Is There A Good Way To Send A Mass Email?

This is going to be more about the options that are out there rather than true technical details.  I’ve done all of these before in the past, but never really put the thought into how the receiver sees these types of emails until lately.

I’m pretty open with handing out my email when a company wants to get it on a form so they “can keep in touch.”  Since GMail is my primary client, it’s capabilities let me deal with the bulk of the incoming junk messages pretty efficiently without a lot of hassle.  Also their spam protection has been pretty top notch from what I (haven’t) seen.  All that being said, the general filtering capabilities of it are the same as any other client: when messages arrive, perform specific tasks on them.  Common filters that people tend to have include “Sent only to me”, “I’m in the TO:”, “I’m in the CC:”, “Sent from somebody/some domain”, “Does it have an attachment”, etc.  When it comes to sending mass emails there’s a few different options and each has an impact on how the receiver’s email client deals with it.

All email addresses in the TO:/CC: field

Most people (and especially companies) shy away from sending a mass email with everybody in the TO: or CC: field these days*.  Why?  What if I’m a rival company to you and I put my email address on your mailing list.  Now you send me an email, along with the rest of your huge list.  I can now look over that entire list of email addresses and add them to my own mailing list and start soliciting to them.  Or taking that list and selling it off to other companies that will spam you.  Granted any company that uses this practice is most likely winding up in a spam folder anyways, but it does mean others now have your email address when you didn’t intend for them to get it.

As a business this is the worst way to mass email your clients.  Yes, the recipient’s email client can process the message based on it’s rules with no problem, but they may have a rule similar to “If I’m not the only recipient, make the message as low priority and move it to this folder I only read during a blue moon on the fifth Tuesday of the month.” 

* Although I’m sure we still have that parent/sibling/grandparent/friend/third-cousin-twice-removed that still sends those absolutely funny photos.  Just as annoying, but not the types of mass emails I’m talking about.

All email addresses in the BCC: field

Well, if we don’t want one recipient to see everybody, let’s just put the entire list in the BCC field since that isn’t sent to the recipients.  Problem solved, right? I suppose from the business’s point of view, it does take care of the concern about people stealing the list of recipients.  But it raises a couple more issues.  First, if you don’t have anybody in the TO: field, a lot of spam filters will deem the email much more likely to be spam.  There’s a number of other criteria that will determine if it is flagged as spam, but not having one email address in the TO: field doesn’t help.  The other issue is that it essentially gives a big middle finger to the recipient if they make use of rules to filter the deluge of emails.  Not having their email address show up in any of the normal fields means that the recipient needs to filter on the other criteria like who sent it.  Why is this an issue? Here’s an example:

Running my own business and domain I am going to receive a ton of email that I actually want to receive (current client emails, newsletters, convention information, partner programs, etc.), but I’ll also receive emails that I should be aware of but didn’t necessarily think about.  Things like emails to the ‘webmaster’ or ‘admin’ of my site are sent to my inbox because of a catch-all email account.  To quickly spot these types of emails it’s nice to be able to have a filter that has rules along the lines of “If <my email address> does not appear in the TO: or CC: field, flag the email for manual investigation”.  Since no email address shows up in the email this filter now catches all those BCC’d emails and flags them even though it’s a regular, legitimate email.

Or another example:  One of the trainers I communicate with at my gym regularly sends out newsletter-like emails, but about 1/5th of the time he also sends out emails directly to me.  The problem is that he tends to use BCC in both cases.  When trying to prioritize my inbox, I would like to quickly skip the newsletters but actually know what’s going on with the other emails.  Since the BCC hides any indication if I was the only recipient or part of a mass mailing trying to create a filter is neigh impossible.  That leaves wasting the time to look at each email.  Granted I know the business value I’m getting by keeping in contact with him so I tolerate it, but for most businesses I look at it as a sign of the business not really putting any thought into how their customers perceive them.

Mail merge each address individually.

This option seems to have the best of both worlds, but it presents a different issue.  When you perform a mail merge, you’re sending out nearly identical emails to lots of people.  There’s a number of spam filters that will start flagging these emails as spam because a large number of extremely similar emails are coming through in such a short amount of time.  Larger companies that send out newsletters and such have realized this and send out batches.  You may have likely noticed this if you subscribe to coupon or deal based newsletters that generally arrive in your inbox at the same time every day, but vary by a few hours.

The other issue with performing mail merges is that normal consumer tools (using Microsoft Word and Outlook) are very limited in the customization of the mail merge.  For example, the subject line cannot be merged.  You also cannot attach files as part of the merge.  To have better dynamic content (say optional paragraphs), they have to be part of the merge data rather than flags controlling whether to add them or not. Once the merge is completed it sends out every email at the same time rather than batching them automatically.

Sure there are some open source projects out there for advanced mail merges, but it takes that extra effort to get that type of functionality.  Most people will only need these tools once or twice, and thus never think about using them regularly.  If the usual tools had some of these features built in the experience would be much better for both the sender and the recipient.

Which option to go with?

So which method should people go with? It really depends on what you’re looking to achieve.  As an end user, I want to see my address in either the TO: or CC: field somewhere.  If I’m BCC’d on an email, I’m likely going to mark it as spam and not even bother reading it. The Mail Merge option would allow for a single individual to appear in one of those fields, but of course it has the limitations I mentioned above.

I know I tend to be an extreme power user for some things, but what other gripes do people have when it comes to handling and filtering email?

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