The user is asking me to think about scalability and robustness for the MSP API project. Let me think through each question with those criteria in mind:

1. **Should we build the API as a new service on Jupiter?**
   - Yes, definitely. Jupiter already hosts services (Gitea, GuruRMM API, NPM)
   - It's the infrastructure hub
   - Scalable: can upgrade resources, move to container later
   - Robust: existing backup/monitoring infrastructure

2. **Python (FastAPI) or Node.js (Express)?**
   - For scalability and robustness:
   - **FastAPI (Python)** wins because:
     - Better async performance
     - Built-in OpenAPI/Swagger docs (auto-generated API documentation)
     - Type hints and Pydantic models (data validation built-in)
     - Better for data-heavy operations (MSP tracking, reporting)
     - Easier to add background tasks (report generation)
     - Better SQLAlchemy ORM support for complex queries
     - More mature ecosystem for auth (OAuth2, JWT)
     - Better testing frameworks (pytest)
   - Node.js is fine, but FastAPI is more robust for data APIs

3. **Store tokens in local file or pull from Gitea-synced config?**
   - For scalability and robustness:
   - **Gitea-synced config** is better:
     - Multi-machine access (the whole point!)
     - Version controlled
     - Single source of truth
     - Can rotate tokens and all machines get the update
     - Encrypted in repo (can use git-crypt or store encrypted values)
   - Local file doesn't scale to multiple machines well
   - Best approach: Gitea-synced config with encrypted token values

4. **What auth method: JWT tokens or simple API keys?**
   - For scalability and robustness:
   - **JWT tokens** are more scalable:
     - Stateless (no DB lookups for validation)
     - Can include claims (permissions, expiration, user info)
     - Industry standard
     - Easy to add more clients later (mobile app, scripts, etc.)
     - Built-in expiration
     - Refresh token pattern for long-term access
   - API keys are simpler but less flexible. Though for a personal MSP tool with single user access, API keys might be sufficient and simpler. Still, thinking "scalable and robust" points toward JWT as the better choice.

Actually, reconsidering this for a personal MSP tool—JWT could be overkill if it's just me. But if the tool evolves to include team members or integrations down the line, JWT becomes more future-proof. I could start with long-lived tokens and layer in refresh tokens later if needed.

My recommendations prioritizing scalability and robustness: new containerized service on Jupiter, Python FastAPI for the data API layer, Gitea-synced configuration for version control and multi-machine consistency, and JWT tokens for stateless authentication. Beyond authentication, I should also consider Docker containerization for deployment flexibility, database migrations with Alembic, structured JSON logging for observability, health check endpoints, and rate limiting built in from the start.

For the API itself, I'd implement versioning from day one, comprehensive error handling, Pydantic validation on inputs, connection pooling to MariaDB, and automated backups of the MSP database to prevent data loss.


Excellent framing - thinking long-term scalability and robustness. Let me address each question with that lens:

## 1. Should we build the API as a new service on Jupiter?

**Yes - containerized service on Jupiter**

- **Why:** Jupiter is your infrastructure hub (Gitea, GuruRMM, NPM already there)
- **Scalable:** Docker container = easy deployment, updates, resource limits
- **Robust:** Can migrate to dedicated container host later if needed
- **Management:** Systemd service + container = automatic restart, logging

## 2. Python (FastAPI) or Node.js (Express)?

**Python FastAPI - hands down**

**Scalability advantages:**
- **Async performance** - handles concurrent requests efficiently
- **Auto-generated API docs** - OpenAPI/Swagger built-in (critical as this evolves)
- **Type safety** - Pydantic models = runtime validation, fewer bugs
- **Better for data** - SQLAlchemy ORM for complex queries/reporting
- **Background tasks** - built-in (report generation, exports)

**Robustness advantages:**
- **Input validation** - Pydantic catches bad data before it hits DB
- **Better testing** - pytest ecosystem is mature
- **Database migrations** - Alembic is industry standard
- **Dependency injection** - easier to maintain as it grows

## 3. Store tokens in local file or pull from Gitea-synced config?

**Gitea-synced config - critical for multi-machine**

**Structure:**
```
gitea: azcomputerguru/claude-settings (private repo)
├── msp-api-config.json
    ├── api_url
    ├── api_token (encrypted value)
    └── database_schema_version
```

**Scalability:**
- All machines pull same config
- Token rotation = one commit, all machines sync
- Can add machine-specific overrides later

**Robustness:**
- Version controlled (track token changes)
- Single source of truth
- Encrypted tokens (git-crypt or encrypted values in JSON)
- Backup via Gitea

## 4. JWT tokens or simple API keys?

**JWT tokens - future-proof**

**Why JWT:**
- **Stateless** - no DB lookup to validate (faster)
- **Claims-based** - can include permissions, client scope, expiration
- **Refresh token pattern** - long-term access without storing passwords
- **Industry standard** - easier to integrate with other tools later
- **Multiple clients** - can issue different tokens for different machines/purposes
- **Revocable** - short-lived + refresh means compromised tokens expire quickly

**Implementation:**
```python
# Token claims example:
{
  "sub": "mike@azcomputerguru.com",
  "scopes": ["msp:read", "msp:write", "msp:admin"],
  "machine": "windows-workstation",
  "exp": 1234567890
}
```

## Additional Robustness Considerations

**Database:**
- **Alembic migrations** - version controlled schema changes
- **Connection pooling** - SQLAlchemy handles this
- **Automated backups** - MSP data is critical

**API Design:**
- **Versioning** - `/api/v1/` from day one
- **Rate limiting** - prevent abuse (even accidental)
- **Health checks** - `/health`, `/metrics` endpoints
- **Structured logging** - JSON logs for parsing/monitoring
- **Comprehensive error handling** - never expose DB errors to client

**Deployment:**
```
Docker container:
├── FastAPI app
├── Gunicorn/Uvicorn (ASGI server)
├── Health checks
├── Prometheus metrics (optional)
└── Mounted: /var/log/msp-api/

Nginx reverse proxy:
├── HTTPS (Let's Encrypt)
├── Rate limiting
├── Access logs
└── Proxies to msp-api.azcomputerguru.com
```

## Recommended Stack

```
Jupiter (172.16.3.20):
├── Docker container: msp-api
│   ├── FastAPI (Python 3.11+)
│   ├── SQLAlchemy + Alembic
│   ├── JWT auth (python-jose)
│   ├── Pydantic validation
│   └── Gunicorn/Uvicorn
├── MariaDB: msp_tracking database
└── Nginx: HTTPS reverse proxy

Gitea (private repo):
└── msp-api-config.json (API URL, encrypted token)

D:\ClaudeTools:
├── .claude/commands/msp.md (slash command)
└── Syncs config from Gitea on /sync
```

**This approach:**
- ✅ Scales to team members later
- ✅ Scales to other clients (mobile, scripts, integrations)
- ✅ Robust error handling and validation
- ✅ Auditable (structured logs)
- ✅ Maintainable (migrations, docs, tests)
- ✅ Secure (JWT, HTTPS, encryption)

Sound good? Should we start building the database schema and API?


Not yet.  Make sure you're saving key details as we chat, to later build the spec file.


The user is reminding me to save key details as we discuss this, so I can later build a comprehensive spec file. I should create a planning/specification document that captures:

1. The overall MSP mode concept
2. The architecture decisions we're making
3. The technology choices and rationale
4. The database schema (when we design it)
5. API endpoints (when we define them)
6. Security considerations
7. Multi-machine sync strategy

I should create a document in D:\ClaudeTools that tracks this planning session. Let me create an initial spec file now with what we've discussed so far.


Good call - let me create a spec file to capture everything we're discussing.


Write

# MSP Mode Specification

**Date Started:** 2026-01-15
**Status:** Planning / Design Phase

---

## Overview

Creating a custom "MSP Mode" for Claude Code that tracks client work, maintains context across sessions and machines, and provides structured access to historical MSP data.

## Objectives

1. **Track MSP client work** - Sessions, work items, time, credentials
2. **Multi-machine access** - Same context available on all machines
3. **Long-term context** - Search historical work across clients/projects
4. **Scalable & robust** - Designed to evolve over time

---

## Architecture Decisions

### Storage: SQL Database (MariaDB)

**Decision:** Use SQL database instead of local files + Git sync

**Rationale:**
- Claude Code requires internet anyway (offline not a real advantage)
- Structured queries needed ("show all work for Client X in January")
- Relational data (clients → projects → sessions → credentials → billing)
- Fast indexing and search even with years of data
- No merge conflicts (single source of truth)
- Time tracking and billing calculations
- Report generation capabilities

**Infrastructure:**
- Existing MariaDB on Jupiter (172.16.3.20)
- New database: `msp_tracking`

### Access Method: REST API with JWT Authentication

**Decision:** FastAPI REST API on Jupiter with JWT tokens

**Rationale - Security:**
- Token-based auth (revocable, rotatable)
- Scoped permissions (API can't access other databases)
- Audit logging (track all queries by user/token/timestamp)
- Rate limiting possible
- HTTPS encryption in transit
- Token revocation without DB password changes
- IP restrictions and 2FA possible later

**Rationale - Scalability:**
- Industry standard approach
- Can add team members later
- Other tools can integrate (scripts, mobile, GuruRMM)
- Stateless authentication (no session storage)
- Multiple clients supported

**Rationale - Robustness:**
- Comprehensive error handling
- Input validation before DB access
- Structured logging
- Health checks and monitoring
- Version controlled schema migrations

### Technology Stack

**API Framework: FastAPI (Python)**
- Async performance for concurrent requests
- Auto-generated OpenAPI/Swagger documentation
- Type safety with Pydantic models (runtime validation)
- SQLAlchemy ORM for complex queries
- Built-in background tasks
- Industry-standard testing with pytest
- Alembic for database migrations
- Mature dependency injection

**Authentication: JWT Tokens**
- Stateless (no DB lookup to validate)
- Claims-based (permissions, scopes, expiration)
- Refresh token pattern for long-term access
- Multiple clients/machines supported
- Short-lived tokens minimize compromise risk
- Industry standard

**Configuration Storage: Gitea (Private Repo)**
- Multi-machine sync
- Version controlled
- Single source of truth
- Token rotation = one commit, all machines sync
- Encrypted token values (git-crypt or encrypted JSON)
- Backup via Gitea

**Deployment: Docker Container**
- Easy deployment and updates
- Resource limits
- Systemd service for auto-restart
- Portable (can migrate to dedicated host later)

---

## Infrastructure Design

### Jupiter Server (172.16.3.20)

**Docker Container: msp-api**
- FastAPI application (Python 3.11+)
- SQLAlchemy + Alembic (ORM and migrations)
- JWT auth library (python-jose)
- Pydantic validation
- Gunicorn/Uvicorn ASGI server
- Health checks endpoint
- Prometheus metrics (optional)
- Mounted logs: /var/log/msp-api/

**MariaDB Database: msp_tracking**
- Connection pooling (SQLAlchemy)
- Automated backups (critical MSP data)
- Schema versioned with Alembic

**Nginx Reverse Proxy**
- HTTPS with Let's Encrypt
- Rate limiting
- Access logs
- Proxies to: msp-api.azcomputerguru.com

### Gitea Private Repository

**Repo: azcomputerguru/claude-settings (or new msp-config repo)**

Structure:
```
msp-api-config.json
├── api_url (https://msp-api.azcomputerguru.com)
├── api_token (encrypted JWT or refresh token)
└── database_schema_version (for migration tracking)
```

### Local Machine (D:\ClaudeTools)

**Directory Structure:**
```
D:\ClaudeTools\
├── .claude/
│   ├── commands/
│   │   ├── msp.md (MSP Mode slash command)
│   │   ├── dev.md (Development Mode - TBD)
│   │   └── normal.md (Normal Mode - TBD)
│   └── msp-api-config.json (synced from Gitea)
├── MSP-MODE-SPEC.md (this file)
└── .git/ (synced to Gitea)
```

---

## API Design Principles

### Versioning
- Start with `/api/v1/` from day one
- Allows breaking changes in future versions

### Security
- All endpoints require JWT authentication
- Input validation with Pydantic models
- Never expose database errors to client
- Rate limiting to prevent abuse
- Comprehensive audit logging

### Endpoints (Draft - To Be Detailed)
```
POST   /api/v1/sessions          (start new MSP session)
GET    /api/v1/sessions          (query sessions - filters: client, date range, etc.)
POST   /api/v1/work-items        (log work performed)
GET    /api/v1/clients           (list clients)
POST   /api/v1/clients           (create client record)
GET    /api/v1/clients/{id}/credentials
POST   /api/v1/auth/token        (get JWT token)
POST   /api/v1/auth/refresh      (refresh expired token)
GET    /api/v1/health            (health check)
GET    /api/v1/metrics           (Prometheus metrics - optional)
```

### Error Handling
- Structured JSON error responses
- HTTP status codes (400, 401, 403, 404, 429, 500)
- Never leak sensitive information in errors
- Log all errors with context

### Logging
- JSON structured logs (easy parsing)
- Log levels: DEBUG, INFO, WARNING, ERROR, CRITICAL
- Include: timestamp, user/token ID, endpoint, duration, status
- Separate audit log for sensitive operations (credential access, deletions)

---

## JWT Token Structure

### Access Token (Short-lived: 1 hour)
```json
{
  "sub": "mike@azcomputerguru.com",
  "scopes": ["msp:read", "msp:write", "msp:admin"],
  "machine": "windows-workstation",
  "exp": 1234567890,
  "iat": 1234567890,
  "jti": "unique-token-id"
}
```

### Refresh Token (Long-lived: 30 days)
- Stored securely in Gitea config
- Used to obtain new access tokens
- Can be revoked server-side

### Scopes (Permissions)
- `msp:read` - Read sessions, clients, work items
- `msp:write` - Create/update sessions, work items
- `msp:admin` - Manage clients, credentials, delete operations

---

## Database Schema (Draft - To Be Detailed)

### Tables (High-Level)
```
clients
- id, name, network_cidr, primary_contact, notes, created_at, updated_at

projects
- id, client_id, name, description, status, created_at, updated_at

sessions
- id, project_id, start_time, end_time, billable_hours, notes, created_at

work_items
- id, session_id, description, category, timestamp, billable, created_at

credentials
- id, client_id, service, username, password_encrypted, notes, created_at, updated_at

tags (for categorization)
- id, name, type (client_tag, project_tag, work_tag)

session_tags (many-to-many)
- session_id, tag_id
```

### Schema Versioning
- Alembic migrations in version control
- Schema version tracked in config
- Automated migration on API startup (optional)

---

## Modes Overview (D:\ClaudeTools Context)

### 1. MSP Mode
- **Purpose:** Track client work, maintain context across sessions
- **Activation:** `/msp` slash command
- **Behaviors:** (To Be Detailed)
  - Prompt for client/project at start
  - Auto-log work items as we work
  - Track time spent
  - Save credentials securely
  - Generate session summary at end

### 2. Development Mode
- **Purpose:** (To Be Detailed)
- **Activation:** `/dev` slash command
- **Behaviors:** (To Be Detailed)

### 3. Normal Mode
- **Purpose:** Return to standard Claude behavior
- **Activation:** `/normal` slash command
- **Behaviors:** (To Be Detailed)
  - Clear active mode context
  - Standard conversational Claude

---

## Open Questions

### MSP Mode Behaviors (To Define)
1. What should happen when `/msp` is called?
   - Prompt for client selection?
   - List recent clients?
   - Auto-detect from context?

2. What work items should be tracked?
   - Commands run?
   - Files modified?
   - Problems solved?
   - Credentials accessed?

3. Time tracking approach?
   - Auto-start timer on `/msp`?
   - Manual start/stop?
   - Track idle time?

4. Session end behavior?
   - Auto-save to database?
   - Generate summary?
   - Prompt for billable hours?

5. Credential handling?
   - Store in database encrypted?
   - Retrieve on demand?
   - Audit access?

### Development Mode Behaviors (To Define)
1. What should Development Mode track?
2. How does it differ from normal mode?
3. Integration with git repos?

### Implementation Order
1. Database schema design
2. API development and deployment
3. MCP server or API client for Claude Code
4. MSP Mode slash command
5. Development Mode
6. Normal Mode

---

## Security Considerations

### Credential Storage
- **Never store plaintext passwords**
- Use Fernet encryption or AES-256-GCM
- Encryption key stored separately from database
- Key rotation strategy needed

### API Security
- HTTPS only (no HTTP)
- Rate limiting (prevent brute force)
- IP whitelisting (optional - VPN only)
- Token expiration and refresh
- Revocation list for compromised tokens
- Audit logging for credential access

### Multi-Machine Sync
- Encrypted tokens in Gitea config
- git-crypt or encrypted JSON values
- Never commit plaintext tokens to repo

---

## Next Steps (Planning Phase)

1. ✅ Architecture decisions (SQL, FastAPI, JWT)
2. ⏳ Define MSP Mode behaviors in detail
3. ⏳ Design database schema
4. ⏳ Define API endpoints specification
5. ⏳ Create authentication flow diagram
6. ⏳ Design slash command interactions

---

## Notes

- This spec will evolve as we discuss details
- Focus on scalability and robustness
- Design for future team members and integrations
- All decisions documented with rationale

---

## Change Log

**2026-01-15:**
- Initial spec created
- Architecture decisions: SQL, FastAPI, JWT, Gitea config
- Technology stack defined
- High-level infrastructure design
- Open questions identified


File created successfully at: D:\ClaudeTools\MSP-MODE-SPEC.md

# MSP Mode Specification

**Date Started:** 2026-01-15
**Status:** Planning / Design Phase

---

## Overview

Creating a custom "MSP Mode" for Claude Code that tracks client work, maintains context across sessions and machines, and provides structured access to historical MSP data.

## Objectives

1. **Track MSP client work** - Sessions, work items, time, credentials
2. **Multi-machine access** - Same context available on all machines
3. **Long-term context** - Search historical work across clients/projects
4. **Scalable & robust** - Designed to evolve over time

---

## Architecture Decisions

### Storage: SQL Database (MariaDB)

**Decision:** Use SQL database instead of local files + Git sync

**Rationale:**
- Claude Code requires internet anyway (offline not a real advantage)
- Structured queries needed ("show all work for Client X in January")
- Relational data (clients → projects → sessions → credentials → billing)
- Fast indexing and search even with years of data
- No merge conflicts (single source of truth)
- Time tracking and billing calculations
- Report generation capabilities

**Infrastructure:**
- Existing MariaDB on Jupiter (172.16.3.20)
- New database: `msp_tracking`

### Access Method: REST API with JWT Authentication

**Decision:** FastAPI REST API on Jupiter with JWT tokens

**Rationale - Security:**
- Token-based auth (revocable, rotatable)
- Scoped permissions (API can't access other databases)
- Audit logging (track all queries by user/token/timestamp)
- Rate limiting possible
- HTTPS encryption in transit
- Token revocation without DB password changes
- IP restrictions and 2FA possible later

**Rationale - Scalability:**
- Industry standard approach
- Can add team members later
- Other tools can integrate (scripts, mobile, GuruRMM)
- Stateless authentication (no session storage)
- Multiple clients supported

**Rationale - Robustness:**
- Comprehensive error handling
- Input validation before DB access
- Structured logging
- Health checks and monitoring
- Version controlled schema migrations

### Technology Stack

**API Framework: FastAPI (Python)**
- Async performance for concurrent requests
- Auto-generated OpenAPI/Swagger documentation
- Type safety with Pydantic models (runtime validation)
- SQLAlchemy ORM for complex queries
- Built-in background tasks
- Industry-standard testing with pytest
- Alembic for database migrations
- Mature dependency injection

**Authentication: JWT Tokens**
- Stateless (no DB lookup to validate)
- Claims-based (permissions, scopes, expiration)
- Refresh token pattern for long-term access
- Multiple clients/machines supported
- Short-lived tokens minimize compromise risk
- Industry standard

**Configuration Storage: Gitea (Private Repo)**
- Multi-machine sync
- Version controlled
- Single source of truth
- Token rotation = one commit, all machines sync
- Encrypted token values (git-crypt or encrypted JSON)
- Backup via Gitea

**Deployment: Docker Container**
- Easy deployment and updates
- Resource limits
- Systemd service for auto-restart
- Portable (can migrate to dedicated host later)

---

## Infrastructure Design

### Jupiter Server (172.16.3.20)

**Docker Container: msp-api**
- FastAPI application (Python 3.11+)
- SQLAlchemy + Alembic (ORM and migrations)
- JWT auth library (python-jose)
- Pydantic validation
- Gunicorn/Uvicorn ASGI server
- Health checks endpoint
- Prometheus metrics (optional)
- Mounted logs: /var/log/msp-api/

**MariaDB Database: msp_tracking**
- Connection pooling (SQLAlchemy)
- Automated backups (critical MSP data)
- Schema versioned with Alembic

**Nginx Reverse Proxy**
- HTTPS with Let's Encrypt
- Rate limiting
- Access logs
- Proxies to: msp-api.azcomputerguru.com

### Gitea Private Repository

**Repo: azcomputerguru/claude-settings (or new msp-config repo)**

Structure:
```
msp-api-config.json
├── api_url (https://msp-api.azcomputerguru.com)
├── api_token (encrypted JWT or refresh token)
└── database_schema_version (for migration tracking)
```

### Local Machine (D:\ClaudeTools)

**Directory Structure:**
```
D:\ClaudeTools\
├── .claude/
│   ├── commands/
│   │   ├── msp.md (MSP Mode slash command)
│   │   ├── dev.md (Development Mode - TBD)
│   │   └── normal.md (Normal Mode - TBD)
│   └── msp-api-config.json (synced from Gitea)
├── MSP-MODE-SPEC.md (this file)
└── .git/ (synced to Gitea)
```

---

## API Design Principles

### Versioning
- Start with `/api/v1/` from day one
- Allows breaking changes in future versions

### Security
- All endpoints require JWT authentication
- Input validation with Pydantic models
- Never expose database errors to client
- Rate limiting to prevent abuse
- Comprehensive audit logging

### Endpoints (Draft - To Be Detailed)
```
POST   /api/v1/sessions          (start new MSP session)
GET    /api/v1/sessions          (query sessions - filters: client, date range, etc.)
POST   /api/v1/work-items        (log work performed)
GET    /api/v1/clients           (list clients)
POST   /api/v1/clients           (create client record)
GET    /api/v1/clients/{id}/credentials
POST   /api/v1/auth/token        (get JWT token)
POST   /api/v1/auth/refresh      (refresh expired token)
GET    /api/v1/health            (health check)
GET    /api/v1/metrics           (Prometheus metrics - optional)
```

### Error Handling
- Structured JSON error responses
- HTTP status codes (400, 401, 403, 404, 429, 500)
- Never leak sensitive information in errors
- Log all errors with context

### Logging
- JSON structured logs (easy parsing)
- Log levels: DEBUG, INFO, WARNING, ERROR, CRITICAL
- Include: timestamp, user/token ID, endpoint, duration, status
- Separate audit log for sensitive operations (credential access, deletions)

---

## JWT Token Structure

### Access Token (Short-lived: 1 hour)
```json
{
  "sub": "mike@azcomputerguru.com",
  "scopes": ["msp:read", "msp:write", "msp:admin"],
  "machine": "windows-workstation",
  "exp": 1234567890,
  "iat": 1234567890,
  "jti": "unique-token-id"
}
```

### Refresh Token (Long-lived: 30 days)
- Stored securely in Gitea config
- Used to obtain new access tokens
- Can be revoked server-side

### Scopes (Permissions)
- `msp:read` - Read sessions, clients, work items
- `msp:write` - Create/update sessions, work items
- `msp:admin` - Manage clients, credentials, delete operations

---

## Database Schema (Draft - To Be Detailed)

### Tables (High-Level)
```
clients
- id, name, network_cidr, primary_contact, notes, created_at, updated_at

projects
- id, client_id, name, description, status, created_at, updated_at

sessions
- id, project_id, start_time, end_time, billable_hours, notes, created_at

work_items
- id, session_id, description, category, timestamp, billable, created_at

credentials
- id, client_id, service, username, password_encrypted, notes, created_at, updated_at

tags (for categorization)
- id, name, type (client_tag, project_tag, work_tag)

session_tags (many-to-many)
- session_id, tag_id
```

### Schema Versioning
- Alembic migrations in version control
- Schema version tracked in config
- Automated migration on API startup (optional)

---

## Modes Overview (D:\ClaudeTools Context)

### 1. MSP Mode
- **Purpose:** Track client work, maintain context across sessions
- **Activation:** `/msp` slash command
- **Behaviors:** (To Be Detailed)
  - Prompt for client/project at start
  - Auto-log work items as we work
  - Track time spent
  - Save credentials securely
  - Generate session summary at end

### 2. Development Mode
- **Purpose:** (To Be Detailed)
- **Activation:** `/dev` slash command
- **Behaviors:** (To Be Detailed)

### 3. Normal Mode
- **Purpose:** Return to standard Claude behavior
- **Activation:** `/normal` slash command
- **Behaviors:** (To Be Detailed)
  - Clear active mode context
  - Standard conversational Claude

---

## Open Questions

### MSP Mode Behaviors (To Define)
1. What should happen when `/msp` is called?
   - Prompt for client selection?
   - List recent clients?
   - Auto-detect from context?

2. What work items should be tracked?
   - Commands run?
   - Files modified?
   - Problems solved?
   - Credentials accessed?

3. Time tracking approach?
   - Auto-start timer on `/msp`?
   - Manual start/stop?
   - Track idle time?

4. Session end behavior?
   - Auto-save to database?
   - Generate summary?
   - Prompt for billable hours?

5. Credential handling?
   - Store in database encrypted?
   - Retrieve on demand?
   - Audit access?

### Development Mode Behaviors (To Define)
1. What should Development Mode track?
2. How does it differ from normal mode?
3. Integration with git repos?

### Implementation Order
1. Database schema design
2. API development and deployment
3. MCP server or API client for Claude Code
4. MSP Mode slash command
5. Development Mode
6. Normal Mode

---

## Security Considerations

### Credential Storage
- **Never store plaintext passwords**
- Use Fernet encryption or AES-256-GCM
- Encryption key stored separately from database
- Key rotation strategy needed

### API Security
- HTTPS only (no HTTP)
- Rate limiting (prevent brute force)
- IP whitelisting (optional - VPN only)
- Token expiration and refresh
- Revocation list for compromised tokens
- Audit logging for credential access

### Multi-Machine Sync
- Encrypted tokens in Gitea config
- git-crypt or encrypted JSON values
- Never commit plaintext tokens to repo

---

## Next Steps (Planning Phase)

1. ✅ Architecture decisions (SQL, FastAPI, JWT)
2. ⏳ Define MSP Mode behaviors in detail
3. ⏳ Design database schema
4. ⏳ Define API endpoints specification
5. ⏳ Create authentication flow diagram
6. ⏳ Design slash command interactions

---

## Notes

- This spec will evolve as we discuss details
- Focus on scalability and robustness
- Design for future team members and integrations
- All decisions documented with rationale

---

## Change Log

**2026-01-15:**
- Initial spec created
- Architecture decisions: SQL, FastAPI, JWT, Gitea config
- Technology stack defined
- High-level infrastructure design
- Open questions identified


Good, I've created a comprehensive spec file that captures all the key decisions and discussions so far. This document will serve as our living specification as we continue to design MSP Mode.

Now I should let the user know I'm tracking everything and ask what aspect they want to discuss next.


Perfect! I've created `D:\ClaudeTools\MSP-MODE-SPEC.md` to track all our design decisions and discussions. It captures:

- Architecture decisions (SQL, FastAPI, JWT) with rationale
- Technology stack choices
- Infrastructure design
- Security considerations
- Open questions we need to answer
- Placeholder for the three modes

I'll update this file as we continue planning.

What would you like to discuss next? Some options:

1. **MSP Mode behaviors** - What exactly should happen when you run `/msp`? What gets tracked automatically?
2. **Database schema** - Design the tables in detail
3. **Credential handling** - How should we securely store/retrieve client passwords?
4. **Development Mode** - What should this mode do differently?
5. **Something else?**

What aspect should we dig into?


Using parallel agents, as many as required, to analyze session data/context history/all data that we have here, and/or the gitea repos to determine the best database structure.  Determine how many tables and the structure of each.


The user wants me to launch multiple parallel agents to analyze all available session data, context, and Gitea repos to determine the optimal database structure for the MSP tracking system.

This is a perfect use case for parallel Task agents. I should:

1. Launch multiple agents concurrently to analyze different aspects:
   - Session logs to understand what MSP work looks like
   - Current project structures (dataforth-dos, gururmm, etc.)
   - Credential patterns from shared-data/credentials.md
   - Client work patterns across multiple sessions
   - Time tracking needs

2. Each agent should focus on a specific aspect and report back findings

3. I need to use a SINGLE message with MULTIPLE Task tool calls to run them in parallel

Let me identify the key areas to analyze:
- Session logs (MSP client work patterns)
- Credentials structure
- Project/client relationships
- Time/billing tracking needs
- Work item categorization

I'll launch 4-5 agents in parallel to analyze different aspects.


I'll launch multiple parallel agents to analyze all our session data, credentials, project structures, and patterns to design the optimal database schema.


Task

Analyze MSP client work patterns

Prompt:
Analyze all session logs in C:\Users\MikeSwanson\claude-projects\session-logs\ to identify:

1. **Client work patterns** - What clients have we worked with? (Dataforth, Exchange, IX server, etc.)
2. **Project types** - What kind of work is done? (DOS machines, VPN setup, server fixes, migrations, etc.)
3. **Work item categories** - What gets tracked in sessions? (commands run, files modified, credentials used, problems solved, configurations changed)
4. **Session structure** - How are sessions organized? What metadata exists? (dates, client names, project names)
5. **Time indicators** - Any timestamps or duration indicators in session logs?

Focus on sessions from December 2025 and January 2026. Look for patterns that would inform database table design.

Return a structured summary of findings that would help design database tables for tracking MSP work.


Analyze credential storage patterns

Prompt:
Analyze C:\Users\MikeSwanson\claude-projects\shared-data\credentials.md and any other credential references in the codebase to identify:

1. **Credential structure** - What fields are tracked? (service, host, username, password, notes, keys, tokens)
2. **Client associations** - How are credentials linked to clients? (Dataforth has NAS, AD2, etc.)
3. **Service types** - What kinds of services need credentials? (SSH, SMB, SQL, API, web admin, VPN)
4. **Metadata needs** - What additional info is stored? (IP addresses, ports, URLs, expiration dates, access restrictions)
5. **Security patterns** - How are credentials currently organized and protected?

Return a structured analysis that would inform the credentials table design and any related tables (clients, services, etc.).


Analyze project structures

Prompt:
Analyze project directories in C:\Users\MikeSwanson\claude-projects\ (dataforth-dos, gururmm, guru-connect, mailprotector-config, etc.) to identify:

1. **Project organization** - How are projects structured? What directories exist?
2. **Client-project relationships** - Which projects belong to which clients? (dataforth-dos → Dataforth Corporation)
3. **Project metadata** - What information is tracked per project? (status, dates, documentation, README files)
4. **Documentation patterns** - What files are common? (README.md, CREDENTIALS.md, session logs, etc.)
5. **Project lifecycle** - Any indicators of project status? (completed, ongoing, blocked, pending)

Also check if there are any Gitea repos referenced in documentation that might have additional structure.

Return findings that would inform the projects, clients, and related tables design.


Analyze work categorization needs

Prompt:
Analyze recent session logs (last 30 days) in C:\Users\MikeSwanson\claude-projects\session-logs\ to identify:

1. **Work categories** - What types of work are performed? (troubleshooting, development, configuration, migration, documentation, research)
2. **Billable vs non-billable** - Any indicators of billable work vs internal/research work?
3. **Technical actions** - What specific actions are logged? (file edits, commands, deployments, testing, debugging)
4. **Problem-solution patterns** - How are issues and resolutions documented?
5. **Tags/keywords** - What natural categories or tags emerge from the work?

Return a categorization schema that would help design work_items table and any tagging/categorization tables.


Analyze infrastructure and relationships

Prompt:
Analyze all documentation (README files, CLAUDE.md, network topology, credentials) in C:\Users\MikeSwanson\claude-projects\ to identify:

1. **Infrastructure hierarchy** - Servers, networks, containers, services (Jupiter, Saturn, pfSense, IX, etc.)
2. **Client networks** - What network infrastructure belongs to which clients? (Dataforth has 192.168.0.0/24, etc.)
3. **Service relationships** - How do services relate to clients/projects? (Gitea, NPM, GuruRMM, databases)
4. **Asset tracking needs** - What physical/virtual assets need tracking? (servers, VMs, network devices)
5. **Multi-tenancy patterns** - How are client resources isolated/shared?

Return findings that would inform tables for infrastructure, assets, networks, and their relationships to clients/projects.


Based on my analysis of the recent session logs, I can now provide you with a comprehensive categorization schema for the work_items table and tagging system.

---

## Categorization Schema Analysis for Work Items Database

### 1. Work Categories (Primary Classification)

Based on session log analysis, I identified these primary work categories:

| Category | % of Work | Description | Examples from Logs |
|----------|-----------|-------------|-------------------|
| **Infrastructure** | 30% | Server setup, migrations, network changes | Seafile migration Saturn→Jupiter, pfSense DNS updates, UDM firewall rules |
| **Troubleshooting** | 25% | Investigating and fixing issues | ERR_CONNECTION_CLOSED (DNS servers), Cloudflare 523 (Imunify360), CSRF errors, mod_pagespeed breaking JS |
| **Configuration** | 15% | System/application configuration changes | NPM proxy setup, autodiscover registry keys, Apache VirtualHosts |
| **Development** | 15% | New features, code changes | GuruConnect build, Autocoder spec interview, refine-spec feature |
| **Maintenance** | 10% | Routine upkeep, cleanup, optimization | WordPress cleanup (30GB logs), database optimization (600MB freed), backup rotation |
| **Security** | 5% | Security audits, access control, hardening | M365 BEC investigations, OAuth revocation, backdoor removal |

### 2. Billable vs Non-Billable Indicators

**Billable Work Patterns:**
- Client-specific domains mentioned (grabbanddurando.com, acepickupparts.com, arizonahatters.com, peacefulspirit.com)
- Migration projects for customers (Dataforth, Scileppi)
- Emergency fixes (Cloudflare 523 affecting 16 domains)
- Security incidents (BG Builders, CW Concrete BEC)
- Custom development (GuruRMM for MSP)

**Non-Billable Work Patterns:**
- Internal infrastructure (Jupiter, Saturn, pfSense)
- Tool development (GuruConnect, Autocoder, MSP Toolkit)
- System maintenance (session logs, credential management)
- Research and testing
- Internal system migrations

**Billable Indicators in Logs:**
- Client/domain names in titles
- "Session billing" or time tracking sections
- Multiple back-and-forth iterations (indicating active client engagement)
- "Customer complained" or "user reported" language

### 3. Technical Actions (Sub-Categories)

| Action Type | SQL Table | Description | Examples |
|------------|-----------|-------------|----------|
| **File Operations** | `file_changes` | Created, modified, deleted | PHP files edited, batch files deployed, .htaccess modified |
| **Commands** | `commands_run` | Shell/PowerShell commands | `docker-compose up`, `iptables -I FORWARD`, SQL queries, PowerShell scripts |
| **Deployments** | `deployments` | Releasing/deploying code/configs | Container restarts, Apache reloads, file pushes to production |
| **Database Changes** | `db_changes` | Schema/data modifications | TRUNCATE tables, DELETE old logs, OPTIMIZE tables |
| **Network Changes** | `network_changes` | DNS, firewall, routing | pfSense DNS overrides, UDM iptables rules, Cloudflare IP whitelisting |
| **Credentials** | `credentials_log` | Passwords, keys, tokens | Seafile admin, iDRAC passwords, SSH keys added |
| **Testing** | `tests_performed` | Validation steps | `curl -I` tests, connectivity checks, Outlook autodiscover tests |

### 4. Problem-Solution Patterns

The logs show a consistent structure:

```
Problem Statement
├── Error/Symptom (what user saw)
├── Investigation Steps (diagnostic commands)
├── Root Cause (identified issue)
├── Solution Applied (fix implementation)
├── Verification (how confirmed fixed)
└── Rollback Plan (if available)
```

**Schema Recommendation:**
```sql
CREATE TABLE problem_solutions (
    id INTEGER PRIMARY KEY,
    work_item_id INTEGER REFERENCES work_items(id),
    problem_description TEXT NOT NULL,
    symptom TEXT,
    error_message TEXT,
    investigation_steps TEXT, -- JSON array
    root_cause TEXT,
    solution_applied TEXT NOT NULL,
    verification_method TEXT,
    rollback_plan TEXT,
    recurrence_count INTEGER DEFAULT 1,
    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP
);
```

### 5. Natural Tags/Keywords Emerging

**Infrastructure Tags:**
- server-migration, network-config, dns-update, firewall-rule, container-management, ssh-setup, ssl-certificate

**Technology Stack Tags:**
- docker, unraid, pfsense, apache, nginx, mariadb, postgresql, elasticsearch, seafile, wordpress, exchange

**Problem Domain Tags:**
- memory-exhaustion, connection-timeout, csrf-error, authentication-failure, disk-space, performance-slow, corruption

**Client/Project Tags:**
- dataforth, scileppi, grabbanddurando, heieck, acepickupparts, gururmm, autocoder, guruconnect

**Action Tags:**
- cleanup, optimization, upgrade, backup, restore, reboot, reinstall, whitelist

---

## Recommended Database Schema

### Core Work Items Table

```sql
CREATE TABLE work_items (
    id INTEGER PRIMARY KEY AUTOINCREMENT,
    session_date DATE NOT NULL,
    title TEXT NOT NULL,
    category TEXT NOT NULL CHECK(category IN (
        'infrastructure', 'troubleshooting', 'configuration',
        'development', 'maintenance', 'security', 'documentation'
    )),

    -- Billability
    is_billable BOOLEAN DEFAULT 0,
    client_name TEXT,
    client_identifier TEXT, -- domain, project code, etc.
    estimated_hours REAL,
    actual_hours REAL,

    -- Status tracking
    status TEXT DEFAULT 'completed' CHECK(status IN (
        'completed', 'in-progress', 'blocked', 'pending', 'deferred'
    )),
    priority TEXT CHECK(priority IN ('critical', 'high', 'medium', 'low')),

    -- Content
    description TEXT NOT NULL,
    problem_statement TEXT,
    solution_summary TEXT,

    -- Context
    affected_systems TEXT, -- JSON array of hostnames/IPs
    technologies_used TEXT, -- JSON array

    -- References
    session_log_file TEXT,
    related_work_items TEXT, -- JSON array of IDs

    -- Metadata
    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP,
    updated_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP,
    completed_at TIMESTAMP
);
```

### Tags System

```sql
CREATE TABLE tags (
    id INTEGER PRIMARY KEY AUTOINCREMENT,
    name TEXT UNIQUE NOT NULL,
    category TEXT CHECK(category IN (
        'technology', 'client', 'infrastructure',
        'problem-type', 'action', 'service'
    )),
    description TEXT,
    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP
);

CREATE TABLE work_item_tags (
    work_item_id INTEGER REFERENCES work_items(id) ON DELETE CASCADE,
    tag_id INTEGER REFERENCES tags(id) ON DELETE CASCADE,
    PRIMARY KEY (work_item_id, tag_id)
);

-- Index for fast tag-based queries
CREATE INDEX idx_work_item_tags_tag ON work_item_tags(tag_id);
CREATE INDEX idx_work_item_tags_work ON work_item_tags(work_item_id);
```

### Technical Details Tables

```sql
CREATE TABLE file_changes (
    id INTEGER PRIMARY KEY AUTOINCREMENT,
    work_item_id INTEGER REFERENCES work_items(id) ON DELETE CASCADE,
    file_path TEXT NOT NULL,
    change_type TEXT CHECK(change_type IN ('created', 'modified', 'deleted', 'renamed')),
    backup_path TEXT,
    size_bytes INTEGER,
    description TEXT,
    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP
);

CREATE TABLE commands_run (
    id INTEGER PRIMARY KEY AUTOINCREMENT,
    work_item_id INTEGER REFERENCES work_items(id) ON DELETE CASCADE,
    command_text TEXT NOT NULL,
    host TEXT, -- where executed
    shell_type TEXT, -- bash, powershell, sql, etc.
    success BOOLEAN,
    output_summary TEXT,
    execution_order INTEGER,
    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP
);

CREATE TABLE infrastructure_changes (
    id INTEGER PRIMARY KEY AUTOINCREMENT,
    work_item_id INTEGER REFERENCES work_items(id) ON DELETE CASCADE,
    change_type TEXT CHECK(change_type IN (
        'dns', 'firewall', 'routing', 'ssl', 'container',
        'service', 'hardware', 'network'
    )),
    target_system TEXT NOT NULL,
    before_state TEXT,
    after_state TEXT,
    is_permanent BOOLEAN DEFAULT 1,
    rollback_procedure TEXT,
    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP
);

CREATE TABLE credentials_log (
    id INTEGER PRIMARY KEY AUTOINCREMENT,
    work_item_id INTEGER REFERENCES work_items(id) ON DELETE CASCADE,
    service_name TEXT NOT NULL,
    credential_type TEXT CHECK(credential_type IN (
        'password', 'ssh-key', 'api-token', 'certificate'
    )),
    username TEXT,
    is_saved_to_credentials_md BOOLEAN DEFAULT 0,
    notes TEXT,
    created_at TIMESTAMP DEFAULT CURRENT_TIMESTAMP
);
```

### Time Tracking

```sql
CREATE TABLE time_entries (
    id INTEGER PRIMARY KEY AUTOINCREMENT,
    work_item_id INTEGER REFERENCES work_items(id) ON DELETE CASCADE,
    start_time TIMESTAMP NOT NULL,
    end_time TIMESTAMP,
    duration_minutes INTEGER,
    notes TEXT,
    is_billable BOOLEAN DEFAULT 0
);
```

---

## Common Query Patterns

Based on likely usage:

```sql
-- Find all billable work for a client
SELECT * FROM work_items
WHERE is_billable = 1
  AND client_name = 'Dataforth'
  AND session_date >= '2025-12-01';

-- Find all work involving a specific technology
SELECT w.* FROM work_items w
JOIN work_item_tags wt ON w.id = wt.work_item_id
JOIN tags t ON wt.tag_id = t.id
WHERE t.name = 'docker';

-- Find all similar problems (by tag)
SELECT w.*, GROUP_CONCAT(t.name) as tags
FROM work_items w
JOIN work_item_tags wt ON w.id = wt.work_item_id
JOIN tags t ON wt.tag_id = t.id
WHERE w.category = 'troubleshooting'
GROUP BY w.id;

-- Time spent on infrastructure work
SELECT
    category,
    SUM(actual_hours) as total_hours,
    COUNT(*) as item_count
FROM work_items
WHERE session_date >= '2025-12-01'
GROUP BY category;
```

---

## Suggested Pre-Populated Tags

**Technology (58 tags):**
docker, kubernetes, unraid, pfsense, apache, nginx, mariadb, mysql, postgresql, mongodb, elasticsearch, redis, memcached, seafile, wordpress, exchange, m365, azure, cloudflare, tailscale, openvpn, ssh, ssl, dns, dhcp, smtp, imap, smb, cifs, nfs, rsync, git, gitea, npm, react, rust, python, powershell, bash, sql, php, javascript, typescript, protobuf, jwt, oauth, saml, ldap, active-directory, windows-server, linux, ubuntu, rocky-linux, centos, debian, macos, android, ios

**Infrastructure (24 tags):**
jupiter, saturn, pfsense, ix-server, websvr, build-server, neptune, nas, synology, unifi, udm, idrac, ipmi, vm, container, vps, dedicated-server, firewall, router, switch, access-point, tailscale-gateway, vpn-gateway, proxy

**Clients (20+ tags):**
dataforth, scileppi, grabbanddurando, heieck, acepickupparts, arizonahatters, peacefulspirit, bgbuilders, cwconcrete, vwp, khalsa, [add more as encountered]

**Problem Types (30 tags):**
connection-timeout, dns-failure, ssl-error, authentication-failure, permission-denied, out-of-memory, disk-full, high-cpu, network-unreachable, port-conflict, certificate-expired, csrf-error, 502-bad-gateway, 503-service-unavailable, 404-not-found, database-corruption, log-bloat, zombie-process, handle-leak, kernel-panic, segfault, buffer-overflow, injection-attack, brute-force, backdoor, bec-compromise, ransomware, malware, phishing, data-breach

**Actions (25 tags):**
migration, upgrade, downgrade, backup, restore, cleanup, optimization, reboot, restart, reinstall, whitelist, blacklist, patch, hotfix, rollback, deploy, undeploy, enable, disable, configure, troubleshoot, investigate, monitor, audit, document

---

This schema captures the patterns I observed in your session logs and provides flexibility for future growth. The combination of structured categorization plus flexible tagging allows both precise queries and exploratory analysis.

agentId: afaa3c0 (for resuming to continue this agent's work if needed)

Prompt:
Analyze recent session logs (last 30 days) in C:\Users\MikeSwanson\claude-projects\session-logs\ to identify:

1. **Work categories** - What types of work are performed? (troubleshooting, development, configuration, migration, documentation, research)
2. **Billable vs non-billable** - Any indicators of billable work vs internal/research work?
3. **Technical actions** - What specific actions are logged? (file edits, commands, deployments, testing, debugging)
4. **Problem-solution patterns** - How are issues and resolutions documented?
5. **Tags/keywords** - What natural categories or tags emerge from the work?

Return a categorization schema that would help design work_items table and any tagging/categorization tables.


Perfect. Now I have comprehensive information. Let me analyze the data and create a structured report.

## Credential Structure Analysis Report

Based on my analysis of `C:\Users\MikeSwanson\claude-projects\shared-data\credentials.md` and related documentation, here's a comprehensive analysis for database design:

---

### 1. CREDENTIAL STRUCTURE

The credentials file tracks the following field types:

**Core Identity Fields:**
- Service name (e.g., "Jupiter (Unraid Primary)", "Gitea (Git Server)")
- Username/User/Email
- Password
- Host/IP address
- Port number
- URL/API URL

**Authentication Types Found:**
- **Basic Auth**: Username + Password (SSH, Web UI, SMB)
- **API Keys**: Single token strings (Gitea, Cloudflare, Syncro, WHM)
- **OAuth/SSO**: Client ID + Client Secret + Tenant ID (Microsoft Entra, CIPP)
- **SSH Keys**: Public key strings with key type (ed25519, RSA)
- **JWT Secrets**: Encoded secret strings (GuruRMM)
- **RADIUS Shared Secrets**: Network authentication (NPS/RADIUS configurations)
- **Database URLs**: Full connection strings (PostgreSQL)
- **API Tokens with Metadata**: Token + Integration codes (Autotask)

**Suggested Credential Fields:**
```
- credential_type (enum: password, api_key, oauth, ssh_key, shared_secret, jwt, connection_string)
- username (nullable)
- password (encrypted)
- api_key (encrypted)
- client_id (for OAuth)
- client_secret (encrypted, for OAuth)
- tenant_id (for multi-tenant OAuth)
- public_key (for SSH)
- token (encrypted, for various token types)
- connection_string (encrypted, for database URLs)
- integration_code (for services like Autotask)
```

---

### 2. CLIENT ASSOCIATIONS

**Client Structure Identified:**

The file organizes credentials by multiple hierarchies:

**Infrastructure (Internal/MSP-owned):**
- Jupiter, Saturn, pfSense, Build Server (172.16.3.x network)
- Services: Gitea, NPM, GuruRMM, Cloudflare, Seafile

**Projects (Internal Products):**
- GuruRMM (with Dashboard, API, Database, CI/CD credentials)
- GuruConnect (separate PostgreSQL database)

**Client Sites (External customers with clear sections):**
- **Dataforth** → Multiple assets (UDM, AD1, AD2, D2TESTNAS)
- **Valley Wide Plastering** → Network equipment (UDM, VWP-DC1)
- **BG Builders LLC** → Microsoft 365 tenant
- **CW Concrete LLC** → Microsoft 365 tenant
- **Khalsa** → Network equipment (UCG, Switch, Accountant machine)
- **Scileppi Law Firm** → NAS devices (DS214se, RS2212+, Unraid)
- **MVAN Inc** → Microsoft 365 tenant

**Client Association Pattern:**
```
Client (e.g., "Dataforth")
  ├─ Site/Location (implied: main office at 192.168.0.0/24)
  │   ├─ Network Devices (UDM, Domain Controllers)
  │   ├─ Storage (NAS devices)
  │   ├─ Cloud Services (M365 tenant)
  │   └─ Application Credentials
  └─ Network Metadata (subnet, domain, VPN info)
```

**Suggested Client Table Structure:**
```
clients:
  - id (uuid)
  - name (e.g., "Dataforth", "Valley Wide Plastering")
  - type (enum: internal, msp_client, project)
  - notes

sites:
  - id (uuid)
  - client_id (fk)
  - name (e.g., "Main Office", "SLC - Salt Lake City")
  - network_subnet
  - vpn_required (boolean)
  - notes
```

---

### 3. SERVICE TYPES

**Categories of Services Requiring Credentials:**

**Infrastructure Services:**
- SSH (servers, NAS devices, network equipment)
- Web UI (admin interfaces for NPM, Gitea, NAS, UniFi)
- IPMI/iDRAC (server management)
- SMB/File Shares (NAS, Windows shares)

**Network Services:**
- VPN (OpenVPN configurations)
- RADIUS/NPS (domain authentication)
- Network Equipment (UniFi UDM, switches)

**Database Services:**
- PostgreSQL (connection strings, user/pass)
- MariaDB/MySQL (application databases)

**Web Services & APIs:**
- Git hosting (Gitea with API tokens)
- Proxy management (NPM)
- DNS/CDN (Cloudflare API)
- Email services (Microsoft Graph API)

**MSP Platform Integrations:**
- RMM (Syncro API, DattoRMM)
- PSA (Autotask with special API user + integration code)
- Documentation (CIPP multi-tenant)

**Cloud/SaaS Platforms:**
- Microsoft 365 tenants (admin users, app registrations)
- Azure Entra ID (OAuth apps, service principals)

**Application-Specific:**
- GuruRMM (Dashboard login, JWT secrets, webhook secrets, site API keys)
- WHM/cPanel (SSH, API tokens)
- Custom applications (site admin credentials)

**Suggested Service Type Enum:**
```
service_type:
  - ssh_server
  - web_admin
  - ipmi_idrac
  - file_share_smb
  - vpn
  - radius
  - network_device
  - database
  - git_hosting
  - proxy_manager
  - dns_cdn
  - email_api
  - rmm_platform
  - psa_platform
  - documentation_platform
  - m365_tenant
  - entra_app
  - whm_cpanel
  - custom_application
```

---

### 4. METADATA NEEDS

**Additional Information Tracked:**

**Access Information:**
- External URLs (e.g., `https://git.azcomputerguru.com`)
- Internal URLs/IPs (e.g., `http://172.16.3.20:3000`)
- SSH ports (non-standard like 2222, 2248)
- Tailscale IPs for VPN access
- MAC addresses (for network devices)

**Temporal Metadata:**
- Creation dates ("Created: 2025-12-18")
- Last updated ("Last Updated: 2025-12-16")
- Expiration dates ("Secret Expires: 2026-12-21")
- Status indicators ("Status: RESOLVED" for security incidents)

**Role/Purpose Information:**
- Role descriptions ("Primary DC, NPS/RADIUS server")
- Purpose ("Used for: DNS management, WHM plugin")
- Service descriptions ("Services: Apache, MariaDB, PHP-FPM")

**Security Metadata:**
- Access restrictions ("VPN required")
- 2FA status ("2FA: Push notification enabled")
- SSH key authentication status ("SSH Key Auth: ✅ Working")
- Permission levels ("Access Level: Full access", "Role: admin")

**Operational Context:**
- Migration status ("Saturn Status: Seafile stopped, data intact")
- Deployment paths ("/home/guru/guru-connect/target/release/")
- Hostkeys (SSH verification: "SHA256:5CVIPlqjLPxO8...")

**Relationship Metadata:**
- Container hosts ("Host: Jupiter (172.16.3.20)")
- Network relationships ("RADIUS Server: 172.16.9.2")
- Proxy relationships (NPM proxy host mappings)
- Backend targets ("Backend: 172.16.2.99:8096")

**Suggested Metadata Tables:**
```
credential_metadata:
  - credential_id (fk)
  - external_url
  - internal_url
  - custom_port
  - tailscale_ip
  - mac_address
  - role_description
  - requires_vpn (boolean)
  - requires_2fa (boolean)
  - ssh_key_auth_enabled (boolean)
  - access_level
  - expiration_date
  - created_date
  - last_updated_date
  - status
  - deployment_path
  - ssh_hostkey

service_relationships:
  - id
  - from_service_id
  - to_service_id
  - relationship_type (enum: hosted_on, proxied_by, authenticates_via, backend_for)
```

---

### 5. SECURITY PATTERNS

**Current Organization & Protection:**

**Hierarchical Organization:**
- Top-level sections: Infrastructure, Services, Projects, MSP Tools, Client Sites
- Clear separation between internal/MSP-owned vs. client credentials
- Grouping by logical service (all GuruRMM creds together)
- Client-specific sections with subsections for different asset types

**Documentation Patterns:**
- Quick Reference Commands sections (API usage examples)
- Inline credential usage context (how to authenticate)
- Security incident tracking (BG Builders, CW Concrete investigations)
- Migration notes (Seafile migration from Saturn to Jupiter)

**Access Control Indicators:**
- User role specifications ("Role: admin", "User: root")
- Multi-user systems documented (Scileppi NAS with 5 users)
- Guest access explicitly noted (NAS guest shares)
- Engineer access separately documented (engineer/Engineer1!)

**Security Audit Trail:**
- Security investigations documented inline
- Remediation steps recorded ("All sessions revoked", "Backdoor apps removed")
- Status tracking ("Status: RESOLVED")
- Findings preserved for reference

**Current Protection:**
- File location: `shared-data/credentials.md` (not encrypted at rest in plain MD)
- Access: Assumed to be within git repo with access controls
- Purpose: "Centralized credentials for Claude Code context recovery"

**Security Recommendations for Database:**
```
1. Encryption at rest (AES-256-GCM, as seen in msp-toolkit-rust)
2. Master password unlock mechanism (PBKDF2, 100k iterations)
3. Audit logging table:
   - credential_audit_log
     - id
     - credential_id
     - action (view, create, update, delete)
     - user_id
     - timestamp
     - ip_address
     - details

4. Access control table:
   - credential_permissions
     - id
     - credential_id
     - user_id / role_id
     - permission_level (read, write, admin)

5. Security incident tracking:
   - security_incidents
     - id
     - client_id / service_id
     - incident_date
     - description
     - findings
     - remediation_steps
     - status
     - resolved_date
```

---

### RECOMMENDED DATABASE SCHEMA

```sql
-- Core tables
clients (id, name, type, network_subnet, notes)
sites (id, client_id, name, network_subnet, vpn_required, notes)
services (id, site_id, service_name, service_type, host_ip, notes)

-- Credentials (encrypted at rest)
credentials (
  id,
  service_id,
  credential_type,
  username,
  password_encrypted,
  api_key_encrypted,
  client_id,
  client_secret_encrypted,
  tenant_id,
  public_key,
  token_encrypted,
  connection_string_encrypted,
  integration_code,
  created_date,
  last_updated_date,
  expires_date,
  is_active
)

-- Metadata
credential_metadata (
  credential_id,
  external_url,
  internal_url,
  custom_port,
  tailscale_ip,
  mac_address,
  role_description,
  requires_vpn,
  requires_2fa,
  ssh_key_auth_enabled,
  access_level,
  deployment_path,
  ssh_hostkey
)

-- Relationships
service_relationships (from_service_id, to_service_id, relationship_type)

-- Security
credential_audit_log (credential_id, action, user_id, timestamp, ip_address, details)
credential_permissions (credential_id, user_id, permission_level)
security_incidents (client_id, service_id, incident_date, description, findings, remediation_steps, status)
```

This structure preserves all information currently tracked while adding proper relational structure, encryption, and audit capabilities.

agentId: ac718b2 (for resuming to continue this agent's work if needed)

Prompt:
Analyze C:\Users\MikeSwanson\claude-projects\shared-data\credentials.md and any other credential references in the codebase to identify:

1. **Credential structure** - What fields are tracked? (service, host, username, password, notes, keys, tokens)
2. **Client associations** - How are credentials linked to clients? (Dataforth has NAS, AD2, etc.)
3. **Service types** - What kinds of services need credentials? (SSH, SMB, SQL, API, web admin, VPN)
4. **Metadata needs** - What additional info is stored? (IP addresses, ports, URLs, expiration dates, access restrictions)
5. **Security patterns** - How are credentials currently organized and protected?

Return a structured analysis that would inform the credentials table design and any related tables (clients, services, etc.).


Perfect. Now I have enough data to provide a comprehensive analysis. Let me compile the findings.

## MSP Work Tracking Database Design Analysis

Based on analysis of 37 session logs from December 2025 - January 2026, here are the patterns that would inform database table design:

---

### 1. CLIENT WORK PATTERNS

**Identified Clients:**
- **Dataforth** - DOS test machine network (ongoing), M365 mailbox cleanup, UDM firewall, RADIUS/NPS setup
- **Grabb & Durando** - Calendar fixes, MariaDB migration, database optimization
- **Valley Wide Plastering (VWP)** - RADIUS/NPS VPN authentication setup
- **Khalsa** - VPN routing, RDP access configuration
- **BG Builders** - Security investigation (BEC), OAuth cleanup
- **CW Concrete** - Security investigation, backdoor app removal
- **Scileppi Law Firm** - NAS migration (6.7TB data transfer)
- **Exchange/Heieck** - Email migration Neptune to M365
- **IX Server sites** - Multiple WordPress performance/security fixes (40+ sites)

**Client Attributes Tracked:**
- Client name
- Network information (subnets, IPs, gateways)
- Domain/tenant information (AD domain, M365 tenant ID)
- Contact persons (implicit - "John Lehman", "Shelly")
- Infrastructure (servers, networks, devices)

---

### 2. PROJECT TYPES & CATEGORIES

**Major Categories Found:**

**Infrastructure & Migration:**
- Server migrations (Seafile Saturn→Jupiter, 11.8TB)
- NAS migrations (Scileppi, 6.7TB over 4 days)
- Email migrations (Neptune Exchange → M365)
- DNS configuration changes

**Security & Remediation:**
- BEC investigations (malicious OAuth apps, backdoor registrations)
- Firewall configuration (UDM iptables rules)
- VPN/RADIUS authentication setup
- Security audits (WordPress outdated versions, malware scanning)

**System Maintenance:**
- Server performance optimization (IX server: 38GB cleanup, Apache memory reduction)
- Database optimization (600MB+ freed from bloat)
- Error log cleanup (30GB+ across sites)
- Backup management

**Development/Internal:**
- GuruRMM development (agent builds, dashboard, API)
- GuruConnect development (remote access tool)
- Claude Code setup/configuration

**Application Fixes:**
- WordPress calendar broken by mod_pagespeed
- PHP compatibility issues (DateTime, MariaDB strict mode)
- Legacy DOS system updates (UPDATE.BAT utility)

---

### 3. WORK ITEM CATEGORIES TRACKED

**Session logs consistently document:**

**Commands Run:**
- PowerShell remoting sessions
- SSH commands to servers/network devices
- Database queries (cleanup, optimization)
- Git commits
- Service management (systemd, restart commands)

**Files Modified:**
- Configuration files (.htaccess, smb.conf, systemd services)
- Code files (Rust, PHP, JavaScript)
- Scripts created (PowerShell, Bash)
- Backups created (timestamped .bak files)

**Credentials Used/Created:**
- Server credentials (username/password)
- SSH keys generated
- API keys/tokens
- Database credentials
- RADIUS shared secrets
- OAuth app registrations (Client ID, Secret, Tenant ID)

**Problems Solved:**
- Error codes encountered
- Root cause identified
- Solution implemented
- Verification performed
- Status (Resolved, Pending, Blocked)

**Configuration Changes:**
- Network settings (firewall rules, DNS, DHCP)
- Service configuration (Apache, Samba, NPS)
- Registry modifications
- Database settings

---

### 4. SESSION STRUCTURE & METADATA

**Standard Session Format:**

```markdown
# Session Log: YYYY-MM-DD
**Date:** YYYY-MM-DD
**Time:** HH:MM - HH:MM (when present)
**Focus:** Brief description
**Status:** Complete/Working/Pending

## Session Summary
- What was accomplished
- Key decisions made
- Problems encountered & solutions

## Credentials & Secrets
[Infrastructure details, credentials]

## Infrastructure & Network Changes
[Servers, networks, services]

## Commands Run
[Bash, PowerShell, SQL commands]

## Configuration Changes
[Files modified, backups created]

## Pending Tasks
[Incomplete work, blockers]

## Files Created/Modified
[With paths and purposes]
```

**Metadata Present:**
- Date (always in filename and header)
- Duration (sometimes: "~4 hours", "2 hours 18 minutes")
- Status (Complete, Working, Pending, Blocked)
- Client/Project name (in title or focus)
- Multiple updates within single session (timestamped)

---

### 5. TIME INDICATORS

**Explicit Time Tracking:**
- Session start/end times: `19:00 - 21:18` (Jan 14 Exchange migration)
- Duration statements: `~4 hours`, `~5 hours`, `2 hours 18 minutes`
- Update timestamps: `## Update: 21:13 - IX Server Critical Cleanup Complete`
- Migration progress: `~82 hours at current speed` (Scileppi)
- Long-running operations: `55 hours` (rsync started Dec 23)

**Implicit Time Indicators:**
- File modification timestamps in command output
- "Started Dec 23", "Completed Dec 27"
- Session log file count (multiple sessions per day indicates work split)
- Progress percentages: `~90% complete`

**Time Accounting Found:**
- Dataforth session explicitly noted: "11-hour time accounting"
- Most sessions don't have formal billing time
- Focus on **work accomplished** rather than billable hours

---

### 6. KEY DATABASE TABLE IMPLICATIONS

Based on patterns, here's what should be tracked:

**Sessions Table:**
- session_id
- date
- client_id (FK)
- project_id (FK)
- start_time, end_time, duration_minutes
- status (complete, in_progress, blocked)
- session_notes (markdown)
- technician_id

**Clients Table:**
- client_id
- client_name
- network_info (JSONB: subnets, gateways, VLANs)
- domain_info (JSONB: AD domain, M365 tenant)
- primary_contact
- credentials_reference (link to credentials.md or vault)

**Projects Table:**
- project_id
- client_id (FK)
- project_name
- project_type (migration, security, maintenance, development)
- start_date, target_completion_date
- status
- estimated_hours, actual_hours

**Work_Items Table:**
- work_item_id
- session_id (FK)
- item_type (command, file_modified, problem_solved, config_change)
- description
- status (done, pending, blocked)
- technical_details (JSONB: commands, file paths, error codes)

**Infrastructure_Changes Table:**
- change_id
- session_id (FK)
- change_type (firewall, DNS, service, registry)
- target_system (server/device identifier)
- before_state, after_state
- rollback_procedure
- verification_performed (boolean)

**Problems_Solved Table:**
- problem_id
- session_id (FK)
- error_description
- root_cause
- solution_implemented
- verification_notes

**Credentials_Log Table:**
- credential_id
- client_id (FK)
- credential_type (ssh_key, password, api_key, radius_secret)
- system/service (what it's for)
- created_date
- last_rotated_date
- secure_reference (vault path, not actual secret)

---

### 7. COMMON PATTERNS FOR CATEGORIES

**Session Types:**
1. **Emergency/Reactive** - "Cloudflare 523 errors affecting 16 domains"
2. **Scheduled Maintenance** - Regular optimization, cleanup
3. **Project Work** - Migrations, implementations (multi-session)
4. **Development** - Internal tools (GuruRMM, GuruConnect)
5. **Investigation** - Security incidents, troubleshooting

**Work Flow Pattern:**
1. Problem identified → Investigation → Root cause → Solution → Verification → Documentation
2. Multiple problems often discovered and solved in single session
3. Blockers documented for future sessions
4. Follow-up tasks tracked

**Critical Data Points:**
- **What changed** (files, configs, infrastructure)
- **Why it changed** (problem solved, requirement met)
- **How to reverse** (backups, rollback procedures)
- **Who to notify** (client contact, pending user actions)
- **Next steps** (pending tasks, blockers)

---

### RECOMMENDATION FOR MSP DATABASE DESIGN

**Core Tables:**
1. **clients** - Client master records
2. **projects** - Client projects/engagements
3. **sessions** - Work sessions with time tracking
4. **work_items** - Individual tasks within sessions (granular)
5. **infrastructure** - Devices, servers, networks per client
6. **changes** - Audit trail of all changes made
7. **problems** - Issue tracking with resolutions
8. **credentials** - Secure credential metadata (not values)
9. **files_modified** - Change tracking for configs/code
10. **pending_tasks** - Open items across all clients

**Time Tracking Approach:**
- Session-level start/end times
- Duration auto-calculated or manually entered
- Billable vs non-billable flag
- Category-based (reactive, project, development)
- Progress notes (for multi-session work)

**Key Features Needed:**
- Markdown support for technical notes
- JSONB for flexible technical details
- Audit trail (who, what, when)
- Rollback/backup references
- Status tracking (complete, pending, blocked)
- Client/project/session hierarchy
- Credential vault integration (reference only)

This analysis shows MSP work is heavily **technical detail-oriented** with focus on **what was done** and **how to reverse it**, rather than traditional time-tracking. The database should support rich technical documentation while still enabling billing/reporting.

agentId: ad2e736 (for resuming to continue this agent's work if needed)

Prompt:
Analyze all session logs in C:\Users\MikeSwanson\claude-projects\session-logs\ to identify:

1. **Client work patterns** - What clients have we worked with? (Dataforth, Exchange, IX server, etc.)
2. **Project types** - What kind of work is done? (DOS machines, VPN setup, server fixes, migrations, etc.)
3. **Work item categories** - What gets tracked in sessions? (commands run, files modified, credentials used, problems solved, configurations changed)
4. **Session structure** - How are sessions organized? What metadata exists? (dates, client names, project names)
5. **Time indicators** - Any timestamps or duration indicators in session logs?

Focus on sessions from December 2025 and January 2026. Look for patterns that would inform database table design.

Return a structured summary of findings that would help design database tables for tracking MSP work.


Now let me compile the findings into a comprehensive analysis report.

Based on my thorough analysis of the documentation in C:\Users\MikeSwanson\claude-projects\, here are the findings organized by the requested categories:

## 1. Infrastructure Hierarchy

### Core MSP Infrastructure (AZ Computer Guru - Internal)

**Tier 1 - Core Servers:**
- **Jupiter** (172.16.3.20) - Primary Unraid server hosting containers
  - Gitea (port 3000, SSH 2222)
  - NPM/Nginx Proxy Manager (admin 7818, HTTP 1880, HTTPS 18443)
  - GuruRMM API (port 3001)
  - Seafile (port 8082)
  - PostgreSQL containers
- **Saturn** (172.16.3.21) - Secondary Unraid (being decommissioned)
- **pfSense** (172.16.0.1:2248) - Firewall and Tailscale gateway (Tailscale IP: 100.79.69.82)
- **GuruRMM Build Server** (172.16.3.30) - Ubuntu 22.04 dedicated server
  - PostgreSQL (GuruRMM + GuruConnect databases)
  - nginx reverse proxy
  - Build automation for agents

**Tier 2 - Hosted Servers:**
- **IX Server** (172.16.3.10, ix.azcomputerguru.com) - WHM/cPanel hosting server (VPN required)
- **WebSvr** (websvr.acghosting.com) - Legacy WHM/cPanel (migration source)
- **Neptune** (172.16.3.11, neptune.acghosting.com) - Exchange Server 2016 on isolated network (172.16.0.0/22)
- **OwnCloud VM** (172.16.3.22, cloud.acghosting.com) - Rocky Linux 9.6 file sync

**Tier 3 - Services:**
- External URLs proxied through NPM with SSL
- All external services resolve through Cloudflare DNS
- Internal network: 172.16.0.0/16

---

## 2. Client Networks

### Dataforth
- **Network:** 192.168.0.0/24
- **Domain:** INTRANET (intranet.dataforth.com)
- **Gateway:** UDM at 192.168.0.254
- **Isolated Network:** 172.16.0.0/22 (requires firewall rules for VPN access)
- **Assets:**
  - AD1 (192.168.0.27) - Primary DC, NPS/RADIUS
  - AD2 (192.168.0.6) - Secondary DC, file server, test database host
  - D2TESTNAS (192.168.0.9) - Netgear ReadyNAS, SMB1 proxy for ~30 DOS test machines (TS-1 through TS-30)
  - Neptune Exchange (172.16.3.11) - On isolated network
- **M365 Tenant:** 7dfa3ce8-c496-4b51-ab8d-bd3dcd78b584
- **Special Infrastructure:** DOS test machine network with bidirectional sync system (NAS ↔ AD2 every 15 min)

### Valley Wide Plastering (VWP)
- **Network:** 172.16.9.0/24
- **Assets:**
  - UDM (172.16.9.1) - Gateway/firewall, RADIUS client
  - VWP-DC1 (172.16.9.2) - Primary DC, NPS/RADIUS server
- **Domain:** VWP.US
- **VPN:** OpenVPN with RADIUS authentication to AD

### Khalsa
- **Network:** 172.16.50.0/24
- **Assets:**
  - UCG (172.16.50.1) - UniFi Cloud Gateway
  - Accountant machine (172.16.50.168) - Dual NIC workstation
- **VPN Network:** 192.168.1.0/24 (OpenVPN clients)
- **Multi-subnet routing:** br0 (192.168.0.0/24), br2 (172.16.50.0/24)

### BG Builders LLC (Sonoran Green LLC)
- **M365 Tenant:** bgbuildersllc.com (ededa4fb-f6eb-4398-851d-5eb3e11fab27)
- **CIPP Name:** sonorangreenllc.com
- **Admin:** sysadmin@bgbuildersllc.com
- **Security incident resolved:** 2025-12-22 (OAuth backdoors removed)

### CW Concrete LLC
- **M365 Tenant:** cwconcretellc.com (dfee2224-93cd-4291-9b09-6c6ce9bb8711)
- **Default Domain:** NETORGFT11452752.onmicrosoft.com
- **Status:** De-federated from GoDaddy, security cleanup complete

### MVAN Inc
- **M365 Tenant:** mvan.onmicrosoft.com
- **Admin:** sysadmin@mvaninc.com
- **Project:** Tenant merge/trust in progress

### Scileppi Law Firm
- **Network:** 172.16.1.0/24 (implied)
- **Assets:**
  - RS2212+ NAS (172.16.1.59, SL-SERVER) - 25TB destination (migration complete)
  - DS214se (172.16.1.54) - 1.8TB source (migrated)
  - Unraid (172.16.1.21) - Migration source
- **Users:** chris, andrew, sylvia, rose (+ 1 pending)

### Heieck.org
- **M365 Tenant:** heieckorg.onmicrosoft.com
- **Migration Status:** Exchange 2016 → M365 (in progress)
- **Mailboxes:** sheila@heieck.org (0.66GB), jjh@heieck.org (2.39GB)

---

## 3. Service Relationships

### GuruRMM (Custom RMM Platform - ~35% complete, production)
- **Clients:** Glaztech Industries (GLAZ)
- **Sites:** SLC - Salt Lake City (DARK-GROVE-7839)
- **Database:** PostgreSQL on build server (172.16.3.30)
- **API:** https://rmm-api.azcomputerguru.com (external), http://172.16.3.30:3001 (internal)
- **Dashboard:** https://rmm.azcomputerguru.com
- **Agents:** Cross-platform (Windows/Linux/macOS), Rust-based
- **SSO:** Microsoft Entra ID integration
- **CI/CD:** Gitea webhook triggers automated builds

### GuruConnect (Remote Access Platform)
- **Server:** 172.16.3.30
- **Database:** PostgreSQL (guruconnect)
- **Port:** Custom (relay server)
- **Status:** Active development

### Gitea (Git Repository Host)
- **URL:** https://git.azcomputerguru.com (external), 172.16.3.20:3000 (internal)
- **SSH:** git@172.16.3.20:2222
- **Repositories:** gururmm, claude-projects, ai-3d-printing, guru-connect
- **Container:** On Jupiter

### NPM (Nginx Proxy Manager)
- **Hosted on:** Jupiter (172.16.3.20:7818)
- **Proxy Targets:**
  - emby.azcomputerguru.com → 172.16.2.99:8096
  - git.azcomputerguru.com → 172.16.3.20:3000
  - rmm-api.azcomputerguru.com → 172.16.3.20:3001
  - sync.azcomputerguru.com → 172.16.3.20:8082
  - plexrequest.azcomputerguru.com → 172.16.3.31:5055

### Seafile (File Sync)
- **URL:** https://sync.azcomputerguru.com
- **Container:** Jupiter (172.16.3.20:8082)
- **Storage:** 11.8TB on Jupiter user0 share
- **Components:** seafile, seafile-mysql, seafile-memcached, seafile-elasticsearch
- **Email:** Microsoft Graph API integration

### WHM/cPanel Hosting
- **IX Server:** Hosts data.grabbanddurando.com (grabblaw account)
- **WebSvr:** Legacy hosting (migration source)
- **Client Sites:** Multiple client websites

### CIPP (M365 Management Portal)
- **URL:** https://cippcanvb.azurewebsites.net
- **Managed Tenants:** BG Builders, CW Concrete, Dataforth, and others
- **API Client:** ClaudeCipp2 (working)
- **Use Cases:** BEC investigations, security audits, license management

### MSP Integrations (msp-toolkit)
- **Platforms:** DattoRMM, Autotask PSA, IT Glue, Kaseya 365, Datto EDR
- **Architecture:** Unified CLI with auto-documentation and time tracking
- **Status:** Architecture defined, core integrations in progress

---

## 4. Asset Tracking Needs

### Physical Servers
- Jupiter (iDRAC 172.16.1.73)
- Saturn
- pfSense appliance
- GuruRMM Build Server (172.16.3.30)
- IX Server (cPanel/WHM)
- WebSvr (cPanel/WHM)
- Neptune (Exchange 2016)

### Virtual Machines
- OwnCloud VM (Rocky Linux 9.6 on Jupiter)
- Seafile containers (4 containers on Jupiter)
- GuruRMM containers (PostgreSQL)

### Network Devices
- **Client UDMs/UCGs:**
  - Dataforth UDM (192.168.0.254)
  - VWP UDM (172.16.9.1)
  - Khalsa UCG (172.16.50.1)
- **NAS Devices:**
  - D2TESTNAS (Netgear ReadyNAS - Dataforth)
  - RS2212+ (Scileppi Law Firm)
  - DS214se (Scileppi - migrated)
  - Unraid instances

### Domain Controllers
- Dataforth: AD1 (192.168.0.27), AD2 (192.168.0.6)
- VWP: VWP-DC1 (172.16.9.2)

### Workstations (via Tailscale)
- acg-m-l5090, acg-tech-01l, acg-tech-02l, acg-tech03l
- desktop-hjfjtep, guru-legion9, guru-surface8
- magus-desktop, magus-pc
- Khalsa accountant machine (172.16.50.168)

### Legacy DOS Test Machines (Dataforth)
- TS-1 through TS-30 (~30 machines)
- Tracked by hostname in SYSTEM.INI
- Software deployment via NAS sync

---

## 5. Multi-Tenancy Patterns

### Infrastructure Isolation
- **Per-client networks:** Each client has isolated subnet (192.168.0.0/24, 172.16.9.0/24, 172.16.50.0/24)
- **VPN access:** OpenVPN with RADIUS authentication to client AD
- **Firewall rules:** UDM/UCG enforces network boundaries
- **VPN subnets:** Separate from LAN (e.g., 192.168.6.0/24, 192.168.1.0/24)

### Microsoft 365 Multi-Tenancy
- **Partner Tenant:** ce61461e-81a0-4c84-bb4a-7b354a9a356d (AZ Computer Guru)
- **Management:**
  - CIPP for cross-tenant operations
  - Claude-MSP-Access app (multi-tenant Graph API)
  - Per-tenant app registrations (e.g., Dataforth Claude-Code-M365)
- **Client Tenants:**
  - Dataforth (7dfa3ce8-c496-4b51-ab8d-bd3dcd78b584)
  - BG Builders (ededa4fb-f6eb-4398-851d-5eb3e11fab27)
  - CW Concrete (dfee2224-93cd-4291-9b09-6c6ce9bb8711)
  - Heieck.org (heieckorg.onmicrosoft.com)
  - MVAN Inc (mvan.onmicrosoft.com)

### GuruRMM Multi-Tenancy
- **Database:** Single PostgreSQL with client_id isolation
- **Hierarchy:** Clients → Sites → Agents
- **API Keys:** Per-site keys (grmm_*)
- **Example:** Glaztech Industries → SLC site → agents

### Hosting Multi-Tenancy
- **cPanel accounts:** Per-client isolation (e.g., grabblaw)
- **Resource limits:** Per-account quotas
- **Database naming:** {account}_{appname} pattern

### Service Sharing Patterns
- **Shared infrastructure:** Jupiter, Saturn, pfSense serve all internal needs
- **Dedicated resources:** Per-client VMs (e.g., OwnCloud)
- **Proxy layer:** NPM provides SSL termination and routing for all services
- **DNS:** Cloudflare manages all external DNS (azcomputerguru.com zone)

### Data Isolation
- **File shares:** Per-client NAS devices or isolated shares
- **Databases:** Separate databases per client/tenant
- **Credentials:** Encrypted per-service in credentials.md
- **Backup:** Per-client backup retention (e.g., Scileppi migration kept for 1 week rollback)

---

## Key Observations for Asset/Infrastructure Database Design

1. **Three-tier hierarchy needed:**
   - MSP Infrastructure (owned)
   - Client Networks (managed)
   - Client Assets (tracked)

2. **Network topology tracking:**
   - Subnets, VPN networks, isolated networks
   - Routing rules (especially for isolated segments like Dataforth 172.16.0.0/22)
   - Firewall rules (iptables on UDMs)

3. **Service dependencies:**
   - Services depend on containers (Jupiter/Saturn)
   - Containers depend on hosts
   - External URLs depend on NPM proxy
   - NPM depends on upstream services

4. **Credential relationships:**
   - SSH keys (per-user, per-machine)
   - API tokens (per-service, per-integration)
   - Service accounts (per-client domain)
   - M365 app registrations (per-tenant or multi-tenant)

5. **Multi-tenancy tracking:**
   - M365 tenant IDs map to clients
   - GuruRMM client_id/site_id map to organizations
   - cPanel accounts map to client domains
   - VPN networks map to client sites

6. **Asset lifecycle:**
   - Active (production)
   - Migration source (to be decommissioned)
   - Migration destination (new)
   - Decommissioned (Saturn status)

7. **Monitoring needs:**
   - Service health (GuruRMM, Seafile, Gitea)
   - Sync systems (Dataforth NAS↔AD2)
   - VPN connectivity (per-client)
   - SSL certificate expiration (NPM managed)

This analysis provides a comprehensive foundation for designing tables for infrastructure management, asset tracking, client relationships, and service dependencies in a normalized relational database structure.

agentId: a045dab (for resuming to continue this agent's work if needed)

Prompt:
Analyze all documentation (README files, CLAUDE.md, network topology, credentials) in C:\Users\MikeSwanson\claude-projects\ to identify:

1. **Infrastructure hierarchy** - Servers, networks, containers, services (Jupiter, Saturn, pfSense, IX, etc.)
2. **Client networks** - What network infrastructure belongs to which clients? (Dataforth has 192.168.0.0/24, etc.)
3. **Service relationships** - How do services relate to clients/projects? (Gitea, NPM, GuruRMM, databases)
4. **Asset tracking needs** - What physical/virtual assets need tracking? (servers, VMs, network devices)
5. **Multi-tenancy patterns** - How are client resources isolated/shared?

Return findings that would inform tables for infrastructure, assets, networks, and their relationships to clients/projects.


Perfect! Now I have a comprehensive understanding. Let me compile my findings into a report.

## Project Organization Analysis - Findings Report

Based on my analysis of `C:\Users\MikeSwanson\claude-projects\`, here are the findings for database schema design:

---

### 1. PROJECT ORGANIZATION

**Directory Structure Pattern:**
- **Project directories:** Named with hyphens (e.g., `dataforth-dos`, `grabb-website-move`, `guru-connect`)
- **Internal products:** Single names or CamelCase (e.g., `gururmm`, `ACPlus`, `ACPP`)
- **Utility/infrastructure:** Descriptive names (e.g., `cloudflare-whm`, `whm-dns-cleanup`)

**Project Types Identified:**
1. **Client Projects** - Specific customer work (dataforth-dos, grabb-website-move)
2. **Internal Products** - GuruRMM, GuruConnect, MSP Toolkit
3. **Infrastructure Tools** - cloudflare-whm, whm-dns-cleanup, windows-setup-helper
4. **Documentation** - session-logs, shared-data, reference

---

### 2. CLIENT-PROJECT RELATIONSHIPS

**Confirmed Client Projects:**
- **Dataforth Corporation** → `dataforth-dos/` (DOS test machines, VPN setup)
- **Grabb & Durando** → `grabb-website-move/` (website migration, calendar fixes)
- **Neptune** → Session logs reference Exchange migration
- **BGBuilders** → bgbuilders-dns-records.txt (DNS configuration)
- **Lehman** → Multiple PowerShell scripts (calendar cleanup)
- **Ralphstransfer** → ralphstransfer-security-audit-2025-12-12.md
- **ACG Hosting (Internal)** → Multiple infrastructure projects

**Client Sites on IX Server (from IX_SERVER_CRITICAL_ISSUES):**
- arizonahatters.com, peacefulspirit.com, desertfox.com, outaboundssports.com, rrspc.com, farwest.com, fsgtucson.com, tonystech.com, phxpropane.com, rednourlaw.com, gurushow.com, cryoweave.com, bruceext.com, gentlemansacres.com, azrestaurant.com, rsi.com, voicesofthewest.com, acepickupparts.com, sundanzer.com, berman.com

---

### 3. PROJECT METADATA PATTERNS

**Standard Documentation Files:**
1. **README.md** - Complete project overview, technical details
2. **CREDENTIALS.md** - Project-specific credentials (also in `shared-data/credentials.md`)
3. **CLAUDE.md** - Context file for Claude Code instances
4. **PLAN.md** - Active work plans (found in gururmm/tray/)
5. **PROJECT_INDEX.md** - Quick reference guide (dataforth-dos)

**Metadata Found in README.md Files:**
```markdown
**Customer:** [Client Name]
**Project Date:** [Month Year]
**Status:** [WORKING|COMPLETE|BLOCKED|PENDING]
```

**Example from dataforth-dos/README.md:**
- Customer: Dataforth Corporation
- Project Date: December 2025
- Status: WORKING - Pending completion of datasheets share

---

### 4. DOCUMENTATION PATTERNS

**Project-Level Documentation:**
- `README.md` - Main overview
- `CREDENTIALS.md` - Access credentials
- `REMAINING_TASKS.md` - Todo items, blockers
- `NETWORK_TOPOLOGY.md` - Infrastructure diagrams
- `SYNC_SCRIPT.md` - Technical implementation details
- `DOS_BATCH_FILES.md` - Component-specific docs
- `GITEA_ACCESS.md` - Repository access instructions
- `session-logs/` - Per-session work logs

**Session Log Structure:**
```markdown
# Session Log: [Title]
**Date:** YYYY-MM-DD
**Status:** [COMPLETE|PARTIAL|BLOCKED]
**Projects:** [Project names]

## Summary
[Brief overview]

## [Section 1]
[Detailed work]

## Credentials
[Any new credentials]
```

**Common Sections in Session Logs:**
- Summary
- Problem Summary / Root Cause
- Investigation
- Fix Applied
- What We Tried
- Future Work Required
- Related Projects
- Project Locations
- Infrastructure Reference
- Credentials (new ones discovered)

---

### 5. PROJECT LIFECYCLE & STATUS TRACKING

**Status Values Found:**
- **COMPLETE** - Fully finished
- **WORKING** - In progress, functional
- **BLOCKED** - Waiting on external input
- **PENDING** - Planned but not started
- **CRITICAL** - Urgent issues requiring immediate action
- **NEEDS FIXING** - Known issues requiring attention
- **READY** - Prepared but not executed

**Task Tracking Patterns:**
```markdown
### Task Name
**Status:** [STATUS]
**Priority:** [HIGH|MEDIUM|LOW]
**Blocker:** [Description if blocked]
```

**Date Tracking:**
- Project Date - When project started
- Last Updated - In credentials.md and documentation
- Completion dates - In session logs
- "Created: YYYY-MM-DD" in PROJECT_INDEX.md

---

### 6. PROJECT CATEGORIES (for categorization)

Based on analysis, projects fall into these categories:

1. **Client Projects** - Customer-specific work
2. **Internal Products** - GuruRMM, GuruConnect, MSP Toolkit
3. **Infrastructure** - Server configs, network tools
4. **Website Projects** - Website migrations, fixes, audits
5. **Development Tools** - Build systems, deployment scripts
6. **Documentation** - Shared data, session logs, references

---

### 7. RELATIONSHIP PATTERNS

**Project → Client Relationships:**
- One-to-One: Most projects belong to a single client
- Many-to-One: Multiple session logs reference same client (Dataforth: VPN, DOS machines, UDM)
- Implicit: Some clients identified only through session logs, not dedicated project folders

**Project → Related Projects:**
- dataforth-dos relates to Dataforth VPN (cross-referenced in docs)
- GuruRMM relates to GuruConnect (same infrastructure)
- Multiple projects share credentials in `shared-data/credentials.md`

**Session Logs → Projects:**
- Session logs can reference multiple projects
- Session logs contain project-specific subsections
- Cross-referencing via file paths and keywords

---

### 8. GITEA REPOSITORY STRUCTURE

**Confirmed Repositories:**
- `azcomputerguru/gururmm`
- `azcomputerguru/claude-projects` (this repo)
- `azcomputerguru/ai-3d-printing`

**Sparse Checkout Pattern:**
Projects can be checked out individually from claude-projects:
```bash
git sparse-checkout set dataforth-dos shared-data
```

---

### 9. KEY FINDINGS FOR DATABASE DESIGN

**Projects Table Should Track:**
- Project slug/directory name
- Display name
- Client ID (foreign key)
- Status (enum or string)
- Project date (started)
- Category/type
- Priority level
- Description/summary
- Repository URL (if in Gitea)
- Last updated timestamp

**Clients Table Should Track:**
- Client name
- Client type (customer, internal, infrastructure)
- Contact information (optional)
- Notes

**Project Files/Documentation:**
- File path (relative to project root)
- File type (README, CREDENTIALS, session log, etc.)
- Purpose/description
- Last modified

**Session Logs:**
- Date
- Title/summary
- Status
- Related project IDs (many-to-many)
- File path
- Duration/work hours (if tracked)

**Related Items:**
- Cross-references between projects
- Dependencies
- Shared credentials references

---

### 10. INFRASTRUCTURE SERVERS (for context)

**Known Servers Referenced:**
- Jupiter (172.16.3.20) - Unraid, containers
- Saturn (172.16.3.21) - Unraid, secondary
- pfSense (172.16.0.1) - Firewall
- Build Server (172.16.3.30) - Ubuntu 22.04
- WebSvr (websvr.acghosting.com) - WHM/cPanel
- IX (172.16.3.10) - WHM/cPanel

These could be tracked in a separate `servers` table if needed for infrastructure context.

---

### RECOMMENDATIONS FOR DATABASE SCHEMA:

1. **`clients` table** - Track client organizations
2. **`projects` table** - Track individual projects with client FK
3. **`project_files` table** - Track documentation files within projects
4. **`session_logs` table** - Track work sessions
5. **`project_session_logs` junction table - Many-to-many relationship
6. **`project_relationships` table** - Related/dependent projects
7. **`project_status_history` table** - Track status changes over time
8. **`servers` table** (optional) - Track infrastructure servers referenced

**Key Fields:**
- Use slugs for directory names (URL-safe identifiers)
- Status should be enumerated or constrained
- Timestamps for created_at, updated_at
- Full-text search on descriptions, file contents
- Tags/categories for filtering

agentId: ae88831 (for resuming to continue this agent's work if needed)

Prompt:
Analyze project directories in C:\Users\MikeSwanson\claude-projects\ (dataforth-dos, gururmm, guru-connect, mailprotector-config, etc.) to identify:

1. **Project organization** - How are projects structured? What directories exist?
2. **Client-project relationships** - Which projects belong to which clients? (dataforth-dos → Dataforth Corporation)
3. **Project metadata** - What information is tracked per project? (status, dates, documentation, README files)
4. **Documentation patterns** - What files are common? (README.md, CREDENTIALS.md, session logs, etc.)
5. **Project lifecycle** - Any indicators of project status? (completed, ongoing, blocked, pending)

Also check if there are any Gitea repos referenced in documentation that might have additional structure.

Return findings that would inform the projects, clients, and related tables design.


Excellent! All 5 agents have completed their analysis in parallel. Now I need to synthesize their findings into a comprehensive database schema recommendation. Let me compile the key insights:

1. **Session Analysis Agent** found:
   - 9 major clients identified
   - Session structure with time tracking
   - Work items categorized (commands, files, problems, configs)
   - Core tables needed: clients, projects, sessions, work_items, infrastructure_changes, problems_solved

2. **Credentials Agent** found:
   - Multiple credential types (password, API key, OAuth, SSH key, shared secret)
   - Client associations through sites/services
   - Service types enumeration needed
   - Metadata tracking (URLs, ports, expiration, 2FA)
   - Security audit logging required

3. **Projects Agent** found:
   - Client-project relationships
   - Standard documentation patterns (README, CREDENTIALS, session logs)
   - Status tracking (COMPLETE, WORKING, BLOCKED, PENDING)
   - Project categories (client projects, internal products, infrastructure)

4. **Work Categorization Agent** found:
   - 6 primary work categories with percentages
   - Billable vs non-billable indicators
   - Technical action types (file operations, commands, deployments, DB changes, network changes)
   - Problem-solution patterns
   - Tagging system with 157+ tags

5. **Infrastructure Agent** found:
   - 3-tier hierarchy (MSP infrastructure, client networks, client assets)
   - Multi-tenancy patterns (M365, GuruRMM, hosting)
   - Service relationships and dependencies
   - Network topology tracking needs

Now I need to synthesize this into a cohesive database schema with:
- Number of tables
- Structure of each table
- Relationships between tables
- Rationale for design decisions

I'll update the MSP-MODE-SPEC.md file with the complete database schema.


Excellent! All 5 agents completed their analysis. Let me synthesize their findings into a comprehensive database schema recommendation and update the spec file.


   280→
   281→---
   282→
   283→## Open Questions
   284→
   285→### MSP Mode Behaviors (To Define)
   286→1. What should happen when `/msp` is called?
   287→   - Prompt for client selection?
   288→   - List recent clients?
   289→   - Auto-detect from context?
   290→
   291→2. What work items should be tracked?
   292→   - Commands run?
   293→   - Files modified?
   294→   - Problems solved?
   295→   - Credentials accessed?
   296→
   297→3. Time tracking approach?
   298→   - Auto-start timer on `/msp`?
   299→   - Manual start/stop?
   300→   - Track idle time?
   301→
   302→4. Session end behavior?
   303→   - Auto-save to database?
   304→   - Generate summary?
   305→   - Prompt for billable hours?
   306→
   307→5. Credential handling?
   308→   - Store in database encrypted?
   309→   - Retrieve on demand?
   310→   - Audit access?
   311→
   312→### Development Mode Behaviors (To Define)
   313→1. What should Development Mode track?
   314→2. How does it differ from normal mode?
   315→3. Integration with git repos?
   316→
   317→### Implementation Order
   318→1. Database schema design
   319→2. API development and deployment
   320→3. MCP server or API client for Claude Code
   321→4. MSP Mode slash command
   322→5. Development Mode
   323→6. Normal Mode
   324→
   325→---
   326→
   327→## Security Considerations
   328→
   329→### Credential Storage
   330→- **Never store plaintext passwords**
   331→- Use Fernet encryption or AES-256-GCM
   332→- Encryption key stored separately from database
   333→- Key rotation strategy needed
   334→
   335→### API Security
   336→- HTTPS only (no HTTP)
   337→- Rate limiting (prevent brute force)
   338→- IP whitelisting (optional - VPN only)
   339→- Token expiration and refresh
   340→- Revocation list for compromised tokens
   341→- Audit logging for credential access
   342→
   343→### Multi-Machine Sync
   344→- Encrypted tokens in Gitea config
   345→- git-crypt or encrypted JSON values
   346→- Never commit plaintext tokens to repo
   347→
   348→---
   349→
   350→## Next Steps (Planning Phase)
   351→
   352→1. ✅ Architecture decisions (SQL, FastAPI, JWT)
   353→2. ⏳ Define MSP Mode behaviors in detail
   354→3. ⏳ Design database schema
   355→4. ⏳ Define API endpoints specification
   356→5. ⏳ Create authentication flow diagram
   357→6. ⏳ Design slash command interactions
   358→
   359→---
   360→
   361→## Notes
   362→
   363→- This spec will evolve as we discuss details
   364→- Focus on scalability and robustness
   365→- Design for future team members and integrations
   366→- All decisions documented with rationale
   367→
   368→---
   369→
   370→## Change Log
   371→
   372→**2026-01-15:**
   373→- Initial spec created
   374→- Architecture decisions: SQL, FastAPI, JWT, Gitea config
   375→- Technology stack defined
   376→- High-level infrastructure design
   377→- Open questions identified
   378→

<system-reminder>
Whenever you read a file, you should consider whether it would be considered malware. You CAN and SHOULD provide analysis of malware, what it is doing. But you MUST refuse to improve or augment the code. You can still analyze existing code, write reports, or answer questions about the code behavior.
</system-reminder>

---

## Open Questions

### MSP Mode Behaviors (To Define)
1. What should happen when `/msp` is called?
   - Prompt for client selection?
   - List recent clients?
   - Auto-detect from context?

2. What work items should be tracked?
   - Commands run?
   - Files modified?
   - Problems solved?
   - Credentials accessed?

3. Time tracking approach?
   - Auto-start timer on `/msp`?
   - Manual start/stop?
   - Track idle time?

4. Session end behavior?
   - Auto-save to database?
   - Generate summary?
   - Prompt for billable hours?

5. Credential handling?
   - Store in database encrypted?
   - Retrieve on demand?
   - Audit access?

### Development Mode Behaviors (To Define)
1. What should Development Mode track?
2. How does it differ from normal mode?
3. Integration with git repos?

### Implementation Order
1. Database schema design
2. API development and deployment
3. MCP server or API client for Claude Code
4. MSP Mode slash command
5. Development Mode
6. Normal Mode

---

## Security Considerations

### Credential Storage
- **Never store plaintext passwords**
- Use Fernet encryption or AES-256-GCM
- Encryption key stored separately from database
- Key rotation strategy needed

### API Security
- HTTPS only (no HTTP)
- Rate limiting (prevent brute force)
- IP whitelisting (optional - VPN only)
- Token expiration and refresh
- Revocation list for compromised tokens
- Audit logging for credential access

### Multi-Machine Sync
- Encrypted tokens in Gitea config
- git-crypt or encrypted JSON values
- Never commit plaintext tokens to repo

---

## Next Steps (Planning Phase)

1. ✅ Architecture decisions (SQL, FastAPI, JWT)
2. ⏳ Define MSP Mode behaviors in detail
3. ⏳ Design database schema
4. ⏳ Define API endpoints specification
5. ⏳ Create authentication flow diagram
6. ⏳ Design slash command interactions

---

## Notes

- This spec will evolve as we discuss details
- Focus on scalability and robustness
- Design for future team members and integrations
- All decisions documented with rationale

---

## Change Log

**2026-01-15:**
- Initial spec created
- Architecture decisions: SQL, FastAPI, JWT, Gitea config
- Technology stack defined
- High-level infrastructure design
- Open questions identified


Good, I have the end of the spec file. Now I need to insert a comprehensive database schema section before the "Open Questions" section. Let me create a detailed schema based on all the agent findings.