diff --git a/ui/src/components/config-form.search.node.test.ts b/ui/src/components/config-form.search.node.test.ts
index 59744756ebc8..35523573d6e2 100644
--- a/ui/src/components/config-form.search.node.test.ts
+++ b/ui/src/components/config-form.search.node.test.ts
@@ -90,4 +90,30 @@ describe("config form search", () => {
 
     expect(matched).toBe(true);
   });
+
+  it("searches additional-property schemas before entries exist", () => {
+    const matched = matchesNodeSearch({
+      schema: {
+        type: "object",
+        additionalProperties: {
+          type: "object",
+          properties: {
+            url: {
+              type: "string",
+            },
+          },
+        },
+      },
+      value: {},
+      path: ["servers"],
+      hints: {
+        "servers.*.url": {
+          help: "Endpoint used by the remote service",
+        },
+      },
+      criteria: parseConfigSearchQuery("remote service"),
+    });
+
+    expect(matched).toBe(true);
+  });
 });
diff --git a/ui/src/components/config-form.search.ts b/ui/src/components/config-form.search.ts
index 6c3d1cd8ad8d..68cd1645d1da 100644
--- a/ui/src/components/config-form.search.ts
+++ b/ui/src/components/config-form.search.ts
@@ -1,8 +1,5 @@
 import type { ConfigUiHints } from "../api/types.ts";
-import {
-  normalizeLowercaseStringOrEmpty,
-  normalizeOptionalLowercaseString,
-} from "../lib/string-coerce.ts";
+import { normalizeLowercaseStringOrEmpty } from "../lib/string-coerce.ts";
 import { hintForPath, humanize, schemaType, type JsonSchema } from "./config-form.shared.ts";
 
 export type ConfigSearchCriteria = {
@@ -16,6 +13,8 @@ export type ConfigFieldMeta = {
   tags: string[];
 };
 
+export type ConfigSearchTextMatcher = (value: string, query: string) => boolean;
+
 export function hasConfigSearchCriteria(criteria: ConfigSearchCriteria | undefined): boolean {
   return Boolean(criteria && (criteria.text.length > 0 || criteria.tags.length > 0));
 }
@@ -79,13 +78,19 @@ export function resolveConfigFieldMeta(
   };
 }
 
-function matchesText(text: string, candidates: Array<string | undefined>): boolean {
+function defaultTextMatcher(value: string, query: string): boolean {
+  return normalizeLowercaseStringOrEmpty(value).includes(normalizeLowercaseStringOrEmpty(query));
+}
+
+function matchesText(
+  text: string,
+  candidates: Array<string | undefined>,
+  textMatcher: ConfigSearchTextMatcher,
+): boolean {
   if (!text) {
     return true;
   }
-  return candidates.some((candidate) =>
-    normalizeOptionalLowercaseString(candidate)?.includes(text),
-  );
+  return candidates.some((candidate) => candidate !== undefined && textMatcher(candidate, text));
 }
 
 function matchesTags(filterTags: string[], fieldTags: string[]): boolean {
@@ -101,8 +106,9 @@ export function matchesNodeSelf(params: {
   path: Array<string | number>;
   hints: ConfigUiHints;
   criteria: ConfigSearchCriteria;
+  textMatcher?: ConfigSearchTextMatcher;
 }): boolean {
-  const { schema, path, hints, criteria } = params;
+  const { schema, path, hints, criteria, textMatcher = defaultTextMatcher } = params;
   if (!hasConfigSearchCriteria(criteria)) {
     return true;
   }
@@ -118,14 +124,11 @@ export function matchesNodeSelf(params: {
     .filter((segment): segment is string => typeof segment === "string")
     .join(".");
   const enumText = schema.enum?.map((value) => String(value)).join(" ") ?? "";
-  return matchesText(criteria.text, [
-    label,
-    help,
-    schema.title,
-    schema.description,
-    pathLabel,
-    enumText,
-  ]);
+  return matchesText(
+    criteria.text,
+    [label, help, schema.title, schema.description, pathLabel, enumText],
+    textMatcher,
+  );
 }
 
 export function matchesNodeSearch(params: {
@@ -134,12 +137,13 @@ export function matchesNodeSearch(params: {
   path: Array<string | number>;
   hints: ConfigUiHints;
   criteria: ConfigSearchCriteria;
+  textMatcher?: ConfigSearchTextMatcher;
 }): boolean {
-  const { schema, value, path, hints, criteria } = params;
+  const { schema, value, path, hints, criteria, textMatcher = defaultTextMatcher } = params;
   if (!hasConfigSearchCriteria(criteria)) {
     return true;
   }
-  if (matchesNodeSelf({ schema, path, hints, criteria })) {
+  if (matchesNodeSelf({ schema, path, hints, criteria, textMatcher })) {
     return true;
   }
 
@@ -159,6 +163,7 @@ export function matchesNodeSearch(params: {
           path: [...path, propertyKey],
           hints,
           criteria,
+          textMatcher,
         })
       ) {
         return true;
@@ -167,15 +172,26 @@ export function matchesNodeSearch(params: {
     const additional = schema.additionalProperties;
     if (additional && typeof additional === "object") {
       const reserved = new Set(Object.keys(properties));
-      for (const [entryKey, entryValue] of Object.entries(obj)) {
+      const dynamicEntries = Object.entries(obj).filter(([entryKey]) => !reserved.has(entryKey));
+      if (dynamicEntries.length === 0) {
+        return matchesNodeSearch({
+          schema: additional,
+          value: undefined,
+          path: [...path, "*"],
+          hints,
+          criteria,
+          textMatcher,
+        });
+      }
+      for (const [entryKey, entryValue] of dynamicEntries) {
         if (
-          !reserved.has(entryKey) &&
           matchesNodeSearch({
             schema: additional,
             value: entryValue,
             path: [...path, entryKey],
             hints,
             criteria,
+            textMatcher,
           })
         ) {
           return true;
@@ -200,6 +216,7 @@ export function matchesNodeSearch(params: {
       path: [...path, 0],
       hints,
       criteria,
+      textMatcher,
     });
   }
   return values.some((entry, index) =>
@@ -209,6 +226,7 @@ export function matchesNodeSearch(params: {
       path: [...path, index],
       hints,
       criteria,
+      textMatcher,
     }),
   );
 }
@@ -221,6 +239,7 @@ export function matchesConfigSectionSearch(params: {
   query: string;
   label?: string;
   description?: string;
+  textMatcher?: ConfigSearchTextMatcher;
 }): boolean {
   if (!params.query) {
     return true;
@@ -230,7 +249,9 @@ export function matchesConfigSectionSearch(params: {
     criteria.tags.length === 0 &&
     criteria.text.length > 0 &&
     [params.key, params.label, params.description].some((candidate) =>
-      normalizeOptionalLowercaseString(candidate)?.includes(criteria.text),
+      candidate !== undefined
+        ? (params.textMatcher ?? defaultTextMatcher)(candidate, criteria.text)
+        : false,
     );
   return (
     metadataMatches ||
@@ -240,6 +261,7 @@ export function matchesConfigSectionSearch(params: {
       path: [params.key],
       hints: params.hints,
       criteria,
+      textMatcher: params.textMatcher,
     })
   );
 }
diff --git a/ui/src/pages/config/settings-search.test.ts b/ui/src/pages/config/settings-search.test.ts
index 02b7ff8a1516..6e5387b0344b 100644
--- a/ui/src/pages/config/settings-search.test.ts
+++ b/ui/src/pages/config/settings-search.test.ts
@@ -95,6 +95,37 @@ describe("findSettingsSearchBlocks", () => {
     ]);
   });
 
+  it("preserves nested schema matches for short prefix queries", () => {
+    const matches = findSettingsSearchBlocks({
+      query: "sa",
+      schema: {
+        type: "object",
+        properties: {
+          tools: {
+            type: "object",
+            properties: {
+              profile: {
+                type: "string",
+                description: "Controls sandbox access",
+              },
+            },
+          },
+        },
+      },
+      value: {},
+      uiHints: {},
+    });
+
+    expect(matches).toEqual([
+      {
+        routeId: "ai-agents",
+        label: "Tools",
+        search: "?section=tools",
+        hash: "#config-section-tools",
+      },
+    ]);
+  });
+
   it("searches and displays static settings blocks in the active locale", async () => {
     await i18n.setLocale("es");
 
diff --git a/ui/src/pages/config/settings-search.ts b/ui/src/pages/config/settings-search.ts
index 2074ff535153..051d02601ddd 100644
--- a/ui/src/pages/config/settings-search.ts
+++ b/ui/src/pages/config/settings-search.ts
@@ -263,24 +263,18 @@ export function findSettingsSearchBlocks(params: {
     return matches;
   }
   const value = params.value ?? {};
-  const usePrefixMatching =
-    criteria.tags.length === 0 && criteria.text.length > 0 && criteria.text.length <= 2;
   for (const [key, sectionSchema] of Object.entries(schema.properties)) {
     const meta = SECTION_META[key];
-    const matchesSection = usePrefixMatching
-      ? [key, meta?.label, meta?.description, sectionSchema.title, sectionSchema.description].some(
-          (candidate) =>
-            typeof candidate === "string" && settingsSearchTextMatches(candidate, criteria.text),
-        )
-      : matchesConfigSectionSearch({
-          key,
-          schema: sectionSchema,
-          value: value[key],
-          hints: params.uiHints,
-          query: params.query,
-          label: meta?.label,
-          description: meta?.description,
-        });
+    const matchesSection = matchesConfigSectionSearch({
+      key,
+      schema: sectionSchema,
+      value: value[key],
+      hints: params.uiHints,
+      query: params.query,
+      label: meta?.label,
+      description: meta?.description,
+      textMatcher: settingsSearchTextMatches,
+    });
     if (!matchesSection) {
       continue;
     }