How to Send Automatic Emails in Outlook? (2025)

I am tired. For real!

Why? Because I spent a whole day trying to test out multiple ways to automate emails from Outlook.

In the end, I realized that Outlook is a relic from the past as there are many tools that have surpassed the in-built automation features of Outlook.

So, if you want to save time, I recommend you use a tool to automate emails from an Outlook account.

But in case you want to use the in-built automation features of Outlook, then I’ve also covered them.

How to Send Automatic (Out-of-Office) Reply Emails in Outlook?

Your email address might get bombarded with a lot of emails when you are on leave.

It’s your responsibility to inform the sender that you are not available till a specific date and direct them to an alternative method if it’s urgent.

How to do that? The answer lies in automated out-of-office replies.

I have shared the process to automate out-of-office replies in Outlook (Classic + New)

• Setup of out-of-office replies in New Outlook
• Setup of out-of-office replies in Classic Outlook

Note: Refer to this guide if you are not sure what version of Outlook you have.

Setup of Out-of-Office replies in New Outlook

Microsoft made it easier to set up automated out-of-office replies in the new Outlook.

Here’s the step-by-step process (the fact that there is only one screenshot of the process makes it easier).

Step 1: Open Outlook ➜ Settings (Gear icon) top right corner

Step 2: Go to ‘Accounts’ ➜ ‘Automatic replies’ ➜ Toggle ‘Automatic replies’ to ‘on’

Step 3: Now select the duration and customize the out-of-office email as per your preference.

Step 4: Save, and you are good to go.

Note: You also get an option to automatically cancel meetings and decline invitations during the out-of-office period.

Setup of Out-of-Office replies in Classic Outlook

Well, the hassle is here.

Because Classic Outlook is outdated and takes a lot of time to automate a simple out-of-office reply.

So hang in there; I have covered the whole process with screenshots.

Step 1: Open Outlook and go to ‘File’ (top left corner)

Step 2: From the menu, select ‘Automatic Replies’
Note: If you’re using an older version of Outlook, the feature might be labeled as ‘out-of-office Assistant.’

Step 3: Customize your automatic reply settings and save it.

Here, you can also set different out-of-office emails for inside and outside the organization. (As shown in the image below)

With this, your automatic out-of-office replies are all set up.

Auto Reply by Setting Rules in Outlook

Outlook Rules are used when you want to perform certain actions (not necessarily a reply) based on the emails you get. It’s pretty easy and convenient.

Here’s what you need to do to set automation by setting Rules in Outlook.

Step 1: Open Outlook ➜ Settings (Gear icon) top right corner

Step 2: Go to Mail ➜ ‘Rules’

Step 3: Set conditions and specify details as shown in the screenshot below

This one is useful when you get certain types of emails. 

For instance, in the above screenshot, you can see that I am forwarding emails that are related to backlinking.

To do that, I simply specified the pattern of those emails based on specific terms. 

So now, whenever I receive such an email, Outlook will automatically forward it to my colleague, who can take care of it without my interference.

How to Send Recurring Emails in Outlook Automatically?

Hang in there, my friend. The process to set up recurring emails in Outlook is a bit tricky for both New and Classic Outlook.

This is why people have been more inclined towards email automation tools that cover up the shortcomings of these ESPs.

Anyway, I recently tested the process of setting up recurring emails in both the New and Classic Outlook versions. Below, I’ve outlined the steps for each:

• How to set up recurring emails in New Outlook
• How to set up recurring emails in Classic Outlook

Note: If you are not sure if you have a new or classic Outlook, then check the version of your Outlook here and follow the process.

How to Set Up Recurring Emails in New Outlook

For the new Outlook, we will have to use ‘Power Automate’ by Microsoft to automate recurring emails.

It’s actually very reliable and works well.

Here’s a step-by-step process you need to follow to send recurring emails in New Outlook.

Step 1: Go to Outlook ➜ Go to Menu (Nine Dots – Top left)

Look for the ‘Power Automate’ option, or else click on more apps.

Step 2: Complete the automation by creating a flow in ‘Power Automate’ (process shared below).

I have created a slide of the process in ‘Power Automate’ – Click on ‘Get Started’ to check the process
(It won’t take you to any shady link. Trust me.)

How to Set Up Recurring Emails in Classic Outlook

If you are still using Classic Editor, then follow this process to set up recurring emails.

Step 1: Open Outlook ➜ Go to the ‘Auto Follow Up’ tab ➜ ‘Recurring Messages’

After that, a ‘Recurring Messages Manager’ dialog box will appear like this, and then click the ‘Add’ button.

Step 2: Write the recurring email you wish to send in the new email window.

Step 3: Customize the timings and frequency of the recurring email (in the right column of the above screenshot).

Note: You can enable the setting to stop the recurring email as per the need.

Step 4: After you’ve set up the recurring email, check and verify the recipients, subject line, and the message before saving.

If everything looks good to go, save the email and close the window.

Here are the types of recurring emails that you can send from Outlook,

1. Reminder Emails: For weekly deadlines, meeting schedules, or task updates.
2. Updates: Regular project progress reports or team status updates.
3. Follow-up Emails: Automated follow-up emails for leads or clients.
4. Emails Regarding Policies or Guidelines: Sending recurring policy reminders or training materials.

Limitations of Sending Automated Emails in Outlook

As I said at the very start of this blog, Outlook is a relic from the past.

It’s like Microsoft has done patchwork in their Classic Outlook and launched the New Outlook.

They made a lot of improvements in Outlook, but it still does not meet the advanced requirements of modern users.

To be precise, here are the 4 major limitations of sending automated emails from Outlook’s in-built features.

1. You Can’t Personalize the Emails Properly

Email personalization is the backbone of a successful emailing niche (especially when you are sending cold emails).

However, since Outlook is made for basic email communication, it does not support advanced personalization features.

For example, it would be ideal if you could mention the sender’s name in the automated out-of-office reply. But you can’t even do that.

This makes your emails sound robotic and leads to a decrease in engagement.

2. You Are Not Allowed to A/B Test

If you want to test out how different email copies are working, you need a basic A/B testing feature. But Outlook does not provide that functionality.

You need to manually create and send multiple versions of emails, which is time-consuming and inefficient.

Without A/B testing, you’re just spraying and praying.

This can eventually hurt your campaign performance and your ROI.

3. You Are Likely To Ruin Your Sender Reputation

When you send multiple emails at the same time, there are chances that it can mess up your sender reputation.

If you want to retain your sender reputation and avoid being flagged by Email Service Providers (ESPs), then you need to use a good email warm-up tool.

Also, there’s another issue with Outlook.

If there is no bounce or spam tracking, then you won’t know if your emails are landing in spam folders or being rejected by servers. For that you need an emailing tool that comes with bounce detection (like Saleshandy).

4. Difficult To Manage Email Campaigns

When you have set up recurring emails for, let’s say reminders or tasks. You will have difficulty in segregating the replies.

For this, you need a campaign management tool that will help you scale your cold email campaigns effectively.

If you’re serious about cold emailing or email marketing, consider using dedicated email automation tools that will offer all the necessary features that Outlook lacks.

Alternatives to Outlook for Sending Automated Emails

If you are reading this, then I am sure you are frustrated with Outlook.

And I am here to suggest an alternate method that will help you automate your emails in Outlook without any headache.

My recommendation – Automate your outreach emails with the help of Saleshandy.

Here’s what you will get:

1. You will be able to create and send hyper-personalized emails (with AI)
2. A/B testing up to 26 variants
3. Fully automated follow-ups and email sequences
4. Get unlimited email warm-ups
5. Advanced email bounce detection with AI
6. Reply management features
7. Advanced analytics

Avoid the Risk of Automating Emails in Outlook – Try Saleshandy Instead

Automating emails in Outlook might seem like a convenient option, but it comes with risks.

So…good luck with the technical glitches and bugs you have to face with Outlook!

But if you want to avoid any risks, then Saleshandy is a great option.

With advanced email sequence automation, real-time tracking, high deliverability, and hyper-personalization, it helps you reach the right people at the right time.

Also, it’s much easier to use than Outlook.

So, why settle for Outlook’s limitations? When you can reach your prospects’ inbox with Saleshandy!

FAQs

1. How to automatically send daily emails in Outlook?

You can use the ‘Recurring Messages’ feature in Outlook to automatically send daily emails to multiple recipients. If you are using new Outlook, then you have to use Power Automate to send recurring messages.

2. How to automate multiple emails in Outlook?

While Outlook doesn’t allow fully automating multiple emails, you can consider creating multiple recurring messages to send multiple emails automatically.

3. What is the difference between Outlook automatic replies and recurring emails?

Automatic replies and recurring emails are completely different in Outlook. Here’s what they actually mean.

• Automatic Replies: Pre-set responses sent when you’re unavailable (e.g., out-of-office). They inform senders you’re away and will respond later.
• Recurring Emails: Scheduled emails sent automatically at set intervals, useful for regular updates or reminders.