#!/usr/bin/env python3
"""
Comprehensive test suite for Gmail elicitation system validation using FastMCP Client SDK.

This test suite validates the complete Gmail elicitation system by testing against
a running MCP server using the FastMCP Client SDK. Tests cover:

- Allow list configuration and parsing
- Management tools (add/remove/view)
- Resource system access
- Elicitation flow simulation
- Integration scenarios
- Edge cases and error handling

Tests are designed to run against a running MCP server instance.
"""

import asyncio
import json
import os
import sys

import pytest

# Server configuration from environment variables with defaults
SERVER_HOST = os.getenv("MCP_SERVER_HOST", "localhost")
SERVER_PORT = os.getenv("MCP_SERVER_PORT", os.getenv("SERVER_PORT", "8002"))
# Force HTTP for now as server is running on HTTP
SERVER_URL = os.getenv("MCP_SERVER_URL", f"http://{SERVER_HOST}:{SERVER_PORT}/mcp/")

# Test email address from environment variable
TEST_EMAIL = os.getenv("TEST_EMAIL_ADDRESS", "test_user@example.com")


class TestGmailElicitationSystem:
    """Comprehensive test suite for Gmail elicitation system using FastMCP Client."""

    # Using the global client fixture from conftest.py

    @pytest.mark.asyncio
    async def test_gmail_tools_available(self, client):
        """Test that Gmail elicitation tools are available."""
        from .test_helpers import assert_tools_registered

        # Check that Gmail elicitation tools are registered
        # Note: Allow list tools have been consolidated into manage_gmail_allow_list
        expected_tools = ["send_gmail_message", "manage_gmail_allow_list"]

        await assert_tools_registered(client, expected_tools, context="Gmail tools")

    @pytest.mark.asyncio
    async def test_gmail_allow_list_resource_available(self, client):
        """Test that Gmail allow list resource is available."""
        resources = await client.list_resources()
        resource_uris = [str(resource.uri) for resource in resources]

        assert "gmail://allow-list" in resource_uris, (
            "gmail://allow-list resource not found"
        )

    # ============================================================================
    # A. ALLOW LIST CONFIGURATION TESTS (Settings Layer)
    # ============================================================================

    @pytest.mark.asyncio
    async def test_view_gmail_allow_list(self, client):
        """Test manage_gmail_allow_list view action returns valid response."""
        result = await client.call_tool(
            "manage_gmail_allow_list",
            {"action": "view", "user_google_email": TEST_EMAIL},
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Response should be valid JSON or error message
        try:
            data = json.loads(content)
            # Should have expected structure
            assert "allowed_emails" in data or "error" in data
        except json.JSONDecodeError:
            # If not JSON, should be descriptive text
            assert (
                "allow list" in content.lower()
                or "authentication" in content.lower()
                or "credentials" in content.lower()
            )

    @pytest.mark.asyncio
    async def test_add_to_gmail_allow_list_valid_email(self, client):
        """Test manage_gmail_allow_list add action with valid email."""
        test_email = "test@example.com"

        result = await client.call_tool(
            "manage_gmail_allow_list",
            {"action": "add", "user_google_email": TEST_EMAIL, "email": test_email},
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should either succeed or indicate authentication issue
        assert (
            "successfully added" in content.lower()
            or "added" in content.lower()
            or "already in the allow list" in content.lower()
            or "authentication" in content.lower()
            or "credentials" in content.lower()
        )

    @pytest.mark.asyncio
    async def test_add_to_gmail_allow_list_invalid_email(self, client):
        """Test manage_gmail_allow_list add action with invalid email format."""
        result = await client.call_tool(
            "manage_gmail_allow_list",
            {
                "action": "add",
                "user_google_email": TEST_EMAIL,
                "email": "invalid-email-format",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should indicate invalid email format or handle gracefully
        assert (
            "invalid" in content.lower()
            or "error" in content.lower()
            or "format" in content.lower()
        )

    @pytest.mark.asyncio
    async def test_remove_from_gmail_allow_list_nonexistent(self, client):
        """Test manage_gmail_allow_list remove action with nonexistent email."""
        result = await client.call_tool(
            "manage_gmail_allow_list",
            {
                "action": "remove",
                "user_google_email": TEST_EMAIL,
                "email": "nonexistent@example.com",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should indicate email not in allow list or authentication issue
        assert (
            "not in the allow list" in content.lower()
            or "removed" in content.lower()
            or "not found" in content.lower()
            or "authentication" in content.lower()
            or "credentials" in content.lower()
        )

    # ============================================================================
    # B. RESOURCE SYSTEM TESTS
    # ============================================================================

    @pytest.mark.asyncio
    async def test_gmail_allow_list_resource_access(self, client):
        """Test accessing gmail://allow-list resource."""
        try:
            content = await client.read_resource("gmail://allow-list")

            assert len(content) > 0
            resource_data = json.loads(content[0].text)

            # Verify resource structure
            expected_fields = [
                "authenticated_user",
                "is_configured",
                "allow_list_count",
                "allow_list",
            ]
            for field in expected_fields:
                assert field in resource_data, (
                    f"Missing field '{field}' in resource response"
                )

            # Should have authentication status
            assert "authenticated" in resource_data or "error" in resource_data

        except Exception as e:
            # Resource access might fail without authentication
            assert "authentication" in str(e).lower() or "user" in str(e).lower()

    # ============================================================================
    # C. ELICITATION FLOW SIMULATION TESTS
    # ============================================================================

    @pytest.mark.asyncio
    async def test_send_gmail_message_requires_elicitation(self, client):
        """Test send_gmail_message triggers elicitation for untrusted recipients."""
        # This test simulates the elicitation flow by attempting to send to untrusted recipients
        result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": ["untrusted@example.com"],
                "subject": "Test Elicitation",
                "body": "This should trigger elicitation",
                "content_type": "plain",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should either trigger elicitation, send successfully, or indicate auth error
        assert (
            "email ready to send" in content.lower()  # Elicitation message
            or "email sent" in content.lower()  # Successful send
            or "authentication" in content.lower()  # Auth error
            or "credentials" in content.lower()
        )  # Auth error

    @pytest.mark.asyncio
    async def test_send_gmail_message_multiple_recipients(self, client):
        """Test send_gmail_message with multiple recipient types."""
        result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": ["recipient1@example.com", "recipient2@example.com"],
                "cc": ["cc@example.com"],
                "bcc": ["bcc@example.com"],
                "subject": "Multi-Recipient Test",
                "body": "Testing multiple recipients",
                "content_type": "plain",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should handle multiple recipients appropriately
        assert (
            "email ready to send" in content.lower()
            or "email sent" in content.lower()
            or "authentication" in content.lower()
            or "credentials" in content.lower()
        )

    @pytest.mark.asyncio
    async def test_send_gmail_message_content_types(self, client):
        """Test send_gmail_message with different content types."""
        content_types = ["plain", "html", "mixed"]

        for content_type in content_types:
            # Note: pytest doesn't have subTest, so we'll just test all content types
            try:
                result = await client.call_tool(
                    "send_gmail_message",
                    {
                        "user_google_email": TEST_EMAIL,
                        "to": ["test@example.com"],
                        "subject": f"Content Type Test - {content_type}",
                        "body": f"Testing {content_type} content",
                        "content_type": content_type,
                        "html_body": (
                            f"<p>Testing {content_type} content</p>"
                            if content_type == "mixed"
                            else None
                        ),
                    },
                )

                assert result is not None and result.content
                content = result.content[0].text

                # Should handle content type appropriately
                assert (
                    "email ready to send" in content.lower()
                    or "email sent" in content.lower()
                    or "authentication" in content.lower()
                    or "credentials" in content.lower()
                )
            except AssertionError as e:
                print(f"Failed for content_type={content_type}: {e}")
                raise

    # ============================================================================
    # D. INTEGRATION TEST SCENARIOS
    # ============================================================================

    @pytest.mark.asyncio
    async def test_allow_list_management_workflow(self, client):
        """Test complete allow list management workflow."""
        test_email = "workflow-test@example.com"

        # Step 1: Add email to allow list
        add_result = await client.call_tool(
            "manage_gmail_allow_list",
            {"action": "add", "user_google_email": TEST_EMAIL, "email": test_email},
        )

        # Step 2: View allow list to verify addition
        view_result = await client.call_tool(
            "manage_gmail_allow_list",
            {"action": "view", "user_google_email": TEST_EMAIL},
        )

        # Step 3: Remove email from allow list
        remove_result = await client.call_tool(
            "manage_gmail_allow_list",
            {"action": "remove", "user_google_email": TEST_EMAIL, "email": test_email},
        )

        # Verify each step handled appropriately - responses may be JSON
        for result in [add_result, view_result, remove_result]:
            assert result is not None and result.content
            content = result.content[0].text
            # Try to parse as JSON first
            try:
                data = json.loads(content)
                # JSON response is valid
                assert isinstance(data, dict)
            except json.JSONDecodeError:
                # Text response - check for expected keywords
                assert (
                    "successfully" in content.lower()
                    or "allow list" in content.lower()
                    or "added" in content.lower()
                    or "removed" in content.lower()
                    or "authentication" in content.lower()
                    or "credentials" in content.lower()
                )

    @pytest.mark.asyncio
    async def test_gmail_elicitation_integration(self, client):
        """Test Gmail elicitation system integration."""
        # Test the complete flow: configure allow list, then send email
        trusted_email = "trusted@example.com"
        untrusted_email = "untrusted@example.com"

        # Step 1: Add trusted email to allow list
        await client.call_tool(
            "manage_gmail_allow_list",
            {"action": "add", "user_google_email": TEST_EMAIL, "email": trusted_email},
        )

        # Step 2: Try to send to trusted email (should not trigger elicitation)
        trusted_result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": [trusted_email],
                "subject": "Trusted Recipient Test",
                "body": "This should not trigger elicitation",
                "content_type": "plain",
            },
        )

        # Step 3: Try to send to untrusted email (should trigger elicitation)
        untrusted_result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": [untrusted_email],
                "subject": "Untrusted Recipient Test",
                "body": "This should trigger elicitation",
                "content_type": "plain",
            },
        )

        # Verify both scenarios handled appropriately
        for result in [trusted_result, untrusted_result]:
            assert result is not None and result.content
            content = result.content[0].text
            assert (
                "email ready to send" in content.lower()
                or "email sent" in content.lower()
                or "authentication" in content.lower()
                or "credentials" in content.lower()
            )

    # ============================================================================
    # E. EDGE CASES AND ERROR HANDLING TESTS
    # ============================================================================

    @pytest.mark.asyncio
    async def test_send_gmail_message_empty_recipients(self, client):
        """Test send_gmail_message with empty recipient lists."""
        result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": [],
                "cc": [],
                "bcc": [],
                "subject": "Empty Recipients Test",
                "body": "Testing with no recipients",
                "content_type": "plain",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should handle empty recipients gracefully
        lower_content = content.lower()
        assert (
            "email sent" in lower_content
            or "authentication" in lower_content
            or "credentials" in lower_content
            or "recipient address required" in lower_content
            or "invalidargument" in lower_content
            or "invalid argument" in lower_content
        )

    @pytest.mark.asyncio
    async def test_send_gmail_message_long_body(self, client):
        """Test send_gmail_message with very long body content."""
        long_body = "This is a very long email body. " * 200  # ~6600 characters

        result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": ["test@example.com"],
                "subject": "Long Body Test",
                "body": long_body,
                "content_type": "plain",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should handle long content appropriately
        assert (
            "email ready to send" in content.lower()
            or "email sent" in content.lower()
            or "authentication" in content.lower()
            or "credentials" in content.lower()
        )

    @pytest.mark.asyncio
    async def test_send_gmail_message_unicode_content(self, client):
        """Test send_gmail_message with unicode characters."""
        unicode_body = (
            "Hello! 👋 This email contains unicode characters: 中文, русский, español"
        )
        unicode_subject = "Unicode Test 📧 中文"

        result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": ["test@example.com"],
                "subject": unicode_subject,
                "body": unicode_body,
                "content_type": "plain",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should handle unicode content appropriately
        assert (
            "email ready to send" in content.lower()
            or "email sent" in content.lower()
            or "authentication" in content.lower()
            or "credentials" in content.lower()
        )

    @pytest.mark.asyncio
    async def test_send_gmail_message_special_characters(self, client):
        """Test send_gmail_message with special characters in subject and body."""
        special_subject = "Special Chars: !@#$%^&*()_+-=[]{}|;:,.<>?"
        special_body = "Body with special chars: ©®™€£¥§¶†‡•…—"

        result = await client.call_tool(
            "send_gmail_message",
            {
                "user_google_email": TEST_EMAIL,
                "to": ["test@example.com"],
                "subject": special_subject,
                "body": special_body,
                "content_type": "plain",
            },
        )

        assert result is not None and result.content
        content = result.content[0].text

        # Should handle special characters appropriately
        assert (
            "email ready to send" in content.lower()
            or "email sent" in content.lower()
            or "authentication" in content.lower()
            or "credentials" in content.lower()
        )

    @pytest.mark.asyncio
    async def test_missing_required_parameters(self, client):
        """Test tools handle missing required parameters gracefully."""
        # Test send_gmail_message without required parameters
        # May raise exception or return error in response
        try:
            result = await client.call_tool(
                "send_gmail_message",
                {
                    "user_google_email": TEST_EMAIL
                    # Missing required: to, subject, body
                },
            )
            # If it returns a result, should indicate error
            if result and result.content:
                content = result.content[0].text.lower()
                assert (
                    "required" in content
                    or "missing" in content
                    or "error" in content
                    or "invalid" in content
                )
        except Exception as e:
            # Exception is expected for missing params
            assert "required" in str(e).lower() or "missing" in str(e).lower()

        # Test manage_gmail_allow_list add action without email
        try:
            result = await client.call_tool(
                "manage_gmail_allow_list",
                {
                    "action": "add",
                    "user_google_email": TEST_EMAIL,
                    # Missing required: email for add action
                },
            )
            # If it returns a result, should indicate error
            if result and result.content:
                content = result.content[0].text.lower()
                assert (
                    "required" in content
                    or "missing" in content
                    or "email" in content
                    or "error" in content
                )
        except Exception as e:
            # Exception is expected for missing params
            assert (
                "required" in str(e).lower()
                or "missing" in str(e).lower()
                or "email" in str(e).lower()
            )

    # ============================================================================
    # F. DOCUMENTATION AND VALIDATION TESTS
    # ============================================================================

    @pytest.mark.asyncio
    async def test_tool_descriptions_and_parameters(self, client):
        """Test that Gmail tools have proper descriptions and parameters."""
        tools = await client.list_tools()

        gmail_tools = [tool for tool in tools if "gmail" in tool.name.lower()]

        for tool in gmail_tools:
            # Each tool should have a description
            assert tool.description, f"Tool '{tool.name}' missing description"

            # Check for elicitation-related tools
            if tool.name == "send_gmail_message":
                assert "elicitation" in tool.description.lower(), (
                    "send_gmail_message should mention elicitation"
                )

            # Tool should have input schema
            assert hasattr(tool, "inputSchema"), (
                f"Tool '{tool.name}' missing input schema"
            )

    @pytest.mark.asyncio
    async def test_resource_descriptions(self, client):
        """Test that Gmail resources have proper descriptions."""
        resources = await client.list_resources()

        gmail_resources = [
            resource for resource in resources if "gmail" in str(resource.uri)
        ]

        for resource in gmail_resources:
            assert resource.description, (
                f"Resource '{resource.uri}' missing description"
            )
            # Gmail resources should have descriptive text
            assert len(resource.description) > 10, (
                f"Resource '{resource.uri}' has too short description"
            )

    # ============================================================================
    # G. PERFORMANCE AND RELIABILITY TESTS
    # ============================================================================

    @pytest.mark.asyncio
    async def test_concurrent_allow_list_operations(self, client):
        """Test concurrent allow list operations."""
        # This test checks if the system can handle concurrent operations
        test_emails = [f"concurrent{i}@example.com" for i in range(3)]

        # Perform concurrent add operations
        tasks = []
        for email in test_emails:
            task = client.call_tool(
                "manage_gmail_allow_list",
                {"action": "add", "user_google_email": TEST_EMAIL, "email": email},
            )
            tasks.append(task)

        # Wait for all operations to complete
        results = await asyncio.gather(*tasks, return_exceptions=True)

        # Verify all operations completed (success or expected failure)
        for result in results:
            if isinstance(result, Exception):
                # Expected for authentication or other issues
                assert (
                    "authentication" in str(result).lower()
                    or "credentials" in str(result).lower()
                    or "unknown tool" in str(result).lower()
                )
            else:
                # Successful operation
                assert result is not None and result.content
                content = result.content[0].text
                assert (
                    "successfully" in content.lower()
                    or "added" in content.lower()
                    or "already in the allow list" in content.lower()
                    or "authentication" in content.lower()
                    or "credentials" in content.lower()
                )


def run_tests():
    """Run the Gmail elicitation system test suite."""
    print("=" * 80)
    print("Gmail Elicitation System Test Suite")
    print("=" * 80)
    print()
    print("This test suite validates the Gmail elicitation system by testing")
    print("against a running MCP server using the FastMCP Client SDK.")
    print()
    print("Prerequisites:")
    print("- MCP server must be running and accessible")
    print("- Set MCP_SERVER_HOST and MCP_SERVER_PORT environment variables if needed")
    print("- Set TEST_EMAIL_ADDRESS for authenticated testing")
    print()
    print("Test Coverage:")
    print("• Allow list configuration and parsing")
    print("• Management tools (add/remove/view)")
    print("• Resource system access")
    print("• Elicitation flow simulation")
    print("• Integration scenarios")
    print("• Edge cases and error handling")
    print("• Documentation validation")
    print("• Performance and reliability")
    print()

    # Run tests with pytest
    import subprocess
    import sys

    try:
        result = subprocess.run(
            [
                sys.executable,
                "-m",
                "pytest",
                __file__,
                "-v",
                "--asyncio-mode=auto",
                "--tb=short",
            ],
            capture_output=False,
            text=True,
        )

        return result.returncode == 0

    except Exception as e:
        print(f"Error running tests: {e}")
        return False


if __name__ == "__main__":
    success = run_tests()
    sys.exit(0 if success else 1)
