diff --git a/apps/cli/src/commands/auth.command.ts b/apps/cli/src/commands/auth.command.ts
index 97fd9683..f9553a04 100644
--- a/apps/cli/src/commands/auth.command.ts
+++ b/apps/cli/src/commands/auth.command.ts
@@ -14,6 +14,7 @@ import {
 	type AuthCredentials
 } from '@tm/core/auth';
 import * as ui from '../utils/ui.js';
+import { ContextCommand } from './context.command.js';
 
 /**
  * Result type from auth command
@@ -351,6 +352,11 @@ export class AuthCommand extends Command {
 				chalk.gray(`  Logged in as: ${credentials.email || credentials.userId}`)
 			);
 
+			// Post-auth: Set up workspace context
+			console.log(); // Add spacing
+			const contextCommand = new ContextCommand();
+			await contextCommand.setupContextInteractive();
+
 			return {
 				success: true,
 				action: 'login',
diff --git a/apps/cli/src/commands/context.command.ts b/apps/cli/src/commands/context.command.ts
index 630ba21f..13e86c60 100644
--- a/apps/cli/src/commands/context.command.ts
+++ b/apps/cli/src/commands/context.command.ts
@@ -720,6 +720,53 @@ export class ContextCommand extends Command {
 		return this.authManager.getContext();
 	}
 
+	/**
+	 * Interactive context setup (for post-auth flow)
+	 * Prompts user to select org and brief
+	 */
+	async setupContextInteractive(): Promise<{
+		success: boolean;
+		orgSelected: boolean;
+		briefSelected: boolean;
+	}> {
+		try {
+			// Ask if user wants to set up workspace context
+			const { setupContext } = await inquirer.prompt([
+				{
+					type: 'confirm',
+					name: 'setupContext',
+					message: 'Would you like to set up your workspace context now?',
+					default: true
+				}
+			]);
+
+			if (!setupContext) {
+				return { success: true, orgSelected: false, briefSelected: false };
+			}
+
+			// Select organization
+			const orgResult = await this.selectOrganization();
+			if (!orgResult.success || !orgResult.context?.orgId) {
+				return { success: false, orgSelected: false, briefSelected: false };
+			}
+
+			// Select brief
+			const briefResult = await this.selectBrief(orgResult.context.orgId);
+			return {
+				success: true,
+				orgSelected: true,
+				briefSelected: briefResult.success
+			};
+		} catch (error) {
+			console.error(
+				chalk.yellow(
+					'\nContext setup skipped due to error. You can set it up later with "tm context"'
+				)
+			);
+			return { success: false, orgSelected: false, briefSelected: false };
+		}
+	}
+
 	/**
 	 * Clean up resources
 	 */