diff --git a/packages/ui/src/components/ui/CommandPalette.tsx b/packages/ui/src/components/ui/CommandPalette.tsx
index 2fe8a942..509d2734 100644
--- a/packages/ui/src/components/ui/CommandPalette.tsx
+++ b/packages/ui/src/components/ui/CommandPalette.tsx
@@ -352,7 +352,7 @@ export const CommandPalette: React.FC = () => {
       return;
     }
     let cancelled = false;
-    void searchFiles(currentRoot, trimmedQuery, 10, { type: 'file' })
+    void searchFiles(currentRoot, trimmedQuery, 40, { type: 'file' })
       .then((results) => {
         if (cancelled) return;
         setFileResults(
diff --git a/packages/ui/src/components/ui/commandPaletteFilesState.test.ts b/packages/ui/src/components/ui/commandPaletteFilesState.test.ts
index d542ef73..3c5de7d3 100644
--- a/packages/ui/src/components/ui/commandPaletteFilesState.test.ts
+++ b/packages/ui/src/components/ui/commandPaletteFilesState.test.ts
@@ -16,4 +16,27 @@ describe('commandPaletteFilesState', () => {
     expect(scoreCommandPaletteFiles(fileResults, 'alpha', freshKey, staleKey)).toEqual([]);
     expect(scoreCommandPaletteFiles(fileResults, 'alpha', freshKey, freshKey)).toHaveLength(1);
   });
+
+  test('matches directory segments of the relative path, not just the basename', () => {
+    const fileResults = [
+      { name: 'index.md', path: '/kb/solo-is-a-team-size/index.md', relativePath: 'solo-is-a-team-size/index.md' },
+      { name: 'index.md', path: '/kb/software-developer/index.md', relativePath: 'software-developer/index.md' },
+    ];
+    const key = buildCommandPaletteFileSearchKey('/kb', 'solo-is-a');
+
+    const scored = scoreCommandPaletteFiles(fileResults, 'solo-is-a', key, key);
+    expect(scored).toHaveLength(1);
+    expect(scored[0].item.relativePath).toBe('solo-is-a-team-size/index.md');
+  });
+
+  test('ranks prefix path matches above later substring matches', () => {
+    const fileResults = [
+      { name: 'index.md', path: '/kb/notes/solo/index.md', relativePath: 'notes/solo/index.md' },
+      { name: 'index.md', path: '/kb/solo-is-a-team-size/index.md', relativePath: 'solo-is-a-team-size/index.md' },
+    ];
+    const key = buildCommandPaletteFileSearchKey('/kb', 'solo');
+
+    const scored = scoreCommandPaletteFiles(fileResults, 'solo', key, key);
+    expect(scored[0].item.relativePath).toBe('solo-is-a-team-size/index.md');
+  });
 });
diff --git a/packages/ui/src/components/ui/commandPaletteFilesState.ts b/packages/ui/src/components/ui/commandPaletteFilesState.ts
index ac5a9b15..0ea03770 100644
--- a/packages/ui/src/components/ui/commandPaletteFilesState.ts
+++ b/packages/ui/src/components/ui/commandPaletteFilesState.ts
@@ -11,7 +11,7 @@ export const buildCommandPaletteFileSearchKey = (
   return JSON.stringify([currentRoot, trimmedQuery]);
 };
 
-export const scoreCommandPaletteFiles = <T extends { name: string }>(
+export const scoreCommandPaletteFiles = <T extends { name: string; relativePath: string }>(
   fileResults: T[],
   trimmedQuery: string,
   fileSearchKey: string,
@@ -21,7 +21,9 @@ export const scoreCommandPaletteFiles = <T extends { name: string }>(
     return [];
   }
 
-  return scoreByFuzzyQuery(fileResults, trimmedQuery, (file) => file.name, {
+  // Score against the full relative path: queries like "solo-is-a" must match
+  // solo-is-a-team-size/index.md even though the basename is just index.md.
+  return scoreByFuzzyQuery(fileResults, trimmedQuery, (file) => file.relativePath || file.name, {
     limit: 10,
     threshold: 0.4,
   });