MSP Documentation Generator Plugin

Automate IT documentation for MSPs managing 20–100 client accounts. This Cowork plugin is an alternative to IT Glue's document generation layer, enabling small teams to generate client intake profiles, asset inventories, network topologies, SOPs, compliance checklists, knowledge base articles, IT health reports, and renewal trackers in minutes—not hours.

MSP Documentation Generator is offline-capable, and designed for MSP operators who need professional documentation without vendor lock-in. Use it to onboard clients faster, maintain compliance with frameworks like HIPAA and PCI-DSS, and deliver comprehensive IT documentation packages.

Prerequisites

• Python 3.8+ — Required for document generation
• python-docx >= 0.8.11 — Installed automatically or manually via pip
• Cowork — Plugin framework for skill orchestration
• ~50 MB disk space — For workspace folders and generated documents

Quick Start

1. Initialize Workspace (One-Time)

/msp:setup --name "Your MSP Name"

This creates folders, configuration files, and validates dependencies:

• Creates: inbound/, processing/, outbound/, archive/, .msp/
• Initializes: .msp/config.json, .msp/client-profiles.json
• Validates: Python 3.8+, python-docx installed

2. Create Client Intake Profile

/msp:new-client --client "Acme Manufacturing"

Answer prompts for:

• Client organization details (industry, size, contact)
• IT environment (OS mix, servers, workstations, network topology)
• Compliance requirements (HIPAA, PCI-DSS, etc.)
• Current IT challenges and MSP engagement scope

Output: Professional client-intake-profile.docx + registry entry

3. Generate Documentation

/msp:generate-docs --client "Acme Manufacturing" --type all

Generates all documents:

• Asset Inventory (with renewal tracking)
• Network Topology (with ASCII diagrams)
• Standard Operating Procedures (5 templates: Backup, Patch, Incident Response, Security Hardening, Onboarding)
• Compliance Checklists (HIPAA, PCI-DSS, SOC 2, GDPR, NIST CSF, ISO 27001)
• Knowledge Base Articles (password reset, VPN, file sharing, etc.)
• Onboarding Checklist (6-phase implementation plan)
• IT Health Report (metrics, accomplishments, risks, recommendations)
• Renewal Tracker (licenses, contracts, SLAs with costs)

Or generate specific types: --type assets, --type network, --type sop, --type compliance, --type kb, --type onboarding, --type report, --type renewal

4. Package for Delivery

/msp:export-package --client "Acme Manufacturing" --format zip

Creates deliverable package in ZIP, PDF, or folder format, ready for client delivery or archival.

Command Reference

Command	Purpose
/msp:setup	Initialize workspace (one-time)
/msp:new-client	Create new client intake profile
/msp:generate-docs	Generate specific document types
/msp:batch-client	Generate docs for multiple clients
/msp:export-package	Package docs for delivery or archive

Skills

Each command is powered by underlying skills:

Skill	Purpose	Output
msp-setup	Initialize workspace	Folders, config, dependency check
msp-client-intake	Gather client info	Client-intake-profile.docx
msp-asset-inventory	Document IT assets	asset-inventory.docx + .csv
msp-network-docs	Network topology	network-topology.docx with ASCII diagrams
msp-sop-generator	Generate procedures	5 × sop-{type}.docx
msp-compliance-checklists	Compliance frameworks	6 × compliance-{framework}-checklist.docx
msp-onboarding-checklist	Implementation plan	onboarding-checklist.docx
msp-kb-articles	Self-service docs	Multiple kb-{topic}.docx articles
msp-client-report	IT health metrics	it-health-report-{period}.docx
msp-renewal-tracker	License tracking	renewal-tracker.docx + .csv

Workspace Structure

After setup, your MSP workspace contains:

workspace/
├── inbound/               # CSV files, bulk imports
├── processing/            # Temporary files (auto-cleaned)
├── outbound/              # Final DOCX outputs (organized by client)
│   ├── acme_manufacturing/
│   │   ├── client-intake-profile.docx
│   │   ├── asset-inventory.docx
│   │   ├── network-topology.docx
│   │   ├── sop-backup.docx
│   │   ├── [... more documents ...]
│   │   └── renewal-tracker.docx
│   └── [... other clients ...]
├── archive/               # Backup packages
└── .msp/
    ├── config.json        # MSP name, legal disclaimer, version
    ├── client-profiles.json  # Client registry
    └── logs/
        ├── setup.log      # Setup history
        ├── errors.log     # Error log
        └── batch-*.log    # Batch run logs

Features

Document Generation

• Client Intake Profiles: Gather environment, compliance, challenges, engagement scope
• Asset Inventories: Track servers, workstations, software, licenses, cloud services with renewal dates
• Network Documentation: Topology diagrams (ASCII), IP addressing tables, DNS, VLANs, security architecture
• Standard Operating Procedures: 5 templates (Backup, Patch, Incident Response, Security Hardening, New User Onboarding)
• Compliance Checklists: Full depth for HIPAA & PCI-DSS; essential controls for SOC 2, GDPR, NIST CSF, ISO 27001
• Knowledge Base Articles: 10 common topics (password reset, VPN, file sharing, email setup, etc.)
• Onboarding Checklists: 6 phases with task breakdown, timelines, escalation procedures, rollback plan
• IT Health Reports: Executive summaries, KPIs, accomplishments, risks, ROI recommendations
• Renewal Trackers: License/contract management with quarterly breakdown and cost analysis

Batch Processing

• Process multiple clients in single command
• Generate specific document types or all documents
• Parallel processing option (4+ clients)
• Comprehensive logging and error handling

Export & Delivery

• ZIP format: Compressed, email-friendly, preserves original structure
• PDF format: Single consolidated document with bookmarks, great for exec review
• Folder format: Organized subdirectories, integrate with document management systems
• Security options: Encrypt ZIP or PDF for sensitive delivery

Data Management

• CSV support: Import asset lists, renewal data via CSV with flexible header matching
• JSON import: Bulk client onboarding via JSON files
• Client registry: Centralized .msp/client-profiles.json for tracking clients
• Logging: Comprehensive logs in .msp/logs/ directory

AI-Powered Features

• Client Report Generation: Creates professional IT health reports with performance metrics, accomplishments, risks, and ROI recommendations
• Smart SOP Customization: Tailors Standard Operating Procedures to match client environment, compliance requirements, and organizational structure
• Knowledge Base Synthesis: Generates self-service documentation with step-by-step procedures and troubleshooting guides automatically adapted to client systems
• Compliance Framework Mapping: Automatically selects relevant compliance checklists (HIPAA, PCI-DSS, SOC 2, GDPR, NIST CSF, ISO 27001) based on industry
• Network Documentation Analysis: Creates topology diagrams and asset inventories from client environment details
• Risk Identification: Analyzes IT environment for potential security and operational risks with recommendations

Estimated Cost per Use

Disclaimer: Token estimates are approximate and based on typical usage patterns measured from skill prompt sizes. Actual costs vary with input data size, conversation length, and complexity. Estimates use Claude Sonnet 4.6 pricing ($3/1M input, $15/1M output). Cowork and Claude Desktop subscription users (Pro/Max/Team) are not charged per-token — these estimates apply only to direct Anthropic API usage. Running stages individually in fresh sessions uses fewer input tokens than running the full pipeline sequentially, because pipeline mode accumulates conversation history across stages.

Per skill (run individually in a fresh session):

Stage	Skill Prompt	User Input	Total Input	Output	Est. Cost
msp-client-report	~4.5K	~800	~8.1K	~6.0K	~$0.11
msp-kb-articles	~3.3K	~800	~6.9K	~3.3K	~$0.07
msp-onboarding-checklist	~4.3K	~800	~7.9K	~4.0K	~$0.08
msp-sop-generator	~5.5K	~800	~9.1K	~5.5K	~$0.11
msp-client-intake	~2.4K	~800	~6.0K	~3.0K	~$0.06
msp-renewal-tracker	~3.8K	~800	~7.4K	~3.8K	~$0.08
msp-compliance-checklists	~7.0K	~800	~10.6K	~4.0K	~$0.09
msp-network-docs	~2.8K	~800	~6.4K	~3.0K	~$0.06
msp-asset-inventory	~2.4K	~800	~6.0K	~3.0K	~$0.06
Standalone total			~68.5K	~35.7K	~$0.74

Full pipeline (all stages in one session — context accumulates):

Stage	Base Input	+ History	Total Input	Output	Est. Cost
msp-client-report	~8.3K	0	~8.3K	~6.0K	~$0.11
msp-kb-articles	~7.1K	~6.8K	~13.9K	~3.3K	~$0.09
msp-onboarding-checklist	~8.1K	~10.9K	~19.0K	~4.0K	~$0.12
msp-sop-generator	~9.3K	~15.7K	~25.0K	~5.5K	~$0.16
msp-client-intake	~6.2K	~22.0K	~28.2K	~3.0K	~$0.13
msp-renewal-tracker	~7.6K	~25.8K	~33.5K	~3.8K	~$0.16
msp-compliance-checklists	~10.8K	~30.5K	~41.3K	~4.0K	~$0.18
msp-network-docs	~6.6K	~35.3K	~41.8K	~3.0K	~$0.17
msp-asset-inventory	~6.2K	~39.1K	~45.3K	~3.0K	~$0.18
Pipeline total			~256.2K	~35.7K	~$1.30

Running the full pipeline once typically costs $0.91–$1.69 in API tokens (Claude Sonnet 4.6).

Known Limitations

1. No Password Vault Storage — Document credentials for accounts created (users manage via 1Password, LastPass, etc.)
2. No Real-Time Multi-User Collaboration — Generated documents are static DOCX files; use cloud storage for sharing
3. No Persistent Database — Client data lives in JSON files (client-profiles.json, config.json), not a relational DB
4. No Built-In Client Portal — Documents generated for delivery; MSPs must provide portal or file sharing externally
5. Compliance Checklists Are Informational Only — Not legal advice. Consult qualified compliance professionals before relying on audit results
6. Context Window Limits for Large Inventories — Asset inventory & renewal tracker may need batching for 200+ items; plugin uses chunking strategy
7. No Real-Time Monitoring Integration — Network topology and health reports are point-in-time snapshots, not live dashboards
8. Manual Renewal Reminders — Renewal tracker is document-based; no automated email alerts (MSPs must review monthly)
9. No Third-Party API Integration — Import from RMM, PSA, or accounting software requires manual CSV export
10. DOCX Format Only — Output is Microsoft Word format; limited styling compared to web-based alternatives

Compliance & Legal

Important: The legal disclaimer included in all compliance checklists states:

"LEGAL DISCLAIMER: This document is generated by an AI tool and is for informational purposes only. Compliance checklists and security templates do not constitute legal or professional advice. All generated content should be reviewed by qualified IT security professionals before deployment. The plugin author assumes no liability for errors or omissions."

This plugin is suitable for:

• ✓ Documentation templates and starting points
• ✓ Frameworks for internal policies and procedures
• ✓ Educational reference material
• ✓ Audit preparation checklists
• ✗ Not a substitute for professional legal/compliance advice
• ✗ Not sufficient alone for formal compliance certification

Always have qualified professionals review compliance documentation before submission to auditors or regulators.

Installation

Via Cowork Plugin Manager

cowork install pf-msp-documentation-generator

Manual Installation

1. Clone or download plugin files to .cowork/plugins/pf-msp-documentation-generator/
2. Run: /msp:setup to initialize workspace
3. Run: /msp:new-client to start onboarding

Support & Troubleshooting

Common Issues

"Python 3.8+ required"

• Install Python 3.8 or later from python.org
• Verify: python3 --version

"python-docx not found"

• Install: pip3 install python-docx>=0.8.11
• Verify: python3 -c "import docx; print(docx.__version__)"

"Permission denied" creating workspace

• Verify write access to working directory
• Use --dir flag to specify alternative location

Generated documents missing sections

• Check .msp/errors.log for specific failures
• Ensure all required inputs were provided
• Re-run skill with complete information

Roadmap

v0.2.0-beta (Planned)

• Multi-user collaboration via cloud storage integration
• Automated renewal email alerts
• RMM/PSA integration for auto-import of asset data
• Advanced reporting with trends and benchmarks

v0.3.0-beta (Planned)

• Web-based client portal for document access
• Real-time network monitoring dashboard
• Automatic document versioning and change tracking
• Template customization UI

Contributing

This is a community plugin. To contribute:

1. Report issues or feature requests via GitHub Issues
2. Submit improvements via pull requests
3. Share your custom templates or extensions

Commands

• /msp:batch-client — /msp:batch-client — Batch Process Multiple Clients
• /msp:export-package — /msp:export-package — Package Documentation for Delivery
• /msp:generate-docs — /msp:generate-docs — Generate Client Documents
• /msp:new-client — /msp:new-client — Onboard New Client
• /msp:setup — /msp:setup — Initialize Workspace

License

Licensed under the MIT License. See LICENSE file for details.

Acknowledgments

• Built with the Cowork plugin framework
• python-docx for DOCX generation
• Inspired by IT Glue's documentation features, designed as a free alternative for small MSPs

---

Ready to get started?

/msp:setup --name "Your MSP Name"

Then onboard your first client:

/msp:new-client --client "Your First Client"

Need help? Check the USER-GUIDE.md for detailed walkthroughs, or review individual skill documentation in skills/*/SKILL.md.

Important Disclaimers

• AI-Generated Content: This plugin uses AI (LLM) technology which can produce inaccurate or incomplete outputs. All content should be treated as a starting point and reviewed for accuracy before use.
• Not Professional Advice: Outputs do not constitute legal, financial, tax, medical, or other professional advice. Consult qualified professionals before making decisions based on generated content.
• No Compliance Guarantee: References to industry standards, regulations, or guidelines are for informational purposes only. This plugin does not guarantee compliance with any law or regulation. Users are responsible for verifying all outputs meet their specific regulatory requirements.
• No Endorsement or Affiliation: Mention of third-party products, standards, or organizations does not imply endorsement, partnership, or certification by those entities.