Critical gaps across all dimensions. Tool names lack action verbs (scan, verify, reindex, status are weak; handle_* prefix is generic). Most tools (20/25) have no visible input schemas in the provided code. Descriptions are present but generic (avg ~60 chars, well below 194-char baseline). No output schemas documented. Parameters lack type definitions and constraints. Error handling and recovery guidance absent. This server prioritizes HTTP transport but definition quality is far below production baseline.

• Rename all handle_* tools to verb_noun format: handle_ask → ask_question, handle_conversation_get → get_conversation, handle_conversations_get → list_conversations, handle_file_get → get_file, handle_files_get → list_files, handle_questions_get → list_questions, handle_courses_get → list_courses, handle_health → get_health, handle_session → get_session, handle_scan → scan_library, handle_upload → upload_files, handle_settings_get → get_settings, handle_settings_post → update_settings.
• Document input and output schemas for all 25 tools. For each, specify parameter types (string, integer, array, object), constraints (enum, min/max, pattern), and return field structure. Example: search should return {results: [{id, title, course, week, category}], total: int, hasMore: bool}.
• Expand descriptions to 50 - 200 characters with WHAT, WHEN, and WHEN-NOT guidance. Current descriptions (avg 60 chars) are too terse. Example: 'search' → 'Search course materials by keyword. Returns matching files, questions, and metadata. Use when user asks for specific topics or materials. Limit: 50 results per page.'
• Add parameter descriptions and constraints. For handle_files_get, document: category enum values (lecture, tutorial, workshop, lab, quiz, assignment, reading, exam, other), offset/limit ranges (offset ≥0, limit 1 - 100), and what each filter does.
• Implement error recovery guidance. For ai-sync, return: {ok: false, error: 'OPENAI_API_KEY not set', recovery: 'Set OPENAI_API_KEY in .env.local and restart server'}. For upload, return per-file success/failure with reasons.