.
- Earlier exploratory queries that were subsequently superseded by cleaner instructions.
- Intermediate draft versions that were replaced — keep only the most recent version state and the decisions made on each revision cycle.
Compression format
Replace older turns with a single, delimited system-style note in this format:
[CONTEXT FROM EARLIER TURNS — COMPRESSED]
Matter: [Document type] — [Party A] x [Party B]
Jurisdiction: [governing law + forum]
Purpose: [one-sentence statement of the matter objective]
Deadline: [if set]
Decisions made:
- [Decision 1] (turn [N])
- [Decision 2] (turn [N])
- [Decision 3] (turn [N])
Open issues:
- [Issue 1] — [status: awaiting client input / pending research / to be drafted]
- [Issue 2] — [status]
User preferences:
- [Preference 1]
- [Preference 2]
Skills invoked: [skill-id-1], [skill-id-2]
[END COMPRESSED CONTEXT]
Example
[CONTEXT FROM EARLIER TURNS — COMPRESSED]
Matter: MSA Negotiation — Acme Group (Provider) x Globex DMCC (Customer)
Jurisdiction: DIFC law; DIFC Courts
Purpose: Closing a 3-year managed technology services agreement within 30 days
Deadline: Execution by 14 June 2025
Decisions made:
- Aggregate liability cap: 100% of fees paid in the prior 12 months (turn 12)
- IP ownership: all custom deliverables assigned to Customer; background IP retained by Provider with license-back (turn 18)
- Dispute resolution: DIAC arbitration, Dubai seat, English language, 3-person tribunal (turn 22)
- Data protection: DIFC DPA addendum to be attached as Exhibit C (turn 28)
Open issues:
- Termination for convenience notice period: Provider wants 90 days; Customer wants 45 days — unresolved (turn 31)
- Material adverse change definition: Provider's counsel has not confirmed acceptance of Globex's proposed language (turn 35)
- Confidentiality survival period: Customer wants 5 years post-term; Provider accepted 3 years; compromise not yet reached (turn 38)
User preferences:
- IRAC structure for legal analyses
- Bilingual AR-EN for the final execution version
- Track-changes / redline style: IILR redline format preferred
Skills invoked: conversation-intake-msa, draft-msa
[END COMPRESSED CONTEXT]
When to notify the user
- Before compressing: notify the user once (briefly) that you are compressing older turns to preserve context quality. Example: "This thread is getting long — I'm compressing earlier turns into a structured summary to preserve context. Here's what I've captured:" (then show the compressed block).
- After compressing: the compressed block is visible to the user and can be edited or corrected.
- Do not compress silently without any notification — the user should know the compression occurred and should have an opportunity to correct any errors in the summary.
Quality standards
- No information loss: a practitioner reading only the compressed block should be able to fully reconstruct the state of the matter without reading any earlier turns.
- Precise language: use the same legal precision as the underlying conversation. Do not paraphrase "24-month aggregate liability cap" as "limited liability" — the precision matters.
- No invented decisions: only record decisions that were actually made in the thread. Do not fill in gaps with assumptions.
- Turn references: include turn numbers for key decisions where feasible — they allow the user to scroll back to verify if needed.
Edge cases
- User corrects the summary: accept corrections immediately and update the compressed block. If a correction reveals that a decision was misrecorded during the session, flag it as an open issue for re-confirmation.
- Multiple matters in one thread: if the thread covers more than one matter (e.g., NDA first, then a follow-on MSA), create separate compressed blocks per matter. Do not conflate them.
- Confidential matter: the compressed block should not be copied out of the session without appropriate privilege and confidentiality review. Flag if the user is about to share the thread.
- Short threads approaching the limit suddenly: a rapid influx of long documents (uploaded contracts, lengthy research) can fill the context faster than turn-count suggests. Trigger compression based on estimated token utilization, not just turn count.
Do not
- Compress without preserving open issues — partial information is worse than no information in a legal context.
- Drop user preferences — they took effort to elicit and re-eliciting them wastes the user's time.
- Over-compress to a single line — the compression block should be as long as it needs to be to capture the matter state completely.
- Compress the most recent 5–10 turns — these are the live working context.
Related skills
- [[conversation-session-memory-recap]]
- [[conversation-professional-b2b]]
- [[conversation-uncertainty-language]]
1---2name: conversation-long-thread-compression3description: Use when a legal AI conversation exceeds approximately 50 turns or approaches 80% of the context window, and Claude must compress older turns into a structured matter-summary without losing any material decisions, open issues, or user preferences. This is a core behavioral skill that applies to all legal matter types across all jurisdictions. Triggers automatically on context pressure, at major matter milestones, or on explicit user request.4license: MIT5---67# Long-Thread Compression89## When this applies1011Activate when any of the following conditions are true:12131. The conversation has exceeded approximately **50 turns** (a "turn" being one user message + one assistant response).142. The estimated context window utilization is **at or above 80%** (based on estimated token count or explicit signal from the runtime environment).153. A major **matter milestone** has been reached: a document has been finalized, a negotiation round has concluded, or a filing has been submitted.164. The user explicitly requests: "summarize this thread", "compress the context", "give me a summary of where we are", or similar.175. Before **exporting or sharing** the thread (e.g., sending a matter summary to a client or colleague).1819This skill does not apply to short, fresh conversations or to single-turn queries with no ongoing matter context.2021## Behavior2223Compress older conversation turns into a single, structured matter-summary block. Replace compressed turns with the block in place. Keep the most recent 5–10 turns full and uncompressed — they contain the live working context that must not be flattened.2425### What to preserve — no exceptions2627Every piece of information in the following categories must survive compression, even if it requires multiple sentences:2829- **Matter context**: parties (full names, roles), document type, purpose of the matter, deadline.30- **Jurisdiction and governing law**: confirmed or tentative.31- **Key decisions made**: any clause, position, or agreement that was reached — include the turn number where confirmed, the precise term agreed, and by whom.32- **Open issues**: explicitly list every unresolved item, every pending question, and every "I'll check this" noted during the thread.33- **User preferences expressed**: drafting style, tone, formatting preferences (e.g., "user prefers IRAC for analysis", "client wants bilingual AR-EN final draft", "use numbered clauses not lettered").34- **Skill IDs invoked**: which skills have already been run (prevents re-running intake already completed).35- **Client instructions and constraints**: deadlines, redline instructions, negotiating positions, budget constraints.3637### What to drop — no exceptions3839- Verbose back-and-forth on questions that have already been resolved.40- Confirmations and simple acknowledgments ("Got it, I'll add that", "OK, proceeding").41- Pleasantries and social exchange.42- Earlier exploratory queries that were subsequently superseded by cleaner instructions.43- Intermediate draft versions that were replaced — keep only the most recent version state and the decisions made on each revision cycle.4445## Compression format4647Replace older turns with a single, delimited system-style note in this format:4849```50[CONTEXT FROM EARLIER TURNS — COMPRESSED]5152Matter: [Document type] — [Party A] x [Party B]53Jurisdiction: [governing law + forum]54Purpose: [one-sentence statement of the matter objective]55Deadline: [if set]5657Decisions made:58- [Decision 1] (turn [N])59- [Decision 2] (turn [N])60- [Decision 3] (turn [N])6162Open issues:63- [Issue 1] — [status: awaiting client input / pending research / to be drafted]64- [Issue 2] — [status]6566User preferences:67- [Preference 1]68- [Preference 2]6970Skills invoked: [skill-id-1], [skill-id-2]7172[END COMPRESSED CONTEXT]73```7475### Example7677```78[CONTEXT FROM EARLIER TURNS — COMPRESSED]7980Matter: MSA Negotiation — Acme Group (Provider) x Globex DMCC (Customer)81Jurisdiction: DIFC law; DIFC Courts82Purpose: Closing a 3-year managed technology services agreement within 30 days83Deadline: Execution by 14 June 20258485Decisions made:86- Aggregate liability cap: 100% of fees paid in the prior 12 months (turn 12)87- IP ownership: all custom deliverables assigned to Customer; background IP retained by Provider with license-back (turn 18)88- Dispute resolution: DIAC arbitration, Dubai seat, English language, 3-person tribunal (turn 22)89- Data protection: DIFC DPA addendum to be attached as Exhibit C (turn 28)9091Open issues:92- Termination for convenience notice period: Provider wants 90 days; Customer wants 45 days — unresolved (turn 31)93- Material adverse change definition: Provider's counsel has not confirmed acceptance of Globex's proposed language (turn 35)94- Confidentiality survival period: Customer wants 5 years post-term; Provider accepted 3 years; compromise not yet reached (turn 38)9596User preferences:97- IRAC structure for legal analyses98- Bilingual AR-EN for the final execution version99- Track-changes / redline style: IILR redline format preferred100101Skills invoked: conversation-intake-msa, draft-msa102103[END COMPRESSED CONTEXT]104```105106## When to notify the user107108- **Before compressing**: notify the user once (briefly) that you are compressing older turns to preserve context quality. Example: *"This thread is getting long — I'm compressing earlier turns into a structured summary to preserve context. Here's what I've captured:"* (then show the compressed block).109- **After compressing**: the compressed block is visible to the user and can be edited or corrected.110- Do not compress silently without any notification — the user should know the compression occurred and should have an opportunity to correct any errors in the summary.111112## Quality standards113114- **No information loss**: a practitioner reading only the compressed block should be able to fully reconstruct the state of the matter without reading any earlier turns.115- **Precise language**: use the same legal precision as the underlying conversation. Do not paraphrase "24-month aggregate liability cap" as "limited liability" — the precision matters.116- **No invented decisions**: only record decisions that were actually made in the thread. Do not fill in gaps with assumptions.117- **Turn references**: include turn numbers for key decisions where feasible — they allow the user to scroll back to verify if needed.118119## Edge cases120121- **User corrects the summary**: accept corrections immediately and update the compressed block. If a correction reveals that a decision was misrecorded during the session, flag it as an open issue for re-confirmation.122- **Multiple matters in one thread**: if the thread covers more than one matter (e.g., NDA first, then a follow-on MSA), create separate compressed blocks per matter. Do not conflate them.123- **Confidential matter**: the compressed block should not be copied out of the session without appropriate privilege and confidentiality review. Flag if the user is about to share the thread.124- **Short threads approaching the limit suddenly**: a rapid influx of long documents (uploaded contracts, lengthy research) can fill the context faster than turn-count suggests. Trigger compression based on estimated token utilization, not just turn count.125126## Do not127128- Compress without preserving open issues — partial information is worse than no information in a legal context.129- Drop user preferences — they took effort to elicit and re-eliciting them wastes the user's time.130- Over-compress to a single line — the compression block should be as long as it needs to be to capture the matter state completely.131- Compress the most recent 5–10 turns — these are the live working context.132133## Related skills134135- [[conversation-session-memory-recap]]136- [[conversation-professional-b2b]]137- [[conversation-uncertainty-language]]
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