By: Chris Lewis

Sometimes it's best to go back to basics to understand some of the issues that can hamper your email distribution efforts. One of those basics is just how email is sent through the internet to the destination.  You may set up the perfect email and it may never reach your destination because it was blocked from getting there.  Most of the "hoops" that need to be jumped through is because of SPAM and open SMTP relays (servers that will allow anyone to send from it).  Below is a quick explanation of how the email system works and how your email interacts with sending and receiving SMTP servers. Here is the path an email takes:

1. Your email client sends an email to your SMTP server, say it was sent to chris@theirdomain.com

2. Your SMTP server grabs the domain name in the email, in this case THEIRDOMAIN.COM

3. Your SMTP server looks up the MX records for THEREDOMAIN.COM from your DNS Server (this is the MXLookup you find in MXToolbox.com website)

4. In the order of priority, your SMTP server attempts to connect to the first destination SMTP server based on the first MX record.

5. If the first destination SMTP is unavailable or busy, your SMTP server will move on to the next destination SMTP server, and so on.

6. Once your SMTP server has connected to a destination SMTP server, before the email is transferred, the full return-path (or FROM) email address to is sent to the destination SMTP server

7. If the destination SMTP is setup correctly, it will take the return-path email address and extract the domain name (in our case ARIALSOFTWARE.COM if we were sending the email)

8. Now the destination SMTP starts authenticating the email by one or more methods. The most common are below:
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• The destination SMTP server looks at all it's subscribing blacklists and sees if your SMTP server's IP address is on the  list.  The destination SMTP server will most of the time reject any emails from any domain from your SMTP server
• The destination SMTP server "sees" the IP address of your SMTP server, which is does a reverse SMTP lookup to see  what domain name is assigned, and if the domain it finds does not match the domain of the return-path of your email than it can be rejected
• The destination SMTP server looks up the SPF record for ARIALSOFTWARE.COM from the ARIALSOFTWARE.COM  DNS entry.  If there is no SPF record for the ARIALSOFTWARE.COM domain, then your SMTP server may not have "authority" to send ARIALSOFTWARE.COM emails so the destination SMTP server can just reject it.  If the SPF record is found for ARIALSOFTWARE.COM, the record is examined to see if your SMTP server has authority to send  ARIALSOFTWARE.COM emails.  If your SMTP Server is not in the list, your emails can be rejected.
• A destination SMTP could have a built in SPAM scoring system like Assassin.  Your mail will be scored and either allowed to go through unscathed, allowed to go through but marked as SPAM, or not allowed to go through at all.

9. Any combination of these above methods plus other methods can be used to determine if an email is just rejected by the destination SMTP server
10. Exceptions - Sometimes these methods will create a SPAM score, and if the score is exceeded then the email is rejected.  So it is possible for one of these to fail but the email still makes it through
 
So, the answers to why an email does not make it is within this flow.  The MXToolbox.com website is a big combination of different tests which may confuse the issues.  Blacklisting ONLY has to do with the "sending" SMTP server and has nothing to do with a particular domain because you could use the same SMTP server to send out emails for multiple domains…so the IP address is king.  If you try to send out emails through your SMTP server that is blacklisted, most of the time the emails will be rejected by the destination SMTP server.

So, to effectively use the MXToolbox.com tool for blacklisting detection, you need to do two things.  First, you need to get the SMTP server they are using in Campaign Enterprise or Email Marketing Director.  You need to translate that SMTP server setting to an IP address if it is not already one.  Then you go to the Blacklisting tab and put that IP address in and then see if your SMTP server is blacklisted.

One last spin on this…if the SMTP server setting they are using is an "internal" IP address, like 10.10.10.1 or 192.168.1.100, then you will have to find out what the "external" IP address of the SMTP server is to see if it is truly blacklisted in the world.

By: Chris Lewis

Here are Arial we get many instances where clients send email perfectly for long time and then bamm! things start falling apart. Many times a software is, like ours, is blamed for the issues because it is a logical thing to look at first.  The truth of the matter is that Campaign Enterprise, Email Marketing Director, or any other emailing software does not change...but the circumstances around it do. Sometimes a dreaded OS update happens overnight and introduce new "support files" that your emailing software requires that causes a difference in functionality than before.  You might have a corruption of some of the email software files, but this is rare.

The #1 culprit of these "it just started happening" scenarios is Blacklisting. The internet is a dynamic place.  New technologies to protect the general public from SPAMers, Phishers and the like come online unknowingly and what was working great before all of a sudden just falls apart.  Email distribution management is not a noun but a verb.  It is an active thing that requires monitoring and maintenance.  Part of your maintenance schedule to make sure everything is working well should include a scan to see if your SMTP server system is on any blacklists.  We recommend using a website called http://mxtoolbox.com. With using this website, you can find out in an instant if you are being blacklisted by many blacklist sites.  It only take a few problems with your SMTP server or a few complaints from cranky recipients to be blacklisted so check it at least weekly or before you send out any major email blasts.

As email distribution professionals, we need to play by the rules and be good internet citizens even if the rules changes.  Remember, it is not IF the rules change, it is WHEN, so stay diligent.

Also, with visiting a free analysis tool like MXToolBox, be sure to visit a few of their advertiser and support their effort.

By: Chris Lewis

Mass Email Professionals have a job to do, and that is to get the emails into INBOXes.  To make an email campaign successful, there are things that need to be in place before you hit the send button or it is possible that even though all your emails seemed to go out, many of your emails could be in the SPAM box which is as good as the recipient not getting the email at all.  So, in order to increase your effectiveness in getting those emails delivered correctly, there are some guidelines you should follow that will be true for many of the big email providers like Gmail, AOL, and hotmail.

Make sure you have an SPF record in your DNS!
This is the #1 problem why email does not make it to the recipient, and many times you wont even know it.  Gmail requires this, and every email sent to it, it makes sure the SPF record is there.  At best, it goes into the Spam folder, at worst, it does not make it at all.

Make sure your links in your emails are not IP addresses and that they use port 80 (HTTP)
Many times you can just cut and past a URL not really noticing that the URL is an IP address or that it may even use a non-standard port.  These are huge red-flags to recipient email systems.  Also, try not to make the "test" part of a hyperlink the same URL.  Use real words like, "Click here to see..." or something.

Make sure your subject line is not too "flower-y"
Using all upper case words or lots of punctuation in your subject line can cause a higher spam score.  You want to attract attention to your subject but it should be done tactfully.  Use some type of useful information that is very specific to the recipient so that you may attract their attention.  Just mentioning their name is not good enough, and can sometimes be annoying and look like SPAM.  Be specific!  Think about what you would click on if you saw your subject line. Getting an email to an INBOX and not having the recipient even open it is a crime!  Bad examples of this are:

YOU HAVE TO SEE THIS!
***Sale now!***
Hello Chris, I think you will like this

It sounds simple, but you would be surprised by how many do this type of thing in the subject.  This happens a lot too when the email is not written by a person not using primary language skills or different cultures.  I don't mean to be harmful here, but many terms and sayings can be outdated or actually repelling, so make sure you edit things before sending out.  Overall, write emails like you were just writing to one person in a normal scenario.

By: Chris Lewis

Well, not really for dummies, but knowing more about this anti-spam system will help you get your emails into the Inbox.  Most of the time, the question is, "should I use DKIM for my email sending..." YES!  "Will it ensure my emails get into Inboxes?"  NO!  But, it helps a ton.  DomainKeys Identified Mail (DKIM) is a method for associating domain name to an email message thereby allowing a person, role, or organization to claim some responsibility for the message.

Here is how it works:

- You send an email using your SMTP server.
- Your SMTP server that has authority to send in behalf of your domain adds a DKIM signiture header to your email and sends it
- The destination SMTP receives the email, sees a DKIM signature in the email, and then looks up the public signature on your domain using via DNS
- If the signature in your email authenticates with the public signature in your email, then the email is "good"

Now, saying that the email is "good" means that the destination SMTP knows it is from you, but the destination mail server will still SPAM score your email by the content.  DKIM adds a ton of "good" SPAM scoring advantage to your email and thus will greatly improve it's inbox-ability.

So, if you are not using DKIM, use it!  Click here is a great link in Wikipedia on the subject

Understand this will not have anything to do with your email sending client, like Outlook or Campaign Enterprise. The system works because it is on a SMTP server level of activity and is based on authority that can only be established by domain owners.

There are several different accepted methods in use now that keep spammers from being successful.  One of those methods is the SPF designation. In order for your emails not to be rejected by the recipients mail system we recommend that you create a Sender Policy Framework (SPF) record for your domain. An SPF record is a type of Domain Name Service (DNS) record that identifies which mail servers are permitted to send email on behalf of your domain.

The purpose of an SPF record is to prevent spammers from sending messages with forged From addresses at your domain. Recipients can refer to the SPF record to determine whether a message purporting to be from your domain comes from an authorized mail server.

For example, suppose that your domain example.com uses Gmail. You create an SPF record that identifies the Google Apps mail servers as the authorized mail servers for your domain. When a recipient's mail server receives a message from user@example.com, it can check the SPF record for example.com to determine whether it is a valid message. If the message comes from a server other than the Gmail's mail servers listed in your domain's SPF record, the recipient's mail server can reject it as spam.

If your domain does not have an SPF record, some recipient domains may reject messages from your users because they cannot validate that the messages come from an authorized mail server.

To Create an SPF record for your domain, you will have to be able to edit your domains DNS information and use a format that specifies your mail servers.

By: Chris Lewis

The choice of the SMTP server you use is as if not more important that the email marketing tool you us. You can create the best looking, most effective email ever but if your SMTP server setup is not set up well then it is like you never sent it.

SMTP servers are the email work-horses of the internet.  In the world of amazing technology, it is sometimes hard to be impressed, but I am constantly amazed by the thought and foreknowledge of the whole SMTP server framework.  As time has moved on, the SMTP framework has changed, and the biggest change is that of SPAM control.  There are to main problem areas we see daily with SMTP servers: How to connect to your SMTP server, and how "good" your SMTP actually functions.

SMTP Connection - The problems that are encountered when connecting to SMTP servers are varied and usually include these:

• The port you need to use is being blocked by your ISP if you SMTP server
• My ISP only allows so many email per day/hour
• Not using the correct connection method (ie: TLS, SSL, NTLM) or wrong domain name
  
• My ISP's SMTP server is not a "good citizen" in the internet world
  

SMTP Configuration - If you have your own SMTP server on-site you are both blessed and cursed.  You will be able to get your emails out to the SMTP server at lightning speeds, but since you have your own SMTP server YOU will have to be responsible for being a "good citizen."  This means you need to do daily duties like making sure your IP address(es) on the SMTP is using is not blacklisted, that major email providers like Hotmail, AOL, and Gmail and not blocking your emails, and making sure you are not overwelming your SMTP server or your connection to the internet.  Needless to say this is a big subject, but these are some of the things to consider.

SMTP Providers - There are specialized companies out there that will act as your SMTP server.  They will ensure your emails going out are appropriately make to conform to SPAM rules, they monitor their servers to make sure they are not blocked, and they will help you resolve issues that do come up is there are any problems with email recipients.  Now it is true this will cost you some money, but if you add up all the time you or someone you will hire to work on these issues I think the value is there.  If you are sending 100,000 emails a month, then the prices are really reasonable.  If you send over a million, then that is maybe when you can start thinking of having your own SMTP server, but it really depends on the connectivity, your budget, and your expertise.  One of our partners is SMTP.com (http://arialsoftware.smtp.com) and they have been a great partner with us for years. There are others, but I think they are the best, so check them out if this seems like a solution for you.

Many email professionals use Microsoft's Exchange server to send out their emails from Campaign Enterprise or Email Marketing director.  The number one complaint we get is usually that it is very slow even though they are on "a super fast system on a fast internet connection."  By default, Exchange Server is not setup to be a mass email system. In fact, they have created many settings by default to stop email from being accepted at a rapid pace. Depending on your Exchange Server version, there are settings you can look at to stop this throttling.  A prominent term used is "tarpitting."  Now the subject of tarpitting mainly concerns a set of parameters you can set in your Exchange Server so that it will accept emails at a rapid pace.  Because of all the version of Exchange Server out there, and with them trying to deal with the SPAM issue through time, there are different settings for each of these versions which we cannot cover, but hopefully this article will uncover a nagging problem you might be having.  Now keep in mind, many Exchange Server administrators may not even know what you are talking about because it is a rare occurrence and they probably have not encounter it before, so you may have to prime the pump with some Google service on "Exchange Server SMTP slowness" and show them some of the settings they will have to deal with.

By: Chris Lewis

Email bounces that occur when you send out email from any email software sending program can occur in two different way:

An Error During Sending - During sending, if your SMTP server deems a certain email address as permanently undeliverable, then your SMTP server will return a 500-series error code which tells Campaign Enterprise or Email Marketing Director to hard bounce that email immediately.  These kind of immediate hard bounces usually only occur for two reasons: The email address was malformed or the mail system you are sending through has "authority" over the domain of the email being sent and can just right on the spot if the email address is good or not. We see this happen a lot with Exchange servers where you both you the Exchange Server for receiving and sending emails.  If your company domain is hosted on the Exchange server then the SMTP server of the Exchange server will only allow valid email addresses to be sent with those domains.

Returned Email - This is the most common way bounces are recorded because most of the time your SMTP server does not have the immediate authority to say whether or not an email address is valid. In this scenario your SMTP server simply relays the email message you sent to the SMTP server that has authority for the domain (from the MX record). When your SMTP server is talking to the target SMTP server, the target SMTP server might say "that email box does not exist" which is a 500 series error.  This triggers your SMTP server to send the email back to you (or your bounce account).  This can take seconds to hours to happen.

So, overall, bounces are somewhat difficult to deal with since they may happen from several different source, and since there is no standard for the formatting of bounces, it become the task of our software to decipher a bounced email which may have all or just part of the original message. In the next article, we will discuss the different ways to deal with the returned emails.

In June 2005, Microsoft began to implement its check for Sender ID records of its Hotmail and MSN email accounts using their version of a specification known as Sender Policy Framework (SPF). Sender ID is only slightly different than SPF, in face Sender ID is specified in the Sender ID string as "v=spf2." Sender ID records are simple identification records attached to the Domain Name Server(s). This identification allows the recipient mail server to determine that email being received is coming from a domain authorized to send that email.

Legitimate email marketers will definitely want to take the time to establish a Sender ID, or risk non-delivery of a substantial portion of their legitimate email messages. Those messages could either be automatically blocked or sent to the recipient’s junk email folder if they fail the check. It will only be a matter of time before other large online email accounts and Internet Service Providers (ISPs) also begin to check Sender ID to authenticate email. MSN and Hotmail already check for Sender ID records, although it does not yet block unauthorized senders.

It is extremely important to test your email messages in a variety of email clients, including Hotmail. If no Sender ID record is associated with the domain name server, the message displays a warning, indicating that the sender could not be verified. Depending on the recipient's filter settings, the message may never even be seen. Each incident will add to the deniability rate, as the ISP learns more about a particular machine’s email practices. It is important to configure your Sender ID as soon as possible.

Here's how to configure your Sender ID

Simply go to the Sender ID Framework wizard at http://www.anti-spamtools.org/SenderIDEmailPolicyTool/Default.aspx and follow the four easy steps (These steps may need to be taken by your network administrator, who should readily understand all the technical instructions that will be requested). Additional configuration may be necessary for companies with multiple name servers, or those who are sending email on behalf of companies with a different domain. Once the initial record is made, there are options for implementing more advanced features of Sender ID.

Once implemented, it is a good idea to check the Sender ID record (this check can also occur ahead of time, in case the network administrator already has Sender ID in place). Go to http://www.dnsreport.com and enter the domain name to check. The results of the Sender ID test appear toward the bottom of the report at the end of the "Mail" section. If there is no record, a yellow warning is displayed, with some information on why you need Sender ID.

Another new term associated with Sender ID and Sender ID is Purported Responsible Address, or PRA. The PRA is a modification to Sender ID on the recipient mail server that should address concerns about blocking forwarded messages. Microsoft will shortly be implementing PRA in their mail servers, namely Hotmail and MSN. As a sender, the only step you need to take for PRA configuration is to ensure that the Sender ID is associated with the proper domain; the recipient mail server determines whether it will simply look for the Sender ID or implement PRA.

For more information about Sender ID, you can visit the Sender ID home page at http://www.microsoft.com/mscorp/safety/technologies/senderid/default.mspx.

One of the most confusing terms regarding email marketing is relaying. Relaying is not a bad word, as some ISPs would lead you to believe; in fact, it is the only way to get emails from point "a" to point "b" while using an SMTP server. Like a baton in a relay race, an email is passed along from one mail server to another, with the goal of getting to the finish line without being dropped. At each transfer, the email is relayed from one server to the next until final delivery. Problems occur if the SMTP server to which the email is first submitted has relay options that are not configured correctly. There are generally two states an SMTP server is in concerning relaying: open relaying or closed relaying.

Open relaying is where all the problems start. It is actually the state of a server sitting out on the Internet to which anybody has access. Email servers that are configured to run wide-open are a major access point for spammers. As soon as an SMTP server is placed online, if it is not configured properly, it is hijacked. Back in the olden days, the default option was to allow anybody and everybody to send through a mail server. Eventually the default for new operating systems was to keep the relaying closed. Some SMTP servers remove the open relaying altogether to prevent accidentally making it open. With open relaying, the server is guaranteed to be used by someone else to send spam messages and cause the server to get blacklisted. Many mail agents check the server settings by sending a test email to see if the SMTP accepts it. If the test is accepted the recipient server may decide not to accept the email from that server, legitimate or not. Never, ever use open relaying.

One of the traditional methods spammers use is finding an SMTP server online without any restrictions in place and use it to send their emails. This can effectively hide their tracks and could cause potential problems for the legitimate server they confiscate. Several online organizations have taken it upon themselves to identify potential spammers and stop them from using other peoples open mail servers to send spam. The IP address of the server that appears to be open, is added to a database that is checked by subscribers and set to deny emails automatically. If this happens to a legitimate business, contact the database administrator to request that your company be removed from the list on the condition that the problem with the server be corrected.

Closed relaying, like open relaying, is merely a description of the state of the server and is not a setting found in the relaying options. Closed relaying means that some sort of authentication must occur before someone can send emails through the SMTP server. The best way is to list a computer's IP address, or a block of addresses can be added to the server in the relay settings section, which vary by product. Enabling these features restricts access to the SMTP server and thereby closes it to people who are not approved. Further restrictions include authenticating with a username and password, and blocking connection requests from all but an approved list of computers. Most mail servers are now closed to all traffic, until a computer is specifically added to the list, or can authenticate.