diff --git a/src/agent/cleanup-manager.ts b/src/agent/cleanup-manager.ts
index dab8f60..86d5ce2 100644
--- a/src/agent/cleanup-manager.ts
+++ b/src/agent/cleanup-manager.ts
@@ -7,7 +7,8 @@
 
 import { promisify } from 'node:util';
 import { execFile } from 'node:child_process';
-import { readFile, readdir, rm } from 'node:fs/promises';
+import { readFile, readdir, rm, cp, mkdir } from 'node:fs/promises';
+import { existsSync } from 'node:fs';
 import { join } from 'node:path';
 import type { AgentRepository } from '../db/repositories/agent-repository.js';
 import type { ProjectRepository } from '../db/repositories/project-repository.js';
@@ -41,6 +42,7 @@ export class CleanupManager {
     private repository: AgentRepository,
     private projectRepository: ProjectRepository,
     private eventBus?: EventBus,
+    private debug: boolean = false,
   ) {}
 
   /**
@@ -212,6 +214,117 @@ export class CleanupManager {
     }
   }
 
+  /**
+   * Check if all project worktrees for an agent are clean (no uncommitted/untracked files).
+   */
+  async isWorkdirClean(alias: string, initiativeId: string | null): Promise<boolean> {
+    const agentWorkdir = this.getAgentWorkdir(alias);
+
+    try {
+      await readdir(agentWorkdir);
+    } catch {
+      // Workdir doesn't exist — treat as clean
+      return true;
+    }
+
+    const worktreePaths: string[] = [];
+
+    if (initiativeId) {
+      const projects = await this.projectRepository.findProjectsByInitiativeId(initiativeId);
+      for (const project of projects) {
+        worktreePaths.push(join(agentWorkdir, project.name));
+      }
+    } else {
+      worktreePaths.push(join(agentWorkdir, 'workspace'));
+    }
+
+    for (const wtPath of worktreePaths) {
+      try {
+        const { stdout } = await execFileAsync('git', ['status', '--porcelain'], { cwd: wtPath });
+        if (stdout.trim().length > 0) {
+          log.info({ alias, worktree: wtPath }, 'workdir has uncommitted changes');
+          return false;
+        }
+      } catch (err) {
+        log.warn({ alias, worktree: wtPath, err: err instanceof Error ? err.message : String(err) }, 'git status failed, treating as dirty');
+        return false;
+      }
+    }
+
+    return true;
+  }
+
+  /**
+   * Archive agent workdir and logs to .cw/debug/ before removal.
+   */
+  async archiveForDebug(alias: string, agentId: string): Promise<void> {
+    const agentWorkdir = this.getAgentWorkdir(alias);
+    const debugWorkdir = join(this.workspaceRoot, '.cw', 'debug', 'workdirs', alias);
+    const logDir = join(this.workspaceRoot, '.cw', 'agent-logs', agentId);
+    const debugLogDir = join(this.workspaceRoot, '.cw', 'debug', 'agent-logs', agentId);
+
+    try {
+      if (existsSync(agentWorkdir)) {
+        await mkdir(join(this.workspaceRoot, '.cw', 'debug', 'workdirs'), { recursive: true });
+        await cp(agentWorkdir, debugWorkdir, { recursive: true });
+        log.debug({ alias, debugWorkdir }, 'archived workdir for debug');
+      }
+    } catch (err) {
+      log.warn({ alias, err: err instanceof Error ? err.message : String(err) }, 'failed to archive workdir for debug');
+    }
+
+    try {
+      if (existsSync(logDir)) {
+        await mkdir(join(this.workspaceRoot, '.cw', 'debug', 'agent-logs'), { recursive: true });
+        await cp(logDir, debugLogDir, { recursive: true });
+        log.debug({ agentId, debugLogDir }, 'archived logs for debug');
+      }
+    } catch (err) {
+      log.warn({ agentId, err: err instanceof Error ? err.message : String(err) }, 'failed to archive logs for debug');
+    }
+  }
+
+  /**
+   * Auto-cleanup agent workdir after successful completion.
+   * Removes worktrees and logs but preserves branches and DB record.
+   */
+  async autoCleanupAfterCompletion(
+    agentId: string,
+    alias: string,
+    initiativeId: string | null,
+  ): Promise<{ clean: boolean; removed: boolean }> {
+    const agentWorkdir = this.getAgentWorkdir(alias);
+
+    // Idempotent: if workdir is already gone, nothing to do
+    if (!existsSync(agentWorkdir)) {
+      return { clean: true, removed: true };
+    }
+
+    const clean = await this.isWorkdirClean(alias, initiativeId);
+    if (!clean) {
+      return { clean: false, removed: false };
+    }
+
+    if (this.debug) {
+      await this.archiveForDebug(alias, agentId);
+    }
+
+    try {
+      await this.removeAgentWorktrees(alias, initiativeId);
+    } catch (err) {
+      log.warn({ agentId, alias, err: err instanceof Error ? err.message : String(err) }, 'auto-cleanup: failed to remove worktrees');
+    }
+
+    try {
+      await this.removeAgentLogs(agentId);
+    } catch (err) {
+      log.warn({ agentId, err: err instanceof Error ? err.message : String(err) }, 'auto-cleanup: failed to remove logs');
+    }
+
+    log.info({ agentId, alias }, 'auto-cleanup: workdir and logs removed');
+    return { clean: true, removed: true };
+  }
+
   /**
    * Reconcile agent state after server restart.
    * Checks all agents in 'running' status:
@@ -233,7 +346,7 @@ export class CleanupManager {
     }>,
     onStreamEvent: (agentId: string, event: StreamEvent) => void,
     onAgentOutput: (agentId: string, rawOutput: string, provider: NonNullable<ReturnType<typeof getProvider>>) => Promise<void>,
-    pollForCompletion: (agentId: string, pid: number) => void,
+    pollForCompletion: (agentId: string, pid: number, outputFilePath?: string) => void,
   ): Promise<void> {
     const runningAgents = await this.repository.findByStatus('running');
     log.info({ runningCount: runningAgents.length }, 'reconciling agents after restart');
@@ -268,7 +381,7 @@ export class CleanupManager {
           outputFilePath: agent.outputFilePath,
         });
 
-        pollForCompletion(agent.id, pid);
+        pollForCompletion(agent.id, pid, agent.outputFilePath);
       } else if (agent.outputFilePath) {
         try {
           const rawOutput = await readFile(agent.outputFilePath, 'utf-8');
diff --git a/src/agent/manager.ts b/src/agent/manager.ts
index 47ce7a0..e9f257c 100644
--- a/src/agent/manager.ts
+++ b/src/agent/manager.ts
@@ -21,6 +21,7 @@ import type {
 import type { AgentRepository } from '../db/repositories/agent-repository.js';
 import type { AccountRepository } from '../db/repositories/account-repository.js';
 import type { ProjectRepository } from '../db/repositories/project-repository.js';
+import type { ProposalRepository } from '../db/repositories/proposal-repository.js';
 import { generateUniqueAlias } from './alias.js';
 import type {
   EventBus,
@@ -32,6 +33,7 @@ import type {
 import { writeInputFiles } from './file-io.js';
 import { getProvider } from './providers/registry.js';
 import { createModuleLogger } from '../logger/index.js';
+import { join } from 'node:path';
 import type { AccountCredentialManager } from './credentials/types.js';
 import { ProcessManager } from './process-manager.js';
 import { CredentialHandler } from './credential-handler.js';
@@ -41,8 +43,11 @@ import { CleanupManager } from './cleanup-manager.js';
 const log = createModuleLogger('agent-manager');
 
 export class MultiProviderAgentManager implements AgentManager {
+  private static readonly MAX_COMMIT_RETRIES = 1;
+
   private activeAgents: Map<string, ActiveAgent> = new Map();
   private outputBuffers: Map<string, string[]> = new Map();
+  private commitRetryCount: Map<string, number> = new Map();
   private processManager: ProcessManager;
   private credentialHandler: CredentialHandler;
   private outputHandler: OutputHandler;
@@ -55,11 +60,13 @@ export class MultiProviderAgentManager implements AgentManager {
     private accountRepository?: AccountRepository,
     private eventBus?: EventBus,
     private credentialManager?: AccountCredentialManager,
+    private proposalRepository?: ProposalRepository,
+    private debug: boolean = false,
   ) {
     this.processManager = new ProcessManager(workspaceRoot, projectRepository, eventBus);
     this.credentialHandler = new CredentialHandler(workspaceRoot, accountRepository, credentialManager);
-    this.outputHandler = new OutputHandler(repository, eventBus);
-    this.cleanupManager = new CleanupManager(workspaceRoot, repository, projectRepository, eventBus);
+    this.outputHandler = new OutputHandler(repository, eventBus, proposalRepository);
+    this.cleanupManager = new CleanupManager(workspaceRoot, repository, projectRepository, eventBus, debug);
   }
 
   /**
@@ -116,11 +123,33 @@ export class MultiProviderAgentManager implements AgentManager {
     // 2. Create isolated worktrees
     let agentCwd: string;
     if (initiativeId) {
+      log.debug({ alias, initiativeId }, 'creating initiative-based worktrees');
       agentCwd = await this.processManager.createProjectWorktrees(alias, initiativeId);
+
+      // Log projects linked to the initiative
+      const projects = await this.projectRepository.findProjectsByInitiativeId(initiativeId);
+      log.info({
+        alias,
+        initiativeId,
+        projectCount: projects.length,
+        projects: projects.map(p => ({ name: p.name, url: p.url })),
+        agentCwd
+      }, 'initiative-based agent workdir created');
     } else {
+      log.debug({ alias }, 'creating standalone worktree');
       agentCwd = await this.processManager.createStandaloneWorktree(alias);
+      log.info({ alias, agentCwd }, 'standalone agent workdir created');
     }
-    log.debug({ alias, agentCwd }, 'worktrees created');
+
+    // Verify the final agentCwd exists
+    const { existsSync: fsExistsSync } = await import('node:fs');
+    const cwdVerified = fsExistsSync(agentCwd);
+    log.info({
+      alias,
+      agentCwd,
+      cwdVerified,
+      initiativeBasedAgent: !!initiativeId
+    }, 'agent workdir setup completed');
 
     // 2b. Write input files
     if (options.inputContext) {
@@ -144,14 +173,39 @@ export class MultiProviderAgentManager implements AgentManager {
 
     // 4. Build spawn command
     const { command, args, env: providerEnv } = this.processManager.buildSpawnCommand(provider, prompt);
-    log.debug({ command, args: args.join(' '), cwd: cwd ?? agentCwd }, 'spawn command built');
+    const finalCwd = cwd ?? agentCwd;
+
+    log.info({
+      agentId,
+      alias,
+      command,
+      args: args.join(' '),
+      finalCwd,
+      customCwdProvided: !!cwd,
+      providerEnv: Object.keys(providerEnv)
+    }, 'spawn command built');
 
     // 5. Set config dir env var if account selected
     const processEnv: Record<string, string> = { ...providerEnv };
     if (accountConfigDir && provider.configDirEnv) {
       processEnv[provider.configDirEnv] = accountConfigDir;
+
+      // Inject CLAUDE_CODE_OAUTH_TOKEN to bypass macOS keychain entirely.
+      // Claude Code prioritizes this env var over keychain/file-based credentials.
+      const accessToken = this.credentialHandler.readAccessToken(accountConfigDir);
+      if (accessToken) {
+        processEnv['CLAUDE_CODE_OAUTH_TOKEN'] = accessToken;
+        log.debug({ alias }, 'CLAUDE_CODE_OAUTH_TOKEN injected for spawn');
+      }
     }
 
+    log.debug({
+      agentId,
+      finalProcessEnv: Object.keys(processEnv),
+      hasAccountConfig: !!accountConfigDir,
+      hasOAuthToken: !!processEnv['CLAUDE_CODE_OAUTH_TOKEN'],
+    }, 'process environment prepared');
+
     // 6. Spawn detached subprocess
     const { pid, outputFilePath, tailer } = this.processManager.spawnDetached(
       agentId, command, args, cwd ?? agentCwd, processEnv, providerName, prompt,
@@ -160,8 +214,32 @@ export class MultiProviderAgentManager implements AgentManager {
 
     await this.repository.update(agentId, { pid, outputFilePath });
 
+    // Write spawn diagnostic file for post-execution verification
+    const { writeFileSync, existsSync: diagnosticExistsSync } = await import('node:fs');
+    const diagnostic = {
+      timestamp: new Date().toISOString(),
+      agentId,
+      alias,
+      intendedCwd: finalCwd,
+      worktreeId: agent.worktreeId,
+      provider: providerName,
+      command,
+      args,
+      env: processEnv,
+      cwdExistsAtSpawn: diagnosticExistsSync(finalCwd),
+      initiativeId: initiativeId || null,
+      customCwdProvided: !!cwd,
+      accountId: accountId || null,
+    };
+
+    writeFileSync(
+      join(finalCwd, '.cw', 'spawn-diagnostic.json'),
+      JSON.stringify(diagnostic, null, 2),
+      'utf-8'
+    );
+
     this.activeAgents.set(agentId, { agentId, pid, tailer, outputFilePath });
-    log.info({ agentId, alias, pid }, 'detached subprocess started');
+    log.info({ agentId, alias, pid, diagnosticWritten: true }, 'detached subprocess started with diagnostic');
 
     // Emit spawned event
     if (this.eventBus) {
@@ -178,6 +256,7 @@ export class MultiProviderAgentManager implements AgentManager {
       agentId, pid,
       () => this.handleDetachedAgentCompletion(agentId),
       () => this.activeAgents.get(agentId)?.tailer,
+      outputFilePath,
     );
 
     return this.toAgentInfo(agent);
@@ -195,7 +274,132 @@ export class MultiProviderAgentManager implements AgentManager {
       active,
       (alias) => this.processManager.getAgentWorkdir(alias),
     );
+
+    // Sync credentials back to DB if the agent had an account
+    await this.syncCredentialsPostCompletion(agentId);
+
     this.activeAgents.delete(agentId);
+
+    // Auto-cleanup workdir after completion
+    await this.tryAutoCleanup(agentId);
+  }
+
+  /**
+   * Attempt auto-cleanup of agent workdir after completion.
+   * If dirty and retries remain, resumes the agent to commit changes.
+   */
+  private async tryAutoCleanup(agentId: string): Promise<void> {
+    try {
+      const agent = await this.repository.findById(agentId);
+      if (!agent || agent.status !== 'idle') return;
+
+      const { clean, removed } = await this.cleanupManager.autoCleanupAfterCompletion(
+        agentId, agent.name, agent.initiativeId,
+      );
+
+      if (removed) {
+        this.commitRetryCount.delete(agentId);
+        log.info({ agentId, alias: agent.name }, 'auto-cleanup completed');
+        return;
+      }
+
+      if (!clean) {
+        const retries = this.commitRetryCount.get(agentId) ?? 0;
+        if (retries < MultiProviderAgentManager.MAX_COMMIT_RETRIES) {
+          this.commitRetryCount.set(agentId, retries + 1);
+          const resumed = await this.resumeForCommit(agentId);
+          if (resumed) {
+            log.info({ agentId, alias: agent.name, retry: retries + 1 }, 'resumed agent to commit uncommitted changes');
+            return;
+          }
+        }
+        log.warn({ agentId, alias: agent.name }, 'agent workdir has uncommitted changes after max retries, leaving in place');
+        this.commitRetryCount.delete(agentId);
+      }
+    } catch (err) {
+      log.warn({ agentId, err: err instanceof Error ? err.message : String(err) }, 'auto-cleanup failed');
+    }
+  }
+
+  /**
+   * Resume an agent's session with a prompt to commit uncommitted changes.
+   * Returns false if the agent can't be resumed (no session, provider doesn't support resume).
+   */
+  private async resumeForCommit(agentId: string): Promise<boolean> {
+    const agent = await this.repository.findById(agentId);
+    if (!agent?.sessionId) return false;
+
+    const provider = getProvider(agent.provider);
+    if (!provider || provider.resumeStyle === 'none') return false;
+
+    const commitPrompt =
+      'You have uncommitted changes in your working directory. ' +
+      'Stage everything with `git add -A` and commit with an appropriate message describing your work. ' +
+      'Do not make any other changes.';
+
+    await this.repository.update(agentId, { status: 'running', pendingQuestions: null, result: null });
+
+    const agentCwd = this.processManager.getAgentWorkdir(agent.worktreeId);
+    const { command, args, env: providerEnv } = this.processManager.buildResumeCommand(provider, agent.sessionId, commitPrompt);
+
+    const processEnv: Record<string, string> = { ...providerEnv };
+    if (agent.accountId && provider.configDirEnv && this.accountRepository) {
+      const { getAccountConfigDir } = await import('./accounts/paths.js');
+      const configDir = getAccountConfigDir(this.workspaceRoot, agent.accountId);
+      const account = await this.accountRepository.findById(agent.accountId);
+      if (account) {
+        this.credentialHandler.writeCredentialsToDisk(account, configDir);
+      }
+      processEnv[provider.configDirEnv] = configDir;
+
+      const accessToken = this.credentialHandler.readAccessToken(configDir);
+      if (accessToken) {
+        processEnv['CLAUDE_CODE_OAUTH_TOKEN'] = accessToken;
+      }
+    }
+
+    const prevActive = this.activeAgents.get(agentId);
+    if (prevActive?.tailer) {
+      await prevActive.tailer.stop();
+    }
+
+    const { pid, outputFilePath, tailer } = this.processManager.spawnDetached(
+      agentId, command, args, agentCwd, processEnv, provider.name, commitPrompt,
+      (event) => this.outputHandler.handleStreamEvent(agentId, event, this.activeAgents.get(agentId), this.outputBuffers),
+    );
+
+    await this.repository.update(agentId, { pid, outputFilePath });
+    this.activeAgents.set(agentId, { agentId, pid, tailer, outputFilePath });
+
+    this.processManager.pollForCompletion(
+      agentId, pid,
+      () => this.handleDetachedAgentCompletion(agentId),
+      () => this.activeAgents.get(agentId)?.tailer,
+      outputFilePath,
+    );
+
+    return true;
+  }
+
+  /**
+   * Sync credentials from agent's config dir back to DB after completion.
+   * The subprocess may have refreshed tokens mid-session; this ensures
+   * the DB stays current and the next spawn uses fresh tokens.
+   */
+  private async syncCredentialsPostCompletion(agentId: string): Promise<void> {
+    if (!this.accountRepository) return;
+
+    try {
+      const agent = await this.repository.findById(agentId);
+      if (!agent?.accountId) return;
+
+      const { getAccountConfigDir } = await import('./accounts/paths.js');
+      const configDir = getAccountConfigDir(this.workspaceRoot, agent.accountId);
+      await this.credentialHandler.persistRefreshedCredentials(agent.accountId, configDir);
+      log.debug({ agentId, accountId: agent.accountId }, 'post-completion credential sync done');
+    } catch (err) {
+      log.warn({ agentId, err: err instanceof Error ? err.message : String(err) }, 'post-completion credential sync failed');
+    }
   }
 
   /**
@@ -213,6 +417,9 @@ export class MultiProviderAgentManager implements AgentManager {
       this.activeAgents.delete(agentId);
     }
 
+    // Sync credentials before marking stopped
+    await this.syncCredentialsPostCompletion(agentId);
+
     await this.repository.update(agentId, { status: 'stopped' });
 
     if (this.eventBus) {
@@ -271,9 +478,7 @@ export class MultiProviderAgentManager implements AgentManager {
 
     const agentCwd = this.processManager.getAgentWorkdir(agent.worktreeId);
     const prompt = this.outputHandler.formatAnswersAsPrompt(answers);
-    await this.repository.update(agentId, { status: 'running' });
-    await this.repository.update(agentId, { pendingQuestions: null });
-    await this.repository.update(agentId, { result: null });
+    await this.repository.update(agentId, { status: 'running', pendingQuestions: null, result: null });
 
     const { command, args, env: providerEnv } = this.processManager.buildResumeCommand(provider, agent.sessionId, prompt);
     log.debug({ command, args: args.join(' ') }, 'resume command built');
@@ -295,6 +500,13 @@ export class MultiProviderAgentManager implements AgentManager {
       if (refreshed) {
         await this.credentialHandler.persistRefreshedCredentials(agent.accountId, resumeAccountConfigDir);
       }
+
+      // Inject CLAUDE_CODE_OAUTH_TOKEN to bypass macOS keychain on resume
+      const accessToken = this.credentialHandler.readAccessToken(resumeAccountConfigDir);
+      if (accessToken) {
+        processEnv['CLAUDE_CODE_OAUTH_TOKEN'] = accessToken;
+        log.debug({ agentId }, 'CLAUDE_CODE_OAUTH_TOKEN injected for resume');
+      }
     }
 
     // Stop previous tailer
@@ -326,6 +538,7 @@ export class MultiProviderAgentManager implements AgentManager {
       agentId, pid,
       () => this.handleDetachedAgentCompletion(agentId),
       () => this.activeAgents.get(agentId)?.tailer,
+      outputFilePath,
     );
   }
 
@@ -432,10 +645,11 @@ export class MultiProviderAgentManager implements AgentManager {
       this.activeAgents,
       (agentId, event) => this.outputHandler.handleStreamEvent(agentId, event, this.activeAgents.get(agentId), this.outputBuffers),
       (agentId, rawOutput, provider) => this.outputHandler.processAgentOutput(agentId, rawOutput, provider, (alias) => this.processManager.getAgentWorkdir(alias)),
-      (agentId, pid) => this.processManager.pollForCompletion(
+      (agentId, pid, outputFilePath) => this.processManager.pollForCompletion(
         agentId, pid,
         () => this.handleDetachedAgentCompletion(agentId),
         () => this.activeAgents.get(agentId)?.tailer,
+        outputFilePath,
       ),
     );
   }
@@ -456,6 +670,7 @@ export class MultiProviderAgentManager implements AgentManager {
     accountId: string | null;
     createdAt: Date;
     updatedAt: Date;
+    userDismissedAt?: Date | null;
   }): AgentInfo {
     return {
       id: agent.id,
@@ -470,6 +685,7 @@ export class MultiProviderAgentManager implements AgentManager {
       accountId: agent.accountId,
       createdAt: agent.createdAt,
       updatedAt: agent.updatedAt,
+      userDismissedAt: agent.userDismissedAt,
     };
   }
 }
diff --git a/src/agent/output-handler.ts b/src/agent/output-handler.ts
index 43ef3e6..7aeabe5 100644
--- a/src/agent/output-handler.ts
+++ b/src/agent/output-handler.ts
@@ -7,7 +7,10 @@
  */
 
 import { readFile } from 'node:fs/promises';
+import { existsSync } from 'node:fs';
+import { join } from 'node:path';
 import type { AgentRepository } from '../db/repositories/agent-repository.js';
+import type { ProposalRepository, CreateProposalData } from '../db/repositories/proposal-repository.js';
 import type {
   EventBus,
   AgentStoppedEvent,
@@ -30,6 +33,7 @@ import {
   readTaskFiles,
   readDecisionFiles,
   readPageFiles,
+  readFrontmatterFile,
 } from './file-io.js';
 import { getProvider } from './providers/registry.js';
 import { createModuleLogger } from '../logger/index.js';
@@ -52,6 +56,8 @@ export interface ActiveAgent {
   streamResultText?: string;
   streamSessionId?: string;
   streamCostUsd?: number;
+  /** True when the stream result indicated an error (e.g. auth failure) */
+  streamIsError?: boolean;
 }
 
 /**
@@ -71,8 +77,30 @@ export class OutputHandler {
   constructor(
     private repository: AgentRepository,
     private eventBus?: EventBus,
+    private proposalRepository?: ProposalRepository,
   ) {}
 
+  /**
+   * Validate that a signal file is complete and properly formatted.
+   */
+  private async validateSignalFile(filePath: string): Promise<boolean> {
+    try {
+      const content = await readFile(filePath, 'utf-8');
+      const trimmed = content.trim();
+      if (!trimmed) return false;
+
+      // Check if JSON is complete (ends with } or ])
+      const endsCorrectly = trimmed.endsWith('}') || trimmed.endsWith(']');
+      if (!endsCorrectly) return false;
+
+      // Try to parse as JSON to ensure it's valid
+      JSON.parse(trimmed);
+      return true;
+    } catch {
+      return false;
+    }
+  }
+
   /**
    * Handle a standardized stream event from a parser.
    */
@@ -112,6 +140,7 @@ export class OutputHandler {
         if (active) {
           active.streamResultText = event.text;
           active.streamCostUsd = event.costUsd;
+          active.streamIsError = event.isError === true;
           if (!active.streamSessionId && event.sessionId) {
             active.streamSessionId = event.sessionId;
           }
@@ -145,14 +174,51 @@ export class OutputHandler {
 
     log.debug({ agentId }, 'detached agent completed');
 
+    // Verify agent worked in correct location by checking for output files
+    const agentWorkdir = getAgentWorkdir(agent.worktreeId);
+    const outputDir = join(agentWorkdir, '.cw', 'output');
+    const expectedPwdFile = join(agentWorkdir, '.cw', 'expected-pwd.txt');
+    const diagnosticFile = join(agentWorkdir, '.cw', 'spawn-diagnostic.json');
+
+    const outputDirExists = existsSync(outputDir);
+    const expectedPwdExists = existsSync(expectedPwdFile);
+    const diagnosticExists = existsSync(diagnosticFile);
+
+    log.info({
+      agentId,
+      agentWorkdir,
+      outputDirExists,
+      expectedPwdExists,
+      diagnosticExists,
+      verification: outputDirExists ? 'PASS' : 'FAIL'
+    }, 'agent workdir verification completed');
+
+    if (!outputDirExists) {
+      log.warn({
+        agentId,
+        agentWorkdir
+      }, 'No output files found in agent workdir! Agent may have run in wrong location.');
+    }
+
     let signalText = active?.streamResultText;
 
+    // If the stream result indicated an error (e.g. auth failure, usage limit),
+    // route directly to error handling instead of trying to parse as signal JSON
+    if (signalText && active?.streamIsError) {
+      log.warn({ agentId, error: signalText }, 'agent returned error result');
+      await this.handleAgentError(agentId, new Error(signalText), provider, getAgentWorkdir);
+      return;
+    }
+
     if (!signalText) {
       try {
-        const fileContent = await readFile(active?.outputFilePath ?? '', 'utf-8');
-        if (fileContent.trim()) {
-          await this.processAgentOutput(agentId, fileContent, provider, getAgentWorkdir);
-          return;
+        const outputFilePath = active?.outputFilePath ?? '';
+        if (outputFilePath && await this.validateSignalFile(outputFilePath)) {
+          const fileContent = await readFile(outputFilePath, 'utf-8');
+          if (fileContent.trim()) {
+            await this.processAgentOutput(agentId, fileContent, provider, getAgentWorkdir);
+            return;
+          }
         }
       } catch { /* file empty or missing */ }
 
@@ -212,23 +278,70 @@ export class OutputHandler {
    */
   private async processOutputFiles(
     agentId: string,
-    agent: { id: string; name: string; taskId: string | null; worktreeId: string; mode: string },
+    agent: { id: string; name: string; taskId: string | null; worktreeId: string; mode: string; initiativeId?: string | null },
     mode: AgentMode,
     getAgentWorkdir: (alias: string) => string,
   ): Promise<void> {
     const agentWorkdir = getAgentWorkdir(agent.worktreeId);
     const summary = readSummary(agentWorkdir);
+    const initiativeId = agent.initiativeId;
+    const canWriteProposals = this.proposalRepository && initiativeId;
 
     let resultMessage = summary?.body ?? 'Task completed';
     switch (mode) {
       case 'breakdown': {
         const phases = readPhaseFiles(agentWorkdir);
-        resultMessage = JSON.stringify({ summary: summary?.body, phases });
+        if (canWriteProposals && phases.length > 0) {
+          const proposalData: CreateProposalData[] = phases.map((p, i) => ({
+            agentId,
+            initiativeId,
+            targetType: 'phase' as const,
+            targetId: null,
+            title: p.title,
+            summary: null,
+            content: p.body || null,
+            metadata: JSON.stringify({ fileId: p.id, number: i + 1, dependencies: p.dependencies }),
+            status: 'pending' as const,
+            sortOrder: i,
+          }));
+          await this.proposalRepository!.createMany(proposalData);
+          resultMessage = summary?.body ?? `${phases.length} phase proposals created`;
+        } else {
+          resultMessage = JSON.stringify({ summary: summary?.body, phases });
+        }
         break;
       }
       case 'decompose': {
         const tasks = readTaskFiles(agentWorkdir);
-        resultMessage = JSON.stringify({ summary: summary?.body, tasks });
+        if (canWriteProposals && tasks.length > 0) {
+          // Read phase info from input context if available
+          const phaseInput = readFrontmatterFile(join(agentWorkdir, '.cw', 'input', 'phase.md'));
+          const phaseId = (phaseInput?.data?.id as string) ?? null;
+
+          const proposalData: CreateProposalData[] = tasks.map((t, i) => ({
+            agentId,
+            initiativeId,
+            targetType: 'task' as const,
+            targetId: null,
+            title: t.title,
+            summary: null,
+            content: t.body || null,
+            metadata: JSON.stringify({
+              fileId: t.id,
+              category: t.category,
+              type: t.type,
+              dependencies: t.dependencies,
+              parentTaskId: agent.taskId,
+              phaseId,
+            }),
+            status: 'pending' as const,
+            sortOrder: i,
+          }));
+          await this.proposalRepository!.createMany(proposalData);
+          resultMessage = summary?.body ?? `${tasks.length} task proposals created`;
+        } else {
+          resultMessage = JSON.stringify({ summary: summary?.body, tasks });
+        }
         break;
       }
       case 'discuss': {
@@ -238,7 +351,44 @@ export class OutputHandler {
       }
       case 'refine': {
         const pages = readPageFiles(agentWorkdir);
-        resultMessage = JSON.stringify({ summary: summary?.body, proposals: pages });
+        if (canWriteProposals) {
+          if (pages.length > 0) {
+            // Create proposals for actual page changes
+            const proposalData: CreateProposalData[] = pages.map((p, i) => ({
+              agentId,
+              initiativeId,
+              targetType: 'page' as const,
+              targetId: p.pageId,
+              title: p.title,
+              summary: p.summary || null,
+              content: p.body || null,
+              metadata: null,
+              status: 'pending' as const,
+              sortOrder: i,
+            }));
+            await this.proposalRepository!.createMany(proposalData);
+            resultMessage = summary?.body ?? `${pages.length} page proposals created`;
+          } else {
+            // Create a synthetic completion proposal when no changes are proposed
+            // This ensures the dismiss flow always goes through proposals domain
+            const completionProposal: CreateProposalData = {
+              agentId,
+              initiativeId,
+              targetType: 'page' as const,
+              targetId: null,
+              title: 'Analysis Complete',
+              summary: 'Agent completed review with no changes proposed',
+              content: summary?.body || 'The agent has finished analyzing the content and determined no changes are needed.',
+              metadata: JSON.stringify({ synthetic: true, reason: 'no_changes' }),
+              status: 'pending' as const,
+              sortOrder: 0,
+            };
+            await this.proposalRepository!.createMany([completionProposal]);
+            resultMessage = summary?.body ?? 'Analysis completed with 1 completion notice';
+          }
+        } else {
+          resultMessage = JSON.stringify({ summary: summary?.body, proposals: pages });
+        }
         break;
       }
     }
@@ -248,8 +398,7 @@ export class OutputHandler {
       message: resultMessage,
       filesModified: summary?.filesModified,
     };
-    await this.repository.update(agentId, { result: JSON.stringify(resultPayload) });
-    await this.repository.update(agentId, { status: 'idle' });
+    await this.repository.update(agentId, { result: JSON.stringify(resultPayload), status: 'idle' });
 
     const reason = this.getStoppedReason(mode);
     if (this.eventBus) {
@@ -280,8 +429,7 @@ export class OutputHandler {
   ): Promise<void> {
     const questionsPayload: PendingQuestions = { questions };
 
-    await this.repository.update(agentId, { pendingQuestions: JSON.stringify(questionsPayload) });
-    await this.repository.update(agentId, { status: 'waiting_for_input' });
+    await this.repository.update(agentId, { pendingQuestions: JSON.stringify(questionsPayload), status: 'waiting_for_input' });
 
     if (this.eventBus) {
       const event: AgentWaitingEvent = {
@@ -309,8 +457,10 @@ export class OutputHandler {
   ): Promise<void> {
     const errorResult: AgentResult = { success: false, message: error };
 
-    await this.repository.update(agentId, { result: JSON.stringify(errorResult) });
-    await this.repository.update(agentId, { status: 'crashed' });
+    await this.repository.update(agentId, {
+      result: JSON.stringify(errorResult),
+      status: 'crashed'
+    });
     this.emitCrashed(agent, error);
   }
 
@@ -342,22 +492,28 @@ export class OutputHandler {
     // Extract session ID using provider's extraction config
     let sessionId: string | null = null;
     if (provider.sessionId) {
-      try {
-        if (provider.sessionId.extractFrom === 'result') {
-          const parsed = JSON.parse(rawOutput);
-          sessionId = parsed[provider.sessionId.field] ?? null;
-        } else if (provider.sessionId.extractFrom === 'event') {
-          const lines = rawOutput.trim().split('\n');
-          for (const line of lines) {
-            try {
-              const event = JSON.parse(line);
-              if (event.type === provider.sessionId.eventType) {
-                sessionId = event[provider.sessionId.field] ?? null;
-              }
-            } catch { /* skip */ }
-          }
+      const outputLines = rawOutput.trim().split('\n');
+      if (provider.sessionId.extractFrom === 'result') {
+        // Find the result line in JSONL output
+        for (const line of outputLines) {
+          try {
+            const parsed = JSON.parse(line);
+            if (parsed.type === 'result' || parsed[provider.sessionId.field]) {
+              sessionId = parsed[provider.sessionId.field] ?? null;
+              if (sessionId) break;
+            }
+          } catch { /* skip */ }
         }
-      } catch { /* parse failure */ }
+      } else if (provider.sessionId.extractFrom === 'event') {
+        for (const line of outputLines) {
+          try {
+            const event = JSON.parse(line);
+            if (event.type === provider.sessionId.eventType) {
+              sessionId = event[provider.sessionId.field] ?? null;
+            }
+          } catch { /* skip */ }
+        }
+      }
     }
 
     if (sessionId) {
@@ -366,14 +522,38 @@ export class OutputHandler {
     log.debug({ agentId, provider: provider.name, hasSessionId: !!sessionId }, 'processing agent output');
 
     if (provider.name === 'claude') {
+      // rawOutput may be a single JSON object or multi-line JSONL — find the result line
+      let cliResult: ClaudeCliResult | null = null;
+      const lines = rawOutput.trim().split('\n');
+      for (const line of lines) {
+        try {
+          const parsed = JSON.parse(line);
+          if (parsed.type === 'result') {
+            cliResult = parsed;
+          }
+        } catch { /* skip non-JSON lines */ }
+      }
+
+      if (!cliResult) {
+        log.error({ agentId }, 'no result event found in agent output');
+        await this.handleAgentError(agentId, new Error('No result event in output'), provider, getAgentWorkdir);
+        return;
+      }
+
+      // Handle error results (auth failure, usage limits, etc.)
+      if (cliResult.is_error) {
+        log.warn({ agentId, error: cliResult.result }, 'agent returned error result from file');
+        await this.handleAgentError(agentId, new Error(cliResult.result), provider, getAgentWorkdir);
+        return;
+      }
+
       let signalText: string;
       try {
-        const cliResult: ClaudeCliResult = JSON.parse(rawOutput);
         const signal = cliResult.structured_output ?? JSON.parse(cliResult.result);
         signalText = JSON.stringify(signal);
       } catch (parseErr) {
-        log.error({ agentId, err: parseErr instanceof Error ? parseErr.message : String(parseErr) }, 'failed to parse agent output');
-        await this.repository.update(agentId, { status: 'crashed' });
+        log.error({ agentId, err: parseErr instanceof Error ? parseErr.message : String(parseErr) }, 'failed to parse agent signal from result');
+        await this.handleAgentError(agentId, new Error('Failed to parse agent signal'), provider, getAgentWorkdir);
         return;
       }
 
@@ -399,7 +579,15 @@ export class OutputHandler {
 
     log.error({ agentId, err: errorMessage }, 'agent error');
 
-    await this.repository.update(agentId, { status: 'crashed' });
+    const errorResult: AgentResult = {
+      success: false,
+      message: errorMessage,
+    };
+
+    await this.repository.update(agentId, {
+      status: 'crashed',
+      result: JSON.stringify(errorResult)
+    });
 
     if (this.eventBus) {
       const event: AgentCrashedEvent = {
@@ -414,12 +602,6 @@ export class OutputHandler {
       };
       this.eventBus.emit(event);
     }
-
-    const errorResult: AgentResult = {
-      success: false,
-      message: errorMessage,
-    };
-    await this.repository.update(agentId, { result: JSON.stringify(errorResult) });
   }
 
   /**
diff --git a/src/agent/process-manager.ts b/src/agent/process-manager.ts
index 91e7fcf..2ed1555 100644
--- a/src/agent/process-manager.ts
+++ b/src/agent/process-manager.ts
@@ -7,7 +7,8 @@
  */
 
 import { spawn } from 'node:child_process';
-import { writeFileSync, mkdirSync, openSync, closeSync } from 'node:fs';
+import { writeFileSync, mkdirSync, openSync, closeSync, existsSync } from 'node:fs';
+import { stat } from 'node:fs/promises';
 import { join } from 'node:path';
 import type { ProjectRepository } from '../db/repositories/project-repository.js';
 import type { EventBus } from '../events/index.js';
@@ -59,10 +60,33 @@ export class ProcessManager {
     const projects = await this.projectRepository.findProjectsByInitiativeId(initiativeId);
     const agentWorkdir = this.getAgentWorkdir(alias);
 
+    log.debug({
+      alias,
+      initiativeId,
+      projectCount: projects.length,
+      agentWorkdir,
+      baseBranch
+    }, 'creating project worktrees');
+
     for (const project of projects) {
       const clonePath = await ensureProjectClone(project, this.workspaceRoot);
       const worktreeManager = new SimpleGitWorktreeManager(clonePath, undefined, agentWorkdir);
-      await worktreeManager.create(project.name, `agent/${alias}`, baseBranch);
+      const worktree = await worktreeManager.create(project.name, `agent/${alias}`, baseBranch);
+      const worktreePath = worktree.path;
+      const pathExists = existsSync(worktreePath);
+
+      log.debug({
+        alias,
+        agentWorkdir,
+        projectName: project.name,
+        worktreePath,
+        pathExists
+      }, 'worktree created');
+
+      if (!pathExists) {
+        log.error({ worktreePath }, 'Worktree path does not exist after creation!');
+        throw new Error(`Worktree creation failed: ${worktreePath}`);
+      }
     }
 
     return agentWorkdir;
@@ -74,7 +98,25 @@ export class ProcessManager {
   async createStandaloneWorktree(alias: string): Promise<string> {
     const agentWorkdir = this.getAgentWorkdir(alias);
     const worktreeManager = new SimpleGitWorktreeManager(this.workspaceRoot, undefined, agentWorkdir);
+
+    log.debug({ alias, agentWorkdir }, 'creating standalone worktree');
+
     const worktree = await worktreeManager.create('workspace', `agent/${alias}`);
+    const worktreePath = worktree.path;
+    const pathExists = existsSync(worktreePath);
+
+    log.debug({
+      alias,
+      agentWorkdir,
+      worktreePath,
+      pathExists
+    }, 'standalone worktree created');
+
+    if (!pathExists) {
+      log.error({ worktreePath }, 'Standalone worktree path does not exist after creation!');
+      throw new Error(`Standalone worktree creation failed: ${worktreePath}`);
+    }
+
     return worktree.path;
   }
 
@@ -195,6 +237,32 @@ export class ProcessManager {
     prompt?: string,
     onEvent?: (event: StreamEvent) => void,
   ): { pid: number; outputFilePath: string; tailer: FileTailer } {
+    // Pre-spawn validation and logging
+    const cwdExists = existsSync(cwd);
+    const commandWithArgs = [command, ...args].join(' ');
+
+    // Log environment variables that might affect working directory
+    const environmentInfo = {
+      PWD: process.env.PWD,
+      HOME: process.env.HOME,
+      CLAUDE_CONFIG_DIR: env.CLAUDE_CONFIG_DIR,
+      CW_CONFIG_DIR: env.CW_CONFIG_DIR
+    };
+
+    log.info({
+      agentId,
+      cwd,
+      cwdExists,
+      commandWithArgs,
+      providerName,
+      environmentInfo
+    }, 'spawning detached process with workdir validation');
+
+    if (!cwdExists) {
+      log.error({ cwd }, 'CWD does not exist before spawn!');
+      throw new Error(`Agent working directory does not exist: ${cwd}`);
+    }
+
     const logDir = join(this.workspaceRoot, '.cw', 'agent-logs', agentId);
     mkdirSync(logDir, { recursive: true });
     const outputFilePath = join(logDir, 'output.jsonl');
@@ -220,7 +288,14 @@ export class ProcessManager {
     child.unref();
 
     const pid = child.pid!;
-    log.debug({ agentId, pid, command }, 'spawned detached process');
+    log.info({
+      agentId,
+      pid,
+      command,
+      args: args.join(' '),
+      cwd,
+      spawnSuccess: true
+    }, 'spawned detached process successfully');
 
     const parser = getStreamParser(providerName);
     const tailer = new FileTailer({
@@ -239,6 +314,33 @@ export class ProcessManager {
     return { pid, outputFilePath, tailer };
   }
 
+  /**
+   * Wait for a file to stabilize (no size changes for 300ms).
+   * More robust than hardcoded delays.
+   */
+  private async waitForFileCompletion(filePath: string, timeout = 10000): Promise<boolean> {
+    const startTime = Date.now();
+    let lastSize = -1;
+    let stableCount = 0;
+
+    while (Date.now() - startTime < timeout) {
+      try {
+        const stats = await stat(filePath);
+        if (stats.size === lastSize) {
+          stableCount++;
+          if (stableCount >= 3) return true; // Stable for 300ms
+        } else {
+          lastSize = stats.size;
+          stableCount = 0;
+        }
+      } catch {
+        // File doesn't exist yet
+      }
+      await new Promise(resolve => setTimeout(resolve, 100));
+    }
+    return false;
+  }
+
   /**
    * Poll for process completion by checking if PID is still alive.
    * When the process exits, calls onComplete callback.
@@ -251,12 +353,25 @@ export class ProcessManager {
     pid: number,
     onComplete: () => Promise<void>,
     getTailer: () => FileTailer | undefined,
+    outputFilePath?: string,
   ): void {
+    const processLog = log.child({ agentId, pid });
+
     const check = async () => {
       if (!isPidAlive(pid)) {
         const tailer = getTailer();
         if (tailer) {
-          await new Promise((resolve) => setTimeout(resolve, 500));
+          // Wait for output file to stabilize instead of hardcoded delay
+          if (outputFilePath) {
+            processLog.debug('waiting for output file completion');
+            const completed = await this.waitForFileCompletion(outputFilePath);
+            if (!completed) {
+              processLog.warn('output file did not stabilize within timeout');
+            }
+          } else {
+            // Fallback to short delay if no output file path
+            await new Promise((resolve) => setTimeout(resolve, 200));
+          }
           await tailer.stop();
         }
         await onComplete();