SMTP Extension Bug Fixes and Enhancements

- Resolves Pull Request 669 - Resolves Issue 667 - Resolves Issue 668
2026-02-06 13:42:03 +00:00 · 2024-02-26 20:13:02 -06:00 · 2024-02-26 20:13:02 -06:00 · 739c5cdcfc
commit 739c5cdcfc
parent 1232b8f317
9 changed files with 488 additions and 105 deletions
--- a/.travis.yml
+++ b/.travis.yml
@ -3,23 +3,47 @@ sudo: false
 script: ./scripts/travis.sh
 os:
  - linux
+
+# env's are redundant, but at global scope additional jobs are created for
+# each env var which I'm sure has a purpose but don't like
 matrix:
  include:
    - python: "3.8"
-      dist: "xenial"
+      dist: "focal"
      sudo: true
+      env:
+        - DOCKER_COMPOSE_VERSION=v2.17.3
+        - SMTP_HOST=localhost
+        - SMTP_PORT=1025
    - python: "3.9"
-      dist: "xenial"
+      dist: "focal"
      sudo: true
+      env:
+        - DOCKER_COMPOSE_VERSION=v2.17.3
+        - SMTP_HOST=localhost
+        - SMTP_PORT=1025
    - python: "3.10"
      dist: "focal"
      sudo: true
+      env:
+        - DOCKER_COMPOSE_VERSION=v2.17.3
+        - SMTP_HOST=localhost
+        - SMTP_PORT=1025
    - python: "3.11"
      dist: "focal"
      sudo: true
+      env:
+        - DOCKER_COMPOSE_VERSION=v2.17.3
+        - SMTP_HOST=localhost
+        - SMTP_PORT=1025
    - python: "3.12"
      dist: "jammy"
      sudo: true
+      env:
+        - DOCKER_COMPOSE_VERSION=v2.17.3
+        - SMTP_HOST=localhost
+        - SMTP_PORT=1025
 services:
  - memcached
  - redis-server
+  - docker
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@ -8,18 +8,27 @@ Bugs:
    - [Issue #310](https://github.com/datafolklabs/cement/issues/310)
 - `[core.foundation]` Quiet mode file is never closed
    - [Issue #653](https://github.com/datafolklabs/cement/issues/653)
+- `[ext.smtp]` Ability to Enable TLS without SSL
+    - [Issue #667](https://github.com/datafolklabs/cement/issues/667)
+- `[ext.smtp]` Empty (wrong) addresses sent when CC/BCC is `None`
+    - [Issue #668](https://github.com/datafolklabs/cement/issues/668)
+

-    
 Features:

 - `[utils.fs]` Add Timestamp Support to fs.backup
    - [Issue #611](https://github.com/datafolklabs/cement/issues/611)
+- `[ext.smtp]` Support for sending file attachements.
+    - [PR #669](https://github.com/datafolklabs/cement/pull/669)
+- `[ext.smtp]` Support for sending both Plain Text and HTML
+    - [PR #669](https://github.com/datafolklabs/cement/pull/669)


 Refactoring: 

 - `[core.plugin]` Deprecate the use of `imp` in favor of `importlib`
    - [Issue #386](https://github.com/datafolklabs/cement/issues/386)
+- `[ext.smtp]` Actually test SMTP against a real server (replace mocks)


 Misc:
@ -34,7 +43,7 @@ Misc:
 - `[dev]` Add `comply-typing` to make helpers, start working toward typing.
    - [Issue #599](https://github.com/datafolklabs/cement/issues/661)
    - [PR #628](https://github.com/datafolklabs/cement/pull/628)
-
+- `[dev]` Add `mailpit` service to docker-compose development config.

 Deprecations:

--- a/cement/ext/ext_smtp.py
+++ b/cement/ext/ext_smtp.py
@ -2,7 +2,6 @@
 Cement smtp extension module.
 """

-import os
 import smtplib
 from email.header import Header
 from email.mime.multipart import MIMEMultipart
@ -10,8 +9,10 @@ from email.mime.base import MIMEBase
 from email.mime.text import MIMEText
 from email import encoders
 from ..core import mail
+from ..utils import fs
 from ..utils.misc import minimal_logger, is_true

+
 LOG = minimal_logger(__name__)


@ -74,7 +75,10 @@ class SMTPMailHandler(mail.MailHandler):
        configuration defaults (cc, bcc, etc).

        Args:
-            body: The message body to send
+            body (list): The message body to send. List is treated as:
+                ``[<text>, <html>]``. If a single string is passed it will be
+                converted to ``[<text>]``. At minimum, a text version is
+                required.

        Keyword Args:
            to (list): List of recipients (generally email addresses)
@ -82,6 +86,9 @@ class SMTPMailHandler(mail.MailHandler):
            cc (list): List of CC Recipients
            bcc (list): List of BCC Recipients
            subject (str): Message subject line
+            subject_prefix (str): Prefix for message subject line (useful to
+                override if you want to remove/change the default prefix).
+            files (list): List of file paths to attach to the message.

        Returns:
            bool:``True`` if message is sent successfully, ``False`` otherwise
@ -107,7 +114,7 @@ class SMTPMailHandler(mail.MailHandler):
        if is_true(params['ssl']):
            server = smtplib.SMTP_SSL(params['host'], params['port'],
                                      params['timeout'])
-            LOG.debug("%s : initiating ssl" % self._meta.label)
+            LOG.debug("%s : initiating smtp over ssl" % self._meta.label)

        else:
            server = smtplib.SMTP(params['host'], params['port'],
@ -143,45 +150,61 @@ class SMTPMailHandler(mail.MailHandler):
        else:
            subject = params['subject']
        msg['Subject'] = Header(subject)
+
        # add body as text and or or as html
        partText = None
        partHtml = None
        if isinstance(body, str):
            partText = MIMEText(body)
        elif isinstance(body, list):
+            # handle plain text
            if len(body) >= 1:
                partText = MIMEText(body[0], 'plain')
+
+            # handle html
            if len(body) >= 2:
                partHtml = MIMEText(body[1], 'html')
-        elif isinstance(body, dict):
-            if 'text' in body:
-                partText = MIMEText(body['text'], 'plain')
-            if 'html' in body:
-                partHtml = MIMEText(body['html'], 'html')
+
        if partText:
            msg.attach(partText)
        if partHtml:
            msg.attach(partHtml)
-        # loop files
+
+        # attach files
        if params['files']:
-            for path in params['files']:
+            for in_path in params['files']:
                part = MIMEBase('application', 'octet-stream')
-                # test filename for a seperate attachement disposition name
+
+                # support for alternative file name if its tuple
                # like (filename.ext=attname.ext)
-                filename = os.path.basename(path)
-                # test for divider in filename
-                i = filename.find('=')
-                # split attname from filename
-                if i < 0:
-                    attname = filename
+                if isinstance(in_path, tuple):
+                    attname = in_path[0]
+                    path = in_path[1]
                else:
-                    attname = filename[i+1:]
-                    filename = filename[0:i]
-                    # update the filename to read from
-                    path = os.path.dirname(path) + '/' + filename
+                    attname = in_path
+                    path = in_path
+
+                path = fs.abspath(path)
+
+                # filename = os.path.basename(path)
+
+                # # test for divider in filename
+                # i = filename.find('=')
+
+                # # split attname from filename
+                # if i < 0:
+                #     attname = filename
+                # else:
+                #     attname = filename[i+1:]
+                #     filename = filename[0:i]
+
+                #     # update the filename to read from
+                #     path = fs.join(os.path.dirname(path), filename)
+
                # add attachment
                with open(path, 'rb') as file:
                    part.set_payload(file.read())
+
                # encode and name
                encoders.encode_base64(part)
                part.add_header(
--- a/docker-compose.yml
+++ b/docker-compose.yml
@ -1,80 +1,104 @@
 version: "3"
+
+volumes:
+  mailpit-data:
+
 services:
-    cement: &DEFAULTS
-        image: "cement:dev"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev
-        hostname: cement
-        stdin_open: true
-        tty: true
-        volumes:
-            - '.:/src'
-        working_dir: '/src'
-        links:
-            - redis:redis
-            - memcached:memcached
-        environment:
-            REDIS_HOST: redis
-            MEMCACHED_HOST: memcached
+  cement: &DEFAULTS
+    image: "cement:dev"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev
+    hostname: cement
+    stdin_open: true
+    tty: true
+    volumes:
+    - '.:/src'
+    working_dir: '/src'
+    links:
+    - redis:redis
+    - memcached:memcached
+    environment:
+      REDIS_HOST: redis
+      MEMCACHED_HOST: memcached
+      SMTP_HOST: mailpit
+      SMTP_PORT: 1025

-    cement-py35:
-        <<: *DEFAULTS
-        image: "cement:dev-py35"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev-py35
-        profiles:
-          - donotstart
+  cement-py35:
+    <<: *DEFAULTS
+    image: "cement:dev-py35"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev-py35
+    profiles:
+    - donotstart

-    cement-py36:
-        <<: *DEFAULTS
-        image: "cement:dev-py36"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev-py36
-        profiles:
-          - donotstart
+  cement-py36:
+    <<: *DEFAULTS
+    image: "cement:dev-py36"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev-py36
+    profiles:
+    - donotstart

-    cement-py37:
-        <<: *DEFAULTS
-        image: "cement:dev-py37"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev-py37
-    
-    cement-py38:
-        <<: *DEFAULTS
-        image: "cement:dev-py38"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev-py38
-    
-    cement-py39:
-        <<: *DEFAULTS
-        image: "cement:dev-py39"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev-py39
-    
-    cement-py310:
-        <<: *DEFAULTS
-        image: "cement:dev-py310"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev-py310
+  cement-py37:
+    <<: *DEFAULTS
+    image: "cement:dev-py37"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev-py37
+  
+  cement-py38:
+    <<: *DEFAULTS
+    image: "cement:dev-py38"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev-py38
+  
+  cement-py39:
+    <<: *DEFAULTS
+    image: "cement:dev-py39"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev-py39
+  
+  cement-py310:
+    <<: *DEFAULTS
+    image: "cement:dev-py310"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev-py310

-    cement-py311:
-        <<: *DEFAULTS
-        image: "cement:dev-py311"
-        build:
-            context: .
-            dockerfile: docker/Dockerfile.dev-py311
+  cement-py311:
+    <<: *DEFAULTS
+    image: "cement:dev-py311"
+    build:
+      context: .
+      dockerfile: docker/Dockerfile.dev-py311

-    redis:
-        image: redis:latest
-        hostname: redis
+  redis:
+    image: redis:latest
+    hostname: redis

-    memcached:
-        image: memcached:latest
-        hostname: memcached
+  memcached:
+    image: memcached:latest
+    hostname: memcached
+  
+  mailpit:
+    image: axllent/mailpit
+    container_name: mailpit
+    restart: always
+    volumes:
+    - mailpit-data:/data
+    - ./docker/mailpit:/certificates
+    ports:
+    - 8025:8025
+    - 1025:1025
+    environment:
+      MP_MAX_MESSAGES: 5000
+      MP_DATA_FILE: /data/mailpit.db
+      MP_SMTP_AUTH_ACCEPT_ANY: 1
+      MP_SMTP_AUTH_ALLOW_INSECURE: 1
+      MP_SMTP_TLS_CERT: /certificates/dev-cert.pem
+      MP_SMTP_TLS_KEY: /certificates/dev-key.pem
--- a/docker/mailpit/dev-cert.pem
+++ b/docker/mailpit/dev-cert.pem
@ -0,0 +1,35 @@
+-----BEGIN CERTIFICATE-----
+MIIGDzCCA/egAwIBAgIULYOgE6JcXKzs9dpXdh0uDfYfdzUwDQYJKoZIhvcNAQEL
+BQAwgZYxCzAJBgNVBAYTAlVTMQ4wDAYDVQQIDAVUZXhhczEUMBIGA1UEBwwLU2Fu
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+-----END CERTIFICATE-----
--- a/docker/mailpit/dev-key.pem
+++ b/docker/mailpit/dev-key.pem
@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----
+MIIJQgIBADANBgkqhkiG9w0BAQEFAASCCSwwggkoAgEAAoICAQC5TQVZOg4LNGfT
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+5djR3JPu5bosaRAtqNd+ZxpDf88QEm0drP+bRLdhVpdOTbEvUAMGErRLs3Z8l4iI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+-----END PRIVATE KEY-----
--- a/scripts/travis.sh
+++ b/scripts/travis.sh
@ -6,6 +6,10 @@ set -e
 # https://travis-ci.community/t/build-error-for-python-3-7-on-two-different-projects/12895/3
 # pip install -U importlib_metadata

+docker-compose up -d mailpit 2>&1 >/dev/null
+
+sleep 10
+
 rm -f .coverage
 pip install -r requirements-dev.txt
 make test
--- a/tests/conftest.py
+++ b/tests/conftest.py
@ -23,4 +23,4 @@ def key(request):

@pytest.fixture(scope="function")
 def rando(request):
-    yield _rando()
+    yield _rando()[:12]
--- a/tests/ext/test_ext_smtp.py
+++ b/tests/ext/test_ext_smtp.py
@ -1,8 +1,26 @@

+import os
 import mock
+import requests
+import json
+from time import sleep
 from cement.utils.test import TestApp
 from cement.utils.misc import init_defaults

+if 'SMTP_HOST' in os.environ.keys():
+    smtp_host = os.environ['SMTP_HOST']
+else:
+    smtp_host = 'mailpit'
+
+
+mailpit_api = f'http://{smtp_host}:8025/api/v1'
+defaults = init_defaults('mail.smtp')
+defaults['mail.smtp']['host'] = smtp_host
+defaults['mail.smtp']['port'] = 1025
+defaults['mail.smtp']['to'] = 'noreply@localhost'
+defaults['mail.smtp']['from_addr'] = 'nobody@localhost'
+defaults['mail.smtp']['subject_prefix'] = 'UNIT TEST >'
+

 class SMTPApp(TestApp):
    class Meta:
@ -10,14 +28,167 @@ class SMTPApp(TestApp):
        mail_handler = 'smtp'


-def test_smtp_defaults():
+def delete_msg(message_id):
+    payload = {
+        "ids": [
+            message_id
+        ]
+    }
+    payload = json.dumps(payload)
+
+    headers = {
+        'accept': 'application/json',
+        'content-type': 'application/json',
+    }
+    requests.delete(f"{mailpit_api}/messages", data=payload, headers=headers)
+
+
+def test_smtp_send(rando):
+    defaults['mail.smtp']['subject'] = rando
+
+    with SMTPApp(config_defaults=defaults) as app:
+        app.run()
+
+        app.mail.send(f"{rando}",
+                      to=[f'to-{rando}@localhost'],
+                      from_addr=f'from-{rando}@localhost')
+        res = requests.get(f"{mailpit_api}/search?query={rando}")
+        data = res.json()
+        assert len(data['messages']) == 1
+        msg = data['messages'][0]
+
+        assert msg['From']['Address'] == f'from-{rando}@localhost'
+        assert msg['To'][0]['Address'] == f'to-{rando}@localhost'
+        assert msg['Subject'] == f'UNIT TEST > {rando}'
+        assert msg['Attachments'] == 0
+        assert msg['Cc'] == []
+        assert msg['Bcc'] == []
+
+        delete_msg(msg['ID'])
+
+
+def test_smtp_html(rando):
+    defaults['mail.smtp']['subject'] = rando
+
+    with SMTPApp(config_defaults=defaults) as app:
+        app.run()
+
+        app.mail.send([f"{rando}", f"<body>{rando}</body>"])
+        sleep(3)
+        res = requests.get(f"{mailpit_api}/search?query={rando}")
+        data = res.json()
+        assert len(data['messages']) == 1
+        msg = data['messages'][0]
+
+        text_url = f"http://{smtp_host}:8025/view/{msg['ID']}.txt"
+        res_text = requests.get(text_url)
+        assert res_text.content.decode('utf-8') == rando
+
+        html_url = f"http://{smtp_host}:8025/view/{msg['ID']}.html"
+        res_html = requests.get(html_url)
+        assert res_html.content.decode('utf-8') == f"<body>{rando}</body>"
+
+        delete_msg(msg['ID'])
+
+
+def test_smtp_cc_bcc(rando):
+    defaults['mail.smtp']['subject'] = rando
+
+    with SMTPApp(config_defaults=defaults) as app:
+        app.run()
+
+        cc = [f"cc1-{rando}@localhost", f"cc2-{rando}@localhost"]
+        bcc = [f"bcc1-{rando}@localhost", f"bcc2-{rando}@localhost"]
+        app.mail.send(f"{rando}",
+                      cc=cc,
+                      bcc=bcc)
+        res = requests.get(f"{mailpit_api}/search?query={rando}")
+        data = res.json()
+        assert len(data['messages']) == 1
+        msg = data['messages'][0]
+
+        cc_verify = [x['Address'] for x in msg['Cc']]
+        bcc_verify = [x['Address'] for x in msg['Bcc']]
+        assert f"cc1-{rando}@localhost" in cc_verify
+        assert f"cc2-{rando}@localhost" in cc_verify
+        assert f"bcc1-{rando}@localhost" in bcc_verify
+        assert f"bcc2-{rando}@localhost" in bcc_verify
+
+        delete_msg(msg['ID'])
+
+
+def test_smtp_files(rando, tmp):
+    defaults['mail.smtp']['subject'] = rando
+
+    with SMTPApp(config_defaults=defaults) as app:
+        app.run()
+
+        files = []
+        for iter in [1, 2, 3]:
+            _file = f"{tmp.file}-{iter}"
+            with open(_file, 'w') as _open_file:
+                _open_file.write(f"{rando}-{iter}")
+            files.append(_file)
+
+        app.mail.send(f"{rando}", files=files)
+        sleep(3)
+        res = requests.get(f"{mailpit_api}/search?query={rando}")
+        data = res.json()
+        assert len(data['messages']) == 1
+        msg = data['messages'][0]
+
+        assert msg['Attachments'] == 3
+
+        delete_msg(msg['ID'])
+
+
+def test_smtp_files_alt_name(rando, tmp):
+    defaults['mail.smtp']['subject'] = rando
+
+    with SMTPApp(config_defaults=defaults) as app:
+        app.run()
+
+        files = [(f"alt-filename-{rando}", tmp.file)]
+        app.mail.send(f"{rando}", files=files)
+        sleep(3)
+        res = requests.get(f"{mailpit_api}/search?query={rando}")
+        data = res.json()
+        assert len(data['messages']) == 1
+        msg = data['messages'][0]
+
+        assert msg['Attachments'] == 1
+
+        res_full = requests.get(f"{mailpit_api}/message/{msg['ID']}")
+        data = res_full.json()
+        assert data['Attachments'][0]['FileName'] == f"alt-filename-{rando}"
+        delete_msg(msg['ID'])
+
+
+def test_smtp_tls(rando):
+    defaults['mail.smtp']['subject'] = rando
+    defaults['mail.smtp']['tls'] = True
+
+    with SMTPApp(config_defaults=defaults, debug=True) as app:
+        app.run()
+        app.mail.send(rando)
+        res = requests.get(f"{mailpit_api}/search?query={rando}")
+        data = res.json()
+        assert len(data['messages']) == 1
+        msg = data['messages'][0]
+
+        delete_msg(msg['ID'])
+
+
+# FIXME: need to replace old mocks with mailpit tests
+
+def test_mock_smtp_defaults():
    defaults = init_defaults('mail.smtp')
-    defaults['mail.smtp']['to'] = 'nobody@localhost'
+    defaults['mail.smtp']['to'] = 'test_smtp_defaults@localhost'
    defaults['mail.smtp']['from_addr'] = 'nobody@localhost'
    defaults['mail.smtp']['cc'] = 'nobody@localhost'
    defaults['mail.smtp']['bcc'] = 'nobody@localhost'
-    defaults['mail.smtp']['subject'] = 'Test Email To nobody@localhost'
-    defaults['mail.smtp']['subject_prefix'] = 'PREFIX >'
+    defaults['mail.smtp']['subject'] = 'test_smtp_defaults'
+    defaults['mail.smtp']['subject_prefix'] = 'UNIT TEST >'

    with mock.patch('smtplib.SMTP') as mock_smtp:
        with SMTPApp(config_defaults=defaults) as app:
@ -28,17 +199,38 @@ def test_smtp_defaults():
            assert instance.send_message.call_count == 1


-def test_smtp_ssl_tls():
+def test_mock_smtp_ssl():
    defaults = init_defaults('mail.smtp')
    defaults['mail.smtp']['ssl'] = True
    defaults['mail.smtp']['tls'] = True
    defaults['mail.smtp']['port'] = 25
+    defaults['mail.smtp']['subject'] = 'test_smtp_ssl'
+    defaults['mail.smtp']['subject_prefix'] = 'UNIT TEST >'

    with mock.patch('smtplib.SMTP_SSL') as mock_smtp:
        with SMTPApp(config_defaults=defaults, debug=True) as app:
            app.run()
            app.mail.send('TEST MESSAGE',
-                          to=['me@localhost'],
+                          to=['test_smtp_ssl@localhost'],
+                          from_addr='noreply@localhost')
+
+            instance = mock_smtp.return_value
+            assert instance.send_message.call_count == 1
+
+
+def test_mock_smtp_tls_no_ssl():
+    defaults = init_defaults('mail.smtp')
+    defaults['mail.smtp']['ssl'] = False
+    defaults['mail.smtp']['tls'] = True
+    defaults['mail.smtp']['port'] = 25
+    defaults['mail.smtp']['subject'] = 'test_smtp_tls_no_ssl'
+    defaults['mail.smtp']['subject_prefix'] = 'UNIT TEST >'
+
+    with mock.patch('smtplib.SMTP') as mock_smtp:
+        with SMTPApp(config_defaults=defaults, debug=True) as app:
+            app.run()
+            app.mail.send('TEST MESSAGE',
+                          to=['test_smtp_tls_no_ssl@localhost'],
                          from_addr='noreply@localhost')

            instance = mock_smtp.return_value
@ -46,7 +238,27 @@ def test_smtp_ssl_tls():
            assert instance.starttls.call_count == 1


-def test_smtp_auth(rando):
+def test_mock_smtp_tls_over_ssl():
+    defaults = init_defaults('mail.smtp')
+    defaults['mail.smtp']['ssl'] = True
+    defaults['mail.smtp']['tls'] = True
+    defaults['mail.smtp']['port'] = 25
+    defaults['mail.smtp']['subject'] = 'test_smtp_tls_over_ssl'
+    defaults['mail.smtp']['subject_prefix'] = 'UNIT TEST >'
+
+    with mock.patch('smtplib.SMTP_SSL') as mock_smtp:
+        with SMTPApp(config_defaults=defaults, debug=True) as app:
+            app.run()
+            app.mail.send('TEST MESSAGE',
+                          to=['test_smtp_tls_no_ssl@localhost'],
+                          from_addr='noreply@localhost')
+
+            instance = mock_smtp.return_value
+            assert instance.send_message.call_count == 1
+            assert instance.starttls.call_count == 1
+
+
+def test_mock_smtp_auth(rando):
    defaults = init_defaults(rando, 'mail.smtp')
    defaults[rando]['debug'] = True
    defaults['mail.smtp']['auth'] = True