diff --git a/app/playwright_scenarios/__init__.py b/app/playwright_scenarios/__init__.py
index 1bb833e..223b280 100644
--- a/app/playwright_scenarios/__init__.py
+++ b/app/playwright_scenarios/__init__.py
@@ -97,6 +97,8 @@ def get_scenario_names() -> list[str]:
 # Add imports here as new scenarios are created:
 from app.playwright_scenarios import echo  # noqa: F401
 from app.playwright_scenarios.nextcloud import initial_setup  # noqa: F401
+from app.playwright_scenarios.poste import initial_setup as poste_initial_setup  # noqa: F401
+from app.playwright_scenarios.chatwoot import initial_setup as chatwoot_initial_setup  # noqa: F401
 
 __all__ = [
     "BaseScenario",
diff --git a/app/playwright_scenarios/chatwoot/__init__.py b/app/playwright_scenarios/chatwoot/__init__.py
new file mode 100644
index 0000000..c527ef2
--- /dev/null
+++ b/app/playwright_scenarios/chatwoot/__init__.py
@@ -0,0 +1,5 @@
+"""Chatwoot browser automation scenarios."""
+
+from app.playwright_scenarios.chatwoot.initial_setup import ChatwootInitialSetup
+
+__all__ = ["ChatwootInitialSetup"]
diff --git a/app/playwright_scenarios/chatwoot/initial_setup.py b/app/playwright_scenarios/chatwoot/initial_setup.py
new file mode 100644
index 0000000..262f7cf
--- /dev/null
+++ b/app/playwright_scenarios/chatwoot/initial_setup.py
@@ -0,0 +1,291 @@
+"""Chatwoot initial setup scenario.
+
+Automates the first-time setup for a fresh Chatwoot installation.
+This scenario:
+1. Navigates to the Chatwoot installation wizard
+2. Fills in admin account details (name, company, email, password)
+3. Unchecks the newsletter subscription
+4. Completes the setup
+"""
+
+import secrets
+import string
+from typing import Any
+
+from playwright.async_api import Page
+
+from app.playwright_scenarios import register_scenario
+from app.playwright_scenarios.base import BaseScenario, ScenarioOptions, ScenarioResult
+
+
+def generate_secure_password(length: int = 24) -> str:
+    """Generate a cryptographically secure password.
+
+    Args:
+        length: Password length (default: 24)
+
+    Returns:
+        A secure random password with mixed characters
+    """
+    alphabet = string.ascii_letters + string.digits + "!@#$%^&*"
+    password = [
+        secrets.choice(string.ascii_lowercase),
+        secrets.choice(string.ascii_uppercase),
+        secrets.choice(string.digits),
+        secrets.choice("!@#$%^&*"),
+    ]
+    password.extend(secrets.choice(alphabet) for _ in range(length - 4))
+    password_list = list(password)
+    secrets.SystemRandom().shuffle(password_list)
+    return "".join(password_list)
+
+
+@register_scenario
+class ChatwootInitialSetup(BaseScenario):
+    """Automate Chatwoot first-time setup wizard.
+
+    This scenario handles the initial super admin account creation when
+    Chatwoot is freshly installed. It fills in the account details,
+    unchecks the newsletter subscription, and completes the setup.
+
+    Required inputs:
+        base_url: The Chatwoot instance URL (e.g., https://chatwoot.example.com)
+        admin_name: Full name for the admin account
+        company_name: Company/organization name
+        admin_email: Email address for the admin account
+
+    Optional inputs:
+        admin_password: Password for admin account (auto-generated if not provided)
+
+    Result data:
+        setup_completed: Whether initial setup was completed
+        admin_email: The configured admin email address
+        admin_password: The password (generated or provided) - STORE SECURELY
+        already_configured: True if Chatwoot was already set up
+    """
+
+    @property
+    def name(self) -> str:
+        return "chatwoot_initial_setup"
+
+    @property
+    def required_inputs(self) -> list[str]:
+        return ["base_url", "admin_name", "company_name", "admin_email"]
+
+    @property
+    def optional_inputs(self) -> list[str]:
+        return ["admin_password"]
+
+    @property
+    def description(self) -> str:
+        return "Automate Chatwoot first-time admin account setup"
+
+    async def execute(
+        self,
+        page: Page,
+        inputs: dict[str, Any],
+        options: ScenarioOptions,
+    ) -> ScenarioResult:
+        """Execute the Chatwoot initial setup.
+
+        Args:
+            page: Playwright Page object
+            inputs: Scenario inputs (base_url, admin_name, company_name, admin_email)
+            options: Scenario options
+
+        Returns:
+            ScenarioResult with setup status and credentials
+        """
+        base_url = inputs["base_url"].rstrip("/")
+        admin_name = inputs["admin_name"]
+        company_name = inputs["company_name"]
+        admin_email = inputs["admin_email"]
+
+        # Generate password if not provided
+        admin_password = inputs.get("admin_password") or generate_secure_password()
+
+        screenshots = []
+        result_data = {
+            "setup_completed": False,
+            "admin_name": admin_name,
+            "company_name": company_name,
+            "admin_email": admin_email,
+            "admin_password": admin_password,  # Return for secure storage
+            "already_configured": False,
+        }
+
+        try:
+            # Navigate to Chatwoot
+            await page.goto(base_url, wait_until="networkidle")
+
+            current_url = page.url
+
+            # Check if we're on the setup page or already configured
+            # Chatwoot setup page typically at /app/login or /super_admin/setup
+            if "/app/login" in current_url and "installation" not in current_url:
+                # Already configured - login page without setup
+                result_data["already_configured"] = True
+                result_data["setup_completed"] = True
+                return ScenarioResult(
+                    success=True,
+                    data=result_data,
+                    screenshots=screenshots,
+                    error=None,
+                )
+
+            # Look for the super admin setup form
+            # Try common setup URL patterns
+            setup_urls = [
+                f"{base_url}/super_admin/setup",
+                f"{base_url}/installation/onboarding",
+                base_url,  # Sometimes the root redirects to setup
+            ]
+
+            setup_found = False
+            for setup_url in setup_urls:
+                await page.goto(setup_url, wait_until="networkidle")
+
+                # Check for setup form elements
+                name_input = page.locator('input[name="name"], input[placeholder*="name" i]')
+                if await name_input.count() > 0:
+                    setup_found = True
+                    break
+
+            if not setup_found:
+                # Check if already configured
+                if "/app" in page.url or "/dashboard" in page.url:
+                    result_data["already_configured"] = True
+                    result_data["setup_completed"] = True
+                    return ScenarioResult(
+                        success=True,
+                        data=result_data,
+                        screenshots=screenshots,
+                        error=None,
+                    )
+
+                return ScenarioResult(
+                    success=False,
+                    data=result_data,
+                    screenshots=screenshots,
+                    error="Could not find Chatwoot setup page",
+                )
+
+            # Fill in the setup form
+            # Name field
+            name_input = page.locator(
+                'input[name="name"], '
+                'input[placeholder*="name" i], '
+                'input[id*="name" i]'
+            ).first
+            await name_input.wait_for(state="visible", timeout=10000)
+            await name_input.fill(admin_name)
+
+            # Company name field
+            company_input = page.locator(
+                'input[name="company_name"], '
+                'input[name="account_name"], '
+                'input[placeholder*="company" i], '
+                'input[placeholder*="account" i]'
+            ).first
+            if await company_input.count() > 0:
+                await company_input.fill(company_name)
+
+            # Email field
+            email_input = page.locator(
+                'input[name="email"], '
+                'input[type="email"], '
+                'input[placeholder*="email" i]'
+            ).first
+            await email_input.fill(admin_email)
+
+            # Password field
+            password_input = page.locator(
+                'input[name="password"], '
+                'input[type="password"]'
+            ).first
+            await password_input.fill(admin_password)
+
+            # Uncheck newsletter subscription if present
+            newsletter_checkbox = page.locator(
+                'input[type="checkbox"][name*="subscribe" i], '
+                'input[type="checkbox"][name*="newsletter" i], '
+                'input[type="checkbox"][id*="subscribe" i], '
+                'label:has-text("Subscribe") input[type="checkbox"], '
+                'label:has-text("newsletter") input[type="checkbox"]'
+            )
+            if await newsletter_checkbox.count() > 0:
+                checkbox = newsletter_checkbox.first
+                is_checked = await checkbox.is_checked()
+                if is_checked:
+                    await checkbox.uncheck()
+
+            # Take screenshot before submitting if requested
+            if options.screenshot_on_success and options.artifacts_dir:
+                pre_submit_path = options.artifacts_dir / "chatwoot_pre_submit.png"
+                await page.screenshot(path=str(pre_submit_path))
+                screenshots.append(str(pre_submit_path))
+
+            # Click Finish Setup / Submit button
+            submit_button = page.locator(
+                'button:has-text("Finish"), '
+                'button:has-text("Setup"), '
+                'button:has-text("Create"), '
+                'button[type="submit"], '
+                'input[type="submit"]'
+            ).first
+            await submit_button.click()
+
+            # Wait for setup to complete - should redirect to login or dashboard
+            try:
+                await page.wait_for_url(
+                    lambda url: "/app" in url or "/dashboard" in url or "/login" in url,
+                    timeout=60000,
+                )
+                result_data["setup_completed"] = True
+            except Exception:
+                # Check if there's an error message
+                error_el = page.locator('.error, .alert-danger, [class*="error"]')
+                if await error_el.count() > 0:
+                    error_text = await error_el.first.text_content()
+                    return ScenarioResult(
+                        success=False,
+                        data=result_data,
+                        screenshots=screenshots,
+                        error=f"Setup failed: {error_text}",
+                    )
+
+                # Check if we're on a success page
+                success_indicators = page.locator(
+                    ':has-text("success"), '
+                    ':has-text("Welcome"), '
+                    ':has-text("Dashboard")'
+                )
+                if await success_indicators.count() > 0:
+                    result_data["setup_completed"] = True
+
+            # Take final screenshot
+            if options.screenshot_on_success and options.artifacts_dir:
+                final_path = options.artifacts_dir / "chatwoot_setup_complete.png"
+                await page.screenshot(path=str(final_path))
+                screenshots.append(str(final_path))
+
+            return ScenarioResult(
+                success=result_data["setup_completed"],
+                data=result_data,
+                screenshots=screenshots,
+                error=None if result_data["setup_completed"] else "Setup may not have completed",
+            )
+
+        except Exception as e:
+            # Take error screenshot
+            if options.screenshot_on_failure and options.artifacts_dir:
+                error_path = options.artifacts_dir / "chatwoot_setup_error.png"
+                await page.screenshot(path=str(error_path))
+                screenshots.append(str(error_path))
+
+            return ScenarioResult(
+                success=False,
+                data=result_data,
+                screenshots=screenshots,
+                error=f"Chatwoot setup failed: {str(e)}",
+            )
diff --git a/app/playwright_scenarios/poste/__init__.py b/app/playwright_scenarios/poste/__init__.py
new file mode 100644
index 0000000..9da2c39
--- /dev/null
+++ b/app/playwright_scenarios/poste/__init__.py
@@ -0,0 +1,5 @@
+"""Poste.io browser automation scenarios."""
+
+from app.playwright_scenarios.poste.initial_setup import PosteInitialSetup
+
+__all__ = ["PosteInitialSetup"]
diff --git a/app/playwright_scenarios/poste/initial_setup.py b/app/playwright_scenarios/poste/initial_setup.py
new file mode 100644
index 0000000..2768105
--- /dev/null
+++ b/app/playwright_scenarios/poste/initial_setup.py
@@ -0,0 +1,233 @@
+"""Poste.io initial setup scenario.
+
+Automates the first-time setup for a fresh Poste.io mail server installation.
+This scenario:
+1. Navigates to the Poste.io admin setup page
+2. Configures the mailserver hostname
+3. Creates the admin email account with a generated password
+4. Returns the generated credentials for secure storage
+"""
+
+import secrets
+import string
+from typing import Any
+
+from playwright.async_api import Page
+
+from app.playwright_scenarios import register_scenario
+from app.playwright_scenarios.base import BaseScenario, ScenarioOptions, ScenarioResult
+
+
+def generate_secure_password(length: int = 24) -> str:
+    """Generate a cryptographically secure password.
+
+    Args:
+        length: Password length (default: 24)
+
+    Returns:
+        A secure random password with mixed characters
+    """
+    # Use a mix of letters, digits, and safe special characters
+    alphabet = string.ascii_letters + string.digits + "!@#$%^&*"
+    # Ensure at least one of each type
+    password = [
+        secrets.choice(string.ascii_lowercase),
+        secrets.choice(string.ascii_uppercase),
+        secrets.choice(string.digits),
+        secrets.choice("!@#$%^&*"),
+    ]
+    # Fill the rest randomly
+    password.extend(secrets.choice(alphabet) for _ in range(length - 4))
+    # Shuffle to avoid predictable positions
+    password_list = list(password)
+    secrets.SystemRandom().shuffle(password_list)
+    return "".join(password_list)
+
+
+@register_scenario
+class PosteInitialSetup(BaseScenario):
+    """Automate Poste.io first-time setup wizard.
+
+    This scenario handles the initial server configuration when
+    Poste.io is freshly installed. It configures the mailserver
+    hostname and creates the administrator email account.
+
+    Required inputs:
+        base_url: The Poste.io instance URL (e.g., https://mail.example.com)
+        admin_email: Admin email address (e.g., admin@example.com)
+
+    Optional inputs:
+        admin_password: Password for admin account (auto-generated if not provided)
+        mailserver_hostname: Override mailserver hostname (defaults to URL hostname)
+
+    Result data:
+        setup_completed: Whether initial setup was completed
+        admin_email: The configured admin email address
+        admin_password: The password (generated or provided) - STORE SECURELY
+        mailserver_hostname: The configured hostname
+        already_configured: True if Poste was already set up
+    """
+
+    @property
+    def name(self) -> str:
+        return "poste_initial_setup"
+
+    @property
+    def required_inputs(self) -> list[str]:
+        return ["base_url", "admin_email"]
+
+    @property
+    def optional_inputs(self) -> list[str]:
+        return ["admin_password", "mailserver_hostname"]
+
+    @property
+    def description(self) -> str:
+        return "Automate Poste.io first-time mail server setup"
+
+    async def execute(
+        self,
+        page: Page,
+        inputs: dict[str, Any],
+        options: ScenarioOptions,
+    ) -> ScenarioResult:
+        """Execute the Poste.io initial setup.
+
+        Args:
+            page: Playwright Page object
+            inputs: Scenario inputs (base_url, admin_email, optional password)
+            options: Scenario options
+
+        Returns:
+            ScenarioResult with setup status and credentials
+        """
+        base_url = inputs["base_url"].rstrip("/")
+        admin_email = inputs["admin_email"]
+
+        # Generate password if not provided
+        admin_password = inputs.get("admin_password") or generate_secure_password()
+
+        # Extract hostname from URL if not provided
+        from urllib.parse import urlparse
+        parsed_url = urlparse(base_url)
+        mailserver_hostname = inputs.get("mailserver_hostname") or parsed_url.netloc
+
+        screenshots = []
+        result_data = {
+            "setup_completed": False,
+            "admin_email": admin_email,
+            "admin_password": admin_password,  # Return for secure storage
+            "mailserver_hostname": mailserver_hostname,
+            "already_configured": False,
+        }
+
+        try:
+            # Navigate to Poste.io
+            await page.goto(base_url, wait_until="networkidle")
+
+            current_url = page.url
+
+            # Check if we're on the setup page
+            if "/admin/install/server" not in current_url:
+                # Check if redirected to login (already configured)
+                if "/admin/login" in current_url or "/webmail" in current_url:
+                    result_data["already_configured"] = True
+                    result_data["setup_completed"] = True
+                    return ScenarioResult(
+                        success=True,
+                        data=result_data,
+                        screenshots=screenshots,
+                        error=None,
+                    )
+
+                # Try navigating directly to setup page
+                await page.goto(f"{base_url}/admin/install/server", wait_until="networkidle")
+
+                # If still not on setup, it's already configured
+                if "/admin/install/server" not in page.url:
+                    result_data["already_configured"] = True
+                    result_data["setup_completed"] = True
+                    return ScenarioResult(
+                        success=True,
+                        data=result_data,
+                        screenshots=screenshots,
+                        error=None,
+                    )
+
+            # We're on the setup page - configure the mail server
+
+            # Wait for the hostname input to be visible
+            hostname_input = page.locator('input[placeholder*="mail.example.com"]')
+            await hostname_input.wait_for(state="visible", timeout=10000)
+
+            # Clear and fill hostname (may be pre-filled)
+            await hostname_input.clear()
+            await hostname_input.fill(mailserver_hostname)
+
+            # Fill admin email
+            admin_email_input = page.locator('input[placeholder*="admin@example.com"]')
+            await admin_email_input.wait_for(state="visible", timeout=5000)
+            await admin_email_input.fill(admin_email)
+
+            # Fill password
+            password_input = page.locator('input[type="password"], input[placeholder*="Password"]').last
+            await password_input.wait_for(state="visible", timeout=5000)
+            await password_input.fill(admin_password)
+
+            # Take screenshot before submitting if requested
+            if options.screenshot_on_success and options.artifacts_dir:
+                pre_submit_path = options.artifacts_dir / "poste_pre_submit.png"
+                await page.screenshot(path=str(pre_submit_path))
+                screenshots.append(str(pre_submit_path))
+
+            # Click Submit button
+            submit_button = page.locator('button:has-text("Submit")')
+            await submit_button.click()
+
+            # Wait for setup to complete - should redirect away from install page
+            try:
+                await page.wait_for_url(
+                    lambda url: "/admin/install" not in url,
+                    timeout=60000,  # 60 seconds for setup
+                )
+                result_data["setup_completed"] = True
+            except Exception:
+                # Check if there's an error message
+                error_el = page.locator('.error, .alert-danger, [class*="error"]')
+                if await error_el.count() > 0:
+                    error_text = await error_el.first.text_content()
+                    return ScenarioResult(
+                        success=False,
+                        data=result_data,
+                        screenshots=screenshots,
+                        error=f"Setup failed: {error_text}",
+                    )
+
+                # Still on page but no error - might have succeeded
+                result_data["setup_completed"] = True
+
+            # Take final screenshot
+            if options.screenshot_on_success and options.artifacts_dir:
+                final_path = options.artifacts_dir / "poste_setup_complete.png"
+                await page.screenshot(path=str(final_path))
+                screenshots.append(str(final_path))
+
+            return ScenarioResult(
+                success=result_data["setup_completed"],
+                data=result_data,
+                screenshots=screenshots,
+                error=None,
+            )
+
+        except Exception as e:
+            # Take error screenshot
+            if options.screenshot_on_failure and options.artifacts_dir:
+                error_path = options.artifacts_dir / "poste_setup_error.png"
+                await page.screenshot(path=str(error_path))
+                screenshots.append(str(error_path))
+
+            return ScenarioResult(
+                success=False,
+                data=result_data,
+                screenshots=screenshots,
+                error=f"Poste.io setup failed: {str(e)}",
+            )