No Global IP whitelist - fixing failed auth response hang, fixing sender authentication.

email_server/auth.py

@@ -32,7 +32,7 @@ class EnhancedAuthenticator:
     def __call__(self, server, session, envelope, mechanism, auth_data):
         if not isinstance(auth_data, LoginPassword):
             logger.warning(f'Invalid auth data format: {type(auth_data)}')
-            return AuthResult(success=False, handled=True, message='535 Authentication failed')
+            return AuthResult(success=False, handled=False, message='535 Authentication failed')
         
         # Decode bytes to string if necessary
         username = auth_data.login
@@ -73,7 +73,7 @@ class EnhancedAuthenticator:
                     message=f'Invalid credentials for {username}'
                 )
                 logger.warning(f'Authentication failed for {username}: invalid credentials')
-                return AuthResult(success=False, handled=True, message='535 Authentication failed')
+                return AuthResult(success=False, handled=False, message='535 Authentication failed')
             
         except Exception as e:
             logger.error(f'Authentication error for {username}: {e}')
@@ -84,7 +84,7 @@ class EnhancedAuthenticator:
                 success=False,
                 message=f'Authentication error: {str(e)}'
             )
-            return AuthResult(success=False, handled=True, message='451 Internal server error')
+            return AuthResult(success=False, handled=False, message='451 Internal server error')
 
 class EnhancedIPAuthenticator:
     """

email_server/server_runner.py

@@ -117,7 +117,7 @@ async def start_server(shutdown_event=None):
     )
     controller_tls.start()
     logger.debug(f'  - Plain SMTP (IP whitelist): {BIND_IP}:{SMTP_PORT}')
-    logger.debug(f'  - STARTTLS SMTP (auth required): {BIND_IP}:{SMTP_TLS_PORT}')
+    logger.debug(f'  - Direct TLS SMTP (SMTPS, auth required): {BIND_IP}:{SMTP_TLS_PORT}')
     logger.debug('Management available via web interface at: http://localhost:5000/email')
     
     try:

email_server/settings_loader.py

@@ -14,8 +14,8 @@ DEFAULTS = {
         '; Server configuration for SMTP ports and hostname': None,
         '; Plain SMTP port for internal/whitelisted IPs': None,
         'SMTP_PORT': '4025',
-        '; STARTTLS SMTP port for authenticated users': None,
-        'SMTP_TLS_PORT': '40587',
+        '; TLS SMTP port for authenticated users': None,
+        'SMTP_TLS_PORT': '40465',
         '; Server hostname for HELO/EHLO identification': None,
         'HOSTNAME': 'mail.example.com',
         '; Override HELO hostname': None,

email_server/smtp_handler.py

@@ -21,7 +21,7 @@ from email_server.tool_box import get_logger
 logger = get_logger()
 
 class CustomSMTP(AIOSMTP):
-    """Custom SMTP class with configurable banner."""
+    """Custom SMTP class with configurable banner and secure AUTH handling."""
     
     def __init__(self, *args, **kwargs):
         # Sets Custom SMTP banner from settings
@@ -30,11 +30,31 @@ class CustomSMTP(AIOSMTP):
         if _banner_message == '""':
             _banner_message = ''
         self.custom_banner = _banner_message
-            
+        
+        # Store authenticator and auth_require_tls for later use
+        self._custom_authenticator = kwargs.get('authenticator', None)
+        self._custom_auth_require_tls = kwargs.get('auth_require_tls', False)
         super().__init__(*args, **kwargs)
         # Override the __ident__ to use our custom banner
         self.__ident__ = self.custom_banner
 
+    def _get_auth_methods(self):
+        # Only advertise AUTH if authenticator is set and (not auth_require_tls or connection is secure)
+        if self._custom_authenticator and (not self._custom_auth_require_tls or self.session and self.session.ssl):
+            return super()._get_auth_methods()
+        return []
+
+    async def smtp_AUTH(self, arg):
+        """
+        Override AUTH command to close connection after failed authentication.
+        """
+        result = await super().smtp_AUTH(arg)
+        # If authentication failed, close the connection immediately
+        if isinstance(result, AuthResult) and not result.success:
+            if hasattr(self, 'session') and hasattr(self.session, 'transport') and self.session.transport:
+                self.session.transport.close()
+        return result
+
 class EnhancedCombinedAuthenticator:
     """
     Enhanced combined authenticator with sender validation support.
@@ -353,7 +373,9 @@ class EnhancedCustomSMTPHandler:
         return '250 OK'
 
 class TLSController(Controller):
-    """Custom controller with TLS support - modeled after the working original."""
+    """
+    Custom controller for direct TLS (SMTPS, port 465) support.
+    """
     
     def __init__(self, handler, ssl_context, hostname='localhost', port=40587):
         logger.debug(f"TLSController __init__: ssl_context={ssl_context is not None}")
@@ -365,10 +387,11 @@ class TLSController(Controller):
         logger.debug(f"TLSController factory: ssl_context={self._ssl_context is not None}")
         logger.debug(f"TLSController factory: ssl_context object={self._ssl_context}")
         logger.debug(f"TLSController factory: hostname={self.smtp_hostname}")
+        # This is direct TLS (SMTPS, port 465 style)
         smtp_instance = CustomSMTP(
             self.handler,
             tls_context=self._ssl_context,
-            require_starttls=False,  # Don't require STARTTLS immediately, but make it available
+            require_starttls=False,  # Direct TLS: do not advertise or require STARTTLS
             auth_require_tls=True,   # If auth is used, require TLS
             authenticator=self.handler.combined_authenticator,
             decode_data=True,
@@ -378,17 +401,18 @@ class TLSController(Controller):
         return smtp_instance
 
 class PlainController(Controller):
-    """Controller for plain SMTP with username/password and IP-based authentication."""
+    """Controller for plain SMTP with authentication and IP whitelist fallback."""
     
     def __init__(self, handler, hostname='localhost', port=4025):
         self.smtp_hostname = hostname  # Store for HELO identification
         super().__init__(handler, hostname='0.0.0.0', port=port)  # Bind to all interfaces
     
     def factory(self):
+        # Pass authenticator and set auth_require_tls=False to enable AUTH on plain port
         return CustomSMTP(
             self.handler,
             authenticator=self.handler.combined_authenticator,
-            auth_require_tls=False,  # Allow AUTH over plain text (not recommended for production)
+            auth_require_tls=False,  # Allow AUTH on plain port
             decode_data=True,
             hostname=self.smtp_hostname  # Use proper hostname for HELO
         )

migrations/README

@@ -1 +0,0 @@
-Single-database configuration for Flask.

migrations/alembic.ini

@@ -1,50 +0,0 @@
-# A generic, single database configuration.
-
-[alembic]
-# template used to generate migration files
-# file_template = %%(rev)s_%%(slug)s
-
-# set to 'true' to run the environment during
-# the 'revision' command, regardless of autogenerate
-# revision_environment = false
-
-
-# Logging configuration
-[loggers]
-keys = root,sqlalchemy,alembic,flask_migrate
-
-[handlers]
-keys = console
-
-[formatters]
-keys = generic
-
-[logger_root]
-level = WARN
-handlers = console
-qualname =
-
-[logger_sqlalchemy]
-level = WARN
-handlers =
-qualname = sqlalchemy.engine
-
-[logger_alembic]
-level = INFO
-handlers =
-qualname = alembic
-
-[logger_flask_migrate]
-level = INFO
-handlers =
-qualname = flask_migrate
-
-[handler_console]
-class = StreamHandler
-args = (sys.stderr,)
-level = NOTSET
-formatter = generic
-
-[formatter_generic]
-format = %(levelname)-5.5s [%(name)s] %(message)s
-datefmt = %H:%M:%S

migrations/env.py

@@ -1,113 +0,0 @@
-import logging
-from logging.config import fileConfig
-
-from flask import current_app
-
-from alembic import context
-
-# this is the Alembic Config object, which provides
-# access to the values within the .ini file in use.
-config = context.config
-
-# Interpret the config file for Python logging.
-# This line sets up loggers basically.
-fileConfig(config.config_file_name)
-logger = logging.getLogger('alembic.env')
-
-
-def get_engine():
-    try:
-        # this works with Flask-SQLAlchemy<3 and Alchemical
-        return current_app.extensions['migrate'].db.get_engine()
-    except (TypeError, AttributeError):
-        # this works with Flask-SQLAlchemy>=3
-        return current_app.extensions['migrate'].db.engine
-
-
-def get_engine_url():
-    try:
-        return get_engine().url.render_as_string(hide_password=False).replace(
-            '%', '%%')
-    except AttributeError:
-        return str(get_engine().url).replace('%', '%%')
-
-
-# add your model's MetaData object here
-# for 'autogenerate' support
-# from myapp import mymodel
-# target_metadata = mymodel.Base.metadata
-config.set_main_option('sqlalchemy.url', get_engine_url())
-target_db = current_app.extensions['migrate'].db
-
-# other values from the config, defined by the needs of env.py,
-# can be acquired:
-# my_important_option = config.get_main_option("my_important_option")
-# ... etc.
-
-
-def get_metadata():
-    if hasattr(target_db, 'metadatas'):
-        return target_db.metadatas[None]
-    return target_db.metadata
-
-
-def run_migrations_offline():
-    """Run migrations in 'offline' mode.
-
-    This configures the context with just a URL
-    and not an Engine, though an Engine is acceptable
-    here as well.  By skipping the Engine creation
-    we don't even need a DBAPI to be available.
-
-    Calls to context.execute() here emit the given string to the
-    script output.
-
-    """
-    url = config.get_main_option("sqlalchemy.url")
-    context.configure(
-        url=url, target_metadata=get_metadata(), literal_binds=True
-    )
-
-    with context.begin_transaction():
-        context.run_migrations()
-
-
-def run_migrations_online():
-    """Run migrations in 'online' mode.
-
-    In this scenario we need to create an Engine
-    and associate a connection with the context.
-
-    """
-
-    # this callback is used to prevent an auto-migration from being generated
-    # when there are no changes to the schema
-    # reference: http://alembic.zzzcomputing.com/en/latest/cookbook.html
-    def process_revision_directives(context, revision, directives):
-        if getattr(config.cmd_opts, 'autogenerate', False):
-            script = directives[0]
-            if script.upgrade_ops.is_empty():
-                directives[:] = []
-                logger.info('No changes in schema detected.')
-
-    conf_args = current_app.extensions['migrate'].configure_args
-    if conf_args.get("process_revision_directives") is None:
-        conf_args["process_revision_directives"] = process_revision_directives
-
-    connectable = get_engine()
-
-    with connectable.connect() as connection:
-        context.configure(
-            connection=connection,
-            target_metadata=get_metadata(),
-            **conf_args
-        )
-
-        with context.begin_transaction():
-            context.run_migrations()
-
-
-if context.is_offline_mode():
-    run_migrations_offline()
-else:
-    run_migrations_online()

migrations/script.py.mako

@@ -1,24 +0,0 @@
-"""${message}
-
-Revision ID: ${up_revision}
-Revises: ${down_revision | comma,n}
-Create Date: ${create_date}
-
-"""
-from alembic import op
-import sqlalchemy as sa
-${imports if imports else ""}
-
-# revision identifiers, used by Alembic.
-revision = ${repr(up_revision)}
-down_revision = ${repr(down_revision)}
-branch_labels = ${repr(branch_labels)}
-depends_on = ${repr(depends_on)}
-
-
-def upgrade():
-    ${upgrades if upgrades else "pass"}
-
-
-def downgrade():
-    ${downgrades if downgrades else "pass"}

migrations/versions/3ce273a1be20_initial_migration.py

@@ -1,108 +0,0 @@
-"""Initial migration
-
-Revision ID: 3ce273a1be20
-Revises: 
-Create Date: 2025-06-07 15:25:35.603295
-
-"""
-from alembic import op
-import sqlalchemy as sa
-
-
-# revision identifiers, used by Alembic.
-revision = '3ce273a1be20'
-down_revision = None
-branch_labels = None
-depends_on = None
-
-
-def upgrade():
-    # ### commands auto generated by Alembic - please adjust! ###
-    op.drop_table('esrv_dkim_keys')
-    op.drop_table('esrv_auth_logs')
-    op.drop_table('esrv_users')
-    op.drop_table('esrv_domains')
-    op.drop_table('esrv_whitelisted_ips')
-    op.drop_table('esrv_email_logs')
-    op.drop_table('esrv_custom_headers')
-    # ### end Alembic commands ###
-
-
-def downgrade():
-    # ### commands auto generated by Alembic - please adjust! ###
-    op.create_table('esrv_custom_headers',
-    sa.Column('id', sa.INTEGER(), nullable=False),
-    sa.Column('domain_id', sa.INTEGER(), nullable=False),
-    sa.Column('header_name', sa.VARCHAR(), nullable=False),
-    sa.Column('header_value', sa.VARCHAR(), nullable=False),
-    sa.Column('is_active', sa.BOOLEAN(), nullable=True),
-    sa.Column('created_at', sa.DATETIME(), nullable=True),
-    sa.PrimaryKeyConstraint('id')
-    )
-    op.create_table('esrv_email_logs',
-    sa.Column('id', sa.INTEGER(), nullable=False),
-    sa.Column('message_id', sa.VARCHAR(), nullable=False),
-    sa.Column('timestamp', sa.DATETIME(), nullable=False),
-    sa.Column('peer', sa.VARCHAR(), nullable=False),
-    sa.Column('mail_from', sa.VARCHAR(), nullable=False),
-    sa.Column('rcpt_tos', sa.VARCHAR(), nullable=False),
-    sa.Column('content', sa.TEXT(), nullable=False),
-    sa.Column('status', sa.VARCHAR(), nullable=False),
-    sa.Column('dkim_signed', sa.BOOLEAN(), nullable=True),
-    sa.Column('from_address', sa.VARCHAR(), server_default=sa.text("'unknown'"), nullable=False),
-    sa.Column('to_address', sa.VARCHAR(), server_default=sa.text("'unknown'"), nullable=False),
-    sa.Column('subject', sa.TEXT(), nullable=True),
-    sa.Column('message', sa.TEXT(), nullable=True),
-    sa.Column('created_at', sa.DATETIME(), nullable=True),
-    sa.PrimaryKeyConstraint('id'),
-    sa.UniqueConstraint('message_id')
-    )
-    op.create_table('esrv_whitelisted_ips',
-    sa.Column('id', sa.INTEGER(), nullable=False),
-    sa.Column('ip_address', sa.VARCHAR(), nullable=False),
-    sa.Column('domain_id', sa.INTEGER(), nullable=False),
-    sa.Column('is_active', sa.BOOLEAN(), nullable=True),
-    sa.Column('created_at', sa.DATETIME(), nullable=True),
-    sa.PrimaryKeyConstraint('id')
-    )
-    op.create_table('esrv_domains',
-    sa.Column('id', sa.INTEGER(), nullable=False),
-    sa.Column('domain_name', sa.VARCHAR(), nullable=False),
-    sa.Column('is_active', sa.BOOLEAN(), nullable=True),
-    sa.Column('created_at', sa.DATETIME(), nullable=True),
-    sa.PrimaryKeyConstraint('id'),
-    sa.UniqueConstraint('domain_name')
-    )
-    op.create_table('esrv_users',
-    sa.Column('id', sa.INTEGER(), nullable=False),
-    sa.Column('email', sa.VARCHAR(), nullable=False),
-    sa.Column('password_hash', sa.VARCHAR(), nullable=False),
-    sa.Column('domain_id', sa.INTEGER(), nullable=False),
-    sa.Column('can_send_as_domain', sa.BOOLEAN(), nullable=True),
-    sa.Column('is_active', sa.BOOLEAN(), nullable=True),
-    sa.Column('created_at', sa.DATETIME(), nullable=True),
-    sa.PrimaryKeyConstraint('id'),
-    sa.UniqueConstraint('email')
-    )
-    op.create_table('esrv_auth_logs',
-    sa.Column('id', sa.INTEGER(), nullable=False),
-    sa.Column('auth_type', sa.VARCHAR(), nullable=False),
-    sa.Column('identifier', sa.VARCHAR(), nullable=False),
-    sa.Column('ip_address', sa.VARCHAR(), nullable=True),
-    sa.Column('success', sa.BOOLEAN(), nullable=False),
-    sa.Column('message', sa.TEXT(), nullable=True),
-    sa.Column('created_at', sa.DATETIME(), nullable=True),
-    sa.PrimaryKeyConstraint('id')
-    )
-    op.create_table('esrv_dkim_keys',
-    sa.Column('id', sa.INTEGER(), nullable=False),
-    sa.Column('domain_id', sa.INTEGER(), nullable=False),
-    sa.Column('selector', sa.VARCHAR(), nullable=False),
-    sa.Column('private_key', sa.TEXT(), nullable=False),
-    sa.Column('public_key', sa.TEXT(), nullable=False),
-    sa.Column('is_active', sa.BOOLEAN(), nullable=True),
-    sa.Column('created_at', sa.DATETIME(), nullable=True),
-    sa.Column('replaced_at', sa.DATETIME(), nullable=True),
-    sa.PrimaryKeyConstraint('id')
-    )
-    # ### end Alembic commands ###

tests/authentication_order_fix.md

@@ -0,0 +1,69 @@
+# SMTP Server Authentication Order and Best Practices
+
+## Summary of Fixes (June 2025)
+
+This document describes the authentication logic and order for the SMTP server, as well as the recent fixes applied to ensure correct sender authentication and IP whitelisting behavior.
+
+### What Was Fixed
+- **Authentication Response:**
+  - The server now immediately responds with an SMTP error (e.g., `535 Authentication failed`) if the username or password is incorrect, instead of hanging the session. This is achieved by returning `AuthResult(success=False, handled=False, message='535 Authentication failed')` from the authenticator, allowing the aiosmtpd framework to send the error to the client.
+- **No Forced Connection Close:**
+  - The server does not forcibly close the connection after failed authentication, but lets the SMTP client decide whether to retry or quit, as per SMTP protocol best practices.
+- **AUTH on Both Ports:**
+  - Both the plain SMTP port (`smtp_port`) and the secure TLS port (`smtp_tls_port`) now advertise and allow authentication (AUTH LOGIN/PLAIN). IP whitelist fallback is also available on both ports.
+
+## Authentication Order and Logic
+
+1. **Connection Handling**
+   - If a client connects to the plain SMTP port, both AUTH and IP whitelisting are available.
+   - If a client connects to the TLS SMTP port, the connection is immediately secured with TLS. Both AUTH and IP whitelisting are available.
+
+2. **Sender Authentication (Username/Password)**
+   - When a client issues the AUTH command (LOGIN or PLAIN) on either port:
+     - The server checks the username and password against the database.
+     - If valid, the session is marked as authenticated and the sender can send as their own address or, if permitted, as any address in their domain.
+     - If invalid, the server responds with `535 Authentication failed` and does not hang the session.
+
+   **Code Snippet for Immediate Authentication Failure Response:**
+   ```python
+   # In email_server/auth.py
+   def __call__(self, server, session, envelope, mechanism, auth_data):
+       # ...existing code...
+       if not isinstance(auth_data, LoginPassword):
+           logger.warning(f'Invalid auth data format: {type(auth_data)}')
+           return AuthResult(success=False, handled=False, message='535 Authentication failed')
+       # ...existing code...
+       try:
+           sender = get_sender_by_email(username)
+           if sender and check_password(password, sender.password_hash):
+               # ...success logic...
+               return AuthResult(success=True, handled=True)
+           else:
+               # ...failure logging...
+               return AuthResult(success=False, handled=False, message='535 Authentication failed')
+       except Exception as e:
+           # ...error logging...
+           return AuthResult(success=False, handled=False, message='451 Internal server error')
+   ```
+   - Returning `handled=False` ensures the SMTP client is immediately informed of the failure and does not hang.
+
+3. **IP Whitelisting (Secondary/Fallback)**
+   - If no AUTH is provided, the server checks if the client's IP is whitelisted for the target domain.
+   - If the IP is whitelisted, the session is authorized to send for that domain.
+   - If not, the server rejects the mail transaction.
+
+## Best Practices for Future Development
+
+- **Always return `handled=False` in `AuthResult` for failed authentication** to ensure the SMTP client receives an error and the session does not hang.
+- **Advertise AUTH on both the plain SMTP and TLS ports**; allow both user authentication and IP whitelist fallback.
+- **Do not use or advertise STARTTLS** on any port if only direct TLS is desired.
+- **Log all authentication attempts** (success and failure) for auditing and troubleshooting.
+- **Keep authentication and IP whitelisting logic modular** for easy updates and security reviews.
+
+## Example Client Setup
+- For user authentication, connect to either the plain SMTP port (e.g., 25 or 4025) or the TLS port (e.g., 40587) and use the correct username and password.
+- For IP whitelisting, connect from an authorized IP to either port; no authentication is required, but the sender must be allowed for the domain.
+
+---
+
+**This document should be updated if the authentication logic or port usage changes in the future.**

tests/bash_send_email.sh

@@ -1,69 +1,110 @@
 #!/bin/bash
-sender="test@example.com"
 receiver="info@example.com"
-password="testpass123"
+EMAIL_SERVER="localhost"   #"pymta.example.com" "localhost"
+EMAIL_SERVER_auth="10.100.111.1"   # IP for authenticated server ( not localhost), use your main interface ip
+
+sender="test@example.com"
+username="test@example.com"
+password="ZjDvcjPSs-nwK2Ghj5vQY7L4LdmTpmn_AEZMokJTFS"  # password you setup for the user!
 domain="example.com"
 body_content_file="@tests/email_body.txt"
 SMTP_PORT=4025
-SMTP_TLS_PORT=40587
-cc_recipient="targetcc@example.com"
-bcc_recipient="targetbcc@example.com"
+SMTP_TLS_PORT=40465
+cc_recipient="ccrecipient@example.com"
+bcc_recipient="bccrecipient@example.com"
 
 <<com
-# Setup domain and user via web interface first
-# Visit http://localhost:5000/email to configure:
-# - Add domain: $domain
-# - Add user: $sender with password $password
-# - Add IP whitelist: 127.0.0.1 and 10.100.111.1
-# - Generate DKIM key for domain
+python -m email_server.cli_tools add-domain $domain
+python -m email_server.cli_tools add-user $username $password $domain
+python -m email_server.cli_tools add-ip 127.0.0.1 $domain
+python -m email_server.cli_tools add-ip 213.249.224.235 $domain
+python -m email_server.cli_tools generate-dkim $domain
+python -m email_server.cli_tools add-custom-header $domain X-Auth-Token "abc123-example-auth"
+python -m email_server.cli_tools add-custom-header $domain X-Server-ID "mail01.example.com"
 
 # options to add CC and BCC recipients for swaks
       --cc $cc_recipient
       --bcc $bcc_recipient
-com
 
 swaks --to $receiver \
       --from $sender \
-      --server localhost \
+      --server $EMAIL_SERVER \
       --port $SMTP_TLS_PORT \
       --auth LOGIN \
-      --auth-user $sender \
+      --auth-user $username \
       --auth-password $password \
       --tls \
       --header "Subject: TLS - Large body email" \
-      --body $body_content_file \
-      --attach tests/email_body.txt \
-      --attach tests/Hello.jpg
+      --body $body_content_file 
+     # --attach @/home/nahaku/Documents/Projects/SMTP_Server/tests/email_body.txt 
+     # --attach @/home/nahaku/Documents/Projects/SMTP_Server/tests/Hello.jpg
 
-swaks --to $receiver \
-      --from $sender \
-      --server localhost \
-      --port $SMTP_PORT \
-      --auth LOGIN \
-      --auth-user $sender \
-      --auth-password $password \
-      --data "Subject: Test Email - authenticated\n\nThis is the message body."
-
-swaks --to $receiver \
-      --from $sender \
-      --server localhost \
-      --port $SMTP_TLS_PORT \
-      --auth LOGIN \
-      --auth-user $sender \
-      --auth-password $password \
-      --tls \
-      --data "Subject: Test via STARTTLS - authenticated\n\nThis is the body."
-
-swaks --to $receiver \
-      --from $sender \
-      --server localhost \
-      --port $SMTP_TLS_PORT \
-      --tls \
-      --data "Subject: Test via STARTTLS - no auth\n\nThis is the body."
 com
+<<com 
 
+com
 swaks --to $receiver \
       --from $sender \
-      --server localhost \
+      --server $EMAIL_SERVER \
       --port $SMTP_PORT \
-      --data "Subject: Test Email - no auth\n\nThis is the message body."
+      --auth LOGIN \
+      --auth-user $username \
+      --auth-password $password \
+      --data "Subject: SMTP - authenticated success\n\nThis is the message body."
+
+# Test with Authentication TLS
+swaks --to $receiver \
+      --from $sender \
+      --server $EMAIL_SERVER \
+      --port $SMTP_TLS_PORT \
+      --auth LOGIN \
+      --auth-user $username \
+      --auth-password $password \
+      --tls \
+      --header "Subject: TLS - authenticated success" \
+      --body "This is the message body with proper headers."
+
+# Test TLS + authentication and IP whitelist
+swaks --to $receiver \
+      --from $sender \
+      --server $EMAIL_SERVER_auth \
+      --port $SMTP_TLS_PORT \
+      --auth LOGIN \
+      --auth-user $username \
+      --auth-password $password \
+      --tls \
+      --data "Subject: TLS - auth + IP Whitelist \n\nTest TLS + authentication and IP whitelist"
+
+
+# Test with IP authentication TLS
+swaks --to $receiver \
+      --from $sender \
+      --server $EMAIL_SERVER_auth \
+      --port $SMTP_TLS_PORT \
+      --tls \
+      --data "Subject: TLS - IP Whitelist - no auth\n\nTest with IP authentication TLS"
+
+# Test with IP authentication SMTP
+swaks --to $receiver \
+      --from $sender \
+      --server $EMAIL_SERVER_auth \
+      --port $SMTP_PORT \
+      --data "Subject: SMTP - IP Whitelist - no auth\n\nTest with IP authentication SMTP"
+
+
+<<com
+com
+# SMTP un-auth test "Email_server - no Whitelist - no auth"
+swaks --to $receiver \
+      --from $sender \
+      --server $EMAIL_SERVER \
+      --port $SMTP_PORT \
+      --data "Subject: SMTP - no Whitelist - no auth\n\nSMTP un-auth test Email_server - no Whitelist - no auth."
+
+# Test TLS un-auth test "Email_server - no Whitelist - no auth"
+swaks --to $receiver \
+      --from $sender \
+      --server $EMAIL_SERVER \
+      --port $SMTP_TLS_PORT \
+      --tls \
+      --data "Subject: TLS - no Whitelist - no auth\n\nTest TLS un-auth test Email_server - no Whitelist - no auth"