Post-Mortem Analysis

Analyze chat histories to identify successes, failures, and improvement opportunities. Generate actionable recommendations for updating project configuration files (.cursorrules , skills, etc.) to prevent similar issues.

When to Use

• User asks for a "post-mortem" or "retrospective"

• User wants to analyze what went well or wrong in a session

• User wants to improve agent behavior based on past interactions

• User provides a chat export file or URL for analysis

Input Sources

The analysis can work with:

• Current session: Analyze the ongoing conversation (default if no file provided)

• File path: Chat export in JSON, markdown, or text format

• URL: Link to a shared chat export

Process

Phase 1: Analysis

Load and analyze chat:

• If no file specified: Analyze the current conversation history

• If file path provided: Read the chat export file

• If URL provided: Fetch the chat export using WebFetch

• Parse the conversation flow and identify key interactions

• Extract tool usage patterns and decision points

• Note any error messages, confusion, or repeated attempts

Categorize interactions:

• Successful patterns: What worked well and why

• Failed patterns: What went wrong and root causes

• Missed opportunities: Where the agent could have been more effective

• User friction points: Where the user had to provide additional guidance

Phase 2: Assessment

Skill usage review:

• Identify skills that were (or should have been) applied

• Locate and read skill files in .cursor/skills/ or ~/.cursor/skills/

• Assess whether skill instructions were clear and complete

Identify root causes:

• Missing context in project rules or skills

• Unclear or ambiguous instructions

• Missing skills or workflow guidance

• Tool selection issues

• Architecture understanding gaps

Pattern analysis:

• Recurring mistakes or confusion

• Successful strategies that should be reinforced

• Dependencies that weren't clear

• Workflow steps that were skipped or misunderstood

Phase 3: Recommendations

Project rules improvements (.cursorrules ):

• Missing architectural context to add

• Workflow patterns to emphasize

• Common pitfalls to warn about

• Examples that would clarify usage

Skill enhancements:

• New skills that should be created

• Existing skills that need updates

• Additional constraints needed

• Process clarifications

• Tool usage guidelines

Phase 4: Implementation

Present findings:

• Summary of what went well

• Key issues identified

• Specific recommendations with rationale

• Proposed changes to configuration files

User confirmation:

• STOP: Present findings and ask "Review these recommendations. Proceed with updating files? (y/n)"

• Allow user to modify or reject specific recommendations

Apply improvements:

• Update .cursorrules with approved changes

• Modify or create skills as needed

• Document changes made

Example Interactions

Analyze current session:

"Do a post-mortem on this chat"

• Review current conversation history

• Identify issues or missed opportunities

• Present recommendations

• Get confirmation before updating files

Analyze external chat:

"Post-mortem this chat export ~/Downloads/session.json - focus on the build process issues"

• Read the chat export file

• Focus analysis on build-related interactions

• Identify missing documentation or skills

• Present recommendations

• Get confirmation before updating files

Output Checklist

• Analysis report: What went well vs. what went wrong

• Root cause analysis: Why issues occurred

• Actionable recommendations: Specific file changes to prevent recurrence

• Updated configuration: Improved rules and skills (after user approval)