Technical Due Diligence
Technical due diligence is a structured investigation of a software product, its architecture, engineering practices, security, dependencies, and team. It replaces deal claims with evidence so an investor or acquirer can identify technical risks, estimate remediation, and decide what those findings mean for the transaction and integration plan.
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Don't Panic
Don't Panic — Technical Due Diligence
Technical due diligence is the practice of checking what a technology asset actually is before a consequential decision makes everybody responsible for it. It appears in acquisitions, investments, software purchases, and supplier reviews. The job is not to admire the architecture diagram or issue a ceremonial code-quality score. The job is to replace claims with evidence and explain what the evidence does to the decision.
Begin with the transaction thesis, meaning the value the transaction expects to create. A buyer interested in intellectual property needs evidence about provenance, third-party components, ownership, and transferability. A buyer expecting rapid growth needs capacity, bottleneck, cost, and delivery evidence. A buyer planning integration needs interfaces, identity, data, deployment boundaries, and migration constraints. One checklist cannot decide which of these matters most, despite checklists being naturally convinced of their own importance.
The central mechanism is an evidence chain. A thesis produces a diligence question. The question identifies a claim. Documents, interviews, repository history, pipeline records, runtime observations, and incident evidence test that claim. The result becomes a finding, and the finding earns its place by changing a decision, cost assumption, pre-close requirement, or integration action.
Evidence is annoyingly specialized. A diagram describes intended architecture but may not match deployment. A repository shows source and change history but does not prove which version runs in production. An interview supplies context but remains a claim until something independent supports it. A software bill of materials identifies components and relationships; it does not wave a small wand over them and pronounce the product secure.
This is why material claims need triangulation, or testing through independent evidence paths. Compare the release process with pipeline history and a recent production change. Compare the architecture walkthrough with infrastructure definitions and runtime inventory. Compare stated knowledge ownership with interviews, contribution history, code review, incident command, and operational access. Contradictions are not courtroom drama. They are directions for the next useful question.
Scope follows risk. Inspect the revenue-critical path, privileged and exposed components, expensive infrastructure, high-change areas, recent incidents, and the interfaces named by the thesis. Record every exclusion and access limit. “The reviewed repository” is a defensible phrase. “The platform” is not, when most of the platform remained behind a door the reviewer did not open.
A finding needs an observed condition, a criterion, a consequence, an evidence-confidence statement, and a response. Keep severity separate from confidence. A potentially severe risk with weak evidence calls for more evidence, a condition, or a contingency. It does not call for a louder adjective.
Read the Intro for the complete review architecture. Use the Cheatsheet to structure evidence and findings. The Practice Reference turns a transaction thesis into a scope and evidence register. The Exercise provides a fictional acquisition where unsupported capacity, stale inventory, and concentrated operational knowledge can be handled without jeopardizing an actual deal.
The final report should say what was tested, what was found, why it matters, how certain it is, and what remains unknown. That is less glamorous than predicting the future. It is also considerably more useful.
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Sources
- https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=961156
Supports
- Due diligence researches and verifies pertinent information about an ICT supplier or product to support informed contracting decisions.
- A due diligence assessment can precede and inform a deeper supply-chain risk assessment.
- An SBOM records components and supply-chain relationships, supports tailored analysis, and does not by itself prove security.
- Component analysis can examine support, contributor concentration, end-of-life status, known vulnerabilities, and unknown components.
- Findings need source traceability, organizational concern levels, risk tolerance, and a defined refresh process.
- https://csrc.nist.gov/pubs/sp/800/218/final
Supports
- The SSDF provides high-level secure-development practices that can be integrated into different software development lifecycles.
- The framework gives software producers, purchasers, and consumers a common vocabulary for acquisition and management discussions.
- Secure-development review includes organizational preparation, software protection, well-secured production, and vulnerability response.
- https://owasp.org/www-project-samm/
Supports
- OWASP SAMM is an open framework for evaluating, measuring, and improving software-security activities according to organizational risk.
- https://www.iso.org/standard/78176.html
Supports
- ISO/IEC 25010 defines nine product-quality characteristics and subcharacteristics for specifying, measuring, and evaluating ICT and software products.
- Acquirers and independent evaluators can use the model for requirements, design objectives, tests, acceptance criteria, and product-quality measures.
- https://www.sei.cmu.edu/library/paying-due-diligence-to-software-architecture-in-acquisition/
Supports
- Availability, security, openness, maintainability, reusability, performance, testability, and usability affect acquisition cost and risk.
- Acquisition work needs early visibility into architecture and quality-attribute tradeoffs because late discovery can cause costly rework.
- Architecture assessment should connect mission and business drivers with observable quality attributes.
- https://saas.group/blog/technical-due-diligence-process-at-saas-group/
Supports
- A serial acquirer reviews product, roadmap, team, intellectual property, technical stack, source code, and supporting materials.
- The process combines a request list, follow-up interviews, source-code review, and direct discussion with the people building the product.
- Contribution statistics can expose founder or key-person concentration that matters when people may leave after a transaction.
- Transparency and contradictions between business and technology behavior affect confidence in the transaction relationship.
- https://akfpartners.com/growth-blog/technical-due-diligence-checklists
Supports
- A practitioner diligence scope spans scalability, failure isolation, recovery, cost, product and delivery processes, operations, organization, and security.
- Useful operational evidence includes monitors, incidents, postmortems, production-change records, capacity headroom, rollback, and recovery practices.
- Development evidence includes code review, tests, continuous integration, deployment, licensing, technical debt, and architectural principles.
- https://circleci.com/resources/tech-due-diligence/
Supports
- Seller-oriented diligence preparation covers infrastructure, code, documentation, tests, security, delivery, and the evidence requested by reviewers.
- The resource is one of the four due-diligence entries curated by Awesome CTO.
- https://github.com/sindresorhus/awesome
Supports
- The required Awesome-list discovery began at the canonical curated-list index.
- The index links to the Awesome CTO list for technology-leadership resources.
- https://github.com/kuchin/awesome-cto
Supports
- The list has a dedicated Due Diligence section containing the AKF checklist, a technical question repository, an IT department checklist, and CircleCI guidance.
- These four items are the discovery basis for the course's Awesome Links.
- https://github.com/altunyurt/technical_due_diligence
Supports
- The open question set spans business, product, team, hiring, technology, code, process, operations, security, and continuity topics.
- It is a learner destination curated by Awesome CTO for constructing a small-company evidence request.
- https://gist.github.com/raphaelbauer/b31d49d91a0af6c1106bfc8ef4bf6d13
Supports
- The checklist extends diligence beyond product source code into IT ownership, infrastructure, access, services, continuity, documentation, and transfer concerns.
- It is a learner destination curated by Awesome CTO.
- https://www.castsoftware.com/products/highlight/how-it-works
Supports
- CAST Highlight derives portfolio evidence about application health, resilience, technical debt, cloud readiness, composition, vulnerabilities, and intellectual-property risk from source.
- The product explicitly supports technical due diligence and multi-application assessment.
- https://www.blackduck.com/solutions/mergers-and-acquisitions.html
Supports
- Black Duck Audits examine open-source, license, security, architecture, quality, technical debt, third-party code, and development-process risk in software transactions.
- The service supports buyers, strategic acquirers, and sellers with code-based evidence and specialist interpretation.
- https://swimm.io/solutions/ma-tech-due-diligence
Supports
- Swimm combines deterministic mapping and specialist interpretation for dependencies, dead code, codebase risks, and modernization fit.
- The offering is a scoped assessment service rather than installed diligence software.
- https://www.techminers.com/
Supports
- TechMiners combines a web-based diligence process, structured evidence extraction, collaboration, expert interviews, and analysis of code, architecture, product, teams, and engineering processes.
- https://techduediligence.co/
Supports
- The platform connects a synchronized evidence room, scanning, findings, diligence reports, escrow, a closing intellectual-property package, and retained transaction evidence.
- https://www.triplekey.com/solutions/mergers-acquisitions
Supports
- TripleScan analyzes code quality, dependencies, technical debt, ownership and provenance, and engineering activity for deal-stage diligence.
- Its repository-derived output is an evidence source that still requires transaction-context interpretation.
