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Automate Email Sending with Python: Complete Guide with Attachments

Alex Rodriguez13 min read

Automate Email Sending with Python: Complete Guide with Attachments

You send the same types of emails every week. Status reports to your team. Invoices to clients. Reminders to stakeholders. Each one takes a few minutes—minutes that add up to hours.

Let Python send your emails while you focus on work that actually matters.

What You'll Learn

  • Sending emails with Python's built-in libraries
  • Using Gmail and other email providers
  • Adding HTML formatting for professional emails
  • Attaching files (PDFs, Excel, images)
  • Creating email templates for reuse

Prerequisites

  • Python 3.8 or higher
  • An email account (Gmail recommended for this tutorial)
  • App Password for Gmail (we'll show you how to set this up)

The Problem

Manual email tasks that eat your time:

  • Weekly status reports to multiple recipients
  • Sending invoices or documents to clients
  • Reminder emails on schedules
  • Bulk notifications to teams
  • Personalizing repetitive emails

The Solution

A Python script that:

  1. Connects to your email provider
  2. Composes professional emails (plain text or HTML)
  3. Attaches files when needed
  4. Sends to one or multiple recipients
  5. Can be scheduled to run automatically

Step 1: Setting Up Gmail App Password

For security, Gmail requires an "App Password" instead of your regular password:

  1. Go to your Google Account (myaccount.google.com)
  2. Select Security on the left
  3. Under "Signing in to Google," select 2-Step Verification (enable if not already)
  4. At the bottom, select App passwords
  5. Select app: "Mail" and device: "Other (Custom name)"
  6. Enter a name like "Python Email Script"
  7. Click Generate
  8. Copy the 16-character password (you'll only see it once!)

Important: Store this password securely, never in your code.

Step 2: Sending a Simple Email

Let's start with the basics:

python
1import smtplib
2from email.mime.text import MIMEText
3from email.mime.multipart import MIMEMultipart
4
5def send_simple_email(to_email, subject, body):
6    """
7    Send a simple text email.
8    
9    Args:
10        to_email: Recipient email address
11        subject: Email subject line
12        body: Email body text
13    """
14    # Your email credentials
15    sender_email = "your.email@gmail.com"
16    app_password = "your-16-char-app-password"  # Use environment variable in production!
17    
18    # Create the email
19    message = MIMEMultipart()
20    message["From"] = sender_email
21    message["To"] = to_email
22    message["Subject"] = subject
23    
24    # Attach the body
25    message.attach(MIMEText(body, "plain"))
26    
27    # Connect to Gmail and send
28    try:
29        with smtplib.SMTP_SSL("smtp.gmail.com", 465) as server:
30            server.login(sender_email, app_password)
31            server.sendmail(sender_email, to_email, message.as_string())
32        
33        print(f"✅ Email sent to {to_email}")
34        return True
35        
36    except Exception as e:
37        print(f"❌ Failed to send email: {e}")
38        return False
39
40# Example usage
41send_simple_email(
42    to_email="colleague@company.com",
43    subject="Quick Update",
44    body="Hi,\n\nJust wanted to share a quick update on the project.\n\nBest regards"
45)

Step 3: Sending HTML Emails

Plain text is fine, but HTML emails look professional:

python
1def send_html_email(to_email, subject, html_content, plain_text=None):
2    """
3    Send an HTML formatted email with plain text fallback.
4    
5    Args:
6        to_email: Recipient email address
7        subject: Email subject line
8        html_content: HTML body content
9        plain_text: Optional plain text alternative
10    """
11    sender_email = "your.email@gmail.com"
12    app_password = "your-16-char-app-password"
13    
14    message = MIMEMultipart("alternative")
15    message["From"] = sender_email
16    message["To"] = to_email
17    message["Subject"] = subject
18    
19    # Plain text version (for email clients that don't support HTML)
20    if plain_text:
21        message.attach(MIMEText(plain_text, "plain"))
22    
23    # HTML version
24    message.attach(MIMEText(html_content, "html"))
25    
26    try:
27        with smtplib.SMTP_SSL("smtp.gmail.com", 465) as server:
28            server.login(sender_email, app_password)
29            server.sendmail(sender_email, to_email, message.as_string())
30        
31        print(f"✅ HTML email sent to {to_email}")
32        return True
33        
34    except Exception as e:
35        print(f"❌ Failed to send email: {e}")
36        return False
37
38# Example HTML email
39html = """
40<html>
41<body style="font-family: Arial, sans-serif; line-height: 1.6;">
42    <h2 style="color: #333;">Weekly Status Report</h2>
43    <p>Hi Team,</p>
44    <p>Here's the update for this week:</p>
45    
46    <table style="border-collapse: collapse; width: 100%;">
47        <tr style="background-color: #4472C4; color: white;">
48            <th style="padding: 10px; border: 1px solid #ddd;">Task</th>
49            <th style="padding: 10px; border: 1px solid #ddd;">Status</th>
50        </tr>
51        <tr>
52            <td style="padding: 10px; border: 1px solid #ddd;">Feature Development</td>
53            <td style="padding: 10px; border: 1px solid #ddd;">✅ Complete</td>
54        </tr>
55        <tr>
56            <td style="padding: 10px; border: 1px solid #ddd;">Testing</td>
57            <td style="padding: 10px; border: 1px solid #ddd;">🔄 In Progress</td>
58        </tr>
59    </table>
60    
61    <p>Best regards,<br>Alex</p>
62</body>
63</html>
64"""
65
66send_html_email(
67    to_email="team@company.com",
68    subject="Weekly Status Report - Week 45",
69    html_content=html
70)

Step 4: Adding Attachments

Emails often need attachments—reports, invoices, images:

python
1from email.mime.base import MIMEBase
2from email import encoders
3import os
4
5def send_email_with_attachment(to_email, subject, body, attachment_paths):
6    """
7    Send an email with one or more attachments.
8    
9    Args:
10        to_email: Recipient email address
11        subject: Email subject line
12        body: Email body text
13        attachment_paths: List of file paths to attach
14    """
15    sender_email = "your.email@gmail.com"
16    app_password = "your-16-char-app-password"
17    
18    message = MIMEMultipart()
19    message["From"] = sender_email
20    message["To"] = to_email
21    message["Subject"] = subject
22    
23    # Add body
24    message.attach(MIMEText(body, "plain"))
25    
26    # Add attachments
27    for filepath in attachment_paths:
28        if not os.path.exists(filepath):
29            print(f"⚠️ Attachment not found: {filepath}")
30            continue
31        
32        filename = os.path.basename(filepath)
33        
34        # Read and encode the file
35        with open(filepath, "rb") as f:
36            attachment = MIMEBase("application", "octet-stream")
37            attachment.set_payload(f.read())
38        
39        encoders.encode_base64(attachment)
40        attachment.add_header(
41            "Content-Disposition",
42            f"attachment; filename={filename}"
43        )
44        
45        message.attach(attachment)
46        print(f"📎 Attached: {filename}")
47    
48    try:
49        with smtplib.SMTP_SSL("smtp.gmail.com", 465) as server:
50            server.login(sender_email, app_password)
51            server.sendmail(sender_email, to_email, message.as_string())
52        
53        print(f"✅ Email with attachments sent to {to_email}")
54        return True
55        
56    except Exception as e:
57        print(f"❌ Failed to send email: {e}")
58        return False
59
60# Example usage
61send_email_with_attachment(
62    to_email="client@company.com",
63    subject="Monthly Report - November 2025",
64    body="Hi,\n\nPlease find the monthly report attached.\n\nBest regards",
65    attachment_paths=["./reports/november_2025.pdf", "./reports/summary.xlsx"]
66)

Step 5: Using Email Templates

Create reusable templates for common emails:

python
1def load_template(template_name, **kwargs):
2    """
3    Load an email template and fill in placeholders.
4    
5    Args:
6        template_name: Name of the template
7        **kwargs: Values to substitute into template
8    
9    Returns:
10        Tuple of (subject, html_content)
11    """
12    templates = {
13        "weekly_report": {
14            "subject": "Weekly Report - {week_date}",
15            "html": """
16            <html>
17            <body style="font-family: Arial, sans-serif;">
18                <h2>Weekly Report</h2>
19                <p>Hi {recipient_name},</p>
20                <p>Here's the weekly summary for {week_date}:</p>
21                
22                <h3>Highlights</h3>
23                <ul>
24                    {highlights}
25                </ul>
26                
27                <h3>Metrics</h3>
28                <p>Tasks Completed: <strong>{tasks_completed}</strong></p>
29                <p>Hours Worked: <strong>{hours_worked}</strong></p>
30                
31                <p>Best regards,<br>{sender_name}</p>
32            </body>
33            </html>
34            """
35        },
36        "invoice_reminder": {
37            "subject": "Invoice #{invoice_number} - Payment Reminder",
38            "html": """
39            <html>
40            <body style="font-family: Arial, sans-serif;">
41                <h2>Payment Reminder</h2>
42                <p>Dear {client_name},</p>
43                
44                <p>This is a friendly reminder that Invoice #{invoice_number} 
45                   for <strong>${amount}</strong> is due on <strong>{due_date}</strong>.</p>
46                
47                <p>If you've already sent payment, please disregard this message.</p>
48                
49                <p>Thank you for your business!</p>
50                <p>Best regards,<br>{company_name}</p>
51            </body>
52            </html>
53            """
54        },
55        "meeting_followup": {
56            "subject": "Follow-up: {meeting_topic}",
57            "html": """
58            <html>
59            <body style="font-family: Arial, sans-serif;">
60                <h2>Meeting Follow-up</h2>
61                <p>Hi {recipient_name},</p>
62                
63                <p>Thank you for meeting with me on {meeting_date} regarding {meeting_topic}.</p>
64                
65                <h3>Action Items</h3>
66                <ul>
67                    {action_items}
68                </ul>
69                
70                <h3>Next Steps</h3>
71                <p>{next_steps}</p>
72                
73                <p>Please let me know if you have any questions.</p>
74                <p>Best regards,<br>{sender_name}</p>
75            </body>
76            </html>
77            """
78        }
79    }
80    
81    if template_name not in templates:
82        raise ValueError(f"Template '{template_name}' not found")
83    
84    template = templates[template_name]
85    
86    subject = template["subject"].format(**kwargs)
87    html = template["html"].format(**kwargs)
88    
89    return subject, html
90
91
92# Example usage
93subject, html = load_template(
94    "weekly_report",
95    recipient_name="Team",
96    week_date="November 10-14, 2025",
97    highlights="<li>Completed feature X</li><li>Fixed 12 bugs</li><li>Onboarded new team member</li>",
98    tasks_completed=25,
99    hours_worked=42,
100    sender_name="Alex"
101)
102
103send_html_email("team@company.com", subject, html)

The Complete Script

python
1#!/usr/bin/env python3
2"""
3Email Automation - Send professional emails with Python.
4Author: Alex Rodriguez
5
6This script sends emails with HTML formatting and attachments.
7Supports templates for common email types.
8"""
9
10import os
11import smtplib
12from email import encoders
13from email.mime.base import MIMEBase
14from email.mime.multipart import MIMEMultipart
15from email.mime.text import MIMEText
16from datetime import datetime
17
18
19# ========================================
20# CONFIGURATION
21# ========================================
22
23# Email credentials - USE ENVIRONMENT VARIABLES IN PRODUCTION!
24SMTP_SERVER = "smtp.gmail.com"
25SMTP_PORT = 465
26SENDER_EMAIL = os.environ.get("EMAIL_ADDRESS", "your.email@gmail.com")
27SENDER_PASSWORD = os.environ.get("EMAIL_PASSWORD", "your-app-password")
28SENDER_NAME = "Alex Rodriguez"
29
30
31# ========================================
32# EMAIL TEMPLATES
33# ========================================
34
35TEMPLATES = {
36    "report": {
37        "subject": "{report_type} Report - {date}",
38        "html": """
39        <html>
40        <body style="font-family: Arial, sans-serif; max-width: 600px; margin: 0 auto;">
41            <div style="background-color: #4472C4; color: white; padding: 20px; text-align: center;">
42                <h1 style="margin: 0;">{report_type} Report</h1>
43                <p style="margin: 5px 0 0 0;">{date}</p>
44            </div>
45            
46            <div style="padding: 20px;">
47                <p>Hi {recipient_name},</p>
48                <p>{intro_text}</p>
49                
50                {content}
51                
52                <p style="margin-top: 30px;">Best regards,<br><strong>{sender_name}</strong></p>
53            </div>
54            
55            <div style="background-color: #f5f5f5; padding: 10px; text-align: center; font-size: 12px; color: #666;">
56                This is an automated message. Please do not reply directly.
57            </div>
58        </body>
59        </html>
60        """
61    },
62    "notification": {
63        "subject": "[{priority}] {title}",
64        "html": """
65        <html>
66        <body style="font-family: Arial, sans-serif;">
67            <div style="border-left: 4px solid {color}; padding-left: 15px;">
68                <h2 style="color: {color};">{title}</h2>
69                <p>{message}</p>
70                {details}
71            </div>
72            <p style="color: #666; font-size: 12px; margin-top: 30px;">
73                Sent at {timestamp}
74            </p>
75        </body>
76        </html>
77        """
78    }
79}
80
81
82def get_priority_color(priority):
83    """Get color based on priority level."""
84    colors = {
85        "high": "#dc3545",
86        "medium": "#ffc107", 
87        "low": "#28a745",
88        "info": "#17a2b8"
89    }
90    return colors.get(priority.lower(), "#6c757d")
91
92
93# ========================================
94# CORE EMAIL FUNCTIONS
95# ========================================
96
97def create_email(to_email, subject, html_content, plain_text=None, attachments=None):
98    """
99    Create an email message with optional attachments.
100    
101    Args:
102        to_email: Recipient(s) - string or list
103        subject: Email subject
104        html_content: HTML body
105        plain_text: Optional plain text alternative
106        attachments: Optional list of file paths
107    
108    Returns:
109        MIMEMultipart message object
110    """
111    message = MIMEMultipart("mixed")
112    message["From"] = f"{SENDER_NAME} <{SENDER_EMAIL}>"
113    message["Subject"] = subject
114    
115    # Handle multiple recipients
116    if isinstance(to_email, list):
117        message["To"] = ", ".join(to_email)
118    else:
119        message["To"] = to_email
120    
121    # Create body container
122    body = MIMEMultipart("alternative")
123    
124    # Add plain text version
125    if plain_text:
126        body.attach(MIMEText(plain_text, "plain", "utf-8"))
127    
128    # Add HTML version
129    body.attach(MIMEText(html_content, "html", "utf-8"))
130    
131    message.attach(body)
132    
133    # Add attachments
134    if attachments:
135        for filepath in attachments:
136            if not os.path.exists(filepath):
137                print(f"⚠️ Attachment not found: {filepath}")
138                continue
139            
140            with open(filepath, "rb") as f:
141                attachment = MIMEBase("application", "octet-stream")
142                attachment.set_payload(f.read())
143            
144            encoders.encode_base64(attachment)
145            filename = os.path.basename(filepath)
146            attachment.add_header(
147                "Content-Disposition",
148                f"attachment; filename={filename}"
149            )
150            message.attach(attachment)
151    
152    return message
153
154
155def send_email(message, to_email):
156    """
157    Send an email message.
158    
159    Args:
160        message: MIMEMultipart message object
161        to_email: Recipient(s) - string or list
162    
163    Returns:
164        True if successful, False otherwise
165    """
166    recipients = to_email if isinstance(to_email, list) else [to_email]
167    
168    try:
169        with smtplib.SMTP_SSL(SMTP_SERVER, SMTP_PORT) as server:
170            server.login(SENDER_EMAIL, SENDER_PASSWORD)
171            server.sendmail(SENDER_EMAIL, recipients, message.as_string())
172        
173        print(f"✅ Email sent to: {', '.join(recipients)}")
174        return True
175        
176    except smtplib.SMTPAuthenticationError:
177        print("❌ Authentication failed. Check your email and app password.")
178    except smtplib.SMTPException as e:
179        print(f"❌ SMTP error: {e}")
180    except Exception as e:
181        print(f"❌ Failed to send email: {e}")
182    
183    return False
184
185
186def send_report(to_email, report_type, content, attachments=None, recipient_name="Team"):
187    """
188    Send a report email using the report template.
189    
190    Args:
191        to_email: Recipient email(s)
192        report_type: Type of report (e.g., "Weekly", "Monthly")
193        content: HTML content for the report body
194        attachments: Optional list of file paths
195        recipient_name: Name to address in email
196    """
197    template = TEMPLATES["report"]
198    
199    subject = template["subject"].format(
200        report_type=report_type,
201        date=datetime.now().strftime("%B %d, %Y")
202    )
203    
204    html = template["html"].format(
205        report_type=report_type,
206        date=datetime.now().strftime("%B %d, %Y"),
207        recipient_name=recipient_name,
208        intro_text="Please find the latest report below.",
209        content=content,
210        sender_name=SENDER_NAME
211    )
212    
213    message = create_email(to_email, subject, html, attachments=attachments)
214    return send_email(message, to_email)
215
216
217def send_notification(to_email, title, message_text, priority="info", details=""):
218    """
219    Send a notification email.
220    
221    Args:
222        to_email: Recipient email(s)
223        title: Notification title
224        message_text: Main message
225        priority: high, medium, low, or info
226        details: Optional additional details (HTML)
227    """
228    template = TEMPLATES["notification"]
229    color = get_priority_color(priority)
230    
231    subject = template["subject"].format(
232        priority=priority.upper(),
233        title=title
234    )
235    
236    html = template["html"].format(
237        color=color,
238        title=title,
239        message=message_text,
240        details=details,
241        timestamp=datetime.now().strftime("%Y-%m-%d %H:%M:%S")
242    )
243    
244    message = create_email(to_email, subject, html)
245    return send_email(message, to_email)
246
247
248def send_bulk_emails(recipients, subject, html_content, personalize_func=None):
249    """
250    Send emails to multiple recipients with optional personalization.
251    
252    Args:
253        recipients: List of dicts with 'email' and any personalization fields
254        subject: Email subject
255        html_content: HTML content (with {placeholders} for personalization)
256        personalize_func: Optional function to customize content per recipient
257    
258    Returns:
259        Dict with success/failure counts
260    """
261    import time
262    
263    results = {"sent": 0, "failed": 0}
264    
265    for i, recipient in enumerate(recipients):
266        email = recipient.get("email")
267        
268        if not email:
269            print(f"⚠️ Skipping recipient {i+1}: no email address")
270            results["failed"] += 1
271            continue
272        
273        # Personalize content
274        if personalize_func:
275            personalized_html = personalize_func(html_content, recipient)
276        else:
277            personalized_html = html_content.format(**recipient)
278        
279        message = create_email(email, subject, personalized_html)
280        
281        if send_email(message, email):
282            results["sent"] += 1
283        else:
284            results["failed"] += 1
285        
286        # Rate limiting - don't spam the server
287        if i < len(recipients) - 1:
288            time.sleep(1)
289    
290    print(f"\n📊 Bulk email results: {results['sent']} sent, {results['failed']} failed")
291    return results
292
293
294# ========================================
295# MAIN
296# ========================================
297
298def main():
299    """Example usage of email automation functions."""
300    
301    print("=" * 60)
302    print("EMAIL AUTOMATION")
303    print("=" * 60)
304    
305    # Check configuration
306    if SENDER_PASSWORD == "your-app-password":
307        print("\n⚠️ Please configure your email credentials!")
308        print("   Set EMAIL_ADDRESS and EMAIL_PASSWORD environment variables")
309        print("   Or update the SENDER_EMAIL and SENDER_PASSWORD constants")
310        return
311    
312    # Example 1: Send a simple report
313    print("\n📧 Example 1: Sending report...")
314    
315    report_content = """
316    <h3>Summary</h3>
317    <ul>
318        <li>Tasks completed: 15</li>
319        <li>Hours logged: 40</li>
320        <li>Issues resolved: 8</li>
321    </ul>
322    
323    <h3>Next Week</h3>
324    <p>Focus areas: Feature development, testing, documentation</p>
325    """
326    
327    send_report(
328        to_email="recipient@example.com",
329        report_type="Weekly",
330        content=report_content,
331        recipient_name="Team"
332    )
333    
334    # Example 2: Send a notification
335    print("\n📧 Example 2: Sending notification...")
336    
337    send_notification(
338        to_email="recipient@example.com",
339        title="Deployment Complete",
340        message_text="Version 2.5.0 has been successfully deployed to production.",
341        priority="info",
342        details="<p>Changes: Bug fixes, performance improvements</p>"
343    )
344    
345    # Example 3: Bulk personalized emails
346    print("\n📧 Example 3: Bulk emails (demo)...")
347    
348    recipients = [
349        {"email": "alice@example.com", "name": "Alice", "role": "Developer"},
350        {"email": "bob@example.com", "name": "Bob", "role": "Designer"},
351    ]
352    
353    html_template = """
354    <html>
355    <body>
356        <h2>Hello {name}!</h2>
357        <p>This is a personalized message for our {role}.</p>
358    </body>
359    </html>
360    """
361    
362    # Uncomment to actually send:
363    # send_bulk_emails(recipients, "Personalized Update", html_template)
364    print("   (Bulk email demo - uncomment to send)")
365    
366    print("\n✅ Email automation examples complete!")
367
368
369if __name__ == "__main__":
370    main()

How to Run This Script

  1. Set up Gmail App Password (see Step 1 above)

  2. Set environment variables:

    bash
    1# Linux/macOS
    2export EMAIL_ADDRESS="your.email@gmail.com"
    3export EMAIL_PASSWORD="your-16-char-app-password"
    4
    5# Windows (Command Prompt)
    6set EMAIL_ADDRESS=your.email@gmail.com
    7set EMAIL_PASSWORD=your-16-char-app-password
  3. Save the script as email_automation.py

  4. Run the script:

    bash
    1python email_automation.py

Customization Options

Use Other Email Providers

python
1# Outlook/Office 365
2SMTP_SERVER = "smtp.office365.com"
3SMTP_PORT = 587
4# Use STARTTLS instead of SSL:
5# with smtplib.SMTP(SMTP_SERVER, SMTP_PORT) as server:
6#     server.starttls()
7
8# Yahoo
9SMTP_SERVER = "smtp.mail.yahoo.com"
10SMTP_PORT = 465

Add CC and BCC

python
1def create_email_with_cc(to, cc, bcc, subject, html):
2    message = MIMEMultipart()
3    message["To"] = to
4    message["Cc"] = cc
5    # BCC is not added to headers
6    
7    # When sending, include all recipients:
8    all_recipients = [to] + cc.split(",") + bcc.split(",")
9    server.sendmail(SENDER_EMAIL, all_recipients, message.as_string())

Schedule Emails

Combine with task scheduling:

python
1# Run at 9 AM every Monday
2# Add to crontab: 0 9 * * 1 /usr/bin/python3 /path/to/email_automation.py

Common Issues & Solutions

IssueSolution
Authentication failedCheck app password; ensure 2FA is enabled
Connection timeoutCheck firewall; try different port
Emails going to spamUse proper HTML; avoid spam trigger words
Attachments not showingCheck file paths; verify files exist
Special characters brokenUse UTF-8 encoding for MIMEText

Taking It Further

Read Replies with IMAP

python
1import imaplib
2import email
3
4def check_inbox():
5    """Read emails from inbox."""
6    mail = imaplib.IMAP4_SSL("imap.gmail.com")
7    mail.login(SENDER_EMAIL, SENDER_PASSWORD)
8    mail.select("inbox")
9    
10    _, messages = mail.search(None, "UNSEEN")
11    
12    for num in messages[0].split():
13        _, data = mail.fetch(num, "(RFC822)")
14        msg = email.message_from_bytes(data[0][1])
15        print(f"From: {msg['from']}")
16        print(f"Subject: {msg['subject']}")
17    
18    mail.close()
19    mail.logout()

Email Queue with Retry

python
1import json
2from datetime import datetime
3
4def queue_email(email_data, queue_file="email_queue.json"):
5    """Add email to send queue."""
6    try:
7        with open(queue_file) as f:
8            queue = json.load(f)
9    except FileNotFoundError:
10        queue = []
11    
12    email_data["queued_at"] = datetime.now().isoformat()
13    email_data["attempts"] = 0
14    queue.append(email_data)
15    
16    with open(queue_file, "w") as f:
17        json.dump(queue, f)
18
19def process_queue(queue_file="email_queue.json", max_attempts=3):
20    """Process queued emails with retry logic."""
21    # Implementation for processing queue
22    pass

Conclusion

You now have a complete email automation system. Send reports, notifications, and personalized bulk emails—all with professional HTML formatting and attachments.

The key is the template system. Once you create templates for your common email types, sending them becomes a single function call. Combine this with scheduling, and your routine email tasks happen automatically.

Start with one email you send regularly. Automate it. See how much time you save. Then expand to more. Before long, you'll wonder how you ever managed without it.

Your inbox, automated.

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