August 5, 2025

There are many reasons you or your firm might need to send numerous emails with the same or similar message. You could need to notify all your clients about a change in staffing, or to notify them of a change in the law. You may need to alert them about overdue invoices or record destruction during file closing. You might also want to send marketing messages to potential clients. The list of reasons for sending mass emails is extensive. Fortunately, there are many ways to simplify this process, including tools you probably already have. However, before doing so, you should assess who you’re sending to and why to ensure you meet your legal and ethical obligations.

What Problem Are You Trying to Solve?

Before you choose a tool to send out email messages to a large group of people, you will need to determine if the message is primarily for communication or marketing purposes. For instance, a client update to a group of people bearing necessary information is different from sending a blast email to promote a service. This analysis is necessary to determine whether the mass email would require compliance with the CAN-SPAM Act, a law that sets rules for commercial email. According to the FTC: the law covers “any electronic mail message the primary purpose of which is the commercial advertisement or promotion of a commercial product or service,” including email that promotes content on commercial websites. The law makes no exception for business-to-business email. That means all email, for example, a message to former customers announcing a new product line, must comply with the law.” This CAN-SPAM Act compliance guide for businesses is very useful in helping determine if your email needs to follow CAN-SPAM requirements, including a physical postal address and opt-out options.

Once you have determined if the email needs to be CAN-SPAM compliant, you can choose the right tool to send your mass email.

Why Can’t I Just Use BCC?

If you have determined that your message does not qualify as CAN-SPAM-defined content, you may ask, “Why can’t I just use BCC to send the message?” While you can, there are a few good reasons not to. If you BCC a group of people, you cannot use any personalization. Generous limits are imposed by most email applications, with professional versions of Gmail and Outlook allowing up to 500 recipients (To, CC, and BCC combined), although system administrators can change those restrictions. However, if you send more than 50 messages at a time via BCC, the email may be flagged by the recipient’s system as spam, and it will go into a spam filter. It may even block your email address. If someone who is Bcc’d uses “reply all,” then anyone in the “to” or “cc” line will receive the response. This could cause a variety of problems, and the risks are described in the article Three Reasons Lawyers Use BCC and Why to Stop.

Options to Consider

Create a Group

If you regularly send emails to multiple people, either internally or externally, and you want that group to be able to communicate, you might consider creating a group in your email app or in a separate service. Microsoft Outlook groups, Google Groups, Groups.io, and others could be options; however, you should think about confidentiality, attachment limits, and other issues before using a group email as an alternative.

Mail Merge via Microsoft Word + Classic Outlook + Excel

If you have the Microsoft Office or 365 suites, you can use Microsoft Word’s Mail Merge feature to send individual emails through Outlook. Add the recipient’s email address, name, and any other information you want to insert into the email in a spreadsheet. Then draft the email in Microsoft Word and use the Mail Merge feature to send a customized email to each individual. You will see all of the sent messages in your “Sent” folder in Outlook.

Be aware that you cannot attach any files to the outbound email, so you will need to set up a link to any documents you need to reference.

New Outlook’s Built-In Mail Merge

In the New Outlook in Microsoft 365 Business subscriptions, you can send multiple people individual emails when drafting an email by clicking the arrow next to “Send” and choosing “Start mail merge”.  This provides a recipient line only and notes “every recipient will receive their own copy of this email without other recipients listed”. Don’t be alarmed when the email messages appear in your Sent mail folder as one message. Like BCC, this method provides no opportunity for personalization or customization.

Outlook Add-Ons

There are a few Outlook add-ons for mail merge without using Excel and Word. One is Standss EmailMerge. It works with classic (Windows) Outlook, and New Outlook/Outlook for Mac. You can send personalized emails in bulk directly from Outlook with attachments. You can also track opens, clicks, and replies. The Classic Windows Outlook add-on is not a subscription, but a license. The Standard edition costs $60 and the Pro edition is $80. The version for New Outlook/Outlook for Mac is a $100 annual subscription.

Email Marketing Platforms (Mailchimp, Constant Contact, etc.)

If you need a mass email management application that helps comply with CAN-SPAM requirements, manages opt-outs, track open rates and click-throughs for marketing, and allows you to create custom personalized templates for marketing and newsletters, there are many options. Commercial business email marketing platforms like MailChimp, Constant Contact, and Drip are reasonably priced and fairly easy to use. Specifically for law firms, some client relationship management applications like Clio Grow and Lawmatics include email marketing and automation.

Conclusion

When sending mass emails, legal professionals must consider both client confidentiality and compliance with CAN-SPAM regulations. Many routine communications, such as non-marketing notices or client updates, may not fall under the CAN-SPAM Act, and can often be sent securely using tools like Microsoft Word Mail Merge and Outlook add-ons. However, if your outreach requires CAN-SPAM compliance, advanced tracking, and personalization with branding, investing in a reputable email marketing platform will offer greater efficiency, automation, and peace of mind. No matter what reason is motivating your need to send mass emails, avoid using BCC, as there are many better alternatives.