[HOWTO] Send Email to a Group

Category: Email

A reader asks: 'I want to send emails to a fairly 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 email to a list of people?' Read on for some good options, and a few you definitely want to avoid...

Sending Email to Many Recipients

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 group of recipients. 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 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. 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 click on the little black triangle next to the word "Gmail" at the top left of your Gmail window. Select "Contacts", and a new Google Contacts tab will open. Click "Create label", enter the list name, and click OK. 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 on the top right that looks like a rectangle pointing to the right. (I told you this was obtuse.) Click the name of the list you just created, 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, Outlook.com, 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 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. See my list of Email Marketing Best Practices for some tips on how to communicate effectively via email to large groups.

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 "[HOWTO] Send Email to a Group"

Posted by:

17 Apr 2018

You forgot to mention that Gmail limits the number of emails in any single batch to 100.

Posted by:

17 Apr 2018

Another great coverage of another great topic!
Thank you, Mr. Rankin.

I don't think Romans were so impersonal in their communication methods. Unless it was for business or they were named Bob Rankin! ;)

Posted by:

Stuart Berg
17 Apr 2018

I really like the email distribution software called Groupmail (https://group-mail.com/). I use it like a listserv to our neighborhood. They have a free version that requires that you send to 100 or less email addresses. ISPs and email servers like Gmail don't complain because Groupmail sends the emails out individually in small groups. For example, I have it set to send 10 emails and then wait 10 seconds and then it just keeps repeating that schedule until all 84 of my emails are sent. It may be a little slower than a bulk email mailing, but it's more easily identified as NOT spam.

Posted by:

17 Apr 2018

I have used MailChimp's free service with great success, and can recommend it. only rub is if some tech-challenged person unsubscribes, they can't be added back by me, but must personally subscribe through a link.

Posted by:

17 Apr 2018

My method for mailing to multiple recipients is having a word processing file(s) of multiple addresses, each separated by a comma. Then I copy-paste that list into the BCC: field. To my knowledge, all the mails go through. A century ago, AOL tried to tag me as a spammer, sending me a nastygram advising me of such. I politely answered that these were friends and relatives (maximum of about 35) and have had no further problems. Still use AOL for those mailings.

Posted by:

Robert Schechter
17 Apr 2018

You showed your age by mentioning Yahoo Groups. Because of failing service groups are leaving Yahoo. I'm moving my groups to Groups.io as a better alternative.

Posted by:

17 Apr 2018

Well, I use Thunderbird & a small, somewhat local ISP for my email. I do a mailing to about 150 once a month. I simply copy the email addresses from the Excel list on which they're kept (along with other data) and paste them into bcc. Early on I worried about their being treated as spam and broke the list up into 2 or 3 chunks but now do the whole list at once. I found out that my ISP has a max of 500 emails allowed in a day (ok, I found out when I had my email hacked by the Russians and 500 plus emails were sent in one day & I was blocked from sending more email that day. Never tangle with Russian trolls on Facebook.) I had thought of using MailChimp but it wanted to go into big plans "campaigns" etc; I just want to notify a bunch of people about a meeting.

Posted by:

17 Apr 2018

I can't believe you *recommended* sending a group of people's emails in the clear using the To: field in Gmail!

Talk about SpaHaM bait. All it takes is one person's computer to be infected with virus/malware and everyone is now harvested. That's what the Bcc: is for!

Also, ActiveCampaign

Posted by:

18 Apr 2018

I use 1and1mail - it allows me to create email templates and a large address book. Using the templates it allows me to send personally addressed emails to each person in the defined email group. I am a volunteer with a Seniors Organisation and we do technology classes, so I use it for class notifications to members and interested seniors.

Posted by:

20 Apr 2018

mknunan is mistaken on the 100 address limitation for gmail. Actually, the following restrictions apply when sending emails from a Google Gmail account: Gmail email send limit - no more than 500 recipients per message for the Gmail web interface, or max 100 recipients if you are using an email client software.

Also, a good practice to remember on multiple address messages is to place the group address (or multiple addresses) into the BCC area to avoid exposing addresses to other addressees or to anyone in general.

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