diff --git a/apprise/plugins/NotifyDiscord.py b/apprise/plugins/NotifyDiscord.py
index 7394ddc4..72e7ac4c 100644
--- a/apprise/plugins/NotifyDiscord.py
+++ b/apprise/plugins/NotifyDiscord.py
@@ -42,7 +42,6 @@
 #
 import re
 import requests
-from json import dumps
 
 from .NotifyBase import NotifyBase
 from ..common import NotifyImageSize
@@ -178,17 +177,12 @@ class NotifyDiscord(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 Discord Notification
         """
 
-        headers = {
-            'User-Agent': self.app_id,
-            'Content-Type': 'multipart/form-data',
-        }
-
-        # Prepare JSON Object
         payload = {
             # Text-To-Speech
             'tts': self.tts,
@@ -258,6 +252,50 @@ class NotifyDiscord(NotifyBase):
             # Optionally override the default username of the webhook
             payload['username'] = self.user
 
+        if not self._send(payload):
+            # We failed to post our message
+            return False
+
+        if attach:
+            # Update our payload; the idea is to preserve it's other detected
+            # and assigned values for re-use here too
+            payload.update({
+                # Text-To-Speech
+                'tts': False,
+                # Wait until the upload has posted itself before continuing
+                'wait': True,
+            })
+
+            # Remove our text/title based content for attachment use
+            if 'embeds' in payload:
+                # Markdown
+                del payload['embeds']
+
+            if 'content' in payload:
+                # Markdown
+                del payload['content']
+
+            # Send our attachments
+            for attachment in attach:
+                self.logger.info(
+                    'Posting Discord Attachment {}'.format(attachment.name))
+                if not self._send(payload, attach=attachment):
+                    # We failed to post our message
+                    return False
+
+        # Otherwise return
+        return True
+
+    def _send(self, payload, attach=None, **kwargs):
+        """
+        Wrapper to the requests (post) object
+        """
+
+        # Our headers
+        headers = {
+            'User-Agent': self.app_id,
+        }
+
         # Construct Notify URL
         notify_url = '{0}/{1}/{2}'.format(
             self.notify_url,
@@ -273,11 +311,19 @@ class NotifyDiscord(NotifyBase):
         # Always call throttle before any remote server i/o is made
         self.throttle()
 
+        # Our attachment path (if specified)
+        files = None
         try:
+
+            # Open our attachment path if required:
+            if attach:
+                files = (attach.name, open(attach.path, 'rb'))
+
             r = requests.post(
                 notify_url,
-                data=dumps(payload),
+                data=payload,
                 headers=headers,
+                files=files,
                 verify=self.verify_certificate,
             )
             if r.status_code not in (
@@ -288,8 +334,9 @@ class NotifyDiscord(NotifyBase):
                     NotifyBase.http_response_code_lookup(r.status_code)
 
                 self.logger.warning(
-                    'Failed to send Discord notification: '
+                    'Failed to send {}to Discord notification: '
                     '{}{}error={}.'.format(
+                        attach.name if attach else '',
                         status_str,
                         ', ' if status_str else '',
                         r.status_code))
@@ -304,12 +351,24 @@ class NotifyDiscord(NotifyBase):
 
         except requests.RequestException as e:
             self.logger.warning(
-                'A Connection error occured sending Discord '
-                'notification.'
-            )
+                'A Connection error occured posting {}to Discord.'.format(
+                    attach.name if attach else ''))
             self.logger.debug('Socket Exception: %s' % str(e))
             return False
 
+        except (OSError, IOError) as e:
+            self.logger.warning(
+                'An I/O error occured while reading {}.'.format(
+                    attach.name if attach else 'attachment'))
+            self.logger.debug('I/O Exception: %s' % str(e))
+            return False
+
+        finally:
+            # Close our file (if it's open) stored in the second element
+            # of our files tuple (index 1)
+            if files:
+                files[1].close()
+
         return True
 
     def url(self, privacy=False, *args, **kwargs):
diff --git a/test/test_discord_plugin.py b/test/test_discord_plugin.py
new file mode 100644
index 00000000..a29e0bec
--- /dev/null
+++ b/test/test_discord_plugin.py
@@ -0,0 +1,191 @@
+# -*- coding: utf-8 -*-
+#
+# All rights reserved.
+#
+# This code is licensed under the MIT License.
+#
+# Permission is hereby granted, free of charge, to any person obtaining a copy
+# of this software and associated documentation files(the "Software"), to deal
+# in the Software without restriction, including without limitation the rights
+# to use, copy, modify, merge, publish, distribute, sublicense, and / or sell
+# copies of the Software, and to permit persons to whom the Software is
+# furnished to do so, subject to the following conditions :
+#
+# The above copyright notice and this permission notice shall be included in
+# all copies or substantial portions of the Software.
+#
+# THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+# IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+# FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT.IN NO EVENT SHALL THE
+# AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+# LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+# 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 apprise import Apprise
+from apprise import AppriseAttachment
+from apprise import plugins
+from apprise import NotifyType
+from apprise import NotifyFormat
+
+# 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')
+
+
+@mock.patch('requests.post')
+def test_discord_plugin(mock_post):
+    """
+    API: NotifyDiscord() General Checks
+
+    """
+    # Disable Throttling to speed testing
+    plugins.NotifyBase.request_rate_per_sec = 0
+
+    # Initialize some generic (but valid) tokens
+    webhook_id = 'A' * 24
+    webhook_token = 'B' * 64
+
+    # Prepare Mock
+    mock_post.return_value = requests.Request()
+    mock_post.return_value.status_code = requests.codes.ok
+
+    # Invalid webhook id
+    with pytest.raises(TypeError):
+        plugins.NotifyDiscord(webhook_id=None, webhook_token=webhook_token)
+    # Invalid webhook id (whitespace)
+    with pytest.raises(TypeError):
+        plugins.NotifyDiscord(webhook_id="  ", webhook_token=webhook_token)
+
+    # Invalid webhook token
+    with pytest.raises(TypeError):
+        plugins.NotifyDiscord(webhook_id=webhook_id, webhook_token=None)
+    # Invalid webhook token (whitespace)
+    with pytest.raises(TypeError):
+        plugins.NotifyDiscord(webhook_id=webhook_id, webhook_token="   ")
+
+    obj = plugins.NotifyDiscord(
+        webhook_id=webhook_id,
+        webhook_token=webhook_token,
+        footer=True, thumbnail=False)
+
+    # Test that we get a string response
+    assert isinstance(obj.url(), six.string_types) is True
+
+    # This call includes an image with it's payload:
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO) is True
+
+    # Test our header parsing
+    test_markdown = "## Heading one\nbody body\n\n" + \
+        "# Heading 2 ##\n\nTest\n\n" + \
+        "more content\n" + \
+        "even more content  \t\r\n\n\n" + \
+        "# Heading 3 ##\n\n\n" + \
+        "normal content\n" + \
+        "# heading 4\n" + \
+        "#### Heading 5"
+
+    results = obj.extract_markdown_sections(test_markdown)
+    assert isinstance(results, list) is True
+    # We should have 5 sections (since there are 5 headers identified above)
+    assert len(results) == 5
+    assert results[0]['name'] == 'Heading one'
+    assert results[0]['value'] == '```md\nbody body\n```'
+    assert results[1]['name'] == 'Heading 2'
+    assert results[1]['value'] == \
+        '```md\nTest\n\nmore content\neven more content\n```'
+    assert results[2]['name'] == 'Heading 3'
+    assert results[2]['value'] == \
+        '```md\nnormal content\n```'
+    assert results[3]['name'] == 'heading 4'
+    assert results[3]['value'] == '```md\n\n```'
+    assert results[4]['name'] == 'Heading 5'
+    assert results[4]['value'] == '```md\n\n```'
+
+    # Test our markdown
+    obj = Apprise.instantiate(
+        'discord://{}/{}/?format=markdown'.format(webhook_id, webhook_token))
+    assert isinstance(obj, plugins.NotifyDiscord)
+    assert obj.notify(
+        body=test_markdown, title='title', notify_type=NotifyType.INFO) is True
+
+    # Empty String
+    results = obj.extract_markdown_sections("")
+    assert isinstance(results, list) is True
+    assert len(results) == 0
+
+    # String without Heading
+    test_markdown = "Just a string without any header entries.\n" + \
+        "A second line"
+    results = obj.extract_markdown_sections(test_markdown)
+    assert isinstance(results, list) is True
+    assert len(results) == 0
+
+    # Use our test markdown string during a notification
+    assert obj.notify(
+        body=test_markdown, title='title', notify_type=NotifyType.INFO) is True
+
+    # Create an apprise instance
+    a = Apprise()
+
+    # Our processing is slightly different when we aren't using markdown
+    # as we do not pre-parse content during our notifications
+    assert a.add(
+        'discord://{webhook_id}/{webhook_token}/'
+        '?format=markdown&footer=Yes'.format(
+            webhook_id=webhook_id,
+            webhook_token=webhook_token)) is True
+
+    # This call includes an image with it's payload:
+    assert a.notify(body=test_markdown, title='title',
+                    notify_type=NotifyType.INFO,
+                    body_format=NotifyFormat.TEXT) is True
+
+    assert a.notify(body=test_markdown, title='title',
+                    notify_type=NotifyType.INFO,
+                    body_format=NotifyFormat.MARKDOWN) is True
+
+    # Toggle our logo availability
+    a.asset.image_url_logo = None
+    assert a.notify(
+        body='body', title='title', notify_type=NotifyType.INFO) is True
+
+
+@mock.patch('requests.post')
+def test_discord_attachments(mock_post):
+    """
+    API: NotifyDiscord() Attachment Checks
+
+    """
+    # Disable Throttling to speed testing
+    plugins.NotifyBase.request_rate_per_sec = 0
+
+    # Initialize some generic (but valid) tokens
+    webhook_id = 'C' * 24
+    webhook_token = 'D' * 64
+
+    # Prepare Mock return object
+    response = mock.Mock()
+    response.status_code = requests.codes.ok
+
+    # Throw an exception on the second call to requests.post()
+    mock_post.side_effect = [response, OSError()]
+
+    # Test our markdown
+    obj = Apprise.instantiate(
+        'discord://{}/{}/?format=markdown'.format(webhook_id, webhook_token))
+
+    # attach our content
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    # We'll fail now because of an internal exception
+    assert obj.send(body="test", attach=attach) is False
diff --git a/test/test_rest_plugins.py b/test/test_rest_plugins.py
index e812f02d..410d7cc0 100644
--- a/test/test_rest_plugins.py
+++ b/test/test_rest_plugins.py
@@ -3849,125 +3849,6 @@ def test_notify_boxcar_plugin(mock_post, mock_get):
     assert len(p.device_tokens) == 3
 
 
-@mock.patch('requests.get')
-@mock.patch('requests.post')
-def test_notify_discord_plugin(mock_post, mock_get):
-    """
-    API: NotifyDiscord() Extra Checks
-
-    """
-    # Disable Throttling to speed testing
-    plugins.NotifyBase.request_rate_per_sec = 0
-
-    # Initialize some generic (but valid) tokens
-    webhook_id = 'A' * 24
-    webhook_token = 'B' * 64
-
-    # Prepare Mock
-    mock_get.return_value = requests.Request()
-    mock_post.return_value = requests.Request()
-    mock_post.return_value.status_code = requests.codes.ok
-    mock_get.return_value.status_code = requests.codes.ok
-
-    # Invalid webhook id
-    with pytest.raises(TypeError):
-        plugins.NotifyDiscord(webhook_id=None, webhook_token=webhook_token)
-    # Invalid webhook id (whitespace)
-    with pytest.raises(TypeError):
-        plugins.NotifyDiscord(webhook_id="  ", webhook_token=webhook_token)
-
-    # Invalid webhook token
-    with pytest.raises(TypeError):
-        plugins.NotifyDiscord(webhook_id=webhook_id, webhook_token=None)
-    # Invalid webhook token (whitespace)
-    with pytest.raises(TypeError):
-        plugins.NotifyDiscord(webhook_id=webhook_id, webhook_token="   ")
-
-    obj = plugins.NotifyDiscord(
-        webhook_id=webhook_id,
-        webhook_token=webhook_token,
-        footer=True, thumbnail=False)
-
-    # This call includes an image with it's payload:
-    assert obj.notify(
-        body='body', title='title', notify_type=NotifyType.INFO) is True
-
-    # Test our header parsing
-    test_markdown = "## Heading one\nbody body\n\n" + \
-        "# Heading 2 ##\n\nTest\n\n" + \
-        "more content\n" + \
-        "even more content  \t\r\n\n\n" + \
-        "# Heading 3 ##\n\n\n" + \
-        "normal content\n" + \
-        "# heading 4\n" + \
-        "#### Heading 5"
-
-    results = obj.extract_markdown_sections(test_markdown)
-    assert isinstance(results, list) is True
-    # We should have 5 sections (since there are 5 headers identified above)
-    assert len(results) == 5
-    assert results[0]['name'] == 'Heading one'
-    assert results[0]['value'] == '```md\nbody body\n```'
-    assert results[1]['name'] == 'Heading 2'
-    assert results[1]['value'] == \
-        '```md\nTest\n\nmore content\neven more content\n```'
-    assert results[2]['name'] == 'Heading 3'
-    assert results[2]['value'] == \
-        '```md\nnormal content\n```'
-    assert results[3]['name'] == 'heading 4'
-    assert results[3]['value'] == '```md\n\n```'
-    assert results[4]['name'] == 'Heading 5'
-    assert results[4]['value'] == '```md\n\n```'
-
-    # Test our markdown
-    obj = Apprise.instantiate(
-        'discord://{}/{}/?format=markdown'.format(webhook_id, webhook_token))
-    assert isinstance(obj, plugins.NotifyDiscord)
-    assert obj.notify(
-        body=test_markdown, title='title', notify_type=NotifyType.INFO) is True
-
-    # Empty String
-    results = obj.extract_markdown_sections("")
-    assert isinstance(results, list) is True
-    assert len(results) == 0
-
-    # String without Heading
-    test_markdown = "Just a string without any header entries.\n" + \
-        "A second line"
-    results = obj.extract_markdown_sections(test_markdown)
-    assert isinstance(results, list) is True
-    assert len(results) == 0
-
-    # Use our test markdown string during a notification
-    assert obj.notify(
-        body=test_markdown, title='title', notify_type=NotifyType.INFO) is True
-
-    # Create an apprise instance
-    a = Apprise()
-
-    # Our processing is slightly different when we aren't using markdown
-    # as we do not pre-parse content during our notifications
-    assert a.add(
-        'discord://{webhook_id}/{webhook_token}/'
-        '?format=markdown&footer=Yes'.format(
-            webhook_id=webhook_id,
-            webhook_token=webhook_token)) is True
-
-    # This call includes an image with it's payload:
-    assert a.notify(body=test_markdown, title='title',
-                    notify_type=NotifyType.INFO,
-                    body_format=NotifyFormat.TEXT) is True
-
-    assert a.notify(body=test_markdown, title='title',
-                    notify_type=NotifyType.INFO,
-                    body_format=NotifyFormat.MARKDOWN) is True
-
-    # Toggle our logo availability
-    a.asset.image_url_logo = None
-    assert a.notify(
-        body='body', title='title', notify_type=NotifyType.INFO) is True
-
-
 @mock.patch('requests.get')
 @mock.patch('requests.post')
 def test_notify_emby_plugin_login(mock_post, mock_get):