Claude silently skips tasks based on unverified assumptions instead of attempting or asking

Problem

When given a multi-part instruction, Claude skipped one part without attempting it or asking clarifying questions. Instead, it assumed the task was impossible and silently moved on.

Reproduction

User instruction:

"create config file and apply to [remote-host]"

Claude's behavior:

1. Created the config file (correct)
2. Did not apply changes to the remote host
3. Did not attempt SSH
4. Did not ask how to access the host
5. Wrote "instructions you can follow on [remote-host]" as if that fulfilled the request

Expected Behavior

When Claude cannot or is unsure how to complete a task, it should:

1. Attempt the obvious approach first (e.g., try SSH)
2. If that fails, ask the user for guidance
3. Never silently skip instructions

Impact

• User's explicit instruction was not followed
• User had to notice the omission and call it out
• Trust eroded when Claude silently drops tasks