diff --git a/apps/cli/src/commands/auth.command.ts b/apps/cli/src/commands/auth.command.ts
index e2878dd8..7c2e03c3 100644
--- a/apps/cli/src/commands/auth.command.ts
+++ b/apps/cli/src/commands/auth.command.ts
@@ -15,6 +15,7 @@ import {
 } from '@tm/core/auth';
 import * as ui from '../utils/ui.js';
 import { ContextCommand } from './context.command.js';
+import { displayError } from '../utils/error-handler.js';
 
 /**
  * Result type from auth command
@@ -117,8 +118,7 @@ export class AuthCommand extends Command {
 				process.exit(0);
 			}, 100);
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -134,8 +134,7 @@ export class AuthCommand extends Command {
 				process.exit(1);
 			}
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -147,8 +146,7 @@ export class AuthCommand extends Command {
 			const result = this.displayStatus();
 			this.setLastResult(result);
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -164,8 +162,7 @@ export class AuthCommand extends Command {
 				process.exit(1);
 			}
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -390,7 +387,7 @@ export class AuthCommand extends Command {
 				message: 'Authentication successful'
 			};
 		} catch (error) {
-			this.handleAuthError(error as AuthenticationError);
+			displayError(error, { skipExit: true });
 
 			return {
 				success: false,
@@ -453,51 +450,6 @@ export class AuthCommand extends Command {
 		}
 	}
 
-	/**
-	 * Handle authentication errors
-	 */
-	private handleAuthError(error: AuthenticationError): void {
-		console.error(chalk.red(`\n✗ ${error.message}`));
-
-		switch (error.code) {
-			case 'NETWORK_ERROR':
-				ui.displayWarning(
-					'Please check your internet connection and try again.'
-				);
-				break;
-			case 'INVALID_CREDENTIALS':
-				ui.displayWarning('Please check your credentials and try again.');
-				break;
-			case 'AUTH_EXPIRED':
-				ui.displayWarning(
-					'Your session has expired. Please authenticate again.'
-				);
-				break;
-			default:
-				if (process.env.DEBUG) {
-					console.error(chalk.gray(error.stack || ''));
-				}
-		}
-	}
-
-	/**
-	 * Handle general errors
-	 */
-	private handleError(error: any): void {
-		if (error instanceof AuthenticationError) {
-			this.handleAuthError(error);
-		} else {
-			const msg = error?.getSanitizedDetails?.() ?? {
-				message: error?.message ?? String(error)
-			};
-			console.error(chalk.red(`Error: ${msg.message || 'Unexpected error'}`));
-
-			if (error.stack && process.env.DEBUG) {
-				console.error(chalk.gray(error.stack));
-			}
-		}
-	}
-
 	/**
 	 * Set the last result for programmatic access
 	 */
diff --git a/apps/cli/src/commands/context.command.ts b/apps/cli/src/commands/context.command.ts
index dc2f0fc7..0d933799 100644
--- a/apps/cli/src/commands/context.command.ts
+++ b/apps/cli/src/commands/context.command.ts
@@ -8,12 +8,9 @@ import chalk from 'chalk';
 import inquirer from 'inquirer';
 import search from '@inquirer/search';
 import ora, { Ora } from 'ora';
-import {
-	AuthManager,
-	AuthenticationError,
-	type UserContext
-} from '@tm/core/auth';
+import { AuthManager, type UserContext } from '@tm/core/auth';
 import * as ui from '../utils/ui.js';
+import { displayError } from '../utils/error-handler.js';
 
 /**
  * Result type from context command
@@ -119,8 +116,7 @@ export class ContextCommand extends Command {
 			const result = this.displayContext();
 			this.setLastResult(result);
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -216,8 +212,7 @@ export class ContextCommand extends Command {
 				process.exit(1);
 			}
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -258,6 +253,7 @@ export class ContextCommand extends Command {
 			this.authManager.updateContext({
 				orgId: selectedOrg.id,
 				orgName: selectedOrg.name,
+				orgSlug: selectedOrg.slug,
 				// Clear brief when changing org
 				briefId: undefined,
 				briefName: undefined
@@ -304,8 +300,7 @@ export class ContextCommand extends Command {
 				process.exit(1);
 			}
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -429,8 +424,7 @@ export class ContextCommand extends Command {
 				process.exit(1);
 			}
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -476,8 +470,7 @@ export class ContextCommand extends Command {
 				process.exit(1);
 			}
 		} catch (error: any) {
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -513,11 +506,13 @@ export class ContextCommand extends Command {
 				process.exit(1);
 			}
 
-			// Fetch org to get a friendly name (optional)
+			// Fetch org to get a friendly name and slug (optional)
 			let orgName: string | undefined;
+			let orgSlug: string | undefined;
 			try {
 				const org = await this.authManager.getOrganization(brief.accountId);
 				orgName = org?.name;
+				orgSlug = org?.slug;
 			} catch {
 				// Non-fatal if org lookup fails
 			}
@@ -528,6 +523,7 @@ export class ContextCommand extends Command {
 			this.authManager.updateContext({
 				orgId: brief.accountId,
 				orgName,
+				orgSlug,
 				briefId: brief.id,
 				briefName
 			});
@@ -549,8 +545,7 @@ export class ContextCommand extends Command {
 			try {
 				if (spinner?.isSpinning) spinner.stop();
 			} catch {}
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -679,26 +674,6 @@ export class ContextCommand extends Command {
 		}
 	}
 
-	/**
-	 * Handle errors
-	 */
-	private handleError(error: any): void {
-		if (error instanceof AuthenticationError) {
-			console.error(chalk.red(`\n✗ ${error.message}`));
-
-			if (error.code === 'NOT_AUTHENTICATED') {
-				ui.displayWarning('Please authenticate first: tm auth login');
-			}
-		} else {
-			const msg = error?.message ?? String(error);
-			console.error(chalk.red(`Error: ${msg}`));
-
-			if (error.stack && process.env.DEBUG) {
-				console.error(chalk.gray(error.stack));
-			}
-		}
-	}
-
 	/**
 	 * Set the last result for programmatic access
 	 */
diff --git a/apps/cli/src/commands/export.command.ts b/apps/cli/src/commands/export.command.ts
index 25b55a93..2b45a835 100644
--- a/apps/cli/src/commands/export.command.ts
+++ b/apps/cli/src/commands/export.command.ts
@@ -7,13 +7,10 @@ import { Command } from 'commander';
 import chalk from 'chalk';
 import inquirer from 'inquirer';
 import ora, { Ora } from 'ora';
-import {
-	AuthManager,
-	AuthenticationError,
-	type UserContext
-} from '@tm/core/auth';
+import { AuthManager, type UserContext } from '@tm/core/auth';
 import { TaskMasterCore, type ExportResult } from '@tm/core';
 import * as ui from '../utils/ui.js';
+import { displayError } from '../utils/error-handler.js';
 
 /**
  * Result type from export command
@@ -197,8 +194,7 @@ export class ExportCommand extends Command {
 			};
 		} catch (error: any) {
 			if (spinner?.isSpinning) spinner.fail('Export failed');
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -334,26 +330,6 @@ export class ExportCommand extends Command {
 		return confirmed;
 	}
 
-	/**
-	 * Handle errors
-	 */
-	private handleError(error: any): void {
-		if (error instanceof AuthenticationError) {
-			console.error(chalk.red(`\n✗ ${error.message}`));
-
-			if (error.code === 'NOT_AUTHENTICATED') {
-				ui.displayWarning('Please authenticate first: tm auth login');
-			}
-		} else {
-			const msg = error?.message ?? String(error);
-			console.error(chalk.red(`Error: ${msg}`));
-
-			if (error.stack && process.env.DEBUG) {
-				console.error(chalk.gray(error.stack));
-			}
-		}
-	}
-
 	/**
 	 * Get the last export result (useful for testing)
 	 */
diff --git a/apps/cli/src/commands/list.command.ts b/apps/cli/src/commands/list.command.ts
index 38e4184b..e6bafcc0 100644
--- a/apps/cli/src/commands/list.command.ts
+++ b/apps/cli/src/commands/list.command.ts
@@ -17,8 +17,9 @@ import {
 } from '@tm/core';
 import type { StorageType } from '@tm/core/types';
 import * as ui from '../utils/ui.js';
+import { displayError } from '../utils/error-handler.js';
+import { displayCommandHeader } from '../utils/display-helpers.js';
 import {
-	displayHeader,
 	displayDashboards,
 	calculateTaskStatistics,
 	calculateSubtaskStatistics,
@@ -106,14 +107,7 @@ export class ListTasksCommand extends Command {
 				this.displayResults(result, options);
 			}
 		} catch (error: any) {
-			const msg = error?.getSanitizedDetails?.() ?? {
-				message: error?.message ?? String(error)
-			};
-			console.error(chalk.red(`Error: ${msg.message || 'Unexpected error'}`));
-			if (error.stack && process.env.DEBUG) {
-				console.error(chalk.gray(error.stack));
-			}
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -257,15 +251,12 @@ export class ListTasksCommand extends Command {
 	 * Display in text format with tables
 	 */
 	private displayText(data: ListTasksResult, withSubtasks?: boolean): void {
-		const { tasks, tag } = data;
+		const { tasks, tag, storageType } = data;
 
-		// Get file path for display
-		const filePath = this.tmCore ? `.taskmaster/tasks/tasks.json` : undefined;
-
-		// Display header without banner (banner already shown by main CLI)
-		displayHeader({
+		// Display header using utility function
+		displayCommandHeader(this.tmCore, {
 			tag: tag || 'master',
-			filePath: filePath
+			storageType
 		});
 
 		// No tasks message
diff --git a/apps/cli/src/commands/next.command.ts b/apps/cli/src/commands/next.command.ts
index 5c037177..50b37169 100644
--- a/apps/cli/src/commands/next.command.ts
+++ b/apps/cli/src/commands/next.command.ts
@@ -9,8 +9,9 @@ import chalk from 'chalk';
 import boxen from 'boxen';
 import { createTaskMasterCore, type Task, type TaskMasterCore } from '@tm/core';
 import type { StorageType } from '@tm/core/types';
+import { displayError } from '../utils/error-handler.js';
 import { displayTaskDetails } from '../ui/components/task-detail.component.js';
-import { displayHeader } from '../ui/index.js';
+import { displayCommandHeader } from '../utils/display-helpers.js';
 
 /**
  * Options interface for the next command
@@ -58,6 +59,7 @@ export class NextCommand extends Command {
 	 * Execute the next command
 	 */
 	private async executeCommand(options: NextCommandOptions): Promise<void> {
+		let hasError = false;
 		try {
 			// Validate options (throws on invalid options)
 			this.validateOptions(options);
@@ -76,16 +78,17 @@ export class NextCommand extends Command {
 				this.displayResults(result, options);
 			}
 		} catch (error: any) {
-			const msg = error?.getSanitizedDetails?.() ?? {
-				message: error?.message ?? String(error)
-			};
-
-			// Allow error to propagate for library compatibility
-			throw new Error(msg.message || 'Unexpected error in next command');
+			hasError = true;
+			displayError(error, { skipExit: true });
 		} finally {
 			// Always clean up resources, even on error
 			await this.cleanup();
 		}
+
+		// Exit after cleanup completes
+		if (hasError) {
+			process.exit(1);
+		}
 	}
 
 	/**
@@ -170,9 +173,10 @@ export class NextCommand extends Command {
 	 * Display in text format
 	 */
 	private displayText(result: NextTaskResult): void {
-		// Display header with tag (no file path for next command)
-		displayHeader({
-			tag: result.tag || 'master'
+		// Display header with storage info
+		displayCommandHeader(this.tmCore, {
+			tag: result.tag || 'master',
+			storageType: result.storageType
 		});
 
 		if (!result.found || !result.task) {
@@ -191,7 +195,6 @@ export class NextCommand extends Command {
 					}
 				)
 			);
-			console.log(`\n${chalk.gray('Storage: ' + result.storageType)}`);
 			console.log(
 				`\n${chalk.dim('Tip: Try')} ${chalk.cyan('task-master list --status pending')} ${chalk.dim('to see all pending tasks')}`
 			);
@@ -208,8 +211,6 @@ export class NextCommand extends Command {
 			headerColor: 'green',
 			showSuggestedActions: true
 		});
-
-		console.log(`\n${chalk.gray('Storage: ' + result.storageType)}`);
 	}
 
 	/**
diff --git a/apps/cli/src/commands/set-status.command.ts b/apps/cli/src/commands/set-status.command.ts
index 25dc40bd..9e08b1cd 100644
--- a/apps/cli/src/commands/set-status.command.ts
+++ b/apps/cli/src/commands/set-status.command.ts
@@ -12,6 +12,7 @@ import {
 	type TaskStatus
 } from '@tm/core';
 import type { StorageType } from '@tm/core/types';
+import { displayError } from '../utils/error-handler.js';
 
 /**
  * Valid task status values for validation
@@ -85,6 +86,7 @@ export class SetStatusCommand extends Command {
 	private async executeCommand(
 		options: SetStatusCommandOptions
 	): Promise<void> {
+		let hasError = false;
 		try {
 			// Validate required options
 			if (!options.id) {
@@ -135,16 +137,15 @@ export class SetStatusCommand extends Command {
 						oldStatus: result.oldStatus,
 						newStatus: result.newStatus
 					});
-				} catch (error) {
-					const errorMessage =
-						error instanceof Error ? error.message : String(error);
-
-					if (!options.silent) {
-						console.error(
-							chalk.red(`Failed to update task ${taskId}: ${errorMessage}`)
-						);
-					}
+				} catch (error: any) {
+					hasError = true;
 					if (options.format === 'json') {
+						const errorMessage = error?.getSanitizedDetails
+							? error.getSanitizedDetails().message
+							: error instanceof Error
+								? error.message
+								: String(error);
+
 						console.log(
 							JSON.stringify({
 								success: false,
@@ -153,8 +154,13 @@ export class SetStatusCommand extends Command {
 								timestamp: new Date().toISOString()
 							})
 						);
+					} else if (!options.silent) {
+						// Show which task failed with context
+						console.error(chalk.red(`\nFailed to update task ${taskId}:`));
+						displayError(error, { skipExit: true });
 					}
-					process.exit(1);
+					// Don't exit here - let finally block clean up first
+					break;
 				}
 			}
 
@@ -170,25 +176,26 @@ export class SetStatusCommand extends Command {
 
 			// Display results
 			this.displayResults(this.lastResult, options);
-		} catch (error) {
-			const errorMessage =
-				error instanceof Error ? error.message : 'Unknown error occurred';
-
-			if (!options.silent) {
-				console.error(chalk.red(`Error: ${errorMessage}`));
-			}
-
+		} catch (error: any) {
+			hasError = true;
 			if (options.format === 'json') {
+				const errorMessage =
+					error instanceof Error ? error.message : 'Unknown error occurred';
 				console.log(JSON.stringify({ success: false, error: errorMessage }));
+			} else if (!options.silent) {
+				displayError(error, { skipExit: true });
 			}
-
-			process.exit(1);
 		} finally {
 			// Clean up resources
 			if (this.tmCore) {
 				await this.tmCore.close();
 			}
 		}
+
+		// Exit after cleanup completes
+		if (hasError) {
+			process.exit(1);
+		}
 	}
 
 	/**
diff --git a/apps/cli/src/commands/show.command.ts b/apps/cli/src/commands/show.command.ts
index f41cb786..121c0819 100644
--- a/apps/cli/src/commands/show.command.ts
+++ b/apps/cli/src/commands/show.command.ts
@@ -9,7 +9,9 @@ import boxen from 'boxen';
 import { createTaskMasterCore, type Task, type TaskMasterCore } from '@tm/core';
 import type { StorageType } from '@tm/core/types';
 import * as ui from '../utils/ui.js';
+import { displayError } from '../utils/error-handler.js';
 import { displayTaskDetails } from '../ui/components/task-detail.component.js';
+import { displayCommandHeader } from '../utils/display-helpers.js';
 
 /**
  * Options interface for the show command
@@ -112,14 +114,7 @@ export class ShowCommand extends Command {
 				this.displayResults(result, options);
 			}
 		} catch (error: any) {
-			const msg = error?.getSanitizedDetails?.() ?? {
-				message: error?.message ?? String(error)
-			};
-			console.error(chalk.red(`Error: ${msg.message || 'Unexpected error'}`));
-			if (error.stack && process.env.DEBUG) {
-				console.error(chalk.gray(error.stack));
-			}
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -257,6 +252,15 @@ export class ShowCommand extends Command {
 			return;
 		}
 
+		// Display header with storage info
+		const activeTag = this.tmCore?.getActiveTag() || 'master';
+		displayCommandHeader(this.tmCore, {
+			tag: activeTag,
+			storageType: result.storageType
+		});
+
+		console.log(); // Add spacing
+
 		// Use the global task details display function
 		displayTaskDetails(result.task, {
 			statusFilter: options.status,
@@ -271,8 +275,12 @@ export class ShowCommand extends Command {
 		result: ShowMultipleTasksResult,
 		_options: ShowCommandOptions
 	): void {
-		// Header
-		ui.displayBanner(`Tasks (${result.tasks.length} found)`);
+		// Display header with storage info
+		const activeTag = this.tmCore?.getActiveTag() || 'master';
+		displayCommandHeader(this.tmCore, {
+			tag: activeTag,
+			storageType: result.storageType
+		});
 
 		if (result.notFound.length > 0) {
 			console.log(chalk.yellow(`\n⚠ Not found: ${result.notFound.join(', ')}`));
@@ -291,8 +299,6 @@ export class ShowCommand extends Command {
 				showDependencies: true
 			})
 		);
-
-		console.log(`\n${chalk.gray('Storage: ' + result.storageType)}`);
 	}
 
 	/**
diff --git a/apps/cli/src/commands/start.command.ts b/apps/cli/src/commands/start.command.ts
index ec82c2e5..dbeb17a7 100644
--- a/apps/cli/src/commands/start.command.ts
+++ b/apps/cli/src/commands/start.command.ts
@@ -16,6 +16,7 @@ import {
 } from '@tm/core';
 import { displayTaskDetails } from '../ui/components/task-detail.component.js';
 import * as ui from '../utils/ui.js';
+import { displayError } from '../utils/error-handler.js';
 
 /**
  * CLI-specific options interface for the start command
@@ -160,8 +161,7 @@ export class StartCommand extends Command {
 			if (spinner) {
 				spinner.fail('Operation failed');
 			}
-			this.handleError(error);
-			process.exit(1);
+			displayError(error);
 		}
 	}
 
@@ -452,22 +452,6 @@ export class StartCommand extends Command {
 		console.log(`\n${chalk.gray('Storage: ' + result.storageType)}`);
 	}
 
-	/**
-	 * Handle general errors
-	 */
-	private handleError(error: any): void {
-		const msg = error?.getSanitizedDetails?.() ?? {
-			message: error?.message ?? String(error)
-		};
-		console.error(chalk.red(`Error: ${msg.message || 'Unexpected error'}`));
-
-		// Show stack trace in development mode or when DEBUG is set
-		const isDevelopment = process.env.NODE_ENV !== 'production';
-		if ((isDevelopment || process.env.DEBUG) && error.stack) {
-			console.error(chalk.gray(error.stack));
-		}
-	}
-
 	/**
 	 * Set the last result for programmatic access
 	 */
diff --git a/apps/cli/src/index.ts b/apps/cli/src/index.ts
index cd010fb1..42f16dc9 100644
--- a/apps/cli/src/index.ts
+++ b/apps/cli/src/index.ts
@@ -24,6 +24,9 @@ export {
 // UI utilities (for other commands to use)
 export * as ui from './utils/ui.js';
 
+// Error handling utilities
+export { displayError, isDebugMode } from './utils/error-handler.js';
+
 // Auto-update utilities
 export {
 	checkForUpdate,
diff --git a/apps/cli/src/ui/components/header.component.ts b/apps/cli/src/ui/components/header.component.ts
index e47337c2..9f3e9984 100644
--- a/apps/cli/src/ui/components/header.component.ts
+++ b/apps/cli/src/ui/components/header.component.ts
@@ -5,6 +5,16 @@
 
 import chalk from 'chalk';
 
+/**
+ * Brief information for API storage
+ */
+export interface BriefInfo {
+	briefId: string;
+	briefName: string;
+	orgSlug?: string;
+	webAppUrl?: string;
+}
+
 /**
  * Header configuration options
  */
@@ -12,16 +22,44 @@ export interface HeaderOptions {
 	title?: string;
 	tag?: string;
 	filePath?: string;
+	storageType?: 'api' | 'file';
+	briefInfo?: BriefInfo;
 }
 
 /**
  * Display the Task Master header with project info
  */
 export function displayHeader(options: HeaderOptions = {}): void {
-	const { filePath, tag } = options;
+	const { filePath, tag, storageType, briefInfo } = options;
 
-	// Display tag and file path info
-	if (tag) {
+	// Display different header based on storage type
+	if (storageType === 'api' && briefInfo) {
+		// API storage: Show brief information
+		const briefDisplay = `🏷  Brief: ${chalk.cyan(briefInfo.briefName)} ${chalk.gray(`(${briefInfo.briefId})`)}`;
+		console.log(briefDisplay);
+
+		// Construct and display the brief URL or ID
+		if (briefInfo.webAppUrl && briefInfo.orgSlug) {
+			const briefUrl = `${briefInfo.webAppUrl}/home/${briefInfo.orgSlug}/briefs/${briefInfo.briefId}/plan`;
+			console.log(`Listing tasks from: ${chalk.dim(briefUrl)}`);
+		} else if (briefInfo.webAppUrl) {
+			// Show web app URL and brief ID if org slug is missing
+			console.log(
+				`Listing tasks from: ${chalk.dim(`${briefInfo.webAppUrl} (Brief: ${briefInfo.briefId})`)}`
+			);
+			console.log(
+				chalk.yellow(
+					`💡 Tip: Run ${chalk.cyan('tm context select')} to set your organization and see the full URL`
+				)
+			);
+		} else {
+			// Fallback: just show the brief ID if we can't get web app URL
+			console.log(
+				`Listing tasks from: ${chalk.dim(`API (Brief ID: ${briefInfo.briefId})`)}`
+			);
+		}
+	} else if (tag) {
+		// File storage: Show tag information
 		let tagInfo = '';
 
 		if (tag && tag !== 'master') {
diff --git a/apps/cli/src/utils/display-helpers.ts b/apps/cli/src/utils/display-helpers.ts
new file mode 100644
index 00000000..acbce710
--- /dev/null
+++ b/apps/cli/src/utils/display-helpers.ts
@@ -0,0 +1,75 @@
+/**
+ * @fileoverview Display helper utilities for commands
+ * Provides DRY utilities for displaying headers and other command output
+ */
+
+import type { TaskMasterCore } from '@tm/core';
+import type { StorageType } from '@tm/core/types';
+import { displayHeader, type BriefInfo } from '../ui/index.js';
+
+/**
+ * Get web app base URL from environment
+ */
+function getWebAppUrl(): string | undefined {
+	const baseDomain =
+		process.env.TM_BASE_DOMAIN || process.env.TM_PUBLIC_BASE_DOMAIN;
+
+	if (!baseDomain) {
+		return undefined;
+	}
+
+	// If it already includes protocol, use as-is
+	if (baseDomain.startsWith('http://') || baseDomain.startsWith('https://')) {
+		return baseDomain;
+	}
+
+	// Otherwise, add protocol based on domain
+	if (baseDomain.includes('localhost') || baseDomain.includes('127.0.0.1')) {
+		return `http://${baseDomain}`;
+	}
+
+	return `https://${baseDomain}`;
+}
+
+/**
+ * Display the command header with appropriate storage information
+ * Handles both API and file storage displays
+ */
+export function displayCommandHeader(
+	tmCore: TaskMasterCore | undefined,
+	options: {
+		tag?: string;
+		storageType: Exclude<StorageType, 'auto'>;
+	}
+): void {
+	const { tag, storageType } = options;
+
+	// Get brief info if using API storage
+	let briefInfo: BriefInfo | undefined;
+	if (storageType === 'api' && tmCore) {
+		const storageInfo = tmCore.getStorageDisplayInfo();
+		if (storageInfo) {
+			// Construct full brief info with web app URL
+			briefInfo = {
+				...storageInfo,
+				webAppUrl: getWebAppUrl()
+			};
+		}
+	}
+
+	// Get file path for display (only for file storage)
+	// Note: The file structure is fixed for file storage and won't change.
+	// This is a display-only relative path, not used for actual file operations.
+	const filePath =
+		storageType === 'file' && tmCore
+			? `.taskmaster/tasks/tasks.json`
+			: undefined;
+
+	// Display header
+	displayHeader({
+		tag: tag || 'master',
+		filePath: filePath,
+		storageType: storageType === 'api' ? 'api' : 'file',
+		briefInfo: briefInfo
+	});
+}
diff --git a/apps/cli/src/utils/error-handler.ts b/apps/cli/src/utils/error-handler.ts
new file mode 100644
index 00000000..900ed796
--- /dev/null
+++ b/apps/cli/src/utils/error-handler.ts
@@ -0,0 +1,60 @@
+/**
+ * @fileoverview Centralized error handling utilities for CLI
+ * Provides consistent error formatting and debug mode detection
+ */
+
+import chalk from 'chalk';
+
+/**
+ * Check if debug mode is enabled via environment variable
+ * Only returns true when DEBUG is explicitly set to 'true' or '1'
+ *
+ * @returns True if debug mode is enabled
+ */
+export function isDebugMode(): boolean {
+	return process.env.DEBUG === 'true' || process.env.DEBUG === '1';
+}
+
+/**
+ * Display an error to the user with optional stack trace in debug mode
+ * Handles both TaskMasterError instances and regular errors
+ *
+ * @param error - The error to display
+ * @param options - Display options
+ */
+export function displayError(
+	error: any,
+	options: {
+		/** Skip exit, useful when caller wants to handle exit */
+		skipExit?: boolean;
+		/** Force show stack trace regardless of debug mode */
+		forceStack?: boolean;
+	} = {}
+): void {
+	// Check if it's a TaskMasterError with sanitized details
+	if (error?.getSanitizedDetails) {
+		const sanitized = error.getSanitizedDetails();
+		console.error(chalk.red(`\n${sanitized.message}`));
+
+		// Show stack trace in debug mode or if forced
+		if ((isDebugMode() || options.forceStack) && error.stack) {
+			console.error(chalk.gray('\nStack trace:'));
+			console.error(chalk.gray(error.stack));
+		}
+	} else {
+		// For other errors, show the message
+		const message = error?.message ?? String(error);
+		console.error(chalk.red(`\nError: ${message}`));
+
+		// Show stack trace in debug mode or if forced
+		if ((isDebugMode() || options.forceStack) && error?.stack) {
+			console.error(chalk.gray('\nStack trace:'));
+			console.error(chalk.gray(error.stack));
+		}
+	}
+
+	// Exit if not skipped
+	if (!options.skipExit) {
+		process.exit(1);
+	}
+}
diff --git a/packages/tm-core/src/auth/types.ts b/packages/tm-core/src/auth/types.ts
index f6108f31..4a6b8c76 100644
--- a/packages/tm-core/src/auth/types.ts
+++ b/packages/tm-core/src/auth/types.ts
@@ -16,6 +16,7 @@ export interface AuthCredentials {
 export interface UserContext {
 	orgId?: string;
 	orgName?: string;
+	orgSlug?: string;
 	briefId?: string;
 	briefName?: string;
 	updatedAt: string;
diff --git a/packages/tm-core/src/errors/task-master-error.ts b/packages/tm-core/src/errors/task-master-error.ts
index 545e6353..d5c8bb5f 100644
--- a/packages/tm-core/src/errors/task-master-error.ts
+++ b/packages/tm-core/src/errors/task-master-error.ts
@@ -52,7 +52,10 @@ export const ERROR_CODES = {
 	INVALID_INPUT: 'INVALID_INPUT',
 	NOT_IMPLEMENTED: 'NOT_IMPLEMENTED',
 	UNKNOWN_ERROR: 'UNKNOWN_ERROR',
-	NOT_FOUND: 'NOT_FOUND'
+	NOT_FOUND: 'NOT_FOUND',
+
+	// Context errors
+	NO_BRIEF_SELECTED: 'NO_BRIEF_SELECTED'
 } as const;
 
 export type ErrorCode = (typeof ERROR_CODES)[keyof typeof ERROR_CODES];
diff --git a/packages/tm-core/src/services/task-service.ts b/packages/tm-core/src/services/task-service.ts
index 60fb7d3c..a30289bf 100644
--- a/packages/tm-core/src/services/task-service.ts
+++ b/packages/tm-core/src/services/task-service.ts
@@ -161,6 +161,16 @@ export class TaskService {
 				storageType: this.getStorageType()
 			};
 		} catch (error) {
+			// If it's a user-facing error (like NO_BRIEF_SELECTED), don't log it as an internal error
+			if (
+				error instanceof TaskMasterError &&
+				error.is(ERROR_CODES.NO_BRIEF_SELECTED)
+			) {
+				// Just re-throw user-facing errors without wrapping
+				throw error;
+			}
+
+			// Log internal errors
 			this.logger.error('Failed to get task list', error);
 			throw new TaskMasterError(
 				'Failed to get task list',
@@ -186,6 +196,14 @@ export class TaskService {
 			// Delegate to storage layer which handles the specific logic for tasks vs subtasks
 			return await this.storage.loadTask(String(taskId), activeTag);
 		} catch (error) {
+			// If it's a user-facing error (like NO_BRIEF_SELECTED), don't wrap it
+			if (
+				error instanceof TaskMasterError &&
+				error.is(ERROR_CODES.NO_BRIEF_SELECTED)
+			) {
+				throw error;
+			}
+
 			throw new TaskMasterError(
 				`Failed to get task ${taskId}`,
 				ERROR_CODES.STORAGE_ERROR,
@@ -522,6 +540,14 @@ export class TaskService {
 				activeTag
 			);
 		} catch (error) {
+			// If it's a user-facing error (like NO_BRIEF_SELECTED), don't wrap it
+			if (
+				error instanceof TaskMasterError &&
+				error.is(ERROR_CODES.NO_BRIEF_SELECTED)
+			) {
+				throw error;
+			}
+
 			throw new TaskMasterError(
 				`Failed to update task status for ${taskIdStr}`,
 				ERROR_CODES.STORAGE_ERROR,
diff --git a/packages/tm-core/src/storage/api-storage.ts b/packages/tm-core/src/storage/api-storage.ts
index 51784c9e..0798e38e 100644
--- a/packages/tm-core/src/storage/api-storage.ts
+++ b/packages/tm-core/src/storage/api-storage.ts
@@ -37,6 +37,13 @@ export interface ApiStorageConfig {
 	maxRetries?: number;
 }
 
+/**
+ * Auth context with a guaranteed briefId
+ */
+type ContextWithBrief = NonNullable<
+	ReturnType<typeof AuthManager.prototype.getContext>
+> & { briefId: string };
+
 /**
  * ApiStorage implementation using repository pattern
  * Provides flexibility to swap between different backend implementations
@@ -126,7 +133,7 @@ export class ApiStorage implements IStorage {
 	private async loadTagsIntoCache(): Promise<void> {
 		try {
 			const authManager = AuthManager.getInstance();
-			const context = await authManager.getContext();
+			const context = authManager.getContext();
 
 			// If we have a selected brief, create a virtual "tag" for it
 			if (context?.briefId) {
@@ -158,15 +165,7 @@ export class ApiStorage implements IStorage {
 		await this.ensureInitialized();
 
 		try {
-			const authManager = AuthManager.getInstance();
-			const context = await authManager.getContext();
-
-			// If no brief is selected in context, throw an error
-			if (!context?.briefId) {
-				throw new Error(
-					'No brief selected. Please select a brief first using: tm context brief <brief-id>'
-				);
-			}
+			const context = this.ensureBriefSelected('loadTasks');
 
 			// Load tasks from the current brief context with filters pushed to repository
 			const tasks = await this.retryOperation(() =>
@@ -181,12 +180,11 @@ export class ApiStorage implements IStorage {
 
 			return tasks;
 		} catch (error) {
-			throw new TaskMasterError(
-				'Failed to load tasks from API',
-				ERROR_CODES.STORAGE_ERROR,
-				{ operation: 'loadTasks', tag, context: 'brief-based loading' },
-				error as Error
-			);
+			this.wrapError(error, 'Failed to load tasks from API', {
+				operation: 'loadTasks',
+				tag,
+				context: 'brief-based loading'
+			});
 		}
 	}
 
@@ -237,16 +235,17 @@ export class ApiStorage implements IStorage {
 		await this.ensureInitialized();
 
 		try {
+			this.ensureBriefSelected('loadTask');
+
 			return await this.retryOperation(() =>
 				this.repository.getTask(this.projectId, taskId)
 			);
 		} catch (error) {
-			throw new TaskMasterError(
-				'Failed to load task from API',
-				ERROR_CODES.STORAGE_ERROR,
-				{ operation: 'loadTask', taskId, tag },
-				error as Error
-			);
+			this.wrapError(error, 'Failed to load task from API', {
+				operation: 'loadTask',
+				taskId,
+				tag
+			});
 		}
 	}
 
@@ -325,7 +324,7 @@ export class ApiStorage implements IStorage {
 
 		try {
 			const authManager = AuthManager.getInstance();
-			const context = await authManager.getContext();
+			const context = authManager.getContext();
 
 			// In our API-based system, we only have one "tag" at a time - the current brief
 			if (context?.briefId) {
@@ -510,6 +509,8 @@ export class ApiStorage implements IStorage {
 		await this.ensureInitialized();
 
 		try {
+			this.ensureBriefSelected('updateTaskStatus');
+
 			const existingTask = await this.retryOperation(() =>
 				this.repository.getTask(this.projectId, taskId)
 			);
@@ -546,12 +547,12 @@ export class ApiStorage implements IStorage {
 				taskId
 			};
 		} catch (error) {
-			throw new TaskMasterError(
-				'Failed to update task status via API',
-				ERROR_CODES.STORAGE_ERROR,
-				{ operation: 'updateTaskStatus', taskId, newStatus, tag },
-				error as Error
-			);
+			this.wrapError(error, 'Failed to update task status via API', {
+				operation: 'updateTaskStatus',
+				taskId,
+				newStatus,
+				tag
+			});
 		}
 	}
 
@@ -769,6 +770,29 @@ export class ApiStorage implements IStorage {
 		}
 	}
 
+	/**
+	 * Ensure a brief is selected in the current context
+	 * @returns The current auth context with a valid briefId
+	 */
+	private ensureBriefSelected(operation: string): ContextWithBrief {
+		const authManager = AuthManager.getInstance();
+		const context = authManager.getContext();
+
+		if (!context?.briefId) {
+			throw new TaskMasterError(
+				'No brief selected',
+				ERROR_CODES.NO_BRIEF_SELECTED,
+				{
+					operation,
+					userMessage:
+						'No brief selected. Please select a brief first using: tm context brief <brief-id> or tm context brief <brief-url>'
+				}
+			);
+		}
+
+		return context as ContextWithBrief;
+	}
+
 	/**
 	 * Retry an operation with exponential backoff
 	 */
@@ -787,4 +811,28 @@ export class ApiStorage implements IStorage {
 			throw error;
 		}
 	}
+
+	/**
+	 * Wrap an error unless it's already a NO_BRIEF_SELECTED error
+	 */
+	private wrapError(
+		error: unknown,
+		message: string,
+		context: Record<string, unknown>
+	): never {
+		// If it's already a NO_BRIEF_SELECTED error, don't wrap it
+		if (
+			error instanceof TaskMasterError &&
+			error.is(ERROR_CODES.NO_BRIEF_SELECTED)
+		) {
+			throw error;
+		}
+
+		throw new TaskMasterError(
+			message,
+			ERROR_CODES.STORAGE_ERROR,
+			context,
+			error as Error
+		);
+	}
 }
diff --git a/packages/tm-core/src/task-master-core.ts b/packages/tm-core/src/task-master-core.ts
index 8b0d07ee..6c958825 100644
--- a/packages/tm-core/src/task-master-core.ts
+++ b/packages/tm-core/src/task-master-core.ts
@@ -201,6 +201,44 @@ export class TaskMasterCore {
 		return this.taskService.getStorageType();
 	}
 
+	/**
+	 * Get storage configuration
+	 */
+	getStorageConfig() {
+		return this.configManager.getStorageConfig();
+	}
+
+	/**
+	 * Get storage display information for headers
+	 * Returns context info for API storage, null for file storage
+	 */
+	getStorageDisplayInfo(): {
+		briefId: string;
+		briefName: string;
+		orgSlug?: string;
+	} | null {
+		// Only return info if using API storage
+		const storageType = this.getStorageType();
+		if (storageType !== 'api') {
+			return null;
+		}
+
+		// Get credentials from auth manager
+		const authManager = AuthManager.getInstance();
+		const credentials = authManager.getCredentials();
+		const selectedContext = credentials?.selectedContext;
+
+		if (!selectedContext?.briefId || !selectedContext?.briefName) {
+			return null;
+		}
+
+		return {
+			briefId: selectedContext.briefId,
+			briefName: selectedContext.briefName,
+			orgSlug: selectedContext.orgSlug
+		};
+	}
+
 	/**
 	 * Get current active tag
 	 */
diff --git a/scripts/modules/commands.js b/scripts/modules/commands.js
index f3032bd5..13361b7b 100644
--- a/scripts/modules/commands.js
+++ b/scripts/modules/commands.js
@@ -19,7 +19,8 @@ import {
 	registerAllCommands,
 	checkForUpdate,
 	performAutoUpdate,
-	displayUpgradeNotification
+	displayUpgradeNotification,
+	displayError
 } from '@tm/cli';
 
 import {
@@ -5156,10 +5157,7 @@ async function runCLI(argv = process.argv) {
 			);
 		} else {
 			// Generic error handling for other errors
-			console.error(chalk.red(`Error: ${error.message}`));
-			if (getDebugFlag()) {
-				console.error(error);
-			}
+			displayError(error);
 		}
 
 		process.exit(1);