diff --git a/apprise/plugins/NotifyMatrix.py b/apprise/plugins/NotifyMatrix.py
index b23f11af96..00b9a2d6bb 100644
--- a/apprise/plugins/NotifyMatrix.py
+++ b/apprise/plugins/NotifyMatrix.py
@@ -590,6 +590,9 @@ def _send_server_notification(self, body, title='',
         attachments = None
         if attach and self.attachment_support:
             attachments = self._send_attachments(attach)
+            if not attachments:
+                # take an early exit
+                return False
 
         while len(rooms) > 0:
 
@@ -687,6 +690,10 @@ def _send_attachments(self, attach):
 
         payloads = []
         for attachment in attach:
+            if not attachment:
+                # invalid attachment (bad file)
+                return False
+
             if not re.match(r'^image/', attachment.mimetype, re.I):
                 # unsuppored at this time
                 continue
@@ -1198,6 +1205,13 @@ def _fetch(self, path, payload=None, params=None, attachment=None,
                 # Return; we're done
                 return (False, response)
 
+            except (OSError, IOError) as e:
+                self.logger.warning(
+                    'An I/O error occurred while reading {}.'.format(
+                        attachment.name if attachment else 'unknown file'))
+                self.logger.debug('I/O Exception: %s' % str(e))
+                return (False, {})
+
             return (True, response)
 
         # If we get here, we ran out of retries
diff --git a/test/test_plugin_matrix.py b/test/test_plugin_matrix.py
index 14a6702a13..624ed99e65 100644
--- a/test/test_plugin_matrix.py
+++ b/test/test_plugin_matrix.py
@@ -32,9 +32,10 @@
 
 from unittest import mock
 
+import os
 import requests
 import pytest
-from apprise import AppriseAsset
+from apprise import Apprise, AppriseAsset, AppriseAttachment, NotifyType
 from json import dumps
 
 from apprise.plugins.NotifyMatrix import NotifyMatrix
@@ -52,6 +53,9 @@
     'home_server': 'localhost',
 })
 
+# Attachment Directory
+TEST_VAR_DIR = os.path.join(os.path.dirname(__file__), 'var')
+
 # Our Testing URLs
 apprise_url_tests = (
     ##################################
@@ -868,3 +872,205 @@ def mock_function_handing(url, data, **kwargs):
     assert obj.access_token is None
 
     assert obj.notify('test', 'test') is True
+
+
+@mock.patch('requests.get')
+@mock.patch('requests.post')
+def test_plugin_matrix_attachments_api_v3(mock_post, mock_get):
+    """
+    NotifyMatrix() Attachment Checks (v3)
+
+    """
+
+    # Prepare a good response
+    response = mock.Mock()
+    response.status_code = requests.codes.ok
+    response.content = MATRIX_GOOD_RESPONSE.encode('utf-8')
+
+    # Prepare a bad response
+    bad_response = mock.Mock()
+    bad_response.status_code = requests.codes.internal_server_error
+
+    # Prepare Mock return object
+    mock_post.return_value = response
+    mock_get.return_value = response
+
+    # Instantiate our object
+    obj = Apprise.instantiate('matrix://user:pass@localhost/#general?v=3')
+
+    # attach our content
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    # Test our call count
+    assert mock_post.call_count == 5
+    assert mock_post.call_args_list[0][0][0] == \
+        'http://localhost/_matrix/client/v3/login'
+    assert mock_post.call_args_list[1][0][0] == \
+        'http://localhost/_matrix/media/v3/upload'
+    assert mock_post.call_args_list[2][0][0] == \
+        'http://localhost/_matrix/client/v3/join/%23general%3Alocalhost'
+    assert mock_post.call_args_list[3][0][0] == \
+        'http://localhost/_matrix/client/v3/rooms/%21abc123%3Alocalhost/' \
+        'send/m.room.message'
+    assert mock_post.call_args_list[4][0][0] == \
+        'http://localhost/_matrix/client/v3/rooms/%21abc123%3Alocalhost/' \
+        'send/m.room.message'
+
+    # Attach an unsupported file type
+    attach = AppriseAttachment(
+        os.path.join(TEST_VAR_DIR, 'apprise-archive.zip'))
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is False
+
+    # An invalid attachment will cause a failure
+    path = os.path.join(TEST_VAR_DIR, '/invalid/path/to/an/invalid/file.jpg')
+    attach = AppriseAttachment(path)
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=path) is False
+
+    # update our attachment to be valid
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    mock_post.return_value = None
+    # Throw an exception on the first call to requests.post()
+    for side_effect in (requests.RequestException(), OSError(), bad_response):
+        mock_post.side_effect = [side_effect]
+
+        # We'll fail now because of our error handling
+        assert obj.send(body="test", attach=attach) is False
+
+    # Throw an exception on the second call to requests.post()
+    for side_effect in (requests.RequestException(), OSError(), bad_response):
+        mock_post.side_effect = [response, side_effect]
+
+        # We'll fail now because of our error handling
+        assert obj.send(body="test", attach=attach) is False
+
+    # handle a bad response
+    bad_response = mock.Mock()
+    bad_response.status_code = requests.codes.internal_server_error
+    mock_post.side_effect = [response, bad_response]
+
+    # We'll fail now because of an internal exception
+    assert obj.send(body="test", attach=attach) is False
+
+
+@mock.patch('requests.get')
+@mock.patch('requests.post')
+def test_plugin_matrix_attachments_api_v2(mock_post, mock_get):
+    """
+    NotifyMatrix() Attachment Checks (v2)
+
+    """
+
+    # Prepare a good response
+    response = mock.Mock()
+    response.status_code = requests.codes.ok
+    response.content = MATRIX_GOOD_RESPONSE.encode('utf-8')
+
+    # Prepare a bad response
+    bad_response = mock.Mock()
+    bad_response.status_code = requests.codes.internal_server_error
+
+    # Prepare Mock return object
+    mock_post.return_value = response
+    mock_get.return_value = response
+
+    # Instantiate our object
+    obj = Apprise.instantiate('matrix://user:pass@localhost/#general?v=3')
+
+    # attach our content
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    # Attach an unsupported file
+    mock_post.return_value = response
+    mock_get.return_value = response
+    mock_post.side_effect = None
+    mock_get.side_effect = None
+
+    # Force a object removal (thus a logout call)
+    del obj
+
+    # Reset our object
+    mock_post.reset_mock()
+    mock_get.reset_mock()
+
+    # Instantiate our object
+    obj = Apprise.instantiate('matrixs://user:pass@localhost/#general?v=2')
+
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is True
+
+    # Test our call count
+    assert mock_post.call_count == 5
+    assert mock_post.call_args_list[0][0][0] == \
+        'https://localhost/_matrix/client/r0/login'
+    assert mock_post.call_args_list[1][0][0] == \
+        'https://localhost/_matrix/media/r0/upload'
+    assert mock_post.call_args_list[2][0][0] == \
+        'https://localhost/_matrix/client/r0/join/%23general%3Alocalhost'
+    assert mock_post.call_args_list[3][0][0] == \
+        'https://localhost/_matrix/client/r0/rooms/%21abc123%3Alocalhost/' \
+        'send/m.room.message'
+    assert mock_post.call_args_list[4][0][0] == \
+        'https://localhost/_matrix/client/r0/rooms/%21abc123%3Alocalhost/' \
+        'send/m.room.message'
+
+    # Attach an unsupported file type
+    attach = AppriseAttachment(
+        os.path.join(TEST_VAR_DIR, 'apprise-archive.zip'))
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=attach) is False
+
+    # An invalid attachment will cause a failure
+    path = os.path.join(TEST_VAR_DIR, '/invalid/path/to/an/invalid/file.jpg')
+    attach = AppriseAttachment(path)
+    assert obj.notify(
+        body='body', title='title', notify_type=NotifyType.INFO,
+        attach=path) is False
+
+    # update our attachment to be valid
+    attach = AppriseAttachment(os.path.join(TEST_VAR_DIR, 'apprise-test.gif'))
+
+    mock_post.return_value = None
+    mock_get.return_value = None
+
+    # Throw an exception on the first call to requests.post()
+    for side_effect in (requests.RequestException(), OSError(), bad_response):
+        mock_post.side_effect = [side_effect]
+        mock_get.side_effect = [side_effect]
+
+        assert obj.send(body="test", attach=attach) is False
+
+    # Throw an exception on the second call to requests.post()
+    for side_effect in (requests.RequestException(), OSError(), bad_response):
+        mock_post.side_effect = [response, side_effect]
+        mock_get.side_effect = [side_effect]
+
+        # We'll fail now because of our error handling
+        assert obj.send(body="test", attach=attach) is False
+
+    # handle a bad response
+    bad_response = mock.Mock()
+    bad_response.status_code = requests.codes.internal_server_error
+    mock_post.side_effect = [response, bad_response]
+    mock_get.side_effect = [response, bad_response]
+
+    # We'll fail now because of an internal exception
+    assert obj.send(body="test", attach=attach) is False