Look closer.

Applied AI: Tokens and Context Windows

Information in this post reflects publicly available sources as of October 18, 2026. Three things happen to the same engineer in one week. A 300-page contract pasted into a chat model is rejected as too long, even though the model advertises a "huge" context window. The monthly API bill reports 40 million tokens for what felt like a few thousand questions. And a frontier model, capable of explaining tax law, miscounts the letter r in &q… Read More

Applied AI: Guardrails

Information in this post reflects publicly available sources as of October 18, 2026. In 2022, a man booking a flight after a death in his family asked Air Canada's website chatbot about bereavement fares. The chatbot told him to buy a regular ticket and apply for the bereavement discount within 90 days. That was not the airline's policy, and when he applied, the airline refused. He took the case to British Columbia's Civil Resolution T… Read More

Applied AI: Memory and Skills

Information in this post reflects publicly available sources as of October 18, 2026. On Monday you spend twenty minutes teaching your coding agent how your project works. Tests run with pytest -x , never through the IDE. Database migrations are off limits. Staging deploys go through a script nobody remembers the flags for. By the end of the session, it is a genuinely useful colleague. On Tuesday you open a new session, and it knows none of it. It ru… Read More

Applied AI: Computer Use

Information in this post reflects publicly available sources as of October 18, 2026. Every month, someone on the finance team spends a morning copying forty receipts from email into a vendor's expense portal. The portal was built in 2009. It has no API, no bulk import, and a date picker that only works if you click it twice. Nobody is going to rebuild it, and no integration project will ever rank high enough to replace it. The agents earlier i… Read More