feat: integrate settings service for auto-load CLAUDE.md functionality

- Updated API routes to accept an optional settings service for loading the autoLoadClaudeMd setting.
- Introduced a new settings helper utility for retrieving project-specific settings.
- Enhanced feature generation and spec generation processes to utilize the autoLoadClaudeMd setting.
- Refactored relevant route handlers to support the new settings integration across various endpoints.

apps/server/src/routes/app-spec/generate-features-from-spec.ts

@@ -10,6 +10,8 @@ import { createFeatureGenerationOptions } from '../../lib/sdk-options.js';
 import { logAuthStatus } from './common.js';
 import { parseAndCreateFeatures } from './parse-and-create-features.js';
 import { getAppSpecPath } from '@automaker/platform';
+import type { SettingsService } from '../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../lib/settings-helpers.js';
 
 const logger = createLogger('SpecRegeneration');
 
@@ -19,7 +21,8 @@ export async function generateFeaturesFromSpec(
   projectPath: string,
   events: EventEmitter,
   abortController: AbortController,
-  maxFeatures?: number
+  maxFeatures?: number,
+  settingsService?: SettingsService
 ): Promise<void> {
   const featureCount = maxFeatures ?? DEFAULT_MAX_FEATURES;
   logger.debug('========== generateFeaturesFromSpec() started ==========');
@@ -91,9 +94,17 @@ IMPORTANT: Do not ask for clarification. The specification is provided above. Ge
     projectPath: projectPath,
   });
 
+  // Load autoLoadClaudeMd setting
+  const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+    projectPath,
+    settingsService,
+    '[FeatureGeneration]'
+  );
+
   const options = createFeatureGenerationOptions({
     cwd: projectPath,
     abortController,
+    autoLoadClaudeMd,
   });
 
   logger.debug('SDK Options:', JSON.stringify(options, null, 2));

apps/server/src/routes/app-spec/generate-spec.ts

@@ -17,6 +17,8 @@ import { createSpecGenerationOptions } from '../../lib/sdk-options.js';
 import { logAuthStatus } from './common.js';
 import { generateFeaturesFromSpec } from './generate-features-from-spec.js';
 import { ensureAutomakerDir, getAppSpecPath } from '@automaker/platform';
+import type { SettingsService } from '../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../lib/settings-helpers.js';
 
 const logger = createLogger('SpecRegeneration');
 
@@ -27,7 +29,8 @@ export async function generateSpec(
   abortController: AbortController,
   generateFeatures?: boolean,
   analyzeProject?: boolean,
-  maxFeatures?: number
+  maxFeatures?: number,
+  settingsService?: SettingsService
 ): Promise<void> {
   logger.info('========== generateSpec() started ==========');
   logger.info('projectPath:', projectPath);
@@ -83,9 +86,17 @@ ${getStructuredSpecPromptInstruction()}`;
     content: 'Starting spec generation...\n',
   });
 
+  // Load autoLoadClaudeMd setting
+  const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+    projectPath,
+    settingsService,
+    '[SpecRegeneration]'
+  );
+
   const options = createSpecGenerationOptions({
     cwd: projectPath,
     abortController,
+    autoLoadClaudeMd,
     outputFormat: {
       type: 'json_schema',
       schema: specOutputSchema,
@@ -269,7 +280,13 @@ ${getStructuredSpecPromptInstruction()}`;
     // Create a new abort controller for feature generation
     const featureAbortController = new AbortController();
     try {
-      await generateFeaturesFromSpec(projectPath, events, featureAbortController, maxFeatures);
+      await generateFeaturesFromSpec(
+        projectPath,
+        events,
+        featureAbortController,
+        maxFeatures,
+        settingsService
+      );
       // Final completion will be emitted by generateFeaturesFromSpec -> parseAndCreateFeatures
     } catch (featureError) {
       logger.error('Feature generation failed:', featureError);

apps/server/src/routes/app-spec/index.ts

@@ -9,13 +9,17 @@ import { createGenerateHandler } from './routes/generate.js';
 import { createGenerateFeaturesHandler } from './routes/generate-features.js';
 import { createStopHandler } from './routes/stop.js';
 import { createStatusHandler } from './routes/status.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
-export function createSpecRegenerationRoutes(events: EventEmitter): Router {
+export function createSpecRegenerationRoutes(
+  events: EventEmitter,
+  settingsService?: SettingsService
+): Router {
   const router = Router();
 
   router.post('/create', createCreateHandler(events));
-  router.post('/generate', createGenerateHandler(events));
-  router.post('/generate-features', createGenerateFeaturesHandler(events));
+  router.post('/generate', createGenerateHandler(events, settingsService));
+  router.post('/generate-features', createGenerateFeaturesHandler(events, settingsService));
   router.post('/stop', createStopHandler());
   router.get('/status', createStatusHandler());
 

apps/server/src/routes/app-spec/routes/generate-features.ts

@@ -13,10 +13,14 @@ import {
   getErrorMessage,
 } from '../common.js';
 import { generateFeaturesFromSpec } from '../generate-features-from-spec.js';
+import type { SettingsService } from '../../../services/settings-service.js';
 
 const logger = createLogger('SpecRegeneration');
 
-export function createGenerateFeaturesHandler(events: EventEmitter) {
+export function createGenerateFeaturesHandler(
+  events: EventEmitter,
+  settingsService?: SettingsService
+) {
   return async (req: Request, res: Response): Promise<void> => {
     logger.info('========== /generate-features endpoint called ==========');
     logger.debug('Request body:', JSON.stringify(req.body, null, 2));
@@ -49,7 +53,7 @@ export function createGenerateFeaturesHandler(events: EventEmitter) {
       setRunningState(true, abortController);
       logger.info('Starting background feature generation task...');
 
-      generateFeaturesFromSpec(projectPath, events, abortController, maxFeatures)
+      generateFeaturesFromSpec(projectPath, events, abortController, maxFeatures, settingsService)
         .catch((error) => {
           logError(error, 'Feature generation failed with error');
           events.emit('spec-regeneration:event', {

apps/server/src/routes/app-spec/routes/generate.ts

@@ -13,10 +13,11 @@ import {
   getErrorMessage,
 } from '../common.js';
 import { generateSpec } from '../generate-spec.js';
+import type { SettingsService } from '../../../services/settings-service.js';
 
 const logger = createLogger('SpecRegeneration');
 
-export function createGenerateHandler(events: EventEmitter) {
+export function createGenerateHandler(events: EventEmitter, settingsService?: SettingsService) {
   return async (req: Request, res: Response): Promise<void> => {
     logger.info('========== /generate endpoint called ==========');
     logger.debug('Request body:', JSON.stringify(req.body, null, 2));
@@ -67,7 +68,8 @@ export function createGenerateHandler(events: EventEmitter) {
         abortController,
         generateFeatures,
         analyzeProject,
-        maxFeatures
+        maxFeatures,
+        settingsService
       )
         .catch((error) => {
           logError(error, 'Generation failed with error');

apps/server/src/routes/context/index.ts

@@ -8,17 +8,19 @@
 import { Router } from 'express';
 import { createDescribeImageHandler } from './routes/describe-image.js';
 import { createDescribeFileHandler } from './routes/describe-file.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
 /**
  * Create the context router
  *
+ * @param settingsService - Optional settings service for loading autoLoadClaudeMd setting
  * @returns Express router with context endpoints
  */
-export function createContextRoutes(): Router {
+export function createContextRoutes(settingsService?: SettingsService): Router {
   const router = Router();
 
-  router.post('/describe-image', createDescribeImageHandler());
-  router.post('/describe-file', createDescribeFileHandler());
+  router.post('/describe-image', createDescribeImageHandler(settingsService));
+  router.post('/describe-file', createDescribeFileHandler(settingsService));
 
   return router;
 }

apps/server/src/routes/context/routes/describe-file.ts

@@ -17,6 +17,8 @@ import { PathNotAllowedError } from '@automaker/platform';
 import { createCustomOptions } from '../../../lib/sdk-options.js';
 import * as secureFs from '../../../lib/secure-fs.js';
 import * as path from 'path';
+import type { SettingsService } from '../../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../../lib/settings-helpers.js';
 
 const logger = createLogger('DescribeFile');
 
@@ -72,9 +74,12 @@ async function extractTextFromStream(
 /**
  * Create the describe-file request handler
  *
+ * @param settingsService - Optional settings service for loading autoLoadClaudeMd setting
  * @returns Express request handler for file description
  */
-export function createDescribeFileHandler(): (req: Request, res: Response) => Promise<void> {
+export function createDescribeFileHandler(
+  settingsService?: SettingsService
+): (req: Request, res: Response) => Promise<void> {
   return async (req: Request, res: Response): Promise<void> => {
     try {
       const { filePath } = req.body as DescribeFileRequestBody;
@@ -165,6 +170,13 @@ File: ${fileName}${truncated ? ' (truncated)' : ''}`;
       // Use the file's directory as the working directory
       const cwd = path.dirname(resolvedPath);
 
+      // Load autoLoadClaudeMd setting
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        cwd,
+        settingsService,
+        '[DescribeFile]'
+      );
+
       // Use centralized SDK options with proper cwd validation
       // No tools needed since we're passing file content directly
       const sdkOptions = createCustomOptions({
@@ -172,6 +184,7 @@ File: ${fileName}${truncated ? ' (truncated)' : ''}`;
         model: CLAUDE_MODEL_MAP.haiku,
         maxTurns: 1,
         allowedTools: [],
+        autoLoadClaudeMd,
         sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
       });
 

apps/server/src/routes/context/routes/describe-image.ts

@@ -17,6 +17,8 @@ import { CLAUDE_MODEL_MAP } from '@automaker/types';
 import { createCustomOptions } from '../../../lib/sdk-options.js';
 import * as fs from 'fs';
 import * as path from 'path';
+import type { SettingsService } from '../../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../../lib/settings-helpers.js';
 
 const logger = createLogger('DescribeImage');
 
@@ -226,9 +228,12 @@ async function extractTextFromStream(
  * Uses Claude SDK query with multi-part content blocks to include the image (base64),
  * matching the agent runner behavior.
  *
+ * @param settingsService - Optional settings service for loading autoLoadClaudeMd setting
  * @returns Express request handler for image description
  */
-export function createDescribeImageHandler(): (req: Request, res: Response) => Promise<void> {
+export function createDescribeImageHandler(
+  settingsService?: SettingsService
+): (req: Request, res: Response) => Promise<void> {
   return async (req: Request, res: Response): Promise<void> => {
     const requestId = `describe-image-${Date.now()}-${Math.random().toString(36).slice(2, 9)}`;
     const startedAt = Date.now();
@@ -325,12 +330,20 @@ export function createDescribeImageHandler(): (req: Request, res: Response) => P
       const cwd = path.dirname(actualPath);
       logger.info(`[${requestId}] Using cwd=${cwd}`);
 
+      // Load autoLoadClaudeMd setting
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        cwd,
+        settingsService,
+        '[DescribeImage]'
+      );
+
       // Use the same centralized option builder used across the server (validates cwd)
       const sdkOptions = createCustomOptions({
         cwd,
         model: CLAUDE_MODEL_MAP.haiku,
         maxTurns: 1,
         allowedTools: [],
+        autoLoadClaudeMd,
         sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
       });
 

apps/server/src/routes/github/index.ts

@@ -16,8 +16,12 @@ import {
   createDeleteValidationHandler,
   createMarkViewedHandler,
 } from './routes/validation-endpoints.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
-export function createGitHubRoutes(events: EventEmitter): Router {
+export function createGitHubRoutes(
+  events: EventEmitter,
+  settingsService?: SettingsService
+): Router {
   const router = Router();
 
   router.post('/check-remote', validatePathParams('projectPath'), createCheckGitHubRemoteHandler());
@@ -26,7 +30,7 @@ export function createGitHubRoutes(events: EventEmitter): Router {
   router.post(
     '/validate-issue',
     validatePathParams('projectPath'),
-    createValidateIssueHandler(events)
+    createValidateIssueHandler(events, settingsService)
   );
 
   // Validation management endpoints

apps/server/src/routes/github/routes/validate-issue.ts

@@ -23,6 +23,8 @@ import {
   logError,
   logger,
 } from './validation-common.js';
+import type { SettingsService } from '../../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../../lib/settings-helpers.js';
 
 /** Valid model values for validation */
 const VALID_MODELS: readonly AgentModel[] = ['opus', 'sonnet', 'haiku'] as const;
@@ -54,7 +56,8 @@ async function runValidation(
   issueLabels: string[] | undefined,
   model: AgentModel,
   events: EventEmitter,
-  abortController: AbortController
+  abortController: AbortController,
+  settingsService?: SettingsService
 ): Promise<void> {
   // Emit start event
   const startEvent: IssueValidationEvent = {
@@ -76,12 +79,20 @@ async function runValidation(
     // Build the prompt
     const prompt = buildValidationPrompt(issueNumber, issueTitle, issueBody, issueLabels);
 
+    // Load autoLoadClaudeMd setting
+    const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+      projectPath,
+      settingsService,
+      '[ValidateIssue]'
+    );
+
     // Create SDK options with structured output and abort controller
     const options = createSuggestionsOptions({
       cwd: projectPath,
       model,
       systemPrompt: ISSUE_VALIDATION_SYSTEM_PROMPT,
       abortController,
+      autoLoadClaudeMd,
       outputFormat: {
         type: 'json_schema',
         schema: issueValidationSchema as Record<string, unknown>,
@@ -190,7 +201,10 @@ async function runValidation(
  * - System prompt guiding the validation process
  * - Async execution with event emission
  */
-export function createValidateIssueHandler(events: EventEmitter) {
+export function createValidateIssueHandler(
+  events: EventEmitter,
+  settingsService?: SettingsService
+) {
   return async (req: Request, res: Response): Promise<void> => {
     try {
       const {
@@ -256,7 +270,8 @@ export function createValidateIssueHandler(events: EventEmitter) {
         issueLabels,
         model,
         events,
-        abortController
+        abortController,
+        settingsService
       )
         .catch((error) => {
           // Error is already handled inside runValidation (event emitted)

apps/server/src/routes/suggestions/generate-suggestions.ts

@@ -9,6 +9,8 @@ import { createSuggestionsOptions } from '../../lib/sdk-options.js';
 import { FeatureLoader } from '../../services/feature-loader.js';
 import { getAppSpecPath } from '@automaker/platform';
 import * as secureFs from '../../lib/secure-fs.js';
+import type { SettingsService } from '../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../lib/settings-helpers.js';
 
 const logger = createLogger('Suggestions');
 
@@ -125,7 +127,8 @@ export async function generateSuggestions(
   projectPath: string,
   suggestionType: string,
   events: EventEmitter,
-  abortController: AbortController
+  abortController: AbortController,
+  settingsService?: SettingsService
 ): Promise<void> {
   const typePrompts: Record<string, string> = {
     features: 'Analyze this project and suggest new features that would add value.',
@@ -154,9 +157,17 @@ The response will be automatically formatted as structured JSON.`;
   // Don't send initial message - let the agent output speak for itself
   // The first agent message will be captured as an info entry
 
+  // Load autoLoadClaudeMd setting
+  const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+    projectPath,
+    settingsService,
+    '[Suggestions]'
+  );
+
   const options = createSuggestionsOptions({
     cwd: projectPath,
     abortController,
+    autoLoadClaudeMd,
     outputFormat: {
       type: 'json_schema',
       schema: suggestionsSchema,

apps/server/src/routes/suggestions/index.ts

@@ -8,11 +8,19 @@ import { validatePathParams } from '../../middleware/validate-paths.js';
 import { createGenerateHandler } from './routes/generate.js';
 import { createStopHandler } from './routes/stop.js';
 import { createStatusHandler } from './routes/status.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
-export function createSuggestionsRoutes(events: EventEmitter): Router {
+export function createSuggestionsRoutes(
+  events: EventEmitter,
+  settingsService?: SettingsService
+): Router {
   const router = Router();
 
-  router.post('/generate', validatePathParams('projectPath'), createGenerateHandler(events));
+  router.post(
+    '/generate',
+    validatePathParams('projectPath'),
+    createGenerateHandler(events, settingsService)
+  );
   router.post('/stop', createStopHandler());
   router.get('/status', createStatusHandler());
 

apps/server/src/routes/suggestions/routes/generate.ts

@@ -7,10 +7,11 @@ import type { EventEmitter } from '../../../lib/events.js';
 import { createLogger } from '@automaker/utils';
 import { getSuggestionsStatus, setRunningState, getErrorMessage, logError } from '../common.js';
 import { generateSuggestions } from '../generate-suggestions.js';
+import type { SettingsService } from '../../../services/settings-service.js';
 
 const logger = createLogger('Suggestions');
 
-export function createGenerateHandler(events: EventEmitter) {
+export function createGenerateHandler(events: EventEmitter, settingsService?: SettingsService) {
   return async (req: Request, res: Response): Promise<void> => {
     try {
       const { projectPath, suggestionType = 'features' } = req.body as {
@@ -37,7 +38,7 @@ export function createGenerateHandler(events: EventEmitter) {
       setRunningState(true, abortController);
 
       // Start generation in background
-      generateSuggestions(projectPath, suggestionType, events, abortController)
+      generateSuggestions(projectPath, suggestionType, events, abortController, settingsService)
         .catch((error) => {
           logError(error, 'Generate suggestions failed (background)');
           events.emit('suggestions:event', {