Some of my recipients didn't receive the mass email I sent. Is that Blackbaud's fault?
It's important to understand that Blackbaud's email servers don't have direct access to individual recipients' email inboxes. The Blackbaud mail servers are only able to hand an email off to the recipient's mail server. From that point forward, the delivery of the message from the receiving mail server to the recipient's email inbox is handled by the receiving mail server and the network and software used by that organization to manage the flow of email.

Sometimes, when Blackbaud attempts to hand an email message off to a mail server, the server will not accept the message. When this occurs, the receiving mail server provides a "bounce" message back to the Blackbaud email server so that we can know why the message was rejected. Blackbaud keeps a record of these bounce messages and most Blackbaud products that send email will show that bounce message for specific recipients when viewing the email statistics.

Note however that when a recipient doesn't receive an email message, what's far more common is that the receiving mail server actually accepts the email message from the Blackbaud email server, but then does not deliver the email to the intended recipient.

The send-from address in my email used my organization's @domain.com domain. Why wouldn't this email be delivered successfully?
Since Blackbaud does not control your organization's domain, email sent from your Blackbaud website is not technically sent from your @domain.org domain, even though you may have entered this in the "send as" or "send from" email address field. The email messages are actually sent from a Blackbaud mail server. Because of this, your receiving mail server may be detecting that even though the "from" domain looks like your organization's actual domain, the email did not actually originate from your domain. It may therefore prevent the message's delivery.

To remedy this, you have a few options. First, your IT staff could "whitelist" the server IP addresses of the Blackbaud mail servers where these emails can originate. Doing this instructs your mail system to not block any emails originating from one of these IP addresses.

Alternatively, you could also whitelist your organization's "@domain.com" domain. Doing this would allow all emails whose sent-from address matches your organization's domain to be delivered without being blocked. Note however that whitelisting your entire domain like this could potentially allow unwanted spam sent from other email senders (masking their emails as though they originated from your domain).

A variation that's also available is to whitelist the specific send-from email address(es) that you use to send email. For example, if all of your Blackbaud website emails are sent from "administrator@domain.org", you could whitelist just this one specific email address instead of the entire "@domain.org" domain. Doing so can reduce the likelihood of unwanted spam from reaching individuals at your organization.

Why would a receiving mail server not "bounce" the message back to Blackbaud but also not deliver it to the intended recipient?
In most cases an organization's anti-SPAM policy aims to do two things: (1) attempt to prevent unwanted SPAM from reaching user mailboxes but (2) still allow legitimate messages that were mistakenly marked as SPAM to be un-marked as SPAM and allowed to route to the recipient. If the receiving mail server were to just bounce all suspected SPAM back to the sending server, it's possible that important messages could get rejected and there would be no way to "unmark" those messages as SPAM and deliver them to the recipient.

How does the email server at a recipient's organization judge whether an email is SPAM or not?
In short, the receiving mail server grades each individual message to judge it's "spamminess". Unfortunately, however, the grading scale is rarely, if ever, published and each organization gets to set the scale however they like. What happens is that the anti-SPAM device uses a set of rules to grade each email on a broad range of characteristics. For each rule that the email satisfies, "points" are added and when the total number of points for that email exceeds a limit set in the anti-SPAM device, the message is deemed to be SPAM and it gets either quarantined or automatically deleted (as determined by settings in the anti-SPAM device).

But the email recipient checked their SPAM folder. Since the email isn't there, doesn't that mean that something happened on Blackbaud's end?
Remember that from the time Blackbaud's mail servers deliver a message to the recipient's mail server, there can be more than one opportunity for messages to be deemed to be SPAM. In most cases, an anti-SPAM appliance, device, or software application (at the recipent's organization) attempts to capture the bulk of spam and prevent it from reaching the recipient at all. This means that when an appliance like this flags a message as SPAM, the message often does not land in the recipient's SPAM folder. It just resides in a server-level quarantine location, typically to be automatically deleted after a certain number of days in quarantine.

For messages to reach a recipient's individual SPAM folder, it often must pass the organization-level anti-SPAM device checks first.

What kinds of things do anti-SPAM devices typically look for when judging "spamminess"?
The main thing to remember here is that there is no single, tell-tale indicator of SPAM. Broadly speaking, SPAM is just unwanted and unsolicited email and because of that, relying on devices to judge whether a given message is SPAM or not is inherently flawed. Some organizations have their SPAM filters set to err on the side of capturing the maximum possible amount of SPAM, knowing that the consequence will be that legitimate email messages will be caught. Other organizations have less restrictive anti-SPAM settings, relying instead on individual recipients to handle unwanted email once it reaches their personal email account.

Here are the main categories of rules that anti-SPAM devices use to rate messages for possible SPAM content.

1) Keywords that could indicate SPAM
It probably doesn't surprise you that words related to certain medical products or adult content can cause an email message to be flagged as SPAM. But other less obvious words are often included in SPAM filter rules:
 
  • Home Based
  • Make money
  • Cash
  • Free
  • Passwords
  • Click
  • Sale
  • % Off
  • Offer
  • Sample
  • Act now
  • Apply now

All of these and many, many more words are often included in extensive lists of complex rules that anti-SPAM devices use to rate messages. Note that just by including a single instance of one of the above words will not necessarily mean that your message will not be deliverable. It will just add a certain number of "points" worth of "spamminess" if the recipient's mail system uses a rule looking for that keyword.

2) Excessive use of images or overly large images
This is a challenging rule to bypass. By its very nature, HTML email tends to be visual and you probably work very hard to make your email messages be as visually appealing as possible. But the fact is that most SPAM is accompanied by a large percentage of the message being image-based instead of being text-based. Make sure to balance the use of a few small images with relevant text-based content to avoid being flagged by this rule.

3) Excessive use of hyperlinks
As with using too many images, having a great number of hyperlinks in an email can add a significant number of "points" worth of "spamminess" to a give message. Try to limit the number of hyperlinks in your message to a small number of relevant links.

4) Complex formatting
The more complex the formatting and layout scheme of a message, the more likely it is to be deemed SPAM. When designing email templates, the best practice is to visualize what your message needs to look like first and then insert a very simple HTML table with only as many rows and columns as is necessary to effectively communicate the message. Once you have a simple and effective table-based layout saved as an email Template, subsequent emails are easy to send using this Template as a starting point.

Are there other things I can do to increase the chances of a recipient receiving my email message?
It's well-documented that the most reliable way to maximize your email deliverability rates is to build a trusted relationship with each of your recipients. This is a slow process and the use of purchased lists and sending of unsolicited messages tend to be ineffective at accelerating the rate at which recipients are willing to opt in to receive mail from your organization. Cultivate that email relationship over time, with simple but effective messages that adhere to the best practices above.

What if the organization not receiving email is my own organization?
In this case, you have a few options to instruct your organization's anti-SPAM device or policy to allow your email messages to pass through without being inspected for "spamminess". You can do what's known as "whitelisting" the IP addresses from which the email messages will originate. This is something that email services staff with responsibility for your email servers would have to implement. Whitelisting these IP addresses essentially tells your mail server to allow all emails originating from one of those IP addresses to pass through without restriction.

Additionally, your email services staff may also be able to whitelist a particular sender email address. For example, if the email that you send from your Blackbaud software product typically originates from Some.Name@MyOrganization.org, your email staff can whitelist this email sender address and allow all messages originating from this address to pass through to the end recipient without restriction.