diff --git a/apprise/plugins/NotifyTwitter.py b/apprise/plugins/NotifyTwitter.py
index 437cd1e8..364eca41 100644
--- a/apprise/plugins/NotifyTwitter.py
+++ b/apprise/plugins/NotifyTwitter.py
@@ -28,6 +28,7 @@
 import re
 import six
 import requests
+from copy import deepcopy
 from datetime import datetime
 from requests_oauthlib import OAuth1
 from json import dumps
@@ -39,6 +40,7 @@ from ..utils import parse_list
 from ..utils import parse_bool
 from ..utils import validate_regex
 from ..AppriseLocale import gettext_lazy as _
+from ..attachment.AttachBase import AttachBase
 
 IS_USER = re.compile(r'^\s*@?(?P<user>[A-Z0-9_]+)$', re.I)
 
@@ -87,9 +89,6 @@ class NotifyTwitter(NotifyBase):
     # Twitter does have titles when creating a message
     title_maxlen = 0
 
-    # Twitter API
-    twitter_api = 'api.twitter.com'
-
     # Twitter API Reference To Acquire Someone's Twitter ID
     twitter_lookup = 'https://api.twitter.com/1.1/users/lookup.json'
 
@@ -103,6 +102,13 @@ class NotifyTwitter(NotifyBase):
     # Twitter API Reference To Send A Public Tweet
     twitter_tweet = 'https://api.twitter.com/1.1/statuses/update.json'
 
+    # it is documented on the site that the maximum images per tweet
+    # is 4 (unless it's a GIF, then it's only 1)
+    __tweet_non_gif_images_batch = 4
+
+    # Twitter Media (Attachment) Upload Location
+    twitter_media = 'https://upload.twitter.com/1.1/media/upload.json'
+
     # Twitter is kind enough to return how many more requests we're allowed to
     # continue to make within it's header response as:
     # X-Rate-Limit-Reset: The epoc time (in seconds) we can expect our
@@ -176,10 +182,15 @@ class NotifyTwitter(NotifyBase):
         'to': {
             'alias_of': 'targets',
         },
+        'batch': {
+            'name': _('Batch Mode'),
+            'type': 'bool',
+            'default': True,
+        },
     })
 
     def __init__(self, ckey, csecret, akey, asecret, targets=None,
-                 mode=TwitterMessageMode.DM, cache=True, **kwargs):
+                 mode=TwitterMessageMode.DM, cache=True, batch=True, **kwargs):
         """
         Initialize Twitter Object
 
@@ -217,6 +228,9 @@ class NotifyTwitter(NotifyBase):
         # Set Cache Flag
         self.cache = cache
 
+        # Prepare Image Batch Mode Flag
+        self.batch = batch
+
         if self.mode not in TWITTER_MESSAGE_MODES:
             msg = 'The Twitter message mode specified ({}) is invalid.' \
                 .format(mode)
@@ -250,42 +264,171 @@ class NotifyTwitter(NotifyBase):
 
         return
 
-    def send(self, body, title='', notify_type=NotifyType.INFO, **kwargs):
+    def send(self, body, title='', notify_type=NotifyType.INFO, attach=None,
+             **kwargs):
         """
         Perform Twitter Notification
         """
 
-        # Call the _send_ function applicable to whatever mode we're in
+        # Build a list of our attachments
+        attachments = []
+
+        if attach:
+            # We need to upload our payload first so that we can source it
+            # in remaining messages
+            for attachment in attach:
+
+                # Perform some simple error checking
+                if not attachment:
+                    # We could not access the attachment
+                    self.logger.error(
+                        'Could not access attachment {}.'.format(
+                            attachment.url(privacy=True)))
+                    return False
+
+                if not re.match(r'^image/.*', attachment.mimetype, re.I):
+                    # Only support images at this time
+                    self.logger.warning(
+                        'Ignoring unsupported Twitter attachment {}.'.format(
+                            attachment.url(privacy=True)))
+                    continue
+
+                self.logger.debug(
+                    'Preparing Twiter attachment {}'.format(
+                        attachment.url(privacy=True)))
+
+                # Upload our image and get our id associated with it
+                # see: https://developer.twitter.com/en/docs/twitter-api/v1/\
+                #         media/upload-media/api-reference/post-media-upload
+                postokay, response = self._fetch(
+                    self.twitter_media,
+                    payload=attachment,
+                )
+
+                if not postokay:
+                    # We can't post our attachment
+                    return False
+
+                if not (isinstance(response, dict)
+                        and response.get('media_id')):
+                    self.logger.debug(
+                        'Could not attach the file to Twitter: %s (mime=%s)',
+                        attachment.name, attachment.mimetype)
+                    continue
+
+                # If we get here, our output will look something like this:
+                # {
+                #   "media_id": 710511363345354753,
+                #   "media_id_string": "710511363345354753",
+                #   "media_key": "3_710511363345354753",
+                #   "size": 11065,
+                #   "expires_after_secs": 86400,
+                #   "image": {
+                #     "image_type": "image/jpeg",
+                #     "w": 800,
+                #     "h": 320
+                #   }
+                # }
+
+                response.update({
+                    # Update our response to additionally include the
+                    # attachment details
+                    'file_name': attachment.name,
+                    'file_mime': attachment.mimetype,
+                    'file_path': attachment.path,
+                })
+
+                # Save our pre-prepared payload for attachment posting
+                attachments.append(response)
+
         # - calls _send_tweet if the mode is set so
         # - calls _send_dm (direct message) otherwise
         return getattr(self, '_send_{}'.format(self.mode))(
-            body=body, title=title, notify_type=notify_type, **kwargs)
+            body=body, title=title, notify_type=notify_type,
+            attachments=attachments, **kwargs)
 
     def _send_tweet(self, body, title='', notify_type=NotifyType.INFO,
-                    **kwargs):
+                    attachments=None, **kwargs):
         """
         Twitter Public Tweet
         """
 
+        # Error Tracking
+        has_error = False
+
         payload = {
             'status': body,
         }
 
-        # Send Tweet
-        postokay, response = self._fetch(
-            self.twitter_tweet,
-            payload=payload,
-            json=False,
-        )
+        payloads = []
+        if not attachments:
+            payloads.append(payload)
+
+        else:
+            # Group our images if batch is set to do so
+            batch_size = 1 if not self.batch \
+                else self.__tweet_non_gif_images_batch
+
+            # Track our batch control in our message generation
+            batches = []
+            batch = []
+            for attachment in attachments:
+                batch.append(str(attachment['media_id']))
+
+                # Twitter supports batching images together.  This allows
+                # the batching of multiple images together.  Twitter also
+                # makes it clear that you can't batch `gif` files; they need
+                # to be separate.  So the below preserves the ordering that
+                # a user passed their attachments in.  if 4-non-gif images
+                # are passed, they are all part of a single message.
+                #
+                # however, if they pass in image, gif, image, gif.  The
+                # gif's inbetween break apart the batches so this would
+                # produce 4 separate tweets.
+                #
+                # If you passed in, image, image, gif, image. <- This would
+                # produce 3 images (as the first 2 images could be lumped
+                # together as a batch)
+                if not re.match(
+                        r'^image/(png|jpe?g)', attachment['file_mime'], re.I) \
+                        or len(batch) >= batch_size:
+                    batches.append(','.join(batch))
+                    batch = []
+
+            if batch:
+                batches.append(','.join(batch))
+
+            for no, media_ids in enumerate(batches):
+                _payload = deepcopy(payload)
+                _payload['media_ids'] = media_ids
+
+                if no:
+                    # strip text and replace it with the image representation
+                    _payload['status'] = \
+                        '{:02d}/{:02d}'.format(no + 1, len(batches))
+                payloads.append(_payload)
+
+        for no, payload in enumerate(payloads, start=1):
+            # Send Tweet
+            postokay, response = self._fetch(
+                self.twitter_tweet,
+                payload=payload,
+                json=False,
+            )
+
+            if not postokay:
+                # Track our error
+                has_error = True
+                continue
 
-        if postokay:
             self.logger.info(
-                'Sent Twitter notification as public tweet.')
+                'Sent [{:02d}/{:02d}] Twitter notification as public tweet.'
+                .format(no, len(payloads)))
 
-        return postokay
+        return not has_error
 
     def _send_dm(self, body, title='', notify_type=NotifyType.INFO,
-                 **kwargs):
+                 attachments=None, **kwargs):
         """
         Twitter Direct Message
         """
@@ -318,24 +461,48 @@ class NotifyTwitter(NotifyBase):
                 'Failed to acquire user(s) to Direct Message via Twitter')
             return False
 
-        for screen_name, user_id in targets.items():
-            # Assign our user
-            payload['event']['message_create']['target']['recipient_id'] = \
-                user_id
+        payloads = []
+        if not attachments:
+            payloads.append(payload)
 
-            # Send Twitter DM
-            postokay, response = self._fetch(
-                self.twitter_dm,
-                payload=payload,
-            )
+        else:
+            for no, attachment in enumerate(attachments):
+                _payload = deepcopy(payload)
+                _data = _payload['event']['message_create']['message_data']
+                _data['attachment'] = {
+                    'type': 'media',
+                    'media': {
+                        'id': attachment['media_id']
+                    },
+                    'additional_owners':
+                    ','.join([str(x) for x in targets.values()])
+                }
+                if no:
+                    # strip text and replace it with the image representation
+                    _data['text'] = \
+                        '{:02d}/{:02d}'.format(no + 1, len(attachments))
+                payloads.append(_payload)
 
-            if not postokay:
-                # Track our error
-                has_error = True
-                continue
+        for no, payload in enumerate(payloads, start=1):
+            for screen_name, user_id in targets.items():
+                # Assign our user
+                target = payload['event']['message_create']['target']
+                target['recipient_id'] = user_id
 
-            self.logger.info(
-                'Sent Twitter DM notification to @{}.'.format(screen_name))
+                # Send Twitter DM
+                postokay, response = self._fetch(
+                    self.twitter_dm,
+                    payload=payload,
+                )
+
+                if not postokay:
+                    # Track our error
+                    has_error = True
+                    continue
+
+                self.logger.info(
+                    'Sent [{:02d}/{:02d}] Twitter DM notification to @{}.'
+                    .format(no, len(payloads), screen_name))
 
         return not has_error
 
@@ -458,13 +625,23 @@ class NotifyTwitter(NotifyBase):
         """
 
         headers = {
-            'Host': self.twitter_api,
             'User-Agent': self.app_id,
         }
 
-        if json:
+        data = None
+        files = None
+
+        # Open our attachment path if required:
+        if isinstance(payload, AttachBase):
+            # prepare payload
+            files = {'media': (payload.name, open(payload.path, 'rb'))}
+
+        elif json:
             headers['Content-Type'] = 'application/json'
-            payload = dumps(payload)
+            data = dumps(payload)
+
+        else:
+            data = payload
 
         auth = OAuth1(
             self.ckey,
@@ -506,7 +683,8 @@ class NotifyTwitter(NotifyBase):
         try:
             r = fn(
                 url,
-                data=payload,
+                data=data,
+                files=files,
                 headers=headers,
                 auth=auth,
                 verify=self.verify_certificate,
@@ -562,6 +740,20 @@ class NotifyTwitter(NotifyBase):
             # Mark our failure
             return (False, content)
 
+        except (OSError, IOError) as e:
+            self.logger.warning(
+                'An I/O error occurred while handling {}.'.format(
+                    payload.name if isinstance(payload, AttachBase)
+                    else payload))
+            self.logger.debug('I/O Exception: %s' % str(e))
+            return (False, content)
+
+        finally:
+            # Close our file (if it's open) stored in the second element
+            # of our files tuple (index 1)
+            if files:
+                files['media'][1].close()
+
         return (True, content)
 
     @property
@@ -581,6 +773,8 @@ class NotifyTwitter(NotifyBase):
         # Define any URL parameters
         params = {
             'mode': self.mode,
+            'batch': 'yes' if self.batch else 'no',
+            'cache': 'yes' if self.cache else 'no',
         }
 
         # Extend our parameters
@@ -653,10 +847,16 @@ class NotifyTwitter(NotifyBase):
         # Store any remaining items as potential targets
         results['targets'].extend(tokens[3:])
 
+        # Get Cache Flag (reduces lookup hits)
         if 'cache' in results['qsd'] and len(results['qsd']['cache']):
             results['cache'] = \
                 parse_bool(results['qsd']['cache'], True)
 
+        # Get Batch Mode Flag
+        results['batch'] = \
+            parse_bool(results['qsd'].get(
+                'batch', NotifyTwitter.template_args['batch']['default']))
+
         # The 'to' makes it easier to use yaml configuration
         if 'to' in results['qsd'] and len(results['qsd']['to']):
             results['targets'] += \
diff --git a/test/test_plugin_twitter.py b/test/test_plugin_twitter.py
index 8c7e62f4..8ac20fde 100644
--- a/test/test_plugin_twitter.py
+++ b/test/test_plugin_twitter.py
@@ -23,19 +23,26 @@
 # OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN
 # THE SOFTWARE.
 
+import os
 import six
 import mock
 import pytest
 import requests
 from json import dumps
 from datetime import datetime
+from apprise import Apprise
 from apprise import plugins
+from apprise import NotifyType
+from apprise import AppriseAttachment
 from helpers import AppriseURLTester
 
 # Disable logging for a cleaner testing output
 import logging
 logging.disable(logging.CRITICAL)
 
+# Attachment Directory
+TEST_VAR_DIR = os.path.join(os.path.dirname(__file__), 'var')
+
 # Our Testing URLs
 apprise_url_tests = (
     ##################################
@@ -77,7 +84,9 @@ apprise_url_tests = (
             # However we'll be okay if we return a proper response
             'requests_response_text': {
                 'id': 12345,
-                'screen_name': 'test'
+                'screen_name': 'test',
+                # For attachment handling
+                'media_id': 123,
             },
         }),
     ('twitter://consumer_key/consumer_secret/access_token/access_secret', {
@@ -86,7 +95,9 @@ apprise_url_tests = (
         # However we'll be okay if we return a proper response
         'requests_response_text': {
             'id': 12345,
-            'screen_name': 'test'
+            'screen_name': 'test',
+            # For attachment handling
+            'media_id': 123,
         },
     }),
     # A duplicate of the entry above, this will cause cache to be referenced
@@ -96,7 +107,9 @@ apprise_url_tests = (
         # However we'll be okay if we return a proper response
         'requests_response_text': {
             'id': 12345,
-            'screen_name': 'test'
+            'screen_name': 'test',
+            # For attachment handling
+            'media_id': 123,
         },
     }),
     # handle cases where the screen_name is missing from the response causing
@@ -107,6 +120,8 @@ apprise_url_tests = (
         # However we'll be okay if we return a proper response
         'requests_response_text': {
             'id': 12345,
+            # For attachment handling
+            'media_id': 123,
         },
         # due to a mangled response_text we'll fail
         'notify_response': False,
@@ -119,8 +134,8 @@ apprise_url_tests = (
         'notify_response': False,
     }),
     ('twitter://user@consumer_key/csecret/access_token/access_secret'
-        '?cache=No', {
-            # No Cache
+        '?cache=No&batch=No', {
+            # No Cache & No Batch
             'instance': plugins.NotifyTwitter,
             'requests_response_text': [{
                 'id': 12345,
@@ -404,3 +419,465 @@ def test_plugin_twitter_edge_cases():
         plugins.NotifyTwitter(
             ckey='value', csecret='value', akey='value', asecret='value',
             targets='%G@rB@g3')
+
+
+@mock.patch('requests.post')
+@mock.patch('requests.get')
+def test_plugin_twitter_dm_attachments(mock_get, mock_post):
+    """
+    NotifyTwitter() DM Attachment Checks
+
+    """
+    ckey = 'ckey'
+    csecret = 'csecret'
+    akey = 'akey'
+    asecret = 'asecret'
+    screen_name = 'apprise'
+
+    good_dm_response_obj = {
+        'screen_name': screen_name,
+        'id': 9876,
+    }
+
+    # Disable Throttling to speed testing
+    plugins.NotifyBase.request_rate_per_sec = 0
+
+    # Prepare a good DM response
+    good_dm_response = mock.Mock()
+    good_dm_response.content = dumps(good_dm_response_obj)
+    good_dm_response.status_code = requests.codes.ok
+
+    # Prepare bad response
+    bad_response = mock.Mock()
+    bad_response.content = dumps({})
+    bad_response.status_code = requests.codes.internal_server_error
+
+    # Prepare a good media response
+    good_media_response = mock.Mock()
+    good_media_response.content = dumps({
+        "media_id": 710511363345354753,
+        "media_id_string": "710511363345354753",
+        "media_key": "3_710511363345354753",
+        "size": 11065,
+        "expires_after_secs": 86400,
+        "image": {
+            "image_type": "image/jpeg",
+            "w": 800,
+            "h": 320
+        }
+    })
+    good_media_response.status_code = requests.codes.ok
+
+    # Prepare a bad media response
+    bad_media_response = mock.Mock()
+    bad_media_response.content = dumps({
+        "errors": [
+            {
+                "code": 93,
+                "message": "This application is not allowed to access or "
+                "delete your direct messages.",
+            }]})
+    bad_media_response.status_code = requests.codes.internal_server_error
+
+    mock_post.side_effect = [good_media_response, good_dm_response]
+    mock_get.return_value = good_dm_response
+
+    twitter_url = 'twitter://{}/{}/{}/{}'.format(ckey, csecret, akey, asecret)
+
+    # attach our content
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    # instantiate our object
+    obj = Apprise.instantiate(twitter_url)
+
+    # Send our notification
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    # Test our call count
+    assert mock_get.call_count == 1
+    assert mock_get.call_args_list[0][0][0] == \
+        'https://api.twitter.com/1.1/account/verify_credentials.json'
+    assert mock_post.call_count == 2
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://api.twitter.com/1.1/direct_messages/events/new.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    # Test case where upload fails
+    mock_get.return_value = good_dm_response
+    mock_post.side_effect = [bad_media_response, good_dm_response]
+
+    # instantiate our object
+    obj = Apprise.instantiate(twitter_url)
+
+    # Send our notification; it will fail because of the media response
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is False
+
+    # Test our call count
+    assert mock_get.call_count == 0
+    # No get request as cached response is used
+    assert mock_post.call_count == 1
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    # Test case where upload fails
+    mock_get.return_value = good_dm_response
+    mock_post.side_effect = [good_media_response, bad_response]
+
+    # instantiate our object
+    obj = Apprise.instantiate(twitter_url)
+
+    # Send our notification; it will fail because of the media response
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is False
+
+    assert mock_get.call_count == 0
+    # No get request as cached response is used
+    assert mock_post.call_count == 2
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://api.twitter.com/1.1/direct_messages/events/new.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    mock_post.side_effect = [good_media_response, good_dm_response]
+    mock_get.return_value = good_dm_response
+
+    # An invalid attachment will cause a failure
+    path = os.path.join(TEST_VAR_DIR, '/invalid/path/to/an/invalid/file.jpg')
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=path) is False
+
+    # No get request as cached response is used
+    assert mock_get.call_count == 0
+
+    # No post request as attachment is no good anyway
+    assert mock_post.call_count == 0
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    mock_post.side_effect = [
+        good_media_response, good_media_response, good_media_response,
+        good_media_response, good_dm_response, good_dm_response,
+        good_dm_response, good_dm_response]
+    mock_get.return_value = good_dm_response
+
+    # 4 images are produced
+    attach = [
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.jpeg'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.png'),
+        # This one is not supported, so it's ignored gracefully
+        os.path.join(TEST_VAR_DIR, 'apprise-test.mp4'),
+    ]
+
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    assert mock_get.call_count == 0
+    # No get request as cached response is used
+    assert mock_post.call_count == 8
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[2][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[3][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[4][0][0] == \
+        'https://api.twitter.com/1.1/direct_messages/events/new.json'
+    assert mock_post.call_args_list[5][0][0] == \
+        'https://api.twitter.com/1.1/direct_messages/events/new.json'
+    assert mock_post.call_args_list[6][0][0] == \
+        'https://api.twitter.com/1.1/direct_messages/events/new.json'
+    assert mock_post.call_args_list[7][0][0] == \
+        'https://api.twitter.com/1.1/direct_messages/events/new.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    # We have an OSError thrown in the middle of our preparation
+    mock_post.side_effect = [good_media_response, OSError()]
+    mock_get.return_value = good_dm_response
+
+    # 2 images are produced
+    attach = [
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.png'),
+        # This one is not supported, so it's ignored gracefully
+        os.path.join(TEST_VAR_DIR, 'apprise-test.mp4'),
+    ]
+
+    # We'll fail to send this time
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is False
+
+    assert mock_get.call_count == 0
+    # No get request as cached response is used
+    assert mock_post.call_count == 2
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+
+
+@mock.patch('requests.post')
+@mock.patch('requests.get')
+def test_plugin_twitter_tweet_attachments(mock_get, mock_post):
+    """
+    NotifyTwitter() Tweet Attachment Checks
+
+    """
+    ckey = 'ckey'
+    csecret = 'csecret'
+    akey = 'akey'
+    asecret = 'asecret'
+    screen_name = 'apprise'
+
+    good_tweet_response_obj = {
+        'screen_name': screen_name,
+        'id': 9876,
+    }
+
+    # Disable Throttling to speed testing
+    plugins.NotifyBase.request_rate_per_sec = 0
+
+    # Prepare a good DM response
+    good_tweet_response = mock.Mock()
+    good_tweet_response.content = dumps(good_tweet_response_obj)
+    good_tweet_response.status_code = requests.codes.ok
+
+    # Prepare bad response
+    bad_response = mock.Mock()
+    bad_response.content = dumps({})
+    bad_response.status_code = requests.codes.internal_server_error
+
+    # Prepare a good media response
+    good_media_response = mock.Mock()
+    good_media_response.content = dumps({
+        "media_id": 710511363345354753,
+        "media_id_string": "710511363345354753",
+        "media_key": "3_710511363345354753",
+        "size": 11065,
+        "expires_after_secs": 86400,
+        "image": {
+            "image_type": "image/jpeg",
+            "w": 800,
+            "h": 320
+        }
+    })
+    good_media_response.status_code = requests.codes.ok
+
+    # Prepare a bad media response
+    bad_media_response = mock.Mock()
+    bad_media_response.content = dumps({
+        "errors": [
+            {
+                "code": 93,
+                "message": "This application is not allowed to access or "
+                "delete your direct messages.",
+            }]})
+    bad_media_response.status_code = requests.codes.internal_server_error
+
+    mock_post.side_effect = [good_media_response, good_tweet_response]
+    mock_get.return_value = good_tweet_response
+
+    twitter_url = 'twitter://{}/{}/{}/{}?mode=tweet'.format(
+        ckey, csecret, akey, asecret)
+
+    # attach our content
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    # instantiate our object
+    obj = Apprise.instantiate(twitter_url)
+
+    # Send our notification
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    # Test our call count
+    assert mock_get.call_count == 0
+    assert mock_post.call_count == 2
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    # Test case where upload fails
+    mock_get.return_value = good_tweet_response
+    mock_post.side_effect = [good_media_response, bad_response]
+
+    # instantiate our object
+    obj = Apprise.instantiate(twitter_url)
+
+    # Send our notification; it will fail because of the media response
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is False
+
+    assert mock_get.call_count == 0
+    assert mock_post.call_count == 2
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    mock_post.side_effect = [good_media_response, good_tweet_response]
+    mock_get.return_value = good_tweet_response
+
+    # An invalid attachment will cause a failure
+    path = os.path.join(TEST_VAR_DIR, '/invalid/path/to/an/invalid/file.jpg')
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=path) is False
+
+    # No get request as cached response is used
+    assert mock_get.call_count == 0
+
+    # No post request as attachment is no good anyway
+    assert mock_post.call_count == 0
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    mock_post.side_effect = [
+        good_media_response, good_media_response, good_media_response,
+        good_media_response, good_tweet_response, good_tweet_response,
+        good_tweet_response, good_tweet_response]
+    mock_get.return_value = good_tweet_response
+
+    # instantiate our object (without a batch mode)
+    obj = Apprise.instantiate(twitter_url + "&batch=no")
+
+    # 4 images are produced
+    attach = [
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.jpeg'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.png'),
+        # This one is not supported, so it's ignored gracefully
+        os.path.join(TEST_VAR_DIR, 'apprise-test.mp4'),
+    ]
+
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    assert mock_get.call_count == 0
+    # No get request as cached response is used
+    assert mock_post.call_count == 8
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[2][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[3][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[4][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+    assert mock_post.call_args_list[5][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+    assert mock_post.call_args_list[6][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+    assert mock_post.call_args_list[7][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    mock_post.side_effect = [
+        good_media_response, good_media_response, good_media_response,
+        good_media_response, good_tweet_response, good_tweet_response,
+        good_tweet_response, good_tweet_response]
+    mock_get.return_value = good_tweet_response
+
+    # instantiate our object
+    obj = Apprise.instantiate(twitter_url)
+
+    # 4 images are produced
+    attach = [
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.jpeg'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.png'),
+        # This one is not supported, so it's ignored gracefully
+        os.path.join(TEST_VAR_DIR, 'apprise-test.mp4'),
+    ]
+
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    assert mock_get.call_count == 0
+    # No get request as cached response is used
+    assert mock_post.call_count == 7
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[2][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[3][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[4][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+    assert mock_post.call_args_list[5][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+    # The 2 images are grouped together (batch mode)
+    assert mock_post.call_args_list[6][0][0] == \
+        'https://api.twitter.com/1.1/statuses/update.json'
+
+    mock_get.reset_mock()
+    mock_post.reset_mock()
+
+    # We have an OSError thrown in the middle of our preparation
+    mock_post.side_effect = [good_media_response, OSError()]
+    mock_get.return_value = good_tweet_response
+
+    # 2 images are produced
+    attach = [
+        os.path.join(TEST_VAR_DIR, 'apprise-test.gif'),
+        os.path.join(TEST_VAR_DIR, 'apprise-test.png'),
+        # This one is not supported, so it's ignored gracefully
+        os.path.join(TEST_VAR_DIR, 'apprise-test.mp4'),
+    ]
+
+    # We'll fail to send this time
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is False
+
+    assert mock_get.call_count == 0
+    # No get request as cached response is used
+    assert mock_post.call_count == 2
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://upload.twitter.com/1.1/media/upload.json'
diff --git a/test/var/apprise-test.mp4 b/test/var/apprise-test.mp4
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index 00000000..74508716
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