Merge branch 'main' into fix/task-execution

apps/server/src/index.ts

@@ -112,10 +112,11 @@ app.use(express.json({ limit: '50mb' }));
 const events: EventEmitter = createEventEmitter();
 
 // Create services
-const agentService = new AgentService(DATA_DIR, events);
-const featureLoader = new FeatureLoader();
-const autoModeService = new AutoModeService(events);
+// Note: settingsService is created first so it can be injected into other services
 const settingsService = new SettingsService(DATA_DIR);
+const agentService = new AgentService(DATA_DIR, events, settingsService);
+const featureLoader = new FeatureLoader();
+const autoModeService = new AutoModeService(events, settingsService);
 const claudeUsageService = new ClaudeUsageService();
 
 // Initialize services
@@ -148,17 +149,17 @@ app.use('/api/enhance-prompt', createEnhancePromptRoutes());
 app.use('/api/worktree', createWorktreeRoutes());
 app.use('/api/git', createGitRoutes());
 app.use('/api/setup', createSetupRoutes());
-app.use('/api/suggestions', createSuggestionsRoutes(events));
+app.use('/api/suggestions', createSuggestionsRoutes(events, settingsService));
 app.use('/api/models', createModelsRoutes());
-app.use('/api/spec-regeneration', createSpecRegenerationRoutes(events));
+app.use('/api/spec-regeneration', createSpecRegenerationRoutes(events, settingsService));
 app.use('/api/running-agents', createRunningAgentsRoutes(autoModeService));
 app.use('/api/workspace', createWorkspaceRoutes());
 app.use('/api/templates', createTemplatesRoutes());
 app.use('/api/terminal', createTerminalRoutes());
 app.use('/api/settings', createSettingsRoutes(settingsService));
 app.use('/api/claude', createClaudeRoutes(claudeUsageService));
-app.use('/api/github', createGitHubRoutes(events));
-app.use('/api/context', createContextRoutes());
+app.use('/api/github', createGitHubRoutes(events, settingsService));
+app.use('/api/context', createContextRoutes(settingsService));
 
 // Create HTTP server
 const server = createServer(app);

apps/server/src/lib/sdk-options.ts

@@ -136,6 +136,59 @@ function getBaseOptions(): Partial<Options> {
   };
 }
 
+/**
+ * Build system prompt configuration based on autoLoadClaudeMd setting.
+ * When autoLoadClaudeMd is true:
+ * - Uses preset mode with 'claude_code' to enable CLAUDE.md auto-loading
+ * - If there's a custom systemPrompt, appends it to the preset
+ * - Sets settingSources to ['project'] for SDK to load CLAUDE.md files
+ *
+ * @param config - The SDK options config
+ * @returns Object with systemPrompt and settingSources for SDK options
+ */
+function buildClaudeMdOptions(config: CreateSdkOptionsConfig): {
+  systemPrompt?: string | SystemPromptConfig;
+  settingSources?: Array<'user' | 'project' | 'local'>;
+} {
+  if (!config.autoLoadClaudeMd) {
+    // Standard mode - just pass through the system prompt as-is
+    return config.systemPrompt ? { systemPrompt: config.systemPrompt } : {};
+  }
+
+  // Auto-load CLAUDE.md mode - use preset with settingSources
+  const result: {
+    systemPrompt: SystemPromptConfig;
+    settingSources: Array<'user' | 'project' | 'local'>;
+  } = {
+    systemPrompt: {
+      type: 'preset',
+      preset: 'claude_code',
+    },
+    // Load both user (~/.claude/CLAUDE.md) and project (.claude/CLAUDE.md) settings
+    settingSources: ['user', 'project'],
+  };
+
+  // If there's a custom system prompt, append it to the preset
+  if (config.systemPrompt) {
+    result.systemPrompt.append = config.systemPrompt;
+  }
+
+  return result;
+}
+
+/**
+ * System prompt configuration for SDK options
+ * When using preset mode with claude_code, CLAUDE.md files are automatically loaded
+ */
+export interface SystemPromptConfig {
+  /** Use preset mode with claude_code to enable CLAUDE.md auto-loading */
+  type: 'preset';
+  /** The preset to use - 'claude_code' enables CLAUDE.md loading */
+  preset: 'claude_code';
+  /** Optional additional prompt to append to the preset */
+  append?: string;
+}
+
 /**
  * Options configuration for creating SDK options
  */
@@ -160,6 +213,9 @@ export interface CreateSdkOptionsConfig {
     type: 'json_schema';
     schema: Record<string, unknown>;
   };
+
+  /** Enable auto-loading of CLAUDE.md files via SDK's settingSources */
+  autoLoadClaudeMd?: boolean;
 }
 
 /**
@@ -169,11 +225,15 @@ export interface CreateSdkOptionsConfig {
  * - Uses read-only tools for codebase analysis
  * - Extended turns for thorough exploration
  * - Opus model by default (can be overridden)
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createSpecGenerationOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     // Override permissionMode - spec generation only needs read-only tools
@@ -184,7 +244,7 @@ export function createSpecGenerationOptions(config: CreateSdkOptionsConfig): Opt
     maxTurns: MAX_TURNS.maximum,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.specGeneration],
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
     ...(config.outputFormat && { outputFormat: config.outputFormat }),
   };
@@ -197,11 +257,15 @@ export function createSpecGenerationOptions(config: CreateSdkOptionsConfig): Opt
  * - Uses read-only tools (just needs to read the spec)
  * - Quick turns since it's mostly JSON generation
  * - Sonnet model by default for speed
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createFeatureGenerationOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     // Override permissionMode - feature generation only needs read-only tools
@@ -210,7 +274,7 @@ export function createFeatureGenerationOptions(config: CreateSdkOptionsConfig):
     maxTurns: MAX_TURNS.quick,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.readOnly],
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }
@@ -222,18 +286,22 @@ export function createFeatureGenerationOptions(config: CreateSdkOptionsConfig):
  * - Uses read-only tools for analysis
  * - Standard turns to allow thorough codebase exploration and structured output generation
  * - Opus model by default for thorough analysis
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createSuggestionsOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('suggestions', config.model),
     maxTurns: MAX_TURNS.extended,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.readOnly],
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
     ...(config.outputFormat && { outputFormat: config.outputFormat }),
   };
@@ -247,6 +315,7 @@ export function createSuggestionsOptions(config: CreateSdkOptionsConfig): Option
  * - Standard turns for interactive sessions
  * - Model priority: explicit model > session model > chat default
  * - Sandbox enabled for bash safety
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createChatOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
@@ -255,6 +324,9 @@ export function createChatOptions(config: CreateSdkOptionsConfig): Options {
   // Model priority: explicit model > session model > chat default
   const effectiveModel = config.model || config.sessionModel;
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('chat', effectiveModel),
@@ -265,7 +337,7 @@ export function createChatOptions(config: CreateSdkOptionsConfig): Options {
       enabled: true,
       autoAllowBashIfSandboxed: true,
     },
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }
@@ -278,11 +350,15 @@ export function createChatOptions(config: CreateSdkOptionsConfig): Options {
  * - Extended turns for thorough feature implementation
  * - Uses default model (can be overridden)
  * - Sandbox enabled for bash safety
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createAutoModeOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('auto', config.model),
@@ -293,7 +369,7 @@ export function createAutoModeOptions(config: CreateSdkOptionsConfig): Options {
       enabled: true,
       autoAllowBashIfSandboxed: true,
     },
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }
@@ -302,6 +378,7 @@ export function createAutoModeOptions(config: CreateSdkOptionsConfig): Options {
  * Create custom SDK options with explicit configuration
  *
  * Use this when the preset options don't fit your use case.
+ * When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createCustomOptions(
   config: CreateSdkOptionsConfig & {
@@ -313,6 +390,9 @@ export function createCustomOptions(
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('default', config.model),
@@ -320,7 +400,7 @@ export function createCustomOptions(
     cwd: config.cwd,
     allowedTools: config.allowedTools ? [...config.allowedTools] : [...TOOL_PRESETS.readOnly],
     ...(config.sandbox && { sandbox: config.sandbox }),
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }

apps/server/src/lib/settings-helpers.ts

@@ -0,0 +1,110 @@
+/**
+ * Helper utilities for loading settings and context file handling across different parts of the server
+ */
+
+import type { SettingsService } from '../services/settings-service.js';
+import type { ContextFilesResult, ContextFileInfo } from '@automaker/utils';
+
+/**
+ * Get the autoLoadClaudeMd setting, with project settings taking precedence over global.
+ * Returns false if settings service is not available.
+ *
+ * @param projectPath - Path to the project
+ * @param settingsService - Optional settings service instance
+ * @param logPrefix - Prefix for log messages (e.g., '[DescribeImage]')
+ * @returns Promise resolving to the autoLoadClaudeMd setting value
+ */
+export async function getAutoLoadClaudeMdSetting(
+  projectPath: string,
+  settingsService?: SettingsService | null,
+  logPrefix = '[SettingsHelper]'
+): Promise<boolean> {
+  if (!settingsService) {
+    console.log(`${logPrefix} SettingsService not available, autoLoadClaudeMd disabled`);
+    return false;
+  }
+
+  try {
+    // Check project settings first (takes precedence)
+    const projectSettings = await settingsService.getProjectSettings(projectPath);
+    if (projectSettings.autoLoadClaudeMd !== undefined) {
+      console.log(
+        `${logPrefix} autoLoadClaudeMd from project settings: ${projectSettings.autoLoadClaudeMd}`
+      );
+      return projectSettings.autoLoadClaudeMd;
+    }
+
+    // Fall back to global settings
+    const globalSettings = await settingsService.getGlobalSettings();
+    const result = globalSettings.autoLoadClaudeMd ?? false;
+    console.log(`${logPrefix} autoLoadClaudeMd from global settings: ${result}`);
+    return result;
+  } catch (error) {
+    console.error(`${logPrefix} Failed to load autoLoadClaudeMd setting:`, error);
+    throw error;
+  }
+}
+
+/**
+ * Filters out CLAUDE.md from context files when autoLoadClaudeMd is enabled
+ * and rebuilds the formatted prompt without it.
+ *
+ * When autoLoadClaudeMd is true, the SDK handles CLAUDE.md loading via settingSources,
+ * so we need to exclude it from the manual context loading to avoid duplication.
+ * Other context files (CODE_QUALITY.md, CONVENTIONS.md, etc.) are preserved.
+ *
+ * @param contextResult - Result from loadContextFiles
+ * @param autoLoadClaudeMd - Whether SDK auto-loading is enabled
+ * @returns Filtered context prompt (empty string if no non-CLAUDE.md files)
+ */
+export function filterClaudeMdFromContext(
+  contextResult: ContextFilesResult,
+  autoLoadClaudeMd: boolean
+): string {
+  // If autoLoadClaudeMd is disabled, return the original prompt unchanged
+  if (!autoLoadClaudeMd || contextResult.files.length === 0) {
+    return contextResult.formattedPrompt;
+  }
+
+  // Filter out CLAUDE.md (case-insensitive)
+  const nonClaudeFiles = contextResult.files.filter((f) => f.name.toLowerCase() !== 'claude.md');
+
+  // If all files were CLAUDE.md, return empty string
+  if (nonClaudeFiles.length === 0) {
+    return '';
+  }
+
+  // Rebuild prompt without CLAUDE.md using the same format as loadContextFiles
+  const formattedFiles = nonClaudeFiles.map((file) => formatContextFileEntry(file));
+
+  return `# Project Context Files
+
+The following context files provide project-specific rules, conventions, and guidelines.
+Each file serves a specific purpose - use the description to understand when to reference it.
+If you need more details about a context file, you can read the full file at the path provided.
+
+**IMPORTANT**: You MUST follow the rules and conventions specified in these files.
+- Follow ALL commands exactly as shown (e.g., if the project uses \`pnpm\`, NEVER use \`npm\` or \`npx\`)
+- Follow ALL coding conventions, commit message formats, and architectural patterns specified
+- Reference these rules before running ANY shell commands or making commits
+
+---
+
+${formattedFiles.join('\n\n---\n\n')}
+
+---
+
+**REMINDER**: Before taking any action, verify you are following the conventions specified above.
+`;
+}
+
+/**
+ * Format a single context file entry for the prompt
+ * (Matches the format used in @automaker/utils/context-loader.ts)
+ */
+function formatContextFileEntry(file: ContextFileInfo): string {
+  const header = `## ${file.name}`;
+  const pathInfo = `**Path:** \`${file.path}\``;
+  const descriptionInfo = file.description ? `\n**Purpose:** ${file.description}` : '';
+  return `${header}\n${pathInfo}${descriptionInfo}\n\n${file.content}`;
+}

apps/server/src/providers/claude-provider.ts

@@ -55,6 +55,8 @@ export class ClaudeProvider extends BaseProvider {
       ...(sdkSessionId && conversationHistory && conversationHistory.length > 0
         ? { resume: sdkSessionId }
         : {}),
+      // Forward settingSources for CLAUDE.md file loading
+      ...(options.settingSources && { settingSources: options.settingSources }),
     };
 
     // Build prompt payload

apps/server/src/providers/types.ts

@@ -26,13 +26,14 @@ export interface ExecuteOptions {
   prompt: string | Array<{ type: string; text?: string; source?: object }>;
   model: string;
   cwd: string;
-  systemPrompt?: string;
+  systemPrompt?: string | { type: 'preset'; preset: 'claude_code'; append?: string };
   maxTurns?: number;
   allowedTools?: string[];
   mcpServers?: Record<string, unknown>;
   abortController?: AbortController;
   conversationHistory?: ConversationMessage[]; // Previous messages for context
   sdkSessionId?: string; // Claude SDK session ID for resuming conversations
+  settingSources?: Array<'user' | 'project' | 'local'>; // Claude filesystem settings to load
 }
 
 /**

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', {

apps/server/src/services/agent-service.ts

@@ -16,6 +16,8 @@ import {
 import { ProviderFactory } from '../providers/provider-factory.js';
 import { createChatOptions, validateWorkingDirectory } from '../lib/sdk-options.js';
 import { PathNotAllowedError } from '@automaker/platform';
+import type { SettingsService } from './settings-service.js';
+import { getAutoLoadClaudeMdSetting, filterClaudeMdFromContext } from '../lib/settings-helpers.js';
 
 interface Message {
   id: string;
@@ -57,11 +59,13 @@ export class AgentService {
   private stateDir: string;
   private metadataFile: string;
   private events: EventEmitter;
+  private settingsService: SettingsService | null = null;
 
-  constructor(dataDir: string, events: EventEmitter) {
+  constructor(dataDir: string, events: EventEmitter, settingsService?: SettingsService) {
     this.stateDir = path.join(dataDir, 'agent-sessions');
     this.metadataFile = path.join(dataDir, 'sessions-metadata.json');
     this.events = events;
+    this.settingsService = settingsService ?? null;
   }
 
   async initialize(): Promise<void> {
@@ -186,12 +190,23 @@ export class AgentService {
       // Determine the effective working directory for context loading
       const effectiveWorkDir = workingDirectory || session.workingDirectory;
 
+      // Load autoLoadClaudeMd setting (project setting takes precedence over global)
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        effectiveWorkDir,
+        this.settingsService,
+        '[AgentService]'
+      );
+
       // Load project context files (CLAUDE.md, CODE_QUALITY.md, etc.)
-      const { formattedPrompt: contextFilesPrompt } = await loadContextFiles({
+      const contextResult = await loadContextFiles({
         projectPath: effectiveWorkDir,
         fsModule: secureFs as Parameters<typeof loadContextFiles>[0]['fsModule'],
       });
 
+      // When autoLoadClaudeMd is enabled, filter out CLAUDE.md to avoid duplication
+      // (SDK handles CLAUDE.md via settingSources), but keep other context files like CODE_QUALITY.md
+      const contextFilesPrompt = filterClaudeMdFromContext(contextResult, autoLoadClaudeMd);
+
       // Build combined system prompt with base prompt and context files
       const baseSystemPrompt = this.getSystemPrompt();
       const combinedSystemPrompt = contextFilesPrompt
@@ -205,6 +220,7 @@ export class AgentService {
         sessionModel: session.model,
         systemPrompt: combinedSystemPrompt,
         abortController: session.abortController!,
+        autoLoadClaudeMd,
       });
 
       // Extract model, maxTurns, and allowedTools from SDK options
@@ -224,11 +240,12 @@ export class AgentService {
         prompt: '', // Will be set below based on images
         model: effectiveModel,
         cwd: effectiveWorkDir,
-        systemPrompt: combinedSystemPrompt,
+        systemPrompt: sdkOptions.systemPrompt,
         maxTurns: maxTurns,
         allowedTools: allowedTools,
         abortController: session.abortController!,
         conversationHistory: conversationHistory.length > 0 ? conversationHistory : undefined,
+        settingSources: sdkOptions.settingSources,
         sdkSessionId: session.sdkSessionId, // Pass SDK session ID for resuming
       };
 

apps/server/src/services/auto-mode-service.ts

@@ -25,8 +25,14 @@ import { promisify } from 'util';
 import path from 'path';
 import * as secureFs from '../lib/secure-fs.js';
 import type { EventEmitter } from '../lib/events.js';
-import { createAutoModeOptions, validateWorkingDirectory } from '../lib/sdk-options.js';
+import {
+  createAutoModeOptions,
+  createCustomOptions,
+  validateWorkingDirectory,
+} from '../lib/sdk-options.js';
 import { FeatureLoader } from './feature-loader.js';
+import type { SettingsService } from './settings-service.js';
+import { getAutoLoadClaudeMdSetting, filterClaudeMdFromContext } from '../lib/settings-helpers.js';
 
 const execAsync = promisify(exec);
 
@@ -341,9 +347,11 @@ export class AutoModeService {
   private autoLoopAbortController: AbortController | null = null;
   private config: AutoModeConfig | null = null;
   private pendingApprovals = new Map<string, PendingApproval>();
+  private settingsService: SettingsService | null = null;
 
-  constructor(events: EventEmitter) {
+  constructor(events: EventEmitter, settingsService?: SettingsService) {
     this.events = events;
+    this.settingsService = settingsService ?? null;
   }
 
   /**
@@ -551,14 +559,25 @@ export class AutoModeService {
       // Update feature status to in_progress
       await this.updateFeatureStatus(projectPath, featureId, 'in_progress');
 
+      // Load autoLoadClaudeMd setting to determine context loading strategy
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        projectPath,
+        this.settingsService,
+        '[AutoMode]'
+      );
+
       // Build the prompt - use continuation prompt if provided (for recovery after plan approval)
       let prompt: string;
       // Load project context files (CLAUDE.md, CODE_QUALITY.md, etc.) - passed as system prompt
-      const { formattedPrompt: contextFilesPrompt } = await loadContextFiles({
+      const contextResult = await loadContextFiles({
         projectPath,
         fsModule: secureFs as Parameters<typeof loadContextFiles>[0]['fsModule'],
       });
 
+      // When autoLoadClaudeMd is enabled, filter out CLAUDE.md to avoid duplication
+      // (SDK handles CLAUDE.md via settingSources), but keep other context files like CODE_QUALITY.md
+      const contextFilesPrompt = filterClaudeMdFromContext(contextResult, autoLoadClaudeMd);
+
       if (options?.continuationPrompt) {
         // Continuation prompt is used when recovering from a plan approval
         // The plan was already approved, so skip the planning phase
@@ -604,6 +623,7 @@ export class AutoModeService {
           planningMode: feature.planningMode,
           requirePlanApproval: feature.requirePlanApproval,
           systemPrompt: contextFilesPrompt || undefined,
+          autoLoadClaudeMd,
         }
       );
 
@@ -746,12 +766,23 @@ export class AutoModeService {
       // No previous context
     }
 
+    // Load autoLoadClaudeMd setting to determine context loading strategy
+    const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+      projectPath,
+      this.settingsService,
+      '[AutoMode]'
+    );
+
     // Load project context files (CLAUDE.md, CODE_QUALITY.md, etc.) - passed as system prompt
-    const { formattedPrompt: contextFilesPrompt } = await loadContextFiles({
+    const contextResult = await loadContextFiles({
       projectPath,
       fsModule: secureFs as Parameters<typeof loadContextFiles>[0]['fsModule'],
     });
 
+    // When autoLoadClaudeMd is enabled, filter out CLAUDE.md to avoid duplication
+    // (SDK handles CLAUDE.md via settingSources), but keep other context files like CODE_QUALITY.md
+    const contextFilesPrompt = filterClaudeMdFromContext(contextResult, autoLoadClaudeMd);
+
     // Build complete prompt with feature info, previous context, and follow-up instructions
     let fullPrompt = `## Follow-up on Feature Implementation
 
@@ -879,6 +910,7 @@ Address the follow-up instructions above. Review the previous work and make the
           planningMode: 'skip', // Follow-ups don't require approval
           previousContent: previousContext || undefined,
           systemPrompt: contextFilesPrompt || undefined,
+          autoLoadClaudeMd,
         }
       );
 
@@ -1065,11 +1097,6 @@ Address the follow-up instructions above. Review the previous work and make the
    * Analyze project to gather context
    */
   async analyzeProject(projectPath: string): Promise<void> {
-    // Validate project path before proceeding
-    // This is called here because analyzeProject builds ExecuteOptions directly
-    // without using a factory function from sdk-options.ts
-    validateWorkingDirectory(projectPath);
-
     const abortController = new AbortController();
 
     const analysisFeatureId = `analysis-${Date.now()}`;
@@ -1097,13 +1124,31 @@ Format your response as a structured markdown document.`;
       const analysisModel = resolveModelString(undefined, DEFAULT_MODELS.claude);
       const provider = ProviderFactory.getProviderForModel(analysisModel);
 
-      const options: ExecuteOptions = {
-        prompt,
+      // Load autoLoadClaudeMd setting
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        projectPath,
+        this.settingsService,
+        '[AutoMode]'
+      );
+
+      // Use createCustomOptions for centralized SDK configuration with CLAUDE.md support
+      const sdkOptions = createCustomOptions({
+        cwd: projectPath,
         model: analysisModel,
         maxTurns: 5,
-        cwd: projectPath,
         allowedTools: ['Read', 'Glob', 'Grep'],
         abortController,
+        autoLoadClaudeMd,
+      });
+
+      const options: ExecuteOptions = {
+        prompt,
+        model: sdkOptions.model ?? analysisModel,
+        cwd: sdkOptions.cwd ?? projectPath,
+        maxTurns: sdkOptions.maxTurns,
+        allowedTools: sdkOptions.allowedTools as string[],
+        abortController,
+        settingSources: sdkOptions.settingSources,
       };
 
       const stream = provider.executeQuery(options);
@@ -1708,6 +1753,7 @@ This helps parse your summary correctly in the output logs.`;
       requirePlanApproval?: boolean;
       previousContent?: string;
       systemPrompt?: string;
+      autoLoadClaudeMd?: boolean;
     }
   ): Promise<void> {
     const finalProjectPath = options?.projectPath || projectPath;
@@ -1780,11 +1826,19 @@ This mock response was generated because AUTOMAKER_MOCK_AGENT=true was set.
       return;
     }
 
+    // Load autoLoadClaudeMd setting (project setting takes precedence over global)
+    // Use provided value if available, otherwise load from settings
+    const autoLoadClaudeMd =
+      options?.autoLoadClaudeMd !== undefined
+        ? options.autoLoadClaudeMd
+        : await getAutoLoadClaudeMdSetting(finalProjectPath, this.settingsService, '[AutoMode]');
+
     // Build SDK options using centralized configuration for feature implementation
     const sdkOptions = createAutoModeOptions({
       cwd: workDir,
       model: model,
       abortController,
+      autoLoadClaudeMd,
     });
 
     // Extract model, maxTurns, and allowedTools from SDK options
@@ -1823,7 +1877,8 @@ This mock response was generated because AUTOMAKER_MOCK_AGENT=true was set.
       cwd: workDir,
       allowedTools: allowedTools,
       abortController,
-      systemPrompt: options?.systemPrompt,
+      systemPrompt: sdkOptions.systemPrompt,
+      settingSources: sdkOptions.settingSources,
     };
 
     // Execute via provider