How to Send Multiple Emails at Once in Outlook: A Step-by-Step Guide

If you’ve ever needed to send the same email to multiple people in Outlook, you know how quickly it can turn into a chore. Maybe it’s a client update, an internal announcement, or an event invitation. And if you’re doing it one by one, it’s not just time-consuming—it’s downright frustrating. Trust me, I’ve been there.

But here’s the thing: Outlook has some great features that can make this process a whole lot easier—you just need to know where to look. Whether it’s sending personalized emails with mail merge or firing off a bulk update to a group, Outlook has tools to help you easily handle these situations. 

In this blog, I’ll walk you through how to send multiple emails at once in Outlook, step by step. Whether you’re new to this or just looking to streamline your process, we’ll cover everything you need to know. Let’s get started!

Table of Contents

• Understanding Microsoft Outlook’s Mass Email Features
• Send Bulk Emails in a Snap with these 3 Outlook Features
• Troubleshooting Mass Emails on Outlook
• Best Practices for Sending Mass Emails in Outlook
• What if You Want More Than Bulk Emailing? Hiver’s Shared Inbox Can Help

Understanding Microsoft Outlook’s Mass Email Features

Outlook has solid features for sending mass emails while keeping things personal and professional. Here’s how to get the most out of them:

#1 BCC (Blind Carbon Copy)

BCC allows you to email several recipients without sharing their email addresses. This is perfect when you must protect your contacts’ privacy while sending the same email to multiple people.

💡Pro Tip: Use BCC to maintain confidentiality and avoid the “Reply All” chaos. However, remember that sending large volumes of emails via BCC could trigger spam filters, so keep it under control.

#2 Mail Merge

Mail merge in Outlook lets you send personalized emails to multiple recipients by automatically inserting specific details into your message, such as the recipient’s name or company. This gives the impression that each email is custom-tailored, even though you’re sending the same core message to everyone.

💡Pro Tip: This method is perfect for sending 10-50 personalized emails simultaneously. But if you’re sending to large lists regularly, consider switching to an email marketing tool to improve deliverability and avoid Outlook flagging your account.

#3 Grouping Contacts

Outlook’s contact groups help you organize your email lists into specific segments, such as departments, customers, or prospects. Once your contacts are grouped, you can send relevant emails to each group without manually selecting individual recipients.

💡Pro Tip: Segment your contact groups based on interests or communication frequency. This will make targeting your audience more effective and reduce the risk of sending irrelevant emails.

#4 Email Templates

Email templates are a huge time-saver when you frequently send similar emails, such as promotional offers, newsletters, or updates. You can create a template once and personalize it for different recipients. Templates are great for recurring emails, but update them regularly so they don’t feel too formulaic.

#5 Tracking and Follow-Up

With Outlook’s tracking feature, you can monitor the performance of your emails—who opens them, clicks on links, and responds. This allows you to adjust your approach and follow up with recipients if needed.

💡Pro Tip: Monitor email performance and follow up when necessary. However, don’t overdo it—timely follow-ups work best, but too many reminders can annoy people.

Send Bulk Emails in a Snap with these 3 Outlook Features

👉 Mail Merge Setup for Personalization

You’re in customer service and must follow up with several customers about their support tickets. Instead of sending the same email to everyone, you can use mail merge to personalize each message quickly.

1.Compose Your Email 

Start by opening MS Word and typing the body of your email. Leave placeholders where you’d like to personalize, such as the recipient’s name or other details.

• Save the document to your computer.

• From the Mailings tab, select Start Mail Merge and choose Email Messages.

2. Create a Mailing List

If you don’t already have one, you can create one using Excel. Include columns for data like names and email addresses.

• Open Excel, add columns for the data you want to personalize and save the file.

3. Select Recipients Link your email to the correct recipients:

• From Outlook: Click Select Recipients > Choose from Outlook Contacts, login, and select your contact list.
• From Excel: Click Select Recipients > Use an Existing List, then choose your saved Excel file.

4. Insert Personalization Fields Personalize your message by adding merge fields (like the recipient’s name):

• Click Insert Merge Field from the Mailings tab and select the field you want to include.

• Optionally, add a Greeting Line for a more personalized touch.

5. Preview Your Email: Check how your email looks before sending it:

• Click Preview Results to see the personalized email for each recipient.

• Adjust formatting using Alt + F9 to view and edit the merge field codes (e.g., for currency formatting) if needed.

6. Finish and Send Once you’re happy with the preview, finish up the merge:

• Click Finish & Merge > Send Email Messages.
• Enter your subject line, and click OK to send the emails.
• If sending to an extensive list, split it into smaller batches using the From and To options.

7. Save Your Work To access the mailing list and email template quickly in the future, save your Word document.

With Mail Merge, you can pull the customer’s name and details from a data file, so each email feels personal without the headache of writing them all from scratch. It’s a huge time-saver! 

👉Distribution List Setup for Easy Communication

Managing communication in a big team spread across different locations and time zones can be tricky. For instance, if you’re on a customer service team and an essential product update isn’t shared in time, it can lead to confusion and support delays. In a finance team, missing fundamental budget changes or deadlines could lead to mistakes or missed opportunities. 

Those gaps can cause significant problems for the whole team without a sound information-sharing system. 

An Outlook distribution list lets you group contacts together, making it easy to email everyone at once. It streamlines communication and helps keep your team connected.

• Start by opening the Microsoft Outlook app or logging in via your browser.
• Head over to the Home tab and click on the Address Book in the top-right corner.

• Next, click on the file and then choose New Entry.

• Select “New Distribution List” and hit OK. Now, give your list a name.

• Click on Select Members to add people to your distribution list.
• Once done, click OK, and then Save & Close to finish up.

👉BCC Method for Privacy

BCC is like a silent CC—recipients get the email, but no one else sees their address, and they’re left out of “Reply All” messages. BCC is commonly used for mass emails where responses aren’t necessary, helping to keep recipients’ email addresses private and preventing them from receiving unwanted replies. It’s perfect for keeping things private and tidy! 

Here’s how to add BCC in Outlook:

• You’ll only see the “To” field when you start a new email.

• Click the “CC” or “BCC” buttons to reveal those options.

• Add the email addresses you want to keep hidden in the BCC field.
• Write your email and hit “Send.”

👉Using Email Templates for Mass Emails

Here are a set of mass email templates customized for different use cases, such as newsletters, event invitations, customer service, and feedback requests. Each template includes best practices for clear, engaging, and effective communication.

Newsletter Email Template: 

Subject: Stay Up to Date with [Your Company Name] – Monthly Newsletter

Hi [Recipient Name],
We’re back with the latest updates, tips, and exclusive offers just for you! Here’s what’s happening at [Your Company Name] this month:

[Headline 1]:
[Brief summary of the topic or news][Link to the full article or more information]
[Headline 2]:
[Brief summary of another update or offer][Link to the full article or more information]

[Special Offer]:
[Details about a current promotion or deal]

We also have exciting events, product launches, and resources lined up for you. Don’t miss out!

Thank you for being a valued subscriber. Please get in touch with me if you have any questions or want to learn more.

Best regards,
[Your Name]
[Your Position] | [Company]

Event Invitation Email Template: 

Subject: Join Us for [Event Name] – [Date] at [Time]

Hi [Recipient Name],
We’re excited to invite you to [Event Name], an exclusive event hosted by [Your Company Name]. Don’t miss this opportunity to [briefly describe the event’s purpose or highlight].

Event Details:
Date: [Event Date]
Time: [Event Time]
Location: [Event Location] (or Virtual Link if online)

Agenda:
[Brief rundown of the event schedule]
[Notable speakers or activities]

RSVP now to secure your spot! Click the Link below:
[RSVP Link]

If you have any questions or need more information, please get in touch with us at [Contact Information]. We look forward to seeing you there!

Best regards,
[Your Name]
[Your Position] | [Company}

Customer Service Email Template: 

Subject: We’re Here to Help – [Issue/Request Number]

Hi [Customer Name],
Thank you for contacting us. We’ve received your request regarding [brief description of the issue or request] and are actively working on a solution.

We understand this is important and want to resolve the matter as quickly as possible. Here’s a summary of the issue and next steps:

Issue Summary:
[Issue description or ticket number]
Next Steps:
[Explain what will be done next or what additional information is needed]

We’ll update you as soon as we have a solution. In the meantime, if you have any further questions or concerns, please don’t hesitate to let us know.

Best regards,
[Your Name]
Customer Support Team |[Company]

Feedback Request Email Template: 

Subject: We Value Your Opinion – Share Your Feedback

Hi [Recipient Name],
We hope you had a positive experience with [Your Company Name]. We’d love to hear from you, and your feedback is crucial in helping us improve our products/services.

How Was Your Experience?
Please take a few moments to share your thoughts. It won’t take more than [X] minutes, and your input will make a real difference.

Click Here to Share Your Feedback:
[Survey Link]

Thank you for your time and being part of [Your Company Name]. We look forward to hearing from you!

Best regards,
[Your Name]
[Your Position] | [Your Company Name]

Troubleshooting Mass Emails on Outlook

When managing mass email campaigns in Outlook, users often face issues like emails going to spam or attachments failing to load. These challenges can hinder delivery and engagement. Here are some quick fixes to address common problems when sending mass emails.

Emails Stuck in Outbox

Fixing connectivity issues and optimizing attachments ensures faster, smoother email delivery without delays.

Quick Fixes:

• Reduce attachments: Large files may block sending. Compress files or images to make them smaller.
• Update Outlook: Make sure your software is up-to-date. Also, clear your cache and close any unnecessary apps to improve performance.

Emails Flagged as Spam

Preventing your emails from landing in spam keeps your messages visible in recipients’ inboxes, improving engagement.

Quick Fixes:

• Avoid spammy language: Don’t use words like “Free” or all caps in your subject lines—they can trigger spam filters.
• Personalize your email: Use merge fields (name, title) to avoid sounding generic, as spam filters flag non-personalized emails.
• Use a trusted sender name: Always send from a recognizable email address to increase trust and reduce the chance of being flagged.
• Test deliverability: Use tools like Mail-Tester to check your email’s spam score before sending it to a large group.

Missing Personalization Fields

Personalization helps make your email more engaging and avoids the negative impact of sending impersonal communication.

Quick Fixes:

• Check Mail Merge fields: Before sending, make sure all merge fields (e.g., names, and company) are correctly mapped in Outlook or Word.
• Send a test email: Always send a test email to yourself or a colleague to check that personalization fields work.
• Review your contact list: If using Excel or Outlook Contacts, verify that all email addresses are accurate and columns are correctly labeled.

GDPR Compliance and Ethical Considerations

Following GDPR and ethical practices ensures compliance and fosters trust with your audience, protecting their privacy and reputation.

Quick Fixes:

• Get consent before emailing: Always secure explicit consent before sending marketing emails, particularly for EU recipients.
• Include opt-out options: Make it easy for recipients to unsubscribe by adding an unsubscribe link in every email.
• Secure your data: Only use and store recipient data for the intended purpose, and ensure it’s stored securely.
• Be transparent: Communicate how you use customer data to build trust and meet legal obligations.

Best Practices for Sending Mass Emails in Outlook

Personalize Your Emails

How to Do It:

• Use Outlook’s Mail Merge to personalize your emails automatically.
• Compose your email in Word and add placeholders like {FirstName}where you want personalized details to appear.
• Connect your contact list (Excel or Outlook contacts) through Mail Merge to fill in these placeholders with accurate data.
• Test the email by sending it to yourself or a colleague to ensure everything looks right.

Why It Works: Personalization makes emails feel more personal and engaging, boosting open rates and interactions.

Avoid Overloading Recipients

How to Do It:

• Organize your emails by relevance—group related information together instead of sending multiple emails on the same topic.
• Use Outlook’s categories to segment contacts by groups like customers, vendors, or team members, and tailor your messages accordingly.
• Keep emails short and to the point. Use bullet points or numbered lists to make your message easy to digest.

Why It Works: Sending fewer, more focused emails makes your messages more effective and prevents overwhelming your audience.

Always Test Before Sending

How to Do It:

• Before hitting ” Send” to a large group, send a test email to yourself or a team member. This will check for formatting issues, broken links, and attachment errors.
• Review the subject line to ensure it’s clear and not too spammy.
• Preview the email with actual recipient data to ensure that any personalization fields (like names or titles) are filled correctly.

Why It Works: Testing ensures your email looks perfect, preventing mistakes that could hurt your credibility or confuse your audience.

Craft a Strong Subject Line

How to Do It:

• Keep it brief and to the point—aim for 6-10 words that clearly convey the purpose of the email.
• Be specific and avoid vague phrases like “Important Info.” Instead, try something like “Meeting Update – Please Review.”
• Avoid “spammy” words like “Free” or excessive punctuation (e.g., “!!!”).
• Consider testing a couple of subject lines with A/B testing to see which one performs better.

Why It Works: A robust and transparent subject line attracts attention and encourages recipients to open the email.

What if You Want More Than Bulk Emailing? Hiver’s Shared Inbox Can Help

When it comes to one-to-many communication in Outlook, distribution lists and similar approaches (as discussed above) get the job done. For instance, if you need to send a company-wide announcement or a newsletter to clients, these tools work well. 

But the moment your recipients start replying with questions or concerns, things can get messy.

There’s no easy way to track responses, assign them to the right person, or collaborate with your team to resolve issues. For customer support or finance teams especially, this can quickly turn into a nightmare.

That’s where Hiver steps in.

Hiver, a customer support platform, simplifies how you manage email addresses like support@ or info@, making it easier for teams to collaborate, stay on top of every email, and keep things moving efficiently—all from a familiar Outlook-like interface.

Here’s how Hiver helps:

• Email delegation: Every email gets the attention it deserves. With Hiver, you can assign emails to team members in just two clicks, making sure no email is overlooked.
• Shared drafts: Collaborate on email replies in real-time. Shared drafts let your team work together on responses, while collision alerts prevent duplicate responses from being sent.
• SLA management: Stay on top of email deadlines with SLA rules. You can also use Hiver’s Analytics to track performance metrics and identify areas for improvement.
• Auto-assign: Automate email assignment based on specific triggers or set up a round-robin system. Prioritize emails that need immediate attention with simple rules.
• Notes and @mentions: Write internal notes using @mentions that loop in specific team members and get their inputs. These notes – attached right next to the main email thread – offer a smooth way to collaborate without cluttering inboxes.

Start with a 7-day free trial!