How to Send a Mass Email (and how NOT to...)

Category: Email

A reader asks: 'I need to send emails to a large group of people on a regular basis. But I've heard that if you do it wrong, you'll get tagged as a spammer, and your emails will never be delivered. What software or services do you recommend for sending emails to a list of people?' Read on for some good options, and a few you definitely want to avoid...

Sending Emails to a List of Addresses

The reason this person wants to send a mass (or bulk) email was not mentioned to me. But there are many legitimate reasons why you might want to send emails to a list of addresses. It could be as simple as keeping in touch with a group of friends or family. Perhaps you want to send out a group, club, or church newsletter. Maybe you're sending invitations to a party or event. Or you run an online business, and want to send a message to your customer list. Hopefully, you're not thinking about sending 50,000 emails to a list of names you purchased from a guy on Craigslist for $49.

You're right to be concerned about the spam issue. Even if your intentions are the best, and your message is benign, sending the same email to a large group of people is one of the "triggers" that anti-spam filters look for, and it can result in your outgoing emails ending up in a black hole, instead of reaching the intended recipients. And it might even violate your Internet Service Provider's terms of service. You don't want to lose your account due to an honest mistake. Let's take a look at several options for mass emailing that will maximize delivery success, and minimize the chances of getting you on the Most Wanted Spammers blacklist.

Sending Mass Email / Bulk Email

Using Your Email Program to Mail to a List

If your intentions are to simply communicate with a group of friends, I recommend using your email program's built-in list or group feature. Every mailer is different, but in general, you'll go into your Contacts or Address Book, tag each of the intended recipients, and save it a list. You can then compose a new email and easily send to the list, instead of tediously entering each address every time you need to email your list.

Normally I love Gmail for its simplicity, but this task is surprisingly obtuse in Gmail. To create a list, you need to open your Contacts tab. To do that, you need to click on the "dashboard apps" icon, which looks like nine little squares, and is located near the top right of your Gmail window. (See illustration below.) Select the "Contacts" icon and a new Google Contacts tab will open. (If you don't see the Contacts icon, click More.) Click "Create label", enter the list name, and click OK.

How to open Gmail Contacts You've created your list. Now click the icon or checkbox next to the people you want in your group. After making your selections, click the icon that looks like a rectangle pointing to the right. (I told you this was obtuse.) Click the name of the list you just created, then click Apply, and your selected contacts will be added to the list. You can now close the Contacts tab and return to the Gmail tab in your browser. To email the list at any time, click the Gmail Compose button, type the list name in the "To" box, and press enter.

If you use another webmail service, such as Yahoo Mail,, or a desktop mailer such as Windows Mail or Thunderbird, there will be a similar capability to create a group or list of contacts, and send to that list. Keep in mind you can use the BCC (blind carbon copy) option to send to a group without revealing everyone's address to all recipients. If you're sending to a dozen or so recipients, this approach should be fine. Some people split their mailings into groups to avoid getting flagged as spam, but management of the list, including removing bad or non-deliverable addresses, can become cumbersome.

If your list is larger, or business-related, there are better options.

Online Alternatives for Group Emails

Yahoo Groups is a free service designed specifically to help groups of people communicate. You can create a group for your club, organization, or a bunch of friends. After inviting people to join the group, you can send messages to the group by email, and they'll be distributed to all the members. Yahoo will maintain an archive of all messages, and offers additional features such as photo albums, group calendars and member polling.

Facebook is another option for informal groups to communicate. Facebook Groups lets you have open groups, or secret groups, so only members will be able to see the group and its postings.

And of course, Google has an iron in this fire as well. Google Groups lets you communicate with a group of friends, Romans, or countrymen via e-mail or a web interface.

What About "Bulk Email" Software?

If you're planning to email a large group of people, you may be tempted to buy software that promises to help you build, manage and broadcast to email lists. I strongly recommend against using these "bulk mailer" programs. Typically, these programs will offer a feature to extract or "harvest" email addresses from websites, and claim to help you avoid blacklists.

Sending high-volume email from a typical home Internet connection (especially if you do not have the permission of the recipients) is a bad idea for several reasons. First, your emails will have very poor deliverability. Spam filters on the receiving mail servers are very good at sensing patterns used by spammers and bulk email programs. If your messages are not silently deleted, they will be bounced back to your inbox as undeliverable. Second, your ISP may cancel or freeze your account. If your abuse of your ISP's mail server causes it to be added to a blacklist, then it could affect the ability of ALL of their customers to send email.

Bulk email software is so 1995. Read on for some better alternatives...

Email Marketing for CLubs, Groups and Businesses

If your bulk emailing is on behalf of a business or organization, my recommendation is to use a web-based email marketing service. Mailchimp's free version is popular with non-profits and small businesses because it lets you send up to 12,000 emails per month, with up to 2000 subscribers. So, for example, you could send to a list of 400 people every day of the month; a list of 1000 people twelve times a month, etc. You don't even need a credit card to sign up.

If you need to send larger volumes, check into Aweber or Constant Contact for more robust email marketing services. MailChimp, Aweber, Constant Contact and similar services all have certain benefits that are important for people who email to large groups on a regular basis. Management of your list, professionally designed email templates, handling of bounced emails, and the ability to customize messages for each recipient are lacking in the do-it-yourself approach. They also have relationships with the major ISPs, to help ensure high delivery rates. In return, they help to minimize unwanted email by requiring that senders have permission, and recipients can easily remove themselves from a mailing list.

In all cases, getting permission is key. If you're sending to people with whom you have no existing personal or business relationship, you're likely to raise red flags and possibly lose your account. Here's a list of best practices for communicating effectively via email to large groups:

  • DON’T: Add people to your list without their permission. Even if you have one of those sneaky pre-checked “add me to your list” opt-in boxes, visitors won’t remember “opting in” and will consider your marketing messages spam.
  • DO: Instead, use “confirmed opt-in” which requires the new subscriber to respond to a confirmation email before they are actually added to your list.
  • DO: Provide a link to an easy opt-out or unsubscribe form in your email marketing messages. It’s required by federal anti-spam law. Test the unsubscribe process occasionally; it’s surprising how many don’t work and no one ever gets around to fixing the problem.
  • DON’T: Include attachments or use scripting such as Javascript, in email marketing messages. Many spam filters will block such messages.
  • DO: Ask subscribers to add your newsletter address to their address book or “safe senders list.” This helps to ensure that your messages won’t be routed to the junk mail folder.
  • DO: Remove invalid email addresses from your mailing list as soon as your become aware of them. A large number of bounced messages can get you blacklisted.

Do you have something to say about sending bulk or mass emails? Post your comment or question below...

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Most recent comments on "How to Send a Mass Email (and how NOT to...)"

Posted by:

Stuart Berg
19 Mar 2019

I use and love GroupMail Lite Edition which is FREE.
It runs on your computer and controls how it sends emails out so that they are not considered spam by Gmail. It sends one email at a time. I have mine set to send 10 consecutive emails and then have it wait 15 seconds before sending the next group of 10 emails. None of my sent messages have been flagged by Gmail as spam. It can easily send emails with attachments and can easily embed images within emails. The restriction of this free "Lite Edition" is a limit of sending no more than 100 emails at a time. For a home user with a need for sending emails to no more than 100 at a time, it's perfect. It does have a very small line at the bottom of each sent email that says "Need Email Marketing for your Business? Learn more about GroupMail", where "GroupMail" is a link to their website. Here is how they describe the GroupMail Lite Edition:

"The GroupMail Lite Edition is wonderful for everyone and especially for the individual home user or community group who want to send personalized group email to smaller mailing lists. The Lite Edition has everything you need to send mass email to groups. Create any number of email groups. Import contacts from .csv and .txt files. Personalize your message for each recipient."

"Easily create and send HTML and/or plain text newsletters
Single connection sending only
39 HTML email marketing templates to get you started
Import contacts from practically any data source as .csv and .txt files
Export email lists
No add-on support
Send to a maximum of 100 recipients at a time"

Posted by:

19 Mar 2019

I am not sure if a privacy 'note' should be appended to your great set of DOs and DON'Ts. The concern would be to make [absolutely] certain that each name/email address is kept [fully] private.

Posted by:

19 Mar 2019

I am a volunteer tutor with a seniors group and when I am running a course I need to send an email to the 200+ seniors on our books about the course. I use 1and1mail (paid for version) this lets me set up an email template explaining about course and using parameters in template personalise the email from recipients details in email database you set up from CSV file. Each recipient gets an individual email sent to them from a gmail account.. I use a spare laptop to do this as it can take some time depending on the time parameters you set for sending the emails.

Posted by:

Eric Bloch
21 Mar 2019

Once a year I solicit for donations for National Multiple Sclerosis Society (NMSS). This requires 2 400 email sends and that quantity does not fit any of the free offerings.

I have the emails in an Excel spreadsheet which I have programmed to groups of 40 concatenated into one cell. I use that cell as BCC in a Gmail email and send 3 or 4 of these per day to eliminate the chance of being branded as spam.

Yes, I manually edit the email list as required. I am in process of making Gmail groups for these emails NMSS01, 02, etc which I will use in a similar fashion as Excel.

Posted by:

top squirrel
21 Mar 2019

(I tried the "question" link but all I got was a request to try existing articles and I lost all the text I prepared.)
Bob's text includes:
"DO: Provide a link to an easy opt-out or unsubscribe form in your email marketing messages. It’s required by federal anti-spam law. Test the unsubscribe process occasionally; it’s surprising how many don’t work and no one ever gets around to fixing the problem."
First I hear of a law that requires an unsub link.
All of the spam I get (lonely beautiful young ladies; health secrets "they" don't want you to know) has an unsub link, but clicking on it goes nowhere and doesn't stop the spam.
If you try to send them an unsub request by hitting the reply button, a totally new address appears in the 'to' field which is always bounced back as undeliverable.
How do I send an unsub request that has any chance of getting there?
Occasionally an unsub request is NOT bounced back.
What federal website do I tell them I will report them to if they don't take my address off?

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