CHAI DART™
Automated Application Portfolio Intelligence for Enterprise Modernization
How to Use This Document
| If you are a... | Start with... | Key sections |
|---|---|---|
| Cloud Architect evaluating modernization tooling | Section 1 (What is CHAI DART) | Sections 1, 2, 5, 7 |
| DevOps / Infrastructure Engineer running discovery | Section 3 (Discovery) | Sections 3, 4, 5 |
| CIO / CDO seeking portfolio rationalization | Section 6 (Reports) | Sections 1, 6, 7 |
| Application Team Lead planning migration waves | Section 5 (Rationalization) | Sections 3, 5, 6 |
| Cloud Cost Analyst estimating AWS migration spend | Section 6.3 (AWS Cost) | Sections 5, 6 |
1. What is CHAI DART™?
CHAI DART™ (Discovery, Assessment & Rationalization Tool) is CloudHedge's AI-powered application portfolio intelligence platform. It provides automated, agentless discovery and deep assessment of enterprise application estates running on Windows and Linux servers — combining live host analysis, network dependency mapping, and automated rationalization into a single intelligence engine.
45% of enterprise cloud migrations fail due to inadequate assessment. Traditional approaches rely on manual interviews, spreadsheets, and static code scans — taking weeks per application and producing error-prone, incomplete intelligence. DART replaces this with automated, AI-driven discovery that delivers complete application context in hours, not weeks.
DART answers three fundamental questions every enterprise must answer before modernizing:
- What do I have? — A complete, accurate inventory of every application, component, service, and network connection across the estate
- How complex is it to migrate? — Automated complexity scoring per application using DART's R6Ai® intelligence engine
- What should I do with each application? — Data-driven 6R rationalization recommendations with AWS cost projections
Key Differentiators
| Capability | Manual Assessment | CHAI DART™ |
|---|---|---|
| Discovery speed | 2–3 weeks per app | Hours per project (50+ hosts) |
| Network dependency mapping | Manual interviews | Automated Netwatch live capture |
| Complexity scoring | Expert opinion, subjective | Formula-based, reproducible |
| 6R recommendation | Spreadsheet | Automated per host/component |
| AWS cost projection | Manual sizing | Automated EC2 mapping per region |
| Graviton readiness | Not assessed | Built-in Graviton readiness indicator |
| Reporting | Manual PowerPoint | DART Report + Practitioner Report, PDF |
2. How DART Discovery Works
2.1 Discovery Architecture
DART uses an agentless architecture. No software is permanently installed on the source servers. CHAI connects to each host over the network using standard protocols (SSH for Linux, WinRM for Windows) to collect system state information.
2.2 Two-Phase Discovery Process
DART discovery operates in two phases:
| Phase | What It Does | Windows | Linux |
|---|---|---|---|
| Phase 1 | Collects static host information: OS, CPU, memory, disk, packages, installed software, running processes, network configuration, environment variables | Supported | Supported |
| Phase 2 (X-Ray) | Attaches dynamic probes to capture live process-to-process communications, outbound connections, file system writes | Not supported | Supported |
Non-Invasive Discovery (Non-X-Ray): For Java application servers (WebLogic, WebSphere, Tomcat, JBoss), DART performs a single-phase discovery. Outgoing connections are determined directly from the application server configuration (DataSource definitions, JMS modules, etc.), making X-Ray unnecessary.
2.3 Projects and Hosts
DART organizes discovery work into Projects. Each project is a logical grouping of hosts:
- Up to 50 hosts per project (Linux and Windows mixed)
- Hosts added by registering credentials (SSH key or password for Linux; WinRM credentials for Windows)
- Hosts can also be added via CSV bulk upload or offline discovery utility
- Projects replaced the legacy "Wave" concept in DART 2.x
3. Windows Host Discovery
DART's Windows discovery is non-intrusive and collects comprehensive system and application state information using WinRM over port 5986.
3.1 What DART Discovers on Windows
IIS Website Discovery (Full Support)
| Data Point | Description |
|---|---|
| Application Pool Name | Pool used by the IIS website |
| Authentication Type | Anonymous, Forms-based, Windows, etc. |
| Network Bindings | All protocols and ports |
| Virtual Directories | Physical paths and drive types |
| SSL Certificates | Issuer, issued-to, validity dates |
| Backing Services | Connection strings used by the site |
| Default Documents | Configured default document list |
Console & Windows Service Discovery (Beta)
For both Console Applications and Windows Services, DART collects:
- List of file/folder paths of all dependencies
- All DLL dependencies
- Process ID, memory usage, ports, command line, platform (32/64-bit), subsystem
Process Ignore List
Specific processes can be excluded from Windows discovery using the Process Ignore List, configurable per project or globally in Settings.
4. Linux Host Discovery
DART connects to Linux hosts over SSH (port 22) and supports both general process discovery and specialized non-X-Ray discovery for major Java application servers.
4.1 General Linux Process Discovery
For any Linux process, Phase 1 collects:
- CPU, memory, disk, OS, DNS configuration
- All running processes and their ports
- Environment variables, scheduled jobs, network configuration
- Static host entries, external DNS servers
Phase 2 (X-Ray) additionally captures:
- Live inbound and outbound network connections per process
- Hard-coded network dependencies
- File system writes
- External services consumed
4.2 Java Application Server Discovery (Non-X-Ray)
For the four major Java application servers, DART performs a specialized single-phase discovery that extracts full application configuration — eliminating the need for X-Ray probes:
Supported Java Application Server Objects
| Object | WebLogic | WebSphere | Tomcat | JBoss |
|---|---|---|---|---|
| Shared Application Libraries | Discover | Discover | Discover | Discover |
| Server Certificates | Discover | Discover | Discover | Discover |
| Data Sources | Discover | Discover | Discover | Discover |
| JMS Modules | Discover | Discover | Discover | Discover |
| JNDI Realms | — | Discover | Discover | Discover |
| Cluster Configuration | Discover | Discover | Discover | Discover |
5. Network Intelligence
5.1 Netwatch — Live Network Dependency Capture
Netwatch is DART's network monitoring capability. It captures all inbound and outbound network connections made to/from each host over a configurable monitoring duration — providing ground-truth evidence of actual application communication patterns.
Netwatch is critical for migration wave planning: it reveals hidden dependencies that no static scan or interview can uncover.
How Netwatch Works:
1. Start Netwatch on selected hosts from the project's Discover view
2. Set monitoring duration; optionally clear previous Netwatch data
3. Netwatch runs in the background — status: waiting → in progress → completed
4. Download results as CSV from the project home page (NetWatch Data)
5. DART automatically identifies IPs shared across projects and suggests logical machine groupings
Netwatch CSV Fields: Project_Wave_Name, Host_Alias, Host_IP, Direction, Port, ProcessID, ProcessName, Connected_Host_IP
5.2 Topology Viewer
DART's Topology view visualizes the connections between all discovered hosts and their processes.
Two Topology Views:
| View | Shows | Use Case |
|---|---|---|
| Host View | All hosts in the project and their process connections | Infrastructure-level dependency map |
| Application View | Processes grouped by defined Applications | Application-level communication map |
Both views support:
- Filtering by host or application
- Customizable layouts
- Double-click on any process, host, or application node for detailed information
6. Rationalization & Assessment
After discovery, DART's Rationalize module applies intelligence to generate actionable migration recommendations.
6.1 The 6R Framework — Host Classification
Every discovered host is classified using the industry-standard 6R migration framework:
| Classification | Definition | CloudHedge Capability |
|---|---|---|
| Reinvest | Strategic apps warranting investment to modernize | Sub-classified as Rehost, Replatform, or Refactor |
| Rehost | Lift-and-shift to cloud, no modifications | Migrate large-scale legacy apps to meet timeline objectives |
| Replatform | Move largely unchanged, replace certain components | Windows-to-Linux migration; leaner cloud options |
| Refactor | Substantial overhaul for cloud-native | Transition to microservices architecture with CHAI Flow™ |
| Retain | No cloud migration | On-premises compliance, performance, or investment constraints |
| Retire | Decommission | Redundant or consolidatable applications |
Classification values are set per host and feed directly into DART report generation.
6.2 Application Complexity Scoring
DART calculates a containerization complexity score for every discovered process. This is a formula-based, reproducible score — not a subjective expert estimate.
Complexity Score Range:
| Score | Complexity |
|---|---|
| 0 – 25 | Low |
| 26 – 35 | Medium |
| 36 and above | High |
Complexity is calculated from:
For Linux X-Ray processes:
- 32-bit process or library detected?
- Hard-coded network dependencies?
- Additional packages required?
- Process user (root vs. service account)?
- Special file permissions or special files detected?
- Hard-coded /etc/hosts entries?
- External DNS servers?
- External services consumed?
- File system writes detected?
For Windows IIS websites:
- Windows features required?
- Additional IIS modules required?
- WebAppPool creation required?
- SSL certificates required?
- Group Managed Service Accounts (gMSAs) required?
- File system writes detected?
- External services consumed?
For Java App Servers (Non-X-Ray — WebSphere, WebLogic, Tomcat):
- External Active Directory integration?
- Database integration (DB2, etc.)?
- Message Queue integration?
- SSL certificates required?
6.3 AWS Cost Comparison
DART calculates the estimated monthly cost of hosting all discovered hosts in an AWS region of your choice.
Cost Calculation Components:
- Compute: EC2 instance selection based on discovered CPU/memory/OS specs
- Storage: EBS/storage based on discovered disk usage
- Network: Data transfer costs
- Business Support: AWS support tier
- VDI: Windows Desktop OS virtualization costs
Features:
- Automatic EC2 instance type mapping per AWS region
- Override instance types to model different cost scenarios
- Compare costs across multiple AWS regions
- Pre- and post-Broadcom VMware cost comparison for savings calculation
- 1-year and 3-year NURI (No Upfront Reserved Instance) options
Prerequisites: Project's Target Cloud must be set to AWS with a preferred region configured.
6.4 AWS Graviton Readiness Assessment
Included by default in every DART project. For each discovered host and component, DART shows:
- Graviton Readiness Indicator (compatible / not compatible)
- Graviton-compatible EC2 instance type recommendations
- Readiness by Application Component Types, Technology Types, and Complexity Levels
7. DART Reports & Dashboards
DART generates two types of reports, available as downloadable PDFs.
7.1 DART Report (CXO / Executive)
The DART Report is the project landing page itself — a live, interactive executive summary automatically generated from discovery data.
7.2 Practitioner Report
The Practitioner Report is the detailed technical report for the IT teams responsible for executing the modernization. It is available per Application, per Component, or per Host.
Sections:
| Section | Contents |
|---|---|
| Executive Summary | Editable workshop notes and summary |
| Host Distribution | Breakdown by OS (Linux, Windows) |
| Complexity Distribution | All applications with calculated complexity scores |
| Technology Stack | Application components by technology |
| Topology | Network dependency map |
| Application Information | Per-application details and rationalization |
| Host Information | OS, IP, CPU cores, memory, CPU family, DNS, storage |
Accessing Practitioner Reports:
- From the Rationalize tab → Hosts tab → View Practitioner Report
- From the Rationalize tab → Applications list → View Practitioner Report
- From the project landing page → Applications, Components, or Hosts sections
7.3 Report Comparison
| Feature | DART Report | Practitioner Report |
|---|---|---|
| Audience | CIO, CDO, Migration Lead | DevOps Engineers, App Owners, Migration Teams |
| Scope | Full portfolio / project | Per application, component, or host |
| Complexity detail | Distribution view | Per-process scoring breakdown |
| Host detail | Summary table | Full OS, CPU, memory, storage, DNS |
| Editable content | No | Yes (Executive Summary) |
| Graviton readiness | Yes | Yes |
| Download |
8. DART Assessment Workflow
The complete end-to-end DART workflow from project setup to report generation:
9. Supported Technology Stack
Application Servers & Middleware
| Technology | Discovery Support | Discovery Type |
|---|---|---|
| Oracle WebLogic 12.1.3, 12.2.1.4 | Full | Non-X-Ray (single phase) |
| IBM WebSphere 8.x, 9.x | Full | Non-X-Ray (single phase) |
| Apache Tomcat 7, 8, 9, 10 | Full | Non-X-Ray (single phase) |
| JBoss EAP 6.1 | Full | Non-X-Ray (single phase) |
| IIS (Windows) | Full | Windows discovery |
| General Linux processes | Full | Phase 1 + Phase 2 (X-Ray) |
| Console Applications (Windows) | Beta | Phase 1 |
| Windows Services | Beta | Phase 1 |
Operating Systems — Host Support
| OS | Version | Discovery Support |
|---|---|---|
| Red Hat Enterprise Linux | 7.x, 8.x | Phase 1 + Phase 2 |
| Ubuntu | 16+ | Phase 1 + Phase 2 |
| Windows Server | 2012 R2 and above | Phase 1 (non-intrusive) |
| Windows Server | 2016 | Phase 1 (non-intrusive) |
Connection Protocols
| Host OS | Protocol | Default Port |
|---|---|---|
| Linux | SSH (key-based or password) | 22 |
| Windows | WinRM (Basic or Kerberos) | 5986 |
| CHAI → OmniDeq | HTTPS | 443 |
10. Business Outcomes
CHAI DART™ delivers measurable, documented outcomes at the project level:
What Organizations Get from DART
| Deliverable | Description |
|---|---|
| Complete host inventory | Every Windows and Linux host with OS, CPU, memory, disk, installed packages |
| Application dependency map | Live Netwatch capture of all network connections — inbound, outbound, ports, processes |
| Application complexity scores | Automated High/Medium/Low scoring per process, based on 10+ containerization factors |
| Technology stack report | Distribution of app servers, databases, OS types across the portfolio |
| OS license expiry timeline | Which hosts are running end-of-life or near-expiry OS versions, with 5-band timeline |
| 6R rationalization | Per-host cloud migration strategy: Rehost, Replatform, Refactor, Retain, Retire |
| AWS cost projection | Monthly cost estimate for hosting the entire discovered portfolio in target AWS region |
| Graviton readiness | Per-component and per-host Graviton compatibility assessment |
| DART Report (PDF) | Executive-ready portfolio summary for CIO/CDO stakeholders |
| Practitioner Report (PDF) | Detailed per-app technical report for migration execution teams |
Appendix A — DART vs. Traditional Assessment
| Dimension | Traditional / Manual | CHAI DART™ |
|---|---|---|
| Data collection | Interviews, questionnaires, spreadsheets | Agentless automated discovery via SSH / WinRM |
| Discovery time | 2–3 weeks per application | Hours for a 50-host project |
| Network dependencies | Self-reported, often incomplete | Netwatch live capture — ground truth |
| Complexity assessment | Subjective expert estimate | Formula-based R6Ai® scoring — reproducible |
| OS lifecycle awareness | Manual research per application | Automatic detection with 5-band expiry timeline |
| AWS cost projection | Manual EC2 sizing spreadsheet | Automated per-host EC2 mapping per region |
| Report quality | Variable, manual effort | Consistent, auto-generated DART + Practitioner PDFs |
| Graviton assessment | Not typically included | Built-in Graviton readiness per host/component |
| Scalability | Bottlenecked by analyst capacity | Parallel discovery across all hosts simultaneously |
Appendix B — Key DART Concepts Glossary
| Term | Definition |
|---|---|
| Project | A logical grouping of up to 50 hosts for discovery and assessment (formerly "Wave" in pre-2.x versions) |
| Host | A physical or virtual machine (Linux or Windows) added to a DART project for discovery |
| Phase 1 | Static discovery — collects OS, hardware, installed packages, and process list |
| Phase 2 (X-Ray) | Dynamic discovery — attaches probes to capture live network connections and file system activity (Linux only) |
| Non-X-Ray Discovery | Single-phase discovery for Java app servers (WebLogic, WebSphere, Tomcat, JBoss) — reads config files instead of probes |
| Netwatch | Network monitoring feature that captures all inbound/outbound connections over a configurable time window |
| Topology | Visual map of connections between all hosts and processes in a project |
| Application | A user-defined grouping of processes belonging to the same logical application (e.g., Web + App + DB tiers) |
| 6R Classification | Per-host migration strategy: Reinvest (Rehost / Replatform / Refactor), Retain, or Retire |
| Complexity Score | Numerical score (0–High, 26–Medium, 36+–High) reflecting containerization effort per process |
| DART Report | Auto-generated executive portfolio report (the project landing page) |
| Practitioner Report | Detailed technical report per application, component, or host for migration teams |
| Vault | CHAI's secure credential store — holds SSH keys, WinRM credentials, cloud access keys |
| Graviton Readiness | AWS Graviton ARM-based processor compatibility assessment per host/component |
| AWS Cost Comparison | Automated EC2 instance mapping and monthly cost projection for a target AWS region |