dm_search

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

No annotations are provided, so the description carries the full behavioral burden. It discloses a real constraint (requires the user token) and the sort order (newest first), which is meaningful context. However, it stays silent on pagination behavior, the shape of results, and any rate-limit implications of searching, which a token-sensitive tool could usefully mention.

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?

The single sentence is tight and front-loaded: purpose first, then scope (DM/group DM), then ordering, then auth. Nothing is wasted, though it is short enough that an explicit sibling pointer would be a justified addition rather than padding.

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?

With 7 parameters, no output schema, and a sibling set containing dm_messages, list_dms, channel_search, and guild_search, the description covers the core (scope, ordering, auth) but leaves the search/dm_messages distinction implicit and says nothing about the return shape. For a search tool, this is adequate but not complete.

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?

Schema description coverage is 100%, so every one of the 7 parameters is already documented with descriptions (has, after, limit, before, content, author_id, channel_id). The description adds only the token and ordering context, nothing parameter-specific, so the baseline 3 applies.

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?

The description states a specific verb ('Search') and resource ('a DM or group DM') plus ordering ('newest first'). The 'DM' resource implicitly differentiates it from guild_search/channel_search siblings, but it does not name those alternatives explicitly the way a 5 would.

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?

'DM or group DM' implies the search scope and rules out guild/channel search, but the description never says 'for guild channels use guild_search' or contrasts with dm_messages. The auth note ('needs the user token') tells the agent when the tool might fail, but no direct when-to-use/when-not-to-use guidance is given.

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