How to Send Email to Multiple Recipients Individually (Gmail, Outlook, & Other ESPs)

It’s a tedious process if you want to separately send emails to multiple recipients (without revealing their email addresses to each other).

But if you want to save your time, then this guide will show you how to send an email to multiple recipients individually in Outlook and Gmail.

I will also share the limitations and explain why you might need a specialized tool to send emails effectively.

How to Send Emails to Multiple Recipients Individually (With Email Automation Tool)

Here are the steps you need to follow ➜

• Step 1: Sign Up on Saleshandy
• Step 2: Connect Your Email Accounts
• Step 3: Craft Your Personalized Email Copies
• Step 4: Add Your Recipients
• Step 5: Launch your Campaign

I have covered the steps in detail below.

Step 1: Sign Up on Saleshandy

Your first step is to create an account on Saleshandy for free.

To sign up, all you have to do is enter your email address or directly sign up with Google!

(That’s it; you don’t have to provide any personal additional information or credit card details.)

Step 2: Connect Your Email Accounts

Go to Saleshandy’s dashboard and click on the “⚙️” settings icon from the sidebar.

Next,

• Go to the user settings and click on “Email Accounts.”
• Click on “Add Email Accounts.”
• Now, choose the email service provider of your choice and start connecting your email accounts.

Step 3: Craft Your Personalized Email Copies

Come back to Saleshandy’s dashboard and click on “Create Sequence” > and then on “Add Step.”

An email composer will appear where you can start writing a catchy subject line.

You can either choose one of the email templates or write your email copy.

Now, to personalize your email copy for each recipient, use the variable or merge tags.

• Examples of Merge Tags:{{First Name}}, {{Company}}, {{Pain Point}}, {{Ice Breaker}} etc.
• Example of Variable Tags:{{PreviousWorkingDay}}, {{NextWorkingDay}}, {{CurrentGreeting}}, etc.

Moreover, you can also use advanced email personalization features like Spintax to send a unique email copy to each recipient.

Once done, preview the email and check how it will appear when it lands in your prospect’s inbox.

Step 4: Add Your Recipients

To upload your email list, follow these steps,

• Click on “Prospects”> “Add Prospects”> “Import your CSV file” with prospect data.

You can add up to 100k prospects at once.

• Verify your contact list to make sure you don’t send emails to invalid email addresses.
• Now, upload your prospects.

Step 5: Launch your Campaign

Once you add the prospect to your sequence, click on “Activate” to launch the email campaign!

How to Send Email to Multiple Recipients With Outlook

In this section, I will explain how to send emails to multiple recipients directly from Outlook and with the “Microsoft Word+Excel+Outlook Method.”

For Outlook, I have covered two ways to send emails to multiple recipients,

1. How to Send Multiple Emails With the BCC Method in Outlook
2. How to Send Email with Mail Merge Method for Outlook

How to Send Multiple Emails With the BCC Method in Outlook

Now, here’s a step-by-step process to send emails to multiple recipients with the BCC method,

• Step 1: Go to Outlook and click on the New button and then on Mail
  
• Step 2: Fill in the subject line & write your email
  
• Step 3: In the “To” field, add your own email address, and in the “BCC” field, add your recipients
  
• Step 4: Check everything and hit the send button. 

How to Send Email with Mail Merge Method for Outlook

Mail merge method is used when you want to send separate emails to multiple recipients using Outlook’s infrastructure (without BCC).

When to use this method – It is best for sending personalized emails or documents to a large number of recipients. It allows you to insert variables and customize your email as per your preference.

For more details, I have covered the process with screenshots below.

Step 1: Create Your Email Copy in Microsoft Word

First, you need to prepare your email in Microsoft Word. For that, you need to go to Word and on the tab click on “Mailings” > “Start Mail Merge” > “E-mail Messages”.

Now, write your email, but remember to insert the placeholder like <<Name>>, <<Company>>, etc., where you want to add the personal information of your recipients.

Don’t “save” or “close” the Word tab, just “minimize” it.

Step 2: Prepare Your Email List in Excel

Now go to Excel and open a new blank workbook.

In the email list along with the email addresses also add additional details like First Name and company and make sure you add correct information.

Save the email list.

Step 3: Upload the List to Word

Now, open the Word document again and click on “select recipients” > “use an existing list”.

Now select the email list, upload it, and click on “ok”.

Step 4: Add Merge Tags

Here comes the important step! Because this step ensures that your emails are personalized. Click on “Insert Merge Tags”, it will display all the merge tags placed in the email.

Replace the placeholders generated by word with that in your email! Don’t forget to do that otherwise, your recipients will not receive personalized emails.

Step 5: Preview Your Email

Don’t forget to preview your email by clicking on the “🔍” icon to access the “Preview results” feature.

To check if customization is done accurately, use the “⏪ ⏩” arrow button, and with the count of 1, 2, 3… and so on, it will keep displaying how the email for each recipient will look.

Step 6: Send the Email

Once everything is in place, click on “Finish & Merge” > select “Send email messages.”

A pop-up will appear. In the “To” field, select “Email Address” and don’t forget to add the subject line as well!

In mail format, select plain text because, for high email deliverability, you should not select HTML format because it hampers your email deliverability.

Click on “Ok” and you are done! Now go and check your Outlook’s sent box.

In addition to these two methods, you can also do a mail merge directly with the new Outlook app and Microsoft Power Automate.

If you want to send emails from Outlook in bulk, then we have covered it in a separate blog.

How to Send Email to Multiple Recipients With Gmail

In this section, I will walk you through the process of sending emails to multiple recipients at once with Gmail.

For this, forums like Google & Reddit recommend that you do it directly by sending emails through Gmail with the BCC method.

Here is how you can do it with screenshots to guide you →

• Step 1: Open Gmail and click the “🖊” Compose icon.
  
• Step 2: Add a subject line and write your email copy.
  
• Step 3: In the “to” field, add your email address, and in the “bcc” field add your recipients.
• Step 4: Before hitting the send button, check that every detail is correct!

However, if you want to send personalized emails to multiple recipients through Gmail but it is only possible through third-party apps (like Saleshandy) or add-on extensions.

How to Send Emails to Multiple Recipients Without Them Knowing in Gmail

When you use the BCC feature along with “undisclosed recipients” in the “To” field, you can send emails to several recipients in Gmail without them knowing that you’ve sent it to other recipients.

For that, here are the steps you can follow:

• Step 1: Create a New Email
• Step 2: Add “Undisclosed Recipients” in the “To” Field
• Step 3: Enter Email Addresses in the BCC Field
• Step 4: Add Email Content and Send

If you want more details or clarity, check out the screenshots and descriptions given below:

Step 1: Create a New Email

For starters, log in to your Gmail account and click the “Compose” button in the top left corner of your screen. This will open a new email window where you can draft your email.

Step 2: Add “Undisclosed Recipients” in the “To” Field

In the “To” field, enter “Undisclosed recipients” followed by your email address in angle brackets (like this “<help@saleshandy.com>”).

It should look something like this: “Undisclosed recipients <your email address>”.

Note: It’s just a display trick; the recipients will see your name and won’t know who else received the email.

Step 3: Enter Email Addresses in the BCC Field

Next, click on the “BCC” button (which stands for “Blind Carbon Copy”) to add the email addresses of your recipients (separated by commas).

This step will ensure that each recipient’s email address is hidden from other recipients. This is good for the recipients’ privacy and also reduces the risk of your email being marked as spam by ESPs.

Step 4: Add Email Content and Send

Once you have added all the email addresses in the BCC field, you can then draft your email.

When you’re ready to send your email, click the “Send” button.

Also, there is a chance that Gmail may display a warning message (based on the number of recipients and the content of your email).

So, make sure that you don’t send too many emails in one go because Gmail has daily sending limits (500 for regular accounts, 2,000 for Google Workspace).

Note: At first go, Gmail seems like a convenient way to send bulk emails, but it’s not designed for sending large volumes of emails at once.

So, if you want to send emails to a large number of recipients on a regular basis, it would be better if you use a dedicated cold email sending platform.

How to Send Emails to Multiple Recipients With Attachments in Outlook

If you want to send personalized emails with different attachments, then you need to do a mail merge with attachments in Outlook. Here’s the process you need to follow:

1. Create an Excel file for a dataset of recipients with a separate column for Attachments. You need to mention the file path for each attachment.
2. Create your mail merge Word document
   Write email copy and add merge fields that will fetch data from your spreadsheet.
   Ensure that the placeholders are in the format <<Name>>.
3. For attachments, you need to use Add-ins or Macros, which are popular when it comes to automated attachment processes.
4. Configure your mail merge
   For this, use your preferred method (I prefer an add-in) to link your Word document template to your data source spreadsheet.
   You need to specify the merge destination (e.g., Outlook) and other options, such as CC, BCC, and subject lines.
5. Attach files & send
   For this, install the add-in (you can use Mail Merge Toolkit) and follow its wizard to link your Excel file, map attachment paths, and send emails.

Potential Issues With Sending Multiple Emails Directly Using Gmail or Outlook

I have explained all the methods to send email to multiple recipients with email automation tools, Gmail and Outlook.

Now, here is the thing. I have sent mass emails directly from ESPs at the start of my entrepreneurial journey to bring new business.

But I won’t recommend doing that!

Here are the major reasons why you should avoid it →

• Your Emails Can Have Low Deliverability
• Constraints on Email Sending Limits
• Not Enough Personalization Email Options
• No Way to Track How Your Emails Performed

1. Your Emails Can Have Low Deliverability

There have been instances where spam filters flagged my emails. Now spam filters can be triggered due to reasons like:

• Sending bulk emails from one email account 
• Not many recipients read the emails 
• Recipients, mark your emails as spam
• ESPs assume that you are sending suspicious emails

Whatever the reason is, if repeatedly your emails are flagged as spam it will definitely harm your sender’s reputation, and make it harder to reach inboxes in the future.

2. Constraints on Email Sending Limits

This was the primary reason that limited my email outreach efforts! All the ESPs have email-sending limits that limit you to reaching out to a wide audience at once.

Here are the email-sending limits for the popular ESPs:

• Gmail: 2,000 emails per day 
• Microsoft Outlook: 5,000 emails per day, with a maximum of 500 recipients per email. 
• Zoho Mail: 2,000 emails per day.

If you don’t follow these limits ESPs will block your account; therefore you have to switch between various email accounts if you want to send more emails! Which is again a task when you are executing it manually!

3. Not Enough Personalization Email Options

2025 is all about targeted personalization!

Gone are the days when basic personalization, i.e., adding the recipient’s first name and company name, was sufficient to get a response. Now, recipients look for more personalized emails, and you have to add specific details about them so that they respond to your email.

And ESPs clearly do not have advanced features to personalize your email copies.

4. No Way to Track How Your Emails Performed

What’s the use of sending emails in bulk and putting in so much work if I can’t track what I’ve sent, how many responses I’ve received, or which recipients show interest? Without proper tracking, even when sending follow-up emails, I might miss potential responses from interested recipients!

So, Which is the Right Way to Send Email To Multiple Recipients Individually?

I know using ESPs seems like a more convenient option for sending multiple emails, but I recommend you avoid it!

Though it can be a great mode of communication for small-scale or business communication, it is not ideal for those looking to scale their outreach and lead generation efforts efficiently.

With a platform like Saleshandy (which is meant for sending cold emails), you can focus on scaling outreach and use features to personalize messages without compromising your sender’s reputation!

FAQs

1. Can I send emails to multiple people with different attachments?

Yes, you can send different attachments to multiple persons. But it’s limited to the method you use. If you use a third party platform like Saleshandy, then you won’t have any issues, but if it’s Gmail or Outlook, then you might face some difficulties in automating it.

2. How do I send a mass email without showing other recipients?

If you use the “Undisclosed method” to send emails, then your recipients won’t be able to see each other. Just add this in the “To” field – “Undisclosed recipients <your email address>”.

3. How do I send a personalized email to multiple recipients?

To send personalized emails, you can use the Mail Merge feature in Outlook. For Gmail users, you need to use an email automation platform. In case of cold emails, it’s best to use Saleshandy.