[UX] --resume with no past conversations should offer to start new session instead of asking to restart

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

When running claude --resume (e.g. claude --resume --chrome --allow-dangerously-skip-permissions) and there are no past conversations to resume, Claude asks the user to restart the shell without the --resume flag.

This adds unnecessary friction — the user has to exit, re-type or edit their command, and re-launch. Since the intent is clear (the user wants to use Claude), there's no reason to force a full restart.

Proposed Solution

Instead of telling the user to restart without --resume, simply display a message like:

No past conversations found. Press Enter to start a new conversation.

On Enter, proceed to start a fresh session with all other flags (e.g. --chrome, --allow-dangerously-skip-permissions) preserved. This keeps the user in flow without requiring them to manually re-invoke the command.

Alternatives Considered

• Keep current behavior (status quo) — works but adds unnecessary friction.
• Auto-start a new session without prompting — could be surprising if the user specifically expected to resume something.

The "press Enter" approach strikes a good balance: it informs the user that no sessions were found, while letting them proceed without leaving the terminal.