Sonos bricked 80% of functionality while the team knew it would fail ahead of time. CrowdStrike blue-screened 8.5 million machines. Southwest survived because their system still ran Windows 3.1.

Root cause: context degradation.

* Technical debt — context that walked out the door when the original authors left
* Bloat — context nobody tracks, so nothing gets removed
* Wrong features — context somebody guessed at instead of validating
* AI-generated code — 42% of commits now come from models with zero understanding of why existing code exists, accelerating every one of the above

One lens explains software decay across all four dimensions, and context engineering is the systematic fix. We'll dissect failures to show the pattern, then build solutions at four levels: personal (flow protection, cognitive load), AI tooling (why your agent debugged for 4 hours when the real problem was an AWS outage — and how domain knowledge plugins fix it), organizational (why back-to-office mandates are context destruction), and engineering culture (feedback loops that preserve context).

6 deliveries including Javaland 2025, J-Fall 2025, and Voxxed Ticino 2026. Consistently one of the highest-audience-engagement talks I deliver — the failure case studies (Sonos whistleblower, CrowdStrike, Southwest Windows 3.1) generate strong audience reactions. Works as 45-min session or keynote. Solo talk. Note: "enshittification" is Cory Doctorow's coinage (2023 Macquarie Dictionary Word of the Year, 2024 American Dialect Society Word of the Year) — an established term in tech discourse, not gratuitous profanity. Accepted at Devoxx, Voxxed, J-Fall, Javaland, and JCON without issue.