session-migration

Session Migration Skill

Converts markdown session logs to JSON format for deterministic validation.

---

Quick Start

# Migrate single file
python3 .claude/skills/session-migration/scripts/convert_session_to_json.py ".agents/sessions/2026-01-09-session-385.md"

# Migrate all sessions in directory
python3 .claude/skills/session-migration/scripts/convert_session_to_json.py ".agents/sessions/"

# Dry run to preview changes
python3 .claude/skills/session-migration/scripts/convert_session_to_json.py ".agents/sessions/" --dry-run

# Force overwrite existing JSON
python3 .claude/skills/session-migration/scripts/convert_session_to_json.py ".agents/sessions/" --force

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Triggers

Use this skill when:

• migrate session logs - Convert markdown to JSON
• convert sessions to JSON - Format migration
• PR has old markdown sessions - In-flight PR migration
• session validation failing - Regex issues with markdown format
• batch migrate sessions - Historical log conversion

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When to Use

Use this skill when:

• PR contains markdown session logs that need conversion to JSON
• Batch migrating historical sessions from markdown to JSON
• Session validation failing due to regex issues with markdown format

Use session-init instead when:

• Creating a new session log (already creates in JSON format)

Use session-log-fixer instead when:

• Fixing validation errors in an existing JSON session log

Context

Why JSON?

Markdown session logs required fragile regex patterns to validate:

• **Branch**: vs Branch: vs Starting Branch:
• Table parsing with varied column orders
• Checkbox detection across different formats

JSON provides:

• Deterministic key-based validation
• Schema enforcement
• No regex, no fuzzy matching
• Clear structure for tooling

Schema Location

JSON sessions follow the schema at:

.agents/schemas/session-log.schema.json

Validator

JSON sessions are validated by:

scripts/validate_session_json.py

---

Process

┌─────────────────────────────────────────────────────────┐
│ 1. INPUT                                                │
│    Markdown session log (.md)                           │
│    OR directory of .md files                            │
└─────────────────────────────────────────────────────────┘
                    │
                    ▼
┌─────────────────────────────────────────────────────────┐
│ 2. PARSE                                                │
│    • Extract session number from filename               │
│    • Extract date from filename                         │
│    • Find branch, commit, objective in content          │
│    • Parse checklist tables for completion status       │
└─────────────────────────────────────────────────────────┘
                    │
                    ▼
┌─────────────────────────────────────────────────────────┐
│ 3. TRANSFORM                                            │
│    • Build session object (number, date, branch, etc.)  │
│    • Build protocolCompliance object                    │
│    • Map checkbox [x] to complete: true                 │
│    • Extract evidence from table cells                  │
└─────────────────────────────────────────────────────────┘
                    │
                    ▼
┌─────────────────────────────────────────────────────────┐
│ 4. OUTPUT                                               │
│    Write .json file alongside .md                       │
│    (same name, different extension)                     │
└─────────────────────────────────────────────────────────┘

---

JSON Structure

{
  "session": {
    "number": 385,
    "date": "2026-01-09",
    "branch": "feat/session-init-skill",
    "startingCommit": "abc1234",
    "objective": "Session protocol validation improvements"
  },
  "protocolCompliance": {
    "sessionStart": {
      "serenaActivated": { "level": "MUST", "complete": true, "evidence": "Tool output" },
      "handoffRead": { "level": "MUST", "complete": true, "evidence": "Content in context" }
    },
    "sessionEnd": {
      "checklistComplete": { "level": "MUST", "complete": true, "evidence": "All [x] checked" },
      "validationPassed": { "level": "MUST", "complete": true, "evidence": "Exit code 0" }
    }
  },
  "workLog": [],
  "endingCommit": "",
  "nextSteps": []
}

---

Parameters

Parameter	Type	Required	Description
-Path	string	Yes	Path to .md file or directory
-Force	switch	No	Overwrite existing .json files
-DryRun	switch	No	Preview without writing files

---

Output

The script returns an array of migrated file paths (string[]) and prints a summary:

=== Migration Summary ===
Migrated: 356
Skipped (JSON exists): 0
Failed: 0

Exit Codes

Code	Meaning	Action
0	Success	All files migrated or skipped (expected behavior)
1	Failure	One or more files failed migration (check error output)

Return Value

The script prints migration summary and returns exit code 0 on success, 1 on failure.

---

PR Migration Workflow

For PRs with in-flight markdown sessions:

1. Check for markdown sessions in PR:

   git diff origin/main --name-only | grep -E '\.agents/sessions/.*\.md$'
   

2. Run migration:

   python3 .claude/skills/session-migration/scripts/convert_session_to_json.py ".agents/sessions/"
   

3. Validate migrated sessions:

   for f in .agents/sessions/*.json; do python3 scripts/validate_session_json.py "$f"; done
   

4. Commit both formats (for transition period):

   git add .agents/sessions/*.json
   git commit -m "chore(session): migrate session logs to JSON format"
   

---

Checklist Mapping

The migration script maps markdown checklist patterns to JSON keys.

Session Start Items

Regex Pattern	JSON Key	Level
activate_project	serenaActivated	MUST
initial_instructions	serenaInstructions	MUST
HANDOFF\.md	handoffRead	MUST
Create.*session.*log|session.*log.*exist|this.*file	sessionLogCreated	MUST
skill.*script	skillScriptsListed	MUST
usage-mandatory	usageMandatoryRead	MUST
CONSTRAINTS	constraintsRead	MUST
memor	memoriesLoaded	MUST
verify.*branch|branch.*verif|declare.*branch	branchVerified	MUST
not.*main|Confirm.*main	notOnMain	MUST
git.*status	gitStatusVerified	SHOULD
starting.*commit|Note.*commit	startingCommitNoted	SHOULD

Session End Items

Regex Pattern	JSON Key	Level
Complete.*session.*log|session.*log.*complete|all.*section	checklistComplete	MUST
HANDOFF.*read-only|Update.*HANDOFF	handoffPreserved	MUST
Serena.*memory|Update.*memory|memory.*updat	serenaMemoryUpdated	MUST
markdownlint|markdown.*lint|Run.*lint	markdownLintRun	MUST
Commit.*change|change.*commit	changesCommitted	MUST
Validate.*Session|validation.*pass|Route.*qa	validationPassed	MUST
PROJECT-PLAN|task.*checkbox	tasksUpdated	SHOULD
retrospective	retrospectiveInvoked	SHOULD

---

Anti-Patterns

Avoid	Why	Instead
Manually converting markdown to JSON	Error-prone, misses edge cases	Use convert_session_to_json.py script
Deleting markdown files after migration	May need originals for reference	Keep both during transition period
Skipping validation after migration	Migrated JSON may still be incomplete	Always validate with validate_session_json.py
Migrating without -DryRun first	Cannot preview changes	Use -DryRun to preview, then run for real

Verification

After migration:

• JSON files created alongside markdown originals
• All migrated JSON files pass validate_session_json.py
• Session numbers and dates match between markdown and JSON
• No migration errors in script output
• Both formats committed (for transition period)

Troubleshooting

JSON already exists

Use -Force to overwrite:

python3 .claude/skills/session-migration/scripts/convert_session_to_json.py ".agents/sessions/" --force

Some sessions fail validation after migration

Expected for genuinely incomplete sessions. The migration preserves the actual state of checkboxes. Review failed sessions manually.

Pattern not detected

If a checklist item isn't detected, the markdown format may be non-standard. The script uses flexible regex but edge cases exist. Update the _find_checklist_item function patterns if needed.

---

Scripts

convert_session_to_json.py

Converts markdown session logs to JSON format.

python3 .claude/skills/session-migration/scripts/convert_session_to_json.py <input-file> [--output <output-file>]

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Related

Skills

Skill	Purpose
session-init	Create new sessions in JSON format
session-log-fixer	Fix validation failures

Schema and Validation

Resource	Location	Purpose
JSON Schema	.agents/schemas/session-log.schema.json	Defines required structure
JSON Validator	scripts/validate_session_json.py	Validates migrated JSON files
Legacy Validator	scripts/validate_session_json.py	Validates markdown (deprecated)

Architecture

• ADR-014: Distributed handoff architecture (context for migration)