Why do my emails sometimes end up in the Junk Folder?

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Occasionally, our Repree support team receives requests about emails and deliverability. “Why did my client never receive it?”, or “why did it end up in my client’s spam, promotion or junk folder?” are probably the two most common questions. So let’s dive into the email and see what is really going on while discussing a few things that can help avoid these issues.

As an email user, we write an email, we hit send, and our expectation is that it will end up in the inbox of the person we sent it to. Most of the time, our expectations are met and we carry on with our day having no need to understand why or how that email made it to the desired destination. However, when an email doesn’t make it through it can send us down a frantic path trying to determine what has happened. At this point, let’s touch on tip #1 and #2 if your email has not been received. We’ll get into details later.

  1. Check the spam, promotions, or junk folder. In many cases, while it may appear that the email you sent was never received, it is in one of these folders. So it isn’t really a case of your recipient not receiving it; rather, it is a case of your recipient not receiving your email to the expected folder.
  2. Search for the sender. In the case of a document for electronic signing, search the word “Repree.” Some mail systems have hidden folders that are not readily noticeable. If the email doesn’t appear in the junk, promotion, or spam folder, a search will more than likely find it.

Now to talk about the why, and for this we will use Repree as an example.

First and foremost, it is actually quite rare that an email just isn’t received by your recipient. The obvious exception here is when an invalid email address is used. To put some statistics behind that, here are some numbers from Repree’s tracking system going back only a short time;

16, 335 emails sent.

16,259 successfully delivered to the recipient.

That equates to a 99.5% success rate when sending emails. Of the 76 emails that couldn’t be delivered, all of them were due to incorrect email addresses or recipients whose mailboxes were full.

But let’s get back to emails appearing in the junk or promotion’s folder. To understand why this happens I will give you a brief overview of how the email system works using the scenario of sending a document for electronic signing from Repree.

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When you hit send, the first thing that happens is our mailing system does a lookup on your recipient’s email address to figure out where we have to deliver it. We’ll say it is Hotmail in this case. Great, the mailing system now knows to make a “phone call” to Hotmail to deliver the message. This is how that call goes;

Repree: “Hey Hotmail, it is Repree, how are you today?”

Hotmail: “Hey Repree, good to see you again, what can I do for you?”

Repree: “Just have a message I would like you to deliver to one of your people.”

Hotmail: “OK, great. Let me just check my list first.”

The list is our potential first point of failure and isn’t very common. The list referenced is Hotmail checking to see if it is allowed to talk to us. We call them blacklists. If Hotmail checks its list and Repree is on it, they basically hang up the phone on us. Repree has never been on this list. So we can continue our conversation;

Hotmail: “OK, you aren’t on my list. What is the message you would like to deliver?”

Repree: “It has a subject that says “Offer to Purchase” and the body says Hi Recipient, please click the link below to start electronic signing”.

Hotmail: “Great, let me check my list again”.

Yup, another list. This one is different than the first though. Here, Hotmail is checking two things;

  1. Repree’s mail reputation. For example, Hotmail is looking to see if we are a known spammer.
  2. Hotmail is looking at the content (subject and body) of the message to determine if the message itself could be spam.

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Mail systems, like Hotmail, “learn”. By that I mean, over the course of weeks and months, it looks at messages Repree has sent and puts all the data together to determine if we are a spammer, or likely to be a spammer. This is how it figures out which folder it should put your email in. It is specifically looking for keywords in the message as well as what action your recipient performs (opens the message, deletes etc) when they receive the email. All of these things are used to determine if the email can be trusted.

This is where we sometimes encounter an issue. A mail system looks at the content and sees key indicators that the email may be spam. It then errs on the side of caution and places that email in junk, promotion’s, spam, or some other folder.

Let’s go back to our conversation between Hotmail and Repree;

Hotmail: “Looks like we may have a bit of a problem here Repree. I am going to deliver this message, but I can see that it contains some words that I am not comfortable with. Furthermore, I can see that the 15 previous emails you sent to us contain similar words. I am not 100% comfortable with this, so I am going to flag it for my people.”

Repree: “But you are going to deliver it, correct”

Hotmail: “I am, and I am going to watch what happens with it and the previous 15 emails. If my people get rid of them immediately I am cutting you off. If they open and click through them, I will add that to my case notes that despite your message containing words I don’t like, you will be approved”

Repree: “Thanks Hotmail. You’re awesome. See you in 12 seconds and we can have this whole conversation again!”

In scenarios where emails hit a junk folder this is normally what is going on. A recipient email system is being cautious to prevent spam. This can and does cause some legitimate emails to end up there incorrectly. However, collectively we can work through it.

Here are some tips that help systems like Hotmail deliver messages to the proper folder, and stop flagging legitimate messages as spam. A lot of this can be rectified by simply changing our emailing habits, specifically in regards to the content of the message.

To start, we need to limit the use of key words typically used by spammers. What is the one word almost every spam email contains that we also use in a good number of legitimate emails?

The word: OFFER.

Think about it for a second. I would bet if you looked back in your email at actual spam, most of them would contain the word OFFER. When Hotmail checks the content of emails to its recipients and sees that word it gets extremely cautious and can set back all the learning it has done (ie. us being a reputable sender). Why? Well, it sees the word “Offer,” or “Offer for you,” or any other variation, and knows in most cases, those sequence of words mean spam, spam, spam. It looks at your legitimate email and says, I have notes that say you are reputable, my people interact with the messages you send, but this message (and a bunch of other messages today) have words I don’t like. For all I know your mailing system was taken over by a spamming robot and this is the start of a mess, so I am going to take two steps back. I am going to put your email in the spam folder until I can be sure you aren’t doing things I don’t want you to.

At that point the mailing system circles back and waits for interactions to happen before it starts to recognize the emails are not spam. And so the cycle continues… on and on. The good news is as time progresses, the steps back will become smaller and smaller until it stops placing important emails in unnecessary folders. It does take time but, in our case, we have already seen substantial improvements with many changes we have implemented coupled with the help of our fantastic user base.

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