How Do I Send Automatic Emails in Outlook? A Step-by-Step Guide

Email automation is essential for professionals and businesses looking to streamline communication, improve response times, and eliminate repetitive tasks. However, while Outlook supports some automation, its capabilities are limited to fully automating recurring emails.

This guide will walk you through the various ways to send automatic emails in Outlook, from basic built-in options to advanced third-party tools. By the end of this guide, you’ll have a clear strategy to automate emails effectively—whether using Outlook’s features or external automation solutions.

What Are Automatic Emails in Outlook?

Before setting up automatic emails, it’s important to understand what they are and how they can enhance workflow efficiency. Automatic emails are pre-written messages that are either scheduled for delivery at a specific time or triggered by predefined actions. These messages help ensure consistency, timeliness, and improved communication across teams, clients, and customers.

Key benefits of automating emails in Outlook:

• Saves Time: Eliminates manual effort in sending repetitive emails.
• Improves Communication: Ensures that responses, follow-ups, and reminders are sent without delay.
• Enhances Customer Engagement: Helps businesses nurture leads, send timely notifications, and build better relationships.

Now, let’s explore how Outlook’s email automation features can be used in various scenarios.

How to Set Up Automatic Emails in Microsoft Outlook

Automating emails in Outlook can help you stay responsive, manage communication efficiently, and save time. Whether you need to set up out-of-office replies, schedule emails in advance, or create recurring messages, Outlook provides various built-in tools. 

However, the available options differ depending on whether you're using Classic Outlook (Microsoft 365) or the New Outlook (2025 update). This section will walk you through the step-by-step process for recurring email settings and provide best practices to ensure they work effectively.

1. Setting Up Automatic Replies (Out-of-Office Emails) in Outlook

‍Out-of-office emails are essential for informing colleagues, clients, and partners that you're unavailable. These automatic replies ensure that important contacts receive an immediate response, reducing the chances of miscommunication or missed opportunities.

How to Set Up Automatic Replies in Classic Outlook (Microsoft 365)

If you're using the classic desktop version of Outlook that comes with Microsoft 365, follow these steps:

1. Open Outlook and go to File > Automatic Replies (Out of Office).
2. Select "Send automatic replies."
3. (Optional) Check “Only send during this time range” and set the start and end times if you want replies to be enabled only during a specific period.
4. Under "Inside My Organization," enter your auto-reply message for colleagues within your company.
5. Under "Outside My Organization," enter a separate message for external contacts (e.g., clients, vendors).
6. (Optional) Select "Send replies only to contacts" to prevent responses from being sent to newsletters, spam, or promotional emails.
7. Click OK to activate automatic replies.

How to Set Up Automatic Replies in New Outlook

If you are using the New Outlook, the process is slightly different:

1. Click Settings (⚙️) > Accounts > Automatic Replies.
2. Toggle “Turn on automatic replies.”
3. (Optional) Set a start and end time for automatic replies to turn on and off automatically.
4. Enter your out-of-office message for both internal and external contacts.
5. Click Save to apply the settings.

Best Practices for an Out-of-Office Message

An out-of-office message should be brief, professional and informative. It should include:

• A greeting – Be polite.
• Your availability – Optional: why you’re out and when you’ll be back.
• Alternative contact – Email or phone number of a colleague for emergencies.
• Closing – Thank them for their patience.

For example:

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"Thanks for your email. I’m out of the office and will be back [return date]. If urgent, contact [alternative contact] at [email/phone number]. Otherwise, I’ll get back to you as soon as I’m back.

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[Your Name]"

2. Scheduling Emails in Microsoft Outlook

‍If you need to send an email at a specific time in the future, Outlook’s Delay Delivery feature allows you to schedule emails in advance.

How to Schedule Emails in Outlook (Classic & New Outlook)

1. Compose a new email in Outlook.
2. Click Options > Delay Delivery.
3. Under Delivery options, check “Do not deliver before” and select the date and time.
4. Click Close, then hit Send—your email will stay in the Outbox until the scheduled time.

Note: Scheduled emails require Outlook to be open and running. If Outlook is closed, the email will not be sent until you open it again.

3. Automating Recurring Emails in Microsoft Outlook

‍If you frequently send daily, weekly, or monthly emails, automating them can save time. However, Outlook does not have a built-in recurring email feature. Below are two workarounds:

‍Use Outlook Calendar for Recurring Email Reminders

‍This method reminds you to send an email manually at a set interval.

1. Open Outlook Calendar and create a new appointment.
2. In the Title field, enter the subject of your email (e.g., “Weekly Team Report”).
3. In the Notes section, draft your email content.
4. Click Recurrence and select how often you want the reminder (daily, weekly, monthly).
5. Save the event—Outlook will now remind you to send the email at the set time.

Drawback: This method does not automate sending the email—it only reminds you to do it manually.

4. Automating Email Responses Using Outlook Rules

‍Outlook’s Rules feature allows you to automatically respond to certain emails, forward messages, or categorize emails based on specific criteria.

How to Create an Automatic Email Response Rule:

1. Go to File > Manage Rules & Alerts.
2. Click New Rule > Apply rule on messages I receive.
3. Set conditions (e.g., emails from a specific sender or with certain keywords).
4. Select “Reply using a specific template” and create your automatic response.
5. Click Next > Finish to activate the rule.

Use Case: Set up an automatic response for customer inquiries or support tickets when you are unavailable.

Best Practices for Sending Automatic Emails in Microsoft Outlook

‍Now that you know how to automate emails in Outlook, optimizing them for maximum effectiveness is essential. Poorly executed automation of multiple emails can lead to miscommunication, overlooked messages, or even emails being marked as spam.

These best practices will ensure your emails are professional, well-received, and achieve their intended purpose:

1. Personalization Is Key

‍Automated emails don’t have to feel robotic. Personalizing your messages can significantly improve engagement and make your communication feel more thoughtful and relevant.

• Use recipient names – Emails with personalized subject lines tend to be noticed and opened more often. A simple “Hi [Name]” can make a difference.
• Reference relevant details—To tailor the email, Include specific information such as prior conversations, project details, or meeting times.
• Leverage AI tools – AI-powered assistants like MailMaestro can generate personalized content while maintaining the consistency of automated responses.

Incorporating personalization will make your automated emails more natural and professional rather than generic and impersonal.

2. Maintain Clarity and Professionalism

‍Since automated emails often serve as out-of-office responses, follow-ups, or reminders, it is crucial to ensure they are clear, concise, and professional.

• Be direct but polite – Automated emails should get straight to the point while maintaining a courteous tone.
• Avoid overly complex or vague language – Ensure your message is easy to understand and contains all necessary details.
• Set the right expectations—If an email confirms receipt of a message or sets a follow-up timeframe, clearly communicate when the recipient can expect a response.
• Use a consistent format – Structure your emails with greetings, key information, and closings for readability and professionalism.

A well-structured automated email prevents confusion and ensures recipients clearly understand the message.

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3. Avoid Spam Filters

‍Even professional automated emails can end up in spam folders if they are not optimized correctly. Following these best practices will help ensure your emails land in the recipient’s inbox:

• Avoid excessive capitalization, exclamation marks, and spammy phrases – Subject lines like “URGENT!!! IMPORTANT!!!” can trigger spam filters.
• Use a verified sender domain – Sending emails from a professional domain (e.g., yourname@company.com) instead of a free email provider (e.g., Gmail, Yahoo) improves deliverability.
• Send emails at appropriate times – Automated emails sent during standard business hours (e.g., mid-morning on weekdays) are more likely to be read.

Optimizing your emails for deliverability ensures they reach the recipient and are not mistakenly flagged as spam.

Final Words

Automating emails in Outlook streamlines communication and saves valuable time by minimizing manual effort. While Outlook provides basic automation features like out-of-office replies, delayed emails, and rules, it lacks built-in support for fully automated recurring emails.

That’s where MailMaestro comes in. With AI-powered tools designed for effortless email writing and management, you can easily manage recurring emails, stay organized, and boost productivity. Experience the convenience of smart email writing and magic templates—try MailMaestro today and take control of your inbox!

FAQs on Sending Automatic Emails in Microsoft Outlook

Can I set automatic replies for specific contacts or groups in Outlook?

Yes, you can customize automatic replies using Rules. You can set different out-of-office messages for internal and external contacts or specify certain groups or email addresses that trigger different responses.

How do I make my automatic replies professional?

To make your automatic replies professional, keep the message polite, brief and informative. Always include the reason for your absence, expected return date and alternative contacts. Don’t use excessive punctuation or informal language, which will make your response look unprofessional.

Can I send an email later in Outlook without using third-party tools?

Yes, you can send an email later in Outlook using the "Delay Delivery" feature. This allows you to compose an email and set a specific time and date for it to be delivered. However, this feature doesn’t support recurring emails, so you would need to schedule each email individually.

How can I prevent my out-of-office messages from going to spam?

To reduce the chance of your out-of-office messages being marked as spam avoid using trigger words like “urgent” or “limited time” and don’t use excessive capitalization or exclamation marks. Also, ensure your email comes from a verified professional domain, not a free email provider.

Can I automate follow-up emails for customer service inquiries in Outlook?

Outlook doesn’t have an out-of-the-box feature for fully automating follow-up emails but you can use the “Rules” feature to set up automatic responses to certain types of emails. For more advanced automation (like sending personalized follow-ups or reminders), you can use Power Automate or integrate third-party tools to create a more customized solution.