How to send automatic emails in Outlook? | Complete Guide

No one is interested in spending a big portion of their time being glued to your inbox and less time with your other to-do list. Well, with Outlook’s automation features you can manage sending email at scale with just one click.

You can stop the endless cycle of sending the same emails over and over again.

This guide will show you exactly how you can effortlessly send automatic email in Outlook, automated marketing campaigns that nurture leads and drive engagement and more. 

How to send automatic emails in Outlook?

Here is a step-by-step guide to set up the automatic sending of emails to Outlook.

Set outlook rules

This method offers more flexibility for creating custom email automation rules based on various criteria. Here’s a general process:

Step 1 – Access Rules & Alerts: Go to the “File” tab and select “Info” or “Manage Rules & Alerts” (depending on your Outlook version).

Step 2 – Create a New Rule:  Click on “New Rule” and choose “Apply rule on messages I receive” or “Start from a blank rule” depending on your desired trigger (incoming vs. any email).

Step 3 – Define Conditions (Optional):  Set specific conditions for when the rule should apply. You can choose criteria like keywords in the subject or sender address.

Step 4 – Choose Actions: Select the action you want the rule to perform. In this case, choose “Send a reply using a specific template” to send an automated reply based on a pre-written template.

Step 5 – Select/Create Template (Optional): If you haven’t already, create an email template containing your automated response content. Choose this template in the rule setup.

Step 6 – Refine & Save:  Review the rule summary, make any adjustments, and click “Finish” to save and activate the rule.

How to set automated Out-Of-Office (OOO) reply on Outlook?

An automatic Out of Office (OOO) reply is a handy way to let people know you’re unavailable to respond to emails immediately. This can be useful when you’re going on vacation, attending a conference, or simply taking a break from checking emails for a set period. 

By setting up an OOO message, you can manage expectations and avoid leaving senders wondering why they haven’t heard back from you.

Here I am going to cover the step to be followed using web application and windows. So first let’s have a look at the web application first.

Step 1: Click on the gear icon on the top right corner.

Step 2: Click on ‘Mail’ and then click on ‘Automatic replies’ 

how to send automatic reply in outlook

Step 3: Toggle Turn on automatic replies to ‘On’. Set start and end dates as per your requirement. 

how to send automatic reply in outlook

Step 4: Outlook provides option to set separate messages for inside and outside the organization. You can set it up as per your requirement. 

how to send automatic reply in outlook

Save and it is done.

Now we will see the steps that you need to follow for the windows system. 

Step 1: Click the File tab. Select Automatic Replies.

In the Automatic Replies box, choose Send automatic replies.

how to send automatic reply in outlook

Step 2: You can set a date and time range for your OOO message by selecting Only send during this time range and entering the start and end times.

how to send automatic reply in outlook

Step 3: Compose your OOO message in the Inside My Organization tab. You can format the text and even include hyperlinks.

Step 4: To create a separate message for external senders, select the Outside My Organization tab and type your desired message.

how to send automatic reply in outlook

Click OK to save your settings.

How to send automatic recurring emails in Outlook?

You can send recurring emails in Outlook using the “Delay Delivery” option. Here is a step by step guide. 

Step 1 – Compose Your Email:  Start by creating a new email message as usual. Include the recipient(s), subject line, and email body content.

Step 2 – Access “Delay Delivery”:  In the new email window, navigate to the “Options” tab on the ribbon at the top.  Within the “Options” tab, find the “Delay Delivery” button and click on it.

Step 3 – Set “Do Not Deliver Before” to Recurring: This will open the “Properties” window for your email.  Look for the “Do Not Deliver Before” dropdown menu and select the “Recurring” option.

Step 4 – Define the Recurrence Pattern:  The “Recurrence” section will now appear. Here, you can choose the frequency for your recurring emails. Options include daily, weekly, monthly, or yearly. You can also define the start and end date for the series of emails.

Step 5 – Send the Email:  Once you’ve configured the recurrence pattern to your liking, click “Close” on the “Properties” window and hit “Send” on your email.  The email will be sent immediately, with the delay set for the next recurrence.

The only disadvantage to this method is there’s no option to edit the original email content after it’s sent. You’d need to create a new email for any changes you want in subsequent recurrences.

You can consider third-party add-ins like Boomerang for Outlook. These offer more control over recurring emails, allowing you to edit the content before each automated send.

Outlook automatic replies Vs recurring emails

Outlook offers two functionalities that deal with sending automated emails, but they serve different purposes. 

Automatic Replies:

  • Function: Informs senders of your absence and sets expectations for response times.
  • Trigger: Manually enabled by you.
  • Content: A pre-written message crafted by you, often including information like your return date and availability for urgent matters.
  • Frequency: Runs continuously for a set period (e.g., while you’re on vacation) or indefinitely until you disable it.
  • Benefits: Lets people know you’re unavailable and manages their expectations for response.

Recurring Emails:

  • Function: Sends a pre-written email at specific intervals.
  • Trigger: Pre-defined by you based on a chosen frequency (e.g., daily, weekly, monthly).
  • Content: A pre-written email that remains the same for each recurrence (though you can create a new one for subsequent iterations).
  • Frequency: Repeats at your chosen interval until you disable it or the end date for the series arrives (if set).
  • Benefits: Automates sending regular updates, reports, reminders, or newsletters.

The table summarizes the difference. 

Automatic Replies Recurring Emails
FunctionInforms of absenceSends pre-written email
TriggerManualPre-defined (daily, weekly, etc.)
FeaturePre-written message (you define)Pre-written email (same for each recurrence)
FrequencyContinuous (set timeframe)Set interval (until disabled or end date)
BenefitsManages sender expectationsAutomates sending regular emails

Types of recurring emails to be used in Outlook

Here’s a breakdown of some recurring email types you can set up, along with details on how to make them work. 

Team Communication

This is required to keep your team on the same page by sending regular updates on project progress, upcoming deadlines, or meeting summaries.

The frequency depends on your team’s needs. Daily updates might be ideal for fast-paced projects, while weekly or bi-weekly updates might suffice for ongoing tasks.

You should craft a clear and concise email template. Here’s what to include:

  • Clearly state the project or topic the update pertains to.
  • Briefly summarize key achievements or milestones reached since the last update.
  • Alert team members of any critical deadlines approaching.
  • If applicable, list any specific tasks or responsibilities that need to be addressed by team members.
  • End with a clear call to action, encouraging team members to review the update or take necessary steps.

Engaging with Clients/Customers

You can automate sending regular newsletters, promotional offers, or educational content to your client/customer base.

The frequency based on your campaign goals.

  • Weekly newsletters might be suitable for keeping your audience informed about industry trends or new product features.
  • Monthly promotions could be used to highlight special offers or discounts.
  • Educational content, like blog posts or articles, could be sent bi-weekly to establish thought leadership.

You should create engaging content that resonates with your target audience.

  • Newsletters: Include relevant industry news, company updates, or success stories.
  • Promotions: Clearly display the offer details, including expiry dates and any terms & conditions.
  • Educational Content: Offer valuable insights or practical tips related to your industry.
  • Personalization: Consider segmenting your audience and personalizing the content based on demographics or interests for a more impactful experience.

Automated Reminders for Internal Teams

The aim is to reduce the risk of missed deadlines and ensure team members stay on top of their tasks by sending automated reminders.

You should set the frequency based on the reminder needs. Daily reminders might be helpful for recurring tasks, while weekly reminders could be suitable for upcoming reports due.

Keep the reminder emails focused and actionable:

  • Clearly state the specific task or report that needs attention.
  • Highlight the due date prominently to ensure timely completion.
  • If necessary, include any specific instructions or resources needed to complete the task.

Automated Reporting and Analytics

The aim is to save time by automating the delivery of reports or analytics summaries to relevant stakeholders.

Make sure to maintain the frequency with your reporting cycles.

  • Weekly reports might be useful for tracking fast-changing metrics like website traffic.
  • Monthly reports could provide valuable insights into sales performance or marketing campaign effectiveness.
  • Quarterly reports often offer a high-level overview of business performance over a longer period.

Ensure the reports are informative and visually appealing:

  • Key Metrics: Focus on the most important metrics that align with stakeholder interests (e.g., sales figures, customer acquisition costs).
  • Graphs and Charts: Use visuals to represent data trends and make the information easier to digest.
  • Insights and Recommendations: Include key takeaways from the data and offer recommendations for improvement where applicable.

Marketing Emails

The goal of these emails are to nurture leads, promote products or services, and drive customer engagement through a series of automated email campaigns.

The frequency depends on your marketing goals and target audience. Here are some examples:

  • Welcome Series: Send a sequence of emails introducing your brand, highlighting key benefits, and offering valuable resources shortly after signup.
  • Promotional Campaigns: Automate emails promoting upcoming sales, new product launches, or limited-time offers based on your campaign schedule.
  • Educational Content: Deliver a series of educational emails sharing industry insights, practical tips, or exclusive content to nurture leads and establish thought leadership.

You should create compelling marketing copy that resonates with your target audience and aligns with your campaign goals.

  • Briefly introduce your brand, showcase your value proposition, and offer a warm welcome.
  • Highlight the benefits of your product or service, showcase the offer details (discounts, expiry dates), and include a clear call to action (e.g., “Shop Now”).
  • Provide valuable and informative content relevant to your audience’s interests. Use storytelling, case studies, or data-driven insights to engage readers.
  • Personalize the emails whenever possible to enhance engagement. You can use subscriber names, purchase history, or browsing behavior to tailor the content and offers.

Follow-Up Emails

Here you try to improve communication and conversion rates by automatically sending follow-up emails after a specific event or interaction (e.g., website abandonment, webinar registration, product demo).

The ideal frequency depends on the context.

  • A first follow-up email might be sent a day or two after website abandonment.
  • A series of follow-up emails might be spread out over a week or more for nurturing leads after a webinar registration.

Craft clear and concise follow-up emails that encourage the recipient to take the desired action. Here’s what to consider including:

  • Context Reminder: Briefly remind the recipient of the initial interaction or event.
  • Value Proposition: Reiterate the benefits of your product or service and how it addresses their needs.
  • Call to Action: Clearly state the desired action you want the recipient to take (e.g., “Schedule a Demo,” “Download the Free Guide”).
  • Offer Incentive (Optional): Consider including a limited-time offer or discount to incentivize action.

Advantage of setting automated email on Outlook

Increase in efficiency

You can automate repetitive email tasks like sending out reports, reminders, or marketing campaigns saves you significant time and effort. This will help you focus on other priorities while your emails get delivered automatically.

Improvement in consistency

Automated emails ensure consistent communication and messaging.  Everyone receives the same information at the same interval, reducing the risk of missed updates or inconsistencies.

Enhanced engagement

Automated email sequences can nurture leads, promote brand awareness, and drive customer engagement more effectively than one-off emails.

Reduction in errors

Manual emails are prone to human error.  Automation minimizes the risk of typos, incorrect information, or missed deliveries.

Improved workflows

Automating emails can help set the workflows within your team or organization.  Automated reports, reminders, or updates keep everyone informed and on the same page.

While the “Delay Delivery” method offers a basic solution, it has limitations. You can consider integration with a sales automation platform like for more advanced functionalities and dynamic content capabilities.

You can check our blog on ‘How to schedule email on Outlook’. 

Frequently Asked Questions (FAQs)

How to send automatic emails in Outlook?

Outlook offers two options: Use “Delay Delivery” for recurring emails (static content) or set up “Automatic Replies” for out-of-office responses.

How can I create recurring emails?

Outlook doesn’t have a built-in feature, but you can use a workaround:

  • Compose your email.
  • Go to Options > Delay Delivery.
  • Set “Do Not Deliver Before” to “Recurring” and define the recurrence pattern (daily, weekly, etc.).
  • Send the email.

What are the limitations of the recurring email workaround?

  • The content remains static for each recurrence.
  • You can’t edit the original email after it’s sent.

Are there alternatives for recurring emails with editable content?

Yes, consider third-party add-ins like Boomerang for Outlook that offer more control over recurring emails and content editing.

Are there any disadvantages to using automated emails?

  • Limited content editing capabilities with the delay delivery workaround.
  • Potential for sending irrelevant emails if the content isn’t reviewed periodically.

How can I set up an automatic Out-of-Office reply?

There are two ways to do this, depending on your Outlook version:

  • Web App: Go to Settings > Mail > Automatic replies.
  • Windows App: Click File > Automatic Replies.

Enable the option and set the start and end dates (if applicable). You can also create separate messages for internal and external senders.

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