diff --git a/.env.example b/.env.example
index 9a48585..1c21eb6 100644
--- a/.env.example
+++ b/.env.example
@@ -6,3 +6,7 @@ VITE_SUPABASE_PUBLISHABLE_KEY=
 # Required in hosted mode; ignored in self-hosted mode.
 # Hosted: the Facet account/billing API base URL (e.g., https://api.facet.app).
 VITE_FACET_API_BASE_URL=
+# Pilot flag (#103): route eligible AI calls through Anthropic native structured
+# outputs (output_config.format) instead of the <result>-sentinel JSON extraction
+# path. Default off; set to "true" to enable. Currently gates bulletReframing only.
+VITE_FACET_STRUCTURED_OUTPUTS=false
diff --git a/src/test/bulletReframing.test.ts b/src/test/bulletReframing.test.ts
index 8702d09..e85963f 100644
--- a/src/test/bulletReframing.test.ts
+++ b/src/test/bulletReframing.test.ts
@@ -1,5 +1,5 @@
 import { beforeEach, describe, expect, it, vi } from 'vitest'
-import { reframeBulletForVector } from '../utils/bulletReframing'
+import { REFRAME_OUTPUT_SCHEMA, reframeBulletForVector } from '../utils/bulletReframing'
 
 describe('bulletReframing', () => {
   const mockEndpoint = 'https://api.example.com/ai'
@@ -242,4 +242,65 @@ describe('bulletReframing', () => {
     expect(body.messages[0]?.content).toContain('<target_vector>Vector 1</target_vector>')
     expect(body.messages[0]?.content).not.toContain('<positioning_strategy>')
   })
+
+  it('sends output_config.format and parses structured JSON directly when enabled', async () => {
+    // Anthropic-style envelope with a pure-JSON text block (no <result> sentinel,
+    // no fence) — what the structured-outputs path returns. The direct-parse path
+    // must consume it without the extraction heuristics.
+    vi.mocked(fetch).mockResolvedValue({
+      ok: true,
+      json: async () => ({
+        content: [
+          {
+            type: 'text',
+            text: JSON.stringify({ reframed: 'Structured rewrite', reasoning: 'Schema-bound' }),
+          },
+        ],
+      }),
+    } as Response)
+
+    const result = await reframeBulletForVector('Original text', 'Vector 1', mockEndpoint, {
+      structuredOutput: true,
+    })
+
+    expect(result).toEqual({
+      original: 'Original text',
+      reframed: 'Structured rewrite',
+      reasoning: 'Schema-bound',
+    })
+
+    const [, init] = vi.mocked(fetch).mock.calls[0] ?? []
+    const body = JSON.parse((init as RequestInit).body as string) as {
+      output_config?: unknown
+    }
+    expect(body.output_config).toEqual({
+      format: { type: 'json_schema', schema: REFRAME_OUTPUT_SCHEMA },
+    })
+  })
+
+  it('omits output_config on the default extraction path', async () => {
+    vi.mocked(fetch).mockResolvedValue({
+      ok: true,
+      json: async () => ({
+        choices: [
+          {
+            message: {
+              content: JSON.stringify({
+                reframed: 'Rewritten text',
+                reasoning: 'Strategic reason',
+              }),
+            },
+          },
+        ],
+      }),
+    } as Response)
+
+    await reframeBulletForVector('Original text', 'Vector 1', mockEndpoint, {
+      structuredOutput: false,
+    })
+
+    const [, init] = vi.mocked(fetch).mock.calls[0] ?? []
+    const body = JSON.parse((init as RequestInit).body as string) as Record<string, unknown>
+    expect(body.output_config).toBeUndefined()
+  })
 })
diff --git a/src/utils/bulletReframing.ts b/src/utils/bulletReframing.ts
index 428f404..65f9340 100644
--- a/src/utils/bulletReframing.ts
+++ b/src/utils/bulletReframing.ts
@@ -1,10 +1,34 @@
+import { facetClientEnv } from './facetEnv'
 import { callLlmProxy, extractJsonBlock, JsonExtractionError } from './llmProxy'
 
 const BULLET_REFRAMING_MODEL = 'sonnet'
 
+/**
+ * Output contract for the structured-outputs path (#103 pilot). Hand-written
+ * rather than Zod-derived so the pilot stays dependency-free and provably within
+ * the constrained-decoding subset: every object sets `additionalProperties: false`
+ * and lists `required`. The broader rollout is expected to adopt Zod
+ * (`z.toJSONSchema()`) for ergonomics + a runtime backstop.
+ */
+export const REFRAME_OUTPUT_SCHEMA = {
+  type: 'object',
+  additionalProperties: false,
+  required: ['reframed', 'reasoning'],
+  properties: {
+    reframed: { type: 'string' },
+    reasoning: { type: 'string' },
+  },
+} as const
+
 export interface BulletReframingOptions {
   apiKey?: string
   strategy?: string
+  /**
+   * Force the structured-outputs path on/off for this call. Defaults to the
+   * `VITE_FACET_STRUCTURED_OUTPUTS` flag (`facetClientEnv.structuredOutputs`).
+   * Primarily a test/escape hatch; production callers inherit the env flag.
+   */
+  structuredOutput?: boolean
 }
 
 export interface ReframedBulletResult {
@@ -41,17 +65,24 @@ ${options.strategy ? `<positioning_strategy>${escapePromptXml(options.strategy)}
 
 Respond in JSON only.`
 
+  const useStructuredOutput = options.structuredOutput ?? facetClientEnv.structuredOutputs
+
   const rawResponse = await callLlmProxy(endpoint, systemPrompt, userPrompt, {
     feature: 'build.bullet-reframe',
     model: BULLET_REFRAMING_MODEL,
     temperature: 0,
     apiKey: options.apiKey,
+    ...(useStructuredOutput
+      ? { outputConfig: { format: { type: 'json_schema', schema: REFRAME_OUTPUT_SCHEMA } } }
+      : {}),
   })
 
   let parsed: Record<string, unknown>
   try {
-    const extracted = extractJsonBlock(rawResponse)
-    parsed = JSON.parse(extracted) as Record<string, unknown>
+    // Structured outputs guarantee the text block is valid JSON matching the
+    // schema, so parse it directly and skip the sentinel/fence/brace heuristics.
+    const jsonText = useStructuredOutput ? rawResponse : extractJsonBlock(rawResponse)
+    parsed = JSON.parse(jsonText) as Record<string, unknown>
   } catch (error) {
     if (error instanceof JsonExtractionError) throw error
     const detail = error instanceof Error ? error.message : 'Unknown error'
diff --git a/src/utils/facetEnv.ts b/src/utils/facetEnv.ts
index 78c7052..2eba85f 100644
--- a/src/utils/facetEnv.ts
+++ b/src/utils/facetEnv.ts
@@ -9,6 +9,13 @@ export interface FacetClientEnv {
   anthropicProxyApiKey: string
   supabaseUrl: string
   supabasePublishableKey: string
+  /**
+   * Pilot flag (#103): route eligible AI calls through Anthropic native
+   * structured outputs instead of the `<result>`-sentinel extraction path.
+   * Env-only (no hosted build-time define yet) while the migration is scoped
+   * to the `bulletReframing` pilot.
+   */
+  structuredOutputs: boolean
 }
 
 export function resolveClientEnvValue(buildValue: BuildEnvValue, viteValue?: string): string {
@@ -19,6 +26,10 @@ export function resolveClientEnvValue(buildValue: BuildEnvValue, viteValue?: str
   return viteValue?.trim() ?? ''
 }
 
+export function resolveBooleanEnvValue(viteValue?: string): boolean {
+  return viteValue?.trim().toLowerCase() === 'true'
+}
+
 export function resolveFacetDeploymentModeValue(
   buildValue: BuildEnvValue,
   viteValue?: FacetDeploymentMode,
@@ -79,6 +90,7 @@ export function getFacetClientEnv(): FacetClientEnv {
       buildSupabasePublishableKey,
       import.meta.env.VITE_SUPABASE_PUBLISHABLE_KEY,
     ),
+    structuredOutputs: resolveBooleanEnvValue(import.meta.env.VITE_FACET_STRUCTURED_OUTPUTS),
   }
 }