restart_debugging

Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

With no annotations, the description carries the full burden and does so: it discloses that the current program is terminated, that breakpoints are re-applied automatically, and that the get_output buffer resets so reads must start at since=0. It also documents the response shape (mirrors start_debugging, can return pending:true) and the session-type restrictions.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Is the description appropriately sized, front-loaded, and free of redundancy?

Front-loaded with the core action and side effects before the edge cases, and virtually every sentence carries needed information. The final clause about answering 'like start_debugging, including "running" with pending:true' is nested and slightly dense but still earns its place.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

For a one-parameter tool with no annotations and no output schema, the description covers side effects (program termination, breakpoint re-application, buffer reset), valid session states, invalid session types, and the response handoff to wait_for_stop. Nothing an agent needs to call this correctly is missing.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

The single parameter sessionId has 0% schema description coverage, and the description never mentions it explicitly. Its meaning is largely self-evident from the surrounding session-oriented tools, so the gap is minor, but the description adds nothing beyond the schema here.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Does the description clearly state what the tool does and how it differs from similar tools?

States a specific verb (restart) and resource (the debuggee), then immediately defines the mechanics: terminate and relaunch with the same configuration as the last start_debugging. That framing cleanly distinguishes it from start_debugging and create_debug_session among the siblings.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Does the description explain when to use this tool, when not to, or what alternatives exist?

Explicitly gives the positive conditions (works while running, paused, or after the program has exited) and the exclusions (not available for attach sessions or sessions never launched). It also names the follow-up tool: call wait_for_stop when the relaunch returns running with pending:true.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.