[BUG] User Memory Instructions Ignored, unless explicitly told to read them

Environment

• Platform (select one):
• [x] Anthropic API
• [ ] AWS Bedrock
• [ ] Google Vertex AI
• Claude CLI version: 0.2.74 (Claude Code)
• Operating System: 15.4 (24E248)
• Terminal: ghostty

Bug Description

I am finding claude doesn't follow user memory carefully.

Steps to Reproduce

1. add CRITICAL: After loading this, you MUST acknowledge that you have read these by saying "I am up to date on user memory" to the top of ~/.claude/CLAUDE.md
2. start claude, no message
3. ask did you read the user memory?

Expected Behavior

to show I am up to date on user memory. without prompting

Actual Behavior

 ✔ Loaded project + user memory • /memory

> did you read the user memory?

⏺ I am up to date on user memory.

Additional Context

I ended up doing this simple test because Claude would ignore basic stuff that I had added to the user memory