diff --git a/django_email_learning/admin.py b/django_email_learning/admin.py
index f6e026b..88f9c07 100644
--- a/django_email_learning/admin.py
+++ b/django_email_learning/admin.py
@@ -10,6 +10,7 @@
     Answer,
     CourseContent,
     Organization,
+    OrganizationUser,
     BlockedEmail,
 )
 
@@ -91,3 +92,4 @@ def get_content_title(self, obj: CourseContent) -> str | None:
 admin.site.register(Answer)
 admin.site.register(Organization)
 admin.site.register(BlockedEmail)
+admin.site.register(OrganizationUser)
diff --git a/django_email_learning/ports/__init__.py b/django_email_learning/ports/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/django_email_learning/ports/email_sender_protocol.py b/django_email_learning/ports/email_sender_protocol.py
new file mode 100644
index 0000000..0b677d6
--- /dev/null
+++ b/django_email_learning/ports/email_sender_protocol.py
@@ -0,0 +1,7 @@
+from typing import Protocol
+from django.core.mail import EmailMultiAlternatives
+
+
+class EmailSenderProtocol(Protocol):
+    def send_email(self, email: EmailMultiAlternatives) -> None:
+        ...
diff --git a/django_email_learning/services/__init__.py b/django_email_learning/services/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/django_email_learning/services/deafults/__init__.py b/django_email_learning/services/deafults/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/django_email_learning/services/deafults/email_sender.py b/django_email_learning/services/deafults/email_sender.py
new file mode 100644
index 0000000..5ff215c
--- /dev/null
+++ b/django_email_learning/services/deafults/email_sender.py
@@ -0,0 +1,33 @@
+import logging
+from django_email_learning.ports.email_sender_protocol import EmailSenderProtocol
+from django.core.mail import EmailMultiAlternatives
+
+logger = logging.getLogger(__name__)
+
+
+class DjangoEmailSender(EmailSenderProtocol):
+    def _mask_email(self, email_address: str) -> str:
+        """Mask email address for logging privacy."""
+        try:
+            username, domain = email_address.split("@")
+            masked_username = username[0] + "***"
+            return f"{masked_username}@{domain}"
+        except ValueError:
+            return "***@***"
+
+    def _mask_recipients(self, recipients: list[str]) -> str:
+        """Mask all recipient email addresses for logging."""
+        if not recipients:
+            return "no recipients"
+        masked = [self._mask_email(recipient) for recipient in recipients]
+        return ", ".join(masked)
+
+    def send_email(self, email: EmailMultiAlternatives) -> None:
+        masked_recipients = self._mask_recipients(email.to)
+        try:
+            logger.info(f"Sending email to {masked_recipients}")
+            email.send()
+            logger.info(f"Email sent successfully to {masked_recipients}")
+        except Exception as e:
+            logger.error(f"Failed to send email to {masked_recipients}: {str(e)}")
+            raise
diff --git a/frontend/course/Course.jsx b/frontend/course/Course.jsx
index fdd1bd6..95aa0b9 100644
--- a/frontend/course/Course.jsx
+++ b/frontend/course/Course.jsx
@@ -21,6 +21,7 @@ function Course() {
     const [lessonCache, setLessonCache] = useState("")
     const [contentLoaded, setContentLoaded] = useState(false)
 
+    const userRole = localStorage.getItem('userRole');
     const apiBaseUrl = localStorage.getItem('apiBaseUrl');
     const organizationId = localStorage.getItem('activeOrganizationId');
 
@@ -120,7 +121,7 @@ function Course() {
         >
             <Grid size={{xs: 12, md: 9}} py={2} pl={2}>
                 <Box p={2} sx={{ border: '1px solid', borderColor: 'grey.300', borderRadius: 1, minHeight: 300 }}>
-                    <Button variant="contained" startIcon={<DescriptionIcon />} sx={{ marginBottom: 2 }} onClick={() => {
+                    {userRole !== 'viewer' && <><Button variant="contained" startIcon={<DescriptionIcon />} sx={{ marginBottom: 2 }} onClick={() => {
                         setDialogContent(<LessonForm
                             header="New Lesson"
                             initialContent={lessonCache}
@@ -134,7 +135,7 @@ function Course() {
                             cancelCallback={() => setDialogOpen(false)}
                             successCallback={resetDialog}
                             courseId={course_id} />);
-                        setDialogOpen(true);}}>Add a Quiz</Button>
+                        setDialogOpen(true);}}>Add a Quiz</Button></> }
                     <ContentTable courseId={course_id} loaded={contentLoaded} eventHandler={(event) => tableEventHandler(event)} />
                 </Box>
             </Grid>
diff --git a/frontend/course/components/ContentTable.jsx b/frontend/course/components/ContentTable.jsx
index 2957b81..9ae0539 100644
--- a/frontend/course/components/ContentTable.jsx
+++ b/frontend/course/components/ContentTable.jsx
@@ -9,6 +9,8 @@ const ContentTable = ({ courseId, eventHandler, loaded = false }) => {
     const apiBaseUrl = localStorage.getItem('apiBaseUrl');
     const organizationId = localStorage.getItem('activeOrganizationId');
 
+    const userRole = localStorage.getItem('userRole');
+
     const formatPeriod = (period) => {
         if (!period) {
             return "";
@@ -97,7 +99,7 @@ const ContentTable = ({ courseId, eventHandler, loaded = false }) => {
                 <TableCell>Waiting time</TableCell>
                 <TableCell>type</TableCell>
                 <TableCell>Published</TableCell>
-                <TableCell align='right'>Actions</TableCell>
+                {userRole !== 'viewer' && <TableCell align='right'>Actions</TableCell>}
               </TableRow>
             </TableHead>
             <TableBody>
@@ -108,12 +110,12 @@ const ContentTable = ({ courseId, eventHandler, loaded = false }) => {
                             color='primary.dark' sx={{ cursor: 'pointer'}}>{content.title}</Typography></TableCell>
                         <TableCell>{formatPeriod(content.waiting_period)}</TableCell>
                         <TableCell>{content.type}</TableCell>
-                        <TableCell><Switch defaultChecked={content.is_published} onChange={() => TogglePublishContent(content.id, !content.is_published)} /></TableCell>
-                        <TableCell align='right'>
+                        <TableCell><Switch defaultChecked={content.is_published} onChange={() => TogglePublishContent(content.id, !content.is_published)} disabled={userRole == 'viewer'} /></TableCell>
+                        {userRole !== 'viewer' && <TableCell align='right'>
                             <IconButton aria-label="delete" onClick={() => deleteContent(content.id)}>
                                 <DeleteIcon />
                             </IconButton>
-                        </TableCell>
+                        </TableCell>}
                     </TableRow>
                 ))}
             </TableBody>
diff --git a/frontend/course/components/LessonForm.jsx b/frontend/course/components/LessonForm.jsx
index d6dc054..8a58c29 100644
--- a/frontend/course/components/LessonForm.jsx
+++ b/frontend/course/components/LessonForm.jsx
@@ -13,6 +13,7 @@ function LessonForm({ header, initialTitle, initialContent, onContentChange, can
     const [contentHelperText, setContentHelperText] = useState("");
     const [errorMessage, setErrorMessage] = useState("");
 
+    const userRole = localStorage.getItem('userRole');
     const apiBaseUrl = localStorage.getItem('apiBaseUrl');
     const orgId = localStorage.getItem('activeOrganizationId');
 
@@ -126,9 +127,9 @@ function LessonForm({ header, initialTitle, initialContent, onContentChange, can
                 {errorMessage}
             </Alert>
         )}
-        <RequiredTextField value={title} label="Lesson Title" name="lesson_title" sx={{ width: '100%' }} onChange={(e) => setTitle(e.target.value)} helperText={titleHelperText}/>
+        <RequiredTextField value={title} label="Lesson Title" name="lesson_title" sx={{ width: '100%' }} onChange={(e) => setTitle(e.target.value)} helperText={titleHelperText} disabled={userRole === 'viewer'} />
         <Box sx={{ my: 2 }}>
-        <ContentEditor initialContent={content} contentUpdateCallback={handleContentChange}/>
+        <ContentEditor initialContent={content} contentUpdateCallback={handleContentChange} disabled={userRole === 'viewer'} />
         <Typography color="errorText.main" sx={{ marginTop: 1, fontSize: '0.75rem' }}>
             {contentHelperText}
         </Typography>
@@ -144,19 +145,20 @@ function LessonForm({ header, initialTitle, initialContent, onContentChange, can
             onChange={(e) => setWaitingPeriod(e.target.value)}
             sx={{ width: '200px', mr: 2 }}
             inputProps={{ min: 1 }}
+            disabled={userRole === 'viewer'}
         />
-        <Select size="small" value={waitingPeriodUnit} onChange={(e) => setWaitingPeriodUnit(e.target.value)} name="waiting_period_unit" sx={{ width: '150px' }}>
+        <Select size="small" value={waitingPeriodUnit} onChange={(e) => setWaitingPeriodUnit(e.target.value)} name="waiting_period_unit" sx={{ width: '150px' }} disabled={userRole === 'viewer'}>
             <MenuItem value="days">Days</MenuItem>
             <MenuItem value="hours">Hours</MenuItem>
         </Select>
         </Tooltip>
         <Box mt={2} textAlign="right">
         <Button variant="outlined" sx={{ mr: 1 }} onClick={cancel}>
-            Cancel
+            Back
         </Button>
-        <Button type="submit" variant="contained" onClick={() => {if(!lessonId) { addLesson(); } else { updateLesson(); }}}>
+        {userRole !== 'viewer' && <Button type="submit" variant="contained" onClick={() => {if(!lessonId) { addLesson(); } else { updateLesson(); }}}>
             Save Lesson
-        </Button>
+        </Button>}
         </Box>
         </Box>
     );
diff --git a/frontend/course/components/QuestionForm.jsx b/frontend/course/components/QuestionForm.jsx
index 08d169e..59359ca 100644
--- a/frontend/course/components/QuestionForm.jsx
+++ b/frontend/course/components/QuestionForm.jsx
@@ -14,8 +14,10 @@ const QuestionForm = ({question, index, eventHandler}) => {
     const [addingOption, setAddingOption] = useState(false);
     const optionInputRef = useRef(null);
 
+    const userRole = localStorage.getItem('userRole');
+
     const editQuestion = () => {
-        if (editMode && questionText.trim() === '') {
+        if (editMode && questionText.trim() === '' || userRole === 'viewer') {
             return;
         }
         triggerUpdateEvent();
@@ -61,7 +63,7 @@ const QuestionForm = ({question, index, eventHandler}) => {
        <Box key={index} sx={{ mb: 1, p: 2, border: '1px solid', borderColor: 'grey.300', borderRadius: 1 }}>
             <Grid container spacing={2} alignItems="center">
                 <Grid size={{ xs: 12, md: 9 }}>
-                    <EditIcon sx={{borderRadius: "50%", display: "inline-block", float: "left", mr: 1, fontSize: "0.9rem", border: 1, borderColor: "grey.200", color: "grey.400", padding: "4px", cursor: "pointer", ':hover': { backgroundColor: "primary.main", color: "white", borderColor: "primary.main" } }} onClick={editQuestion}/>
+                    {userRole !== 'viewer' && <EditIcon sx={{borderRadius: "50%", display: "inline-block", float: "left", mr: 1, fontSize: "0.9rem", border: 1, borderColor: "grey.200", color: "grey.400", padding: "4px", cursor: "pointer", ':hover': { backgroundColor: "primary.main", color: "white", borderColor: "primary.main" } }} onClick={editQuestion}/>}
                     {!editMode ? (
                         <Typography onClick={editQuestion}>{index + 1}. {questionText}</Typography>
                     ) : (
@@ -77,12 +79,12 @@ const QuestionForm = ({question, index, eventHandler}) => {
                     )}
                 </Grid>
                 <Grid size={{ xs: 12, md: 3 }} sx={{ textAlign: 'right' }}>
-                    <Button variant="outlined" color="primary" sx={{ fontSize: '0.75rem', mt: 1 }} onClick={() => setAddingOption(true)} >
+                    {userRole !== 'viewer' && <><Button variant="outlined" color="primary" sx={{ fontSize: '0.75rem', mt: 1 }} onClick={() => setAddingOption(true)} >
                         <RuleIcon /><Typography variant="button" sx={{ ml: 1, fontSize: '0.75rem' }}>Add Option</Typography>
                     </Button>
                     <Button variant="outlined" onClick={deleteCallback} sx={{ ml: 1, mt: 1, fontSize: '0.75rem' }}>
                         Delete
-                    </Button>
+                    </Button></>}
                 </Grid>
                 {addingOption && (<>
                     <Grid size={{ xs: 9 }} sx={{ display: 'flex', alignItems: 'center' }}>
@@ -125,7 +127,7 @@ const QuestionForm = ({question, index, eventHandler}) => {
                                 <TableRow>
                                     <TableCell>Options</TableCell>
                                     <TableCell>Correct Answer</TableCell>
-                                    <TableCell align='right'>Actions</TableCell>
+                                    {userRole !== 'viewer' && <TableCell align='right'>Actions</TableCell>}
                                 </TableRow>
                             </TableHead>
                             <TableBody>
@@ -146,8 +148,8 @@ const QuestionForm = ({question, index, eventHandler}) => {
                                                 }}
                                             />
                                         )}</TableCell>
-                                        <TableCell><Switch onChange={(e)=>updateOption(idx, e.target.checked)} checked={option.isCorrect} /></TableCell>
-                                        <TableCell align='right'>
+                                        <TableCell><Switch onChange={(e)=>updateOption(idx, e.target.checked)} checked={option.isCorrect} disabled={userRole === 'viewer'} /></TableCell>
+                                        {userRole !== 'viewer' && <TableCell align='right'>
                                             <EditIcon sx={{ cursor: 'pointer', mr: 1 }} onClick={() => {
                                                 setOptions(options.map((opt, i) => i === idx ? { ...opt, editMode: !opt.editMode } : opt));
                                             }} />
@@ -155,7 +157,7 @@ const QuestionForm = ({question, index, eventHandler}) => {
                                                 const updatedOptions = options.filter((_, i) => i !== idx);
                                                 setOptions(updatedOptions);
                                             }} />
-                                        </TableCell>
+                                        </TableCell>}
                                     </TableRow>
                                 ))}
                             </TableBody>
diff --git a/frontend/course/components/QuizForm.jsx b/frontend/course/components/QuizForm.jsx
index 06363e9..cf82cf2 100644
--- a/frontend/course/components/QuizForm.jsx
+++ b/frontend/course/components/QuizForm.jsx
@@ -19,7 +19,7 @@ const QuizForm = ({cancelCallback, successCallback, courseId, quizId, contentId,
     const dialogRef = useRef(null);
     const apiBaseUrl = localStorage.getItem('apiBaseUrl');
     const organizationId = localStorage.getItem('activeOrganizationId');
-
+    const userRole = localStorage.getItem('userRole');
 
     const addQuiz = () => {
         if (!validateQuiz()) {
@@ -201,9 +201,9 @@ const QuizForm = ({cancelCallback, successCallback, courseId, quizId, contentId,
         }} tabIndex={0} focusable="true">
             <Typography variant="h2" sx={{ my: 2, fontSize: '1.5rem' }}>{ quizId ? "Update Quiz" : "New Quiz" }</Typography>
             {errorMessage && <Alert severity="error" sx={{ mb: 2 }}>{errorMessage}</Alert>}
-            <RequiredTextField label="Quiz Title" value={title} onChange={(e) => setTitle(e.target.value)} sx={{ mb: 2, width: '100%' }} />
-            <Button variant="outlined" sx={{ mb: 2 }} onClick={() => setShowQuestionField(true)}>
-                <QuizIcon sx={{ mr: 1 }} /> Add Question</Button>
+            <RequiredTextField label="Quiz Title" value={title} onChange={(e) => setTitle(e.target.value)} sx={{ mb: 2, width: '100%' }} disabled={userRole === 'viewer'} />
+            {userRole !== 'viewer' && <Button variant="outlined" sx={{ mb: 2 }} onClick={() => setShowQuestionField(true)}>
+                <QuizIcon sx={{ mr: 1 }} /> Add Question</Button>}
             { showQuestionField && (
                 <Box sx={{ mb: 2, border: '1px solid', borderColor: 'grey.300', borderRadius: 1, p: 2 }}>
                     <Grid container spacing={2} alignItems="center">
@@ -240,6 +240,7 @@ const QuizForm = ({cancelCallback, successCallback, courseId, quizId, contentId,
                 onChange={(e) => setRequiredScore(e.target.value)}
                 sx={{ width: '200px', mr: 2 }}
                 inputProps={{ min: 0, max: 100 }}
+                disabled={userRole === 'viewer'}
                 >
             </RequiredTextField>
             </Box>
@@ -254,19 +255,20 @@ const QuizForm = ({cancelCallback, successCallback, courseId, quizId, contentId,
                     onChange={(e) => setWaitingPeriod(e.target.value)}
                     sx={{ width: '200px', mr: 2 }}
                     inputProps={{ min: 1 }}
+                    disabled={userRole === 'viewer'}
                 />
-                <Select size="small" value={waitingPeriodUnit} onChange={(e) => setWaitingPeriodUnit(e.target.value)} name="waiting_period_unit" sx={{ width: '150px' }}>
+                <Select size="small" value={waitingPeriodUnit} onChange={(e) => setWaitingPeriodUnit(e.target.value)} name="waiting_period_unit" sx={{ width: '150px' }} disabled={userRole === 'viewer'}>
                     <MenuItem value="days">Days</MenuItem>
                     <MenuItem value="hours">Hours</MenuItem>
                 </Select>
             </Tooltip>
             <Box mt={2} textAlign="right">
                 <Button variant="outlined" sx={{ mr: 1, boxShadow: 'none' }} onClick={cancel}>
-                    Cancel
+                    Back
                 </Button>
-                <Button type="submit" variant="contained" color="primary" sx={{ boxShadow: 'none' }} onClick={() => {if(!quizId) { addQuiz(); } else { updateQuiz(); }}}>
+                {userRole !== 'viewer' && <Button type="submit" variant="contained" color="primary" sx={{ boxShadow: 'none' }} onClick={() => {if(!quizId) { addQuiz(); } else { updateQuiz(); }}}>
                     Save Quiz
-                </Button>
+                </Button>}
             </Box>
         </Box>
     );
diff --git a/frontend/courses/Courses.jsx b/frontend/courses/Courses.jsx
index 53e731f..297a395 100644
--- a/frontend/courses/Courses.jsx
+++ b/frontend/courses/Courses.jsx
@@ -20,6 +20,7 @@ function Courses() {
   const [courses, setCourses] = useState([])
   const [organizationId, setOrganizationId] = useState(null);
   const [queryParameters, setQueryParameters] = useState("");
+  const userRole = localStorage.getItem('userRole');
   const apiBaseUrl = localStorage.getItem('apiBaseUrl');
   const platformBaseUrl = localStorage.getItem('platformBaseUrl');
 
@@ -106,7 +107,7 @@ function Courses() {
     >
       <Grid size={{xs: 12, md: 9}} py={2} pl={2}>
         <Box p={2} sx={{ border: '1px solid', borderColor: 'border.main', backgroundColor: 'background.main', borderRadius: 1, minHeight: 300 }}>
-        <Button variant="contained" startIcon={<SchoolIcon />} sx={{ marginBottom: 2 }} onClick={() => {
+        {userRole !== 'viewer' && <Button variant="contained" startIcon={<SchoolIcon />} sx={{ marginBottom: 2 }} onClick={() => {
           setDialogContent(<CourseForm
             successCallback={handleCourseCreated}
             failureCallback={handleCourseCreationFailed}
@@ -114,7 +115,7 @@ function Courses() {
             activeOrganizationId={organizationId}
             createMode={true}
           />);
-          setDialogOpen(true);}}>Add a Course</Button>
+          setDialogOpen(true);}}>Add a Course</Button>}
         <TableContainer component={Paper}>
           <Table sx={{ width: "100%" }} aria-label="Courses">
             <TableHead>
@@ -122,7 +123,7 @@ function Courses() {
                 <TableCell>Title</TableCell>
                 <TableCell>Slug</TableCell>
                 <TableCell>Enabled</TableCell>
-                <TableCell align='right'>Actions</TableCell>
+                {userRole !== 'viewer' && <TableCell align='right'>Actions</TableCell>}
               </TableRow>
             </TableHead>
             <TableBody>
@@ -140,9 +141,10 @@ function Courses() {
                       checked={course.enabled}
                       onChange={showEnableCoursePopup(course.id, course.enabled ? 'disable' : 'enable', course.title)}
                       slotProps={{ input: { 'aria-label': course.enabled ? 'Disable Course' : 'Enable Course' } }}
+                      disabled={userRole === 'viewer'}
                     />
                   </TableCell>
-                  <TableCell align="right">
+                  {userRole !== 'viewer' && <TableCell align="right">
                     <IconButton onClick={() => {
                       showEditCourseDialog(course);}}><EditIcon fontSize="small" /></IconButton>
                     <IconButton aria-label={`Delete ${course.title}`} onClick={() => {
@@ -152,7 +154,7 @@ function Courses() {
                     }} />);
                     setDialogOpen(true);
                   }}><DeleteIcon fontSize="small" /></IconButton>
-                  </TableCell>
+                  </TableCell>}
                 </TableRow>
               ))}
             </TableBody>
diff --git a/frontend/src/components/ContentEditor.jsx b/frontend/src/components/ContentEditor.jsx
index 132414b..6cc44f8 100644
--- a/frontend/src/components/ContentEditor.jsx
+++ b/frontend/src/components/ContentEditor.jsx
@@ -20,7 +20,7 @@ import FormatBoldIcon from '@mui/icons-material/FormatBold';
 import ImageIcon from '@mui/icons-material/Image';
 
 
-function ContentEditor({ initialContent, contentUpdateCallback }) {
+function ContentEditor({ initialContent, contentUpdateCallback, disabled = false }) {
     const editor = useEditor({
         extensions: [
             Document,
@@ -40,6 +40,7 @@ function ContentEditor({ initialContent, contentUpdateCallback }) {
             }),
             Dropcursor,],
         content: initialContent,
+        editable: !disabled,
         autofocus: true,
         onUpdate: ({ editor }) => {
             contentUpdateCallback(editor.getHTML());
@@ -54,7 +55,7 @@ function ContentEditor({ initialContent, contentUpdateCallback }) {
         <Paper elevation={2} sx={{ width: '100%' }}>
             <EditorContext.Provider value={{ editor }}>
                 {/* Material UI Toolbar */}
-                <Toolbar variant="dense" sx={{
+                {!disabled && <Toolbar variant="dense" sx={{
                     backgroundColor: 'background.nav',
                     borderBottom: '1px solid',
                     borderColor: 'divider'
@@ -111,7 +112,7 @@ function ContentEditor({ initialContent, contentUpdateCallback }) {
                         <CodeIcon />
                     </IconButton>
                     </Tooltip>
-                </Toolbar>
+                </Toolbar>}
 
                 {/* TipTap Editor wrapped in Material UI Box */}
                 <Box
diff --git a/tests/services/__init__.py b/tests/services/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/tests/services/defaults/__init__.py b/tests/services/defaults/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/tests/services/defaults/test_email_sender.py b/tests/services/defaults/test_email_sender.py
new file mode 100644
index 0000000..47ab536
--- /dev/null
+++ b/tests/services/defaults/test_email_sender.py
@@ -0,0 +1,40 @@
+from django_email_learning.services.deafults.email_sender import DjangoEmailSender
+from django.core.mail import EmailMultiAlternatives
+from unittest.mock import Mock
+import pytest
+
+
+@pytest.fixture
+def email_sender() -> DjangoEmailSender:
+    return DjangoEmailSender()
+
+
+@pytest.fixture
+def email_multi_alternatives() -> EmailMultiAlternatives:
+    email = Mock(spec=EmailMultiAlternatives)
+    email.to = ["recipient@example.com"]
+    return email
+
+
+def test_email_sender_logs_success_with_masked_recipients(
+    email_sender: DjangoEmailSender,
+    email_multi_alternatives: EmailMultiAlternatives,
+    caplog,
+):
+    with caplog.at_level("INFO"):
+        email_sender.send_email(email_multi_alternatives)
+    assert "Sending email to r***@example.com" in caplog.text
+
+
+def test_email_sender_logs_failure_with_masked_recipients(
+    email_sender: DjangoEmailSender,
+    email_multi_alternatives: EmailMultiAlternatives,
+    caplog,
+):
+    email_multi_alternatives.send.side_effect = Exception("SMTP error")
+
+    with caplog.at_level("ERROR"):
+        with pytest.raises(Exception):
+            email_sender.send_email(email_multi_alternatives)
+
+    assert "Failed to send email to r***@example.com" in caplog.text