diff --git a/src/tools/registry.ts b/src/tools/registry.ts
index 8b99159d..a80ad770 100644
--- a/src/tools/registry.ts
+++ b/src/tools/registry.ts
@@ -3,6 +3,7 @@ import { textContent } from "../engine/content-helpers.ts";
 import type { ToolCall, ToolResult, ToolRouter, ToolSchema } from "../engine/types.ts";
 import type { PermissionStore } from "../permissions/permission-store.ts";
 import type { McpSource } from "./mcp-source.ts";
+import { rankToolSearchResults } from "./search-ranking.ts";
 import type { Tool, ToolSource } from "./types.ts";
 
 /**
@@ -189,12 +190,10 @@ export class ToolRegistry implements ToolRouter {
     return source.execute(localName, call.input, signal);
   }
 
-  /** Search all tools by keyword (substring match on name + description). */
+  /** Search all tools by natural-language terms over name + description. */
   private async searchTools(query: string): Promise<Array<{ name: string; description: string }>> {
-    const q = query.toLowerCase();
     const all = await this.availableTools();
-    return all
-      .filter((t) => t.name.toLowerCase().includes(q) || t.description.toLowerCase().includes(q))
+    return rankToolSearchResults(all, query)
       .slice(0, 5)
       .map((t) => ({ name: t.name, description: t.description }));
   }
diff --git a/src/tools/search-ranking.ts b/src/tools/search-ranking.ts
new file mode 100644
index 00000000..52be8be0
--- /dev/null
+++ b/src/tools/search-ranking.ts
@@ -0,0 +1,89 @@
+import type { ToolSchema } from "../engine/types.ts";
+
+export type ToolSearchResult = Pick<ToolSchema, "name" | "description">;
+
+interface ScoredTool<T extends ToolSearchResult> {
+  tool: T;
+  score: number;
+  matchedTerms: number;
+}
+
+function tokenize(value: string): string[] {
+  return value
+    .toLowerCase()
+    .split(/[^a-z0-9]+/)
+    .filter(Boolean);
+}
+
+function tokenVariants(token: string): string[] {
+  if (token.length > 3 && token.endsWith("s")) return [token, token.slice(0, -1)];
+  return [token];
+}
+
+function tokenSet(value: string): Set<string> {
+  const tokens = new Set<string>();
+  for (const token of tokenize(value)) {
+    for (const variant of tokenVariants(token)) tokens.add(variant);
+  }
+  return tokens;
+}
+
+function hasTerm(tokens: Set<string>, term: string): boolean {
+  for (const variant of tokenVariants(term)) {
+    if (tokens.has(variant)) return true;
+  }
+  return false;
+}
+
+/**
+ * Rank installed tools for natural-language discovery queries.
+ *
+ * Matching is deterministic and dependency-free: full-query substring matches
+ * still work, but multi-term queries also match tokenized source names, tool
+ * names, and descriptions. Full query-term coverage ranks above partial hits.
+ */
+export function rankToolSearchResults<T extends ToolSearchResult>(tools: T[], query: string): T[] {
+  const normalizedQuery = query.toLowerCase().trim();
+  const queryTerms = [...new Set(tokenize(normalizedQuery))];
+  if (queryTerms.length === 0) return tools;
+
+  const scored: ScoredTool<T>[] = [];
+  for (const tool of tools) {
+    const name = tool.name.toLowerCase();
+    const description = tool.description.toLowerCase();
+    const nameSubstringMatch = name.includes(normalizedQuery);
+    const descriptionSubstringMatch = description.includes(normalizedQuery);
+    const nameTokens = tokenSet(tool.name);
+    const descriptionTokens = tokenSet(tool.description);
+
+    let score = 0;
+    if (nameSubstringMatch) score += 200;
+    if (descriptionSubstringMatch) score += 100;
+
+    let matchedTerms = 0;
+    for (const term of queryTerms) {
+      const nameMatch = hasTerm(nameTokens, term);
+      const descriptionMatch = hasTerm(descriptionTokens, term);
+      if (!nameMatch && !descriptionMatch) continue;
+
+      matchedTerms++;
+      score += nameMatch ? 20 : 0;
+      score += descriptionMatch ? 10 : 0;
+    }
+
+    if (matchedTerms === 0 && !nameSubstringMatch && !descriptionSubstringMatch) continue;
+    const fullCoverage = matchedTerms === queryTerms.length;
+    score += matchedTerms * 1000;
+    if (fullCoverage) score += 500;
+
+    scored.push({ tool, score, matchedTerms });
+  }
+
+  scored.sort((a, b) => {
+    if (b.matchedTerms !== a.matchedTerms) return b.matchedTerms - a.matchedTerms;
+    if (b.score !== a.score) return b.score - a.score;
+    return a.tool.name.localeCompare(b.tool.name);
+  });
+
+  return scored.map((s) => s.tool);
+}
diff --git a/src/tools/system-tools.ts b/src/tools/system-tools.ts
index c9d64d7d..034d5df0 100644
--- a/src/tools/system-tools.ts
+++ b/src/tools/system-tools.ts
@@ -19,6 +19,7 @@ import { McpSource } from "./mcp-source.ts";
 import { createManageToolsToolDefs } from "./platform/manage-tools.ts";
 import type { ToolRegistry } from "./registry.ts";
 import { createManageRegistriesTool } from "./registry-tools.ts";
+import { rankToolSearchResults } from "./search-ranking.ts";
 import { createManageUsersTool, type ManageUsersContext } from "./user-tools.ts";
 import {
   createManageWorkspacesTool,
@@ -95,7 +96,7 @@ export async function createSystemTools(
           query: {
             type: "string",
             description:
-              "Search query (substring match on name + description). Optional — omit to list everything in scope.",
+              "Search query (natural-language terms over name + description). Optional — omit to list everything in scope.",
           },
         },
         required: ["scope"],
@@ -136,7 +137,7 @@ export async function createSystemTools(
         }
 
         // scope === "tools" (default)
-        const q = query.toLowerCase();
+        const q = query.toLowerCase().trim();
         // Identity-level discovery: search the identity's full
         // cross-workspace tool union (the aggregator), not just the
         // calling workspace. The aggregator namespaces nb__search per
@@ -153,16 +154,16 @@ export async function createSystemTools(
             toolEligibilityCtx?.isToolEligible(t) ?? !t.annotations?.["ai.nimblebrain/internal"],
         );
         if (!q) return groupToolsBySource(all);
-        const matches = all.filter(
-          (t) => t.name.toLowerCase().includes(q) || t.description.toLowerCase().includes(q),
-        );
+        const matches = rankToolSearchResults(all, q);
         if (matches.length === 0)
           return { content: textContent(`No tools matched "${query}".`), isError: false };
-        const lines = [`Found ${matches.length} tool(s) for "${query}":\n`];
-        for (const t of matches) lines.push(`- **${t.name}**: ${t.description}`);
+        const shown = matches.slice(0, 25);
+        const suffix = matches.length > shown.length ? ` (showing top ${shown.length})` : "";
+        const lines = [`Found ${matches.length} tool(s) for "${query}"${suffix}:\n`];
+        for (const t of shown) lines.push(`- **${t.name}**: ${t.description}`);
         return {
           content: textContent(lines.join("\n")),
-          structuredContent: { tools: matches.map((t) => ({ name: t.name })) },
+          structuredContent: { tools: shown.map((t) => ({ name: t.name })) },
           isError: false,
         };
       },
diff --git a/test/unit/system-tools.test.ts b/test/unit/system-tools.test.ts
index d2657653..ccf96725 100644
--- a/test/unit/system-tools.test.ts
+++ b/test/unit/system-tools.test.ts
@@ -53,6 +53,50 @@ async function makeRegistry(): Promise<ToolRegistry> {
 	return registry;
 }
 
+async function makeTodoSearchRegistry(): Promise<ToolRegistry> {
+	const registry = new ToolRegistry();
+	const todoSource = await makeInProcessSource("synapse-todo-board", [
+		{
+			name: "create_board_task",
+			description: "Create a task on a specific board",
+			inputSchema: { type: "object", properties: {} },
+			handler: async () => ({ content: textContent("ok"), isError: false }),
+		},
+		{
+			name: "list_boards",
+			description: "List available boards",
+			inputSchema: { type: "object", properties: {} },
+			handler: async () => ({ content: textContent("ok"), isError: false }),
+		},
+	]);
+	const genericSource = await makeInProcessSource("scratch", [
+		{
+			name: "create_task_template",
+			description: "Create a reusable task template",
+			inputSchema: { type: "object", properties: {} },
+			handler: async () => ({ content: textContent("ok"), isError: false }),
+		},
+	]);
+	registry.addSource(todoSource);
+	registry.addSource(genericSource);
+	return registry;
+}
+
+async function makeManyMatchingToolsRegistry(count: number): Promise<ToolRegistry> {
+	const registry = new ToolRegistry();
+	const source = await makeInProcessSource(
+		"many",
+		Array.from({ length: count }, (_, i) => ({
+			name: `common_tool_${String(i).padStart(2, "0")}`,
+			description: "Common searchable helper",
+			inputSchema: { type: "object", properties: {} },
+			handler: async () => ({ content: textContent("ok"), isError: false }),
+		})),
+	);
+	registry.addSource(source);
+	return registry;
+}
+
 function getStructured<T>(result: { structuredContent?: unknown }): T | undefined {
 	return result.structuredContent as T | undefined;
 }
@@ -72,6 +116,91 @@ describe("System Tools", () => {
 		]);
 	});
 
+	it("search with scope=tools preserves single-word prefix substring matches", async () => {
+		const registry = new ToolRegistry();
+		const source = await makeInProcessSource("test", [
+			{
+				name: "greeting",
+				description: "Friendly salutation helper",
+				inputSchema: { type: "object", properties: {} },
+				handler: async () => ({ content: textContent("ok"), isError: false }),
+			},
+		]);
+		registry.addSource(source);
+		const systemTools = await createSystemTools(() => registry);
+		const result = await systemTools.execute("search", {
+			scope: "tools",
+			query: "greet",
+		});
+
+		expect(result.isError).toBe(false);
+		expect(getStructured<{ tools?: Array<{ name: string }> }>(result)?.tools).toEqual([
+			{ name: "test__greeting" },
+		]);
+	});
+
+	it("search with scope=tools matches natural-language terms across source, name, and description", async () => {
+		const registry = await makeTodoSearchRegistry();
+		const systemTools = await createSystemTools(() => registry);
+		const result = await systemTools.execute("search", {
+			scope: "tools",
+			query: "todo task create",
+		});
+
+		expect(result.isError).toBe(false);
+		expect(getStructured<{ tools?: Array<{ name: string }> }>(result)?.tools?.[0]).toEqual({
+			name: "synapse-todo-board__create_board_task",
+		});
+		expect(extractText(result.content)).toContain("synapse-todo-board__create_board_task");
+	});
+
+	it("search with scope=tools tokenizes hyphenated source names", async () => {
+		const registry = await makeTodoSearchRegistry();
+		const systemTools = await createSystemTools(() => registry);
+		const result = await systemTools.execute("search", {
+			scope: "tools",
+			query: "todo board",
+		});
+
+		expect(result.isError).toBe(false);
+		const names = getStructured<{ tools?: Array<{ name: string }> }>(result)?.tools?.map(
+			(t) => t.name,
+		);
+		expect(names).toContain("synapse-todo-board__create_board_task");
+		expect(names).toContain("synapse-todo-board__list_boards");
+	});
+
+	it("search with scope=tools matches description terms", async () => {
+		const registry = await makeTodoSearchRegistry();
+		const systemTools = await createSystemTools(() => registry);
+		const result = await systemTools.execute("search", {
+			scope: "tools",
+			query: "specific board",
+		});
+
+		expect(result.isError).toBe(false);
+		expect(getStructured<{ tools?: Array<{ name: string }> }>(result)?.tools?.[0]).toEqual({
+			name: "synapse-todo-board__create_board_task",
+		});
+	});
+
+	it("search with scope=tools caps broad matches at the top 25 results", async () => {
+		const registry = await makeManyMatchingToolsRegistry(30);
+		const systemTools = await createSystemTools(() => registry);
+		const result = await systemTools.execute("search", {
+			scope: "tools",
+			query: "common",
+		});
+
+		expect(result.isError).toBe(false);
+		expect(extractText(result.content)).toContain(
+			'Found 30 tool(s) for "common" (showing top 25):',
+		);
+		expect(getStructured<{ tools?: Array<{ name: string }> }>(result)?.tools).toHaveLength(25);
+		expect(extractText(result.content)).toContain("many__common_tool_24");
+		expect(extractText(result.content)).not.toContain("many__common_tool_25");
+	});
+
 	it("search with scope=tools and empty query returns all tools grouped", async () => {
 		const registry = await makeRegistry();
 		const systemTools = await createSystemTools(() => registry);