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

Annotations already declare readOnlyHint=true, so safety is covered. The description adds that the search is server-side and that results carry emails and phone numbers, which is meaningful behavioral context for a read tool with no output schema.

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?

Two short sentences, front-loaded with the verb and the filter/sort/paging capabilities. The trailing "Shopmonkey: POST /v3/customer/search" endpoint note is mildly redundant but not wasteful.

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 no output schema, the description usefully states what is returned (customers with emails and phone numbers), and the schema fully documents paging and filtering. An agent has enough to call it correctly, though tool-selection guidance relative to siblings is the remaining gap.

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% and each of the four parameters (skip, limit, where, orderBy) has an example-bearing description, so the schema does the heavy lifting. The description adds nothing about parameter syntax, making the baseline 3 appropriate.

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+resource ("Search customers") and qualifies it with server-side filter, sort and paging, which separates it from the narrower find_customers_by_email/phone siblings. It does not, however, explicitly name those siblings to route the agent.

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?

The mention of a server-side filter implies this is the general-purpose lookup tool, but no when-to-use/when-not guidance is given against the many alternatives (find_customers_by_email, find_customers_by_phone, get_customer, list_customer_orders). Usage must be inferred.

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