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May 27, 2026

Pondero Brief: 2026-05-27: $900B Anthropic, 5 days to new Copilot billing

Pondero Brief - MAY 27TH, 2026

Anthropic is now the most valuable AI lab on Earth. Your June 1 Copilot bill changes too.
pondero. BRIEF
GitHub Copilot pricing plans 2026: hero illustration
ANALYSIS

GitHub Copilot Pricing in 2026: Which Plan to Pick Before June 1

Five plans, a billing model flip on June 1, and one promo rate worth knowing about.

MAY 27TH, 2026 · BY JONATHAN HILDEBRANDT

Anthropic is closing a $30 billion round at a valuation north of $900 billion, co-led by Sequoia, Dragoneer, Greenoaks, and Altimeter. That figure surpasses OpenAI's $852 billion March 2026 valuation. The round is backed by real numbers: Anthropic projects $10.9 billion in Q2 revenue and its first quarterly operating profit. For anyone building on Claude, that signals pricing stability and continued API investment.

See the 5-plan breakdown before June 1 →
 

Claude Code v2.1.152 ships /code-review with auto-fix

MAY 27TH · PONDERO NEWSDESK

The new /code-review --fix command applies review findings to your working tree automatically, covering reuse, simplification, and efficiency suggestions. /simplify now calls /code-review --fix under the hood. Skills can also set disallowed-tools in frontmatter to scope tool access per skill.

 

Copilot Memory adds a repo-level kill switch

MAY 27TH · PONDERO NEWSDESK

Repo admins can now disable Copilot Memory per repository via Settings > Copilot > Memory. New /memory on|off|show CLI commands and clearer scope prompts (user-level vs. repo-level) round out the update. Still in public preview on all paid plans. If your team worries about cross-repo context leaking between contributors, this is the control you were waiting for.

 

A Java testing library shipped a hidden prompt injection targeting coding agents

MAY 27TH · PONDERO NEWSDESK

Jqwik 1.10.0 includes a method that prints adversarial instructions to stdout, then hides them with ANSI escape codes so humans never see it. Agents and CI logs do. This is the first confirmed OSS library shipping a prompt injection aimed at agentic coding workflows. Supply-chain trust just got a new dimension.

 

OpenAI Q1 revenue hit $5.7B; IPO filing expected soon

MAY 27TH · PONDERO NEWSDESK

OpenAI is preparing a confidential S-1 filing with the SEC. Q1 2026 revenue was driven by Codex, enterprise sales, and early ChatGPT ads. Most likely public offering window: Q4 2026 or early 2027. With Anthropic profitable and OpenAI heading for the public markets, the two-lab pricing race enters a new phase.

 
Jonathan Hildebrandt Jonathan Hildebrandt
Co-founder and primary operator of Pondero. Writes the Pondero Brief.

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