Vista's Junk Mail Filter: Users' Tips

Friday Mar 30th 2007 by Tony Piltzecker
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Technologies like SmartScreen help you get ahead of the scammers. Here’s an overview of Vista’s many options for keeping your inbox manageable.

It would seem that everyone on planet Earth has received spam. In fact, it is probably not unrealistic to think that spam has been somehow transmitted across the wireless waves in space to our yet undetected cosmic neighbors who can only conclude that we are obsessed with online meetings, free prescription refills, and miraculous growth enhancers. Indeed, the Internet is as much a place of “dodging” unwanted material as it is “searching” for the content of choice.

No network administrator is unfamiliar with the pains associated with spam filtering. Many enterprises turn to a third-party solution out on the perimeter, and yet others opt for a separate service provider who will accept and filter all their mail for them and then relay mail to their organization once it has been sanitized. Few organizations rely solely on client-side applications.

Often, a layered approach to battling spam is what is required, one that utilizes each of the avenues through which spam can make its way into the organization’s e-mail system. As such, the client-side fight will always remain; spam or virus-generated mail could come from within the organization, or from a visiting consultant or a poorly protected laptop that is brought into the company. So, taking yet another step forward in improving the e-mail experience for former Outlook Express users, the Windows Mail design team has integrated a Junk E-mail filter into Windows Mail.

SmartScreen

Contrary to popular belief, the Junk E-mail filter built into Windows Mail is not simply another Bayesian filter. The algorithms that compose the learning engine for this product are more sophisticated than that. In fact, this product is not a client-side application; what ships with Windows Mail’s Junk E-mail filter are filters derived from the Microsoft SmartScreen spam-filtering solution that has been refined over the past few years at the enterprise level.

First deployed to its Hotmail servers, the SmartScreen technology leveraged learning algorithms against large sets of data (hence Hotmail and eventually Windows Live Mail). The design team that is focused exclusively on the antispam effort at Microsoft found higher levels of “learning” with a broader user base and deeper concentration of mail. Based on user input, the algorithms adjust their detection settings and then generate filters accordingly. This approach has provided SmartScreen with such a high success rate at the identification of spam (95 percent, according to Microsoft) that the product was eventually incorporated into the Exchange 2003 and Outlook 2003 products, as well as their respective 2007 versions.

Because of the nature of the algorithms, the application does not learn at the client level, that is, no “personal” settings or adjustments are made to tailor the filtering to a user’s preference. To do so would be to take these finely tuned enterprise-level algorithms and point them at a ridiculously small subset of data, which would essentially stunt the learning process. However, like in Outlook, the Windows Mail Junk E-mail filter is set to pull filter updates from Microsoft via the Microsoft Update service. In this way, the filter settings in use for Exchange are at work on your local machine from the first use of Windows Mail.

Configuring Junk E-Mail Options

Enabled by default, the Junk E-mail filter sits silently; in effect, watching all e-mail. Virtually no setup is required. In fact, when a user first launches Windows Mail and sets up the account information for either a POP or an IMAP account (the only two account types the Junk E-mail filter supports), there is neither an indication that junk e-mail filtering is enabled nor a prompt to configure settings.

Once you are up and running with an account, any new mail is run through the filter. If a message is identified as spam, it is moved immediately to the Junk E-mail folder, which notifies you that there are messages waiting there for your review, just like your Inbox.

Although the Junk E-mail filter functionality is on by default, some settings are available to the user. You can access these settings in the main menu in Windows Mail via Tools | Junk E-mail options.

A five-tab window is opened where you can finely tune the Junk E-mail filter to your liking.

The Junk E-Mail Options Tab

The first tab offers you the ability to manage the level of sensitivity that the application will apply to messages. This essentially amounts to a degree of filtering. By default, the Junk E-mail filter is set to “Low: Move the most obvious junk e-mail to the Junk E-mail folder.” Adjusting the sensitivity is as simple as choosing a radio button.

During testing, we found that the High setting provided the best results. Certain companies that we have received e-mail from saw fit to send us advertisements for related products, even on behalf of their partners. On the High setting, these less personal e-mails were moved to the Junk E-mail folder, allowing us to quickly discern what we cared for and what was likely irrelevant mail.

The first and last radio button options under “Choose the level of junk e-mail protection you want” provide the opposite ends of the spectrum. The No Automatic Filtering and Safe List Only settings rely not on the SmartScreen algorithms, but simply on block or allow lists. These lists specify who is allowed to send mail to the recipient, and who is not. In Windows Mail, these lists are Safe Senders and Blocked Senders, respectively.

Let’s take a moment to discuss the Blocked Senders and the Safe Senders lists, both of which are easily administered through dedicated tabs. The Safe Senders and Blocked Senders tabs are fairly straightforward. Both allow you to add, remove, and edit entries. When “Add” an entry is chosen, Windows Mail provides you with a simple interface for data entry.

The Junk E-Mail Options Tab

The first tab offers you the ability to manage the level of sensitivity that the application will apply to messages. This essentially amounts to a degree of filtering. By default, the Junk E-mail filter is set to “Low: Move the most obvious junk e-mail to the Junk E-mail folder.” Adjusting the sensitivity is as simple as choosing a radio button.

During testing, we found that the High setting provided the best results. Certain companies that we have received e-mail from saw fit to send us advertisements for related products, even on behalf of their partners. On the High setting, these less personal e-mails were moved to the Junk E-mail folder, allowing us to quickly discern what we cared for and what was likely irrelevant mail.

The first and last radio button options under “Choose the level of junk e-mail protection you want” provide the opposite ends of the spectrum. The No Automatic Filtering and Safe List Only settings rely not on the SmartScreen algorithms, but simply on block or allow lists. These lists specify who is allowed to send mail to the recipient, and who is not. In Windows Mail, these lists are Safe Senders and Blocked Senders, respectively.

Let’s take a moment to discuss the Blocked Senders and the Safe Senders lists, both of which are easily administered through dedicated tabs. The Safe Senders and Blocked Senders tabs are fairly straightforward. Both allow you to add, remove, and edit entries. When “Add” an entry is chosen, Windows Mail provides you with a simple interface for data entry.

The Address or Domain Prompt for the Senders List

As is clearly stated, you add not only e-mail addresses, but also entire domains. This is both a good and a bad thing. You can add entire organizations in one fell swoop by choosing to place a domain (Syngress.com, for example) into the Safe Senders list. Now, everyone from the editor-in-chief to the cafeteria janitor can e-mail you, allowing you to avoid the administrative nightmare of having to add each and every employee.

Obviously, there is a flip side to this coin. If you choose to block an entire domain because a very odd employee of that company seems to have taken a particular interest in you, don’t be surprised when your friend in Marketing can’t e-mail you to inform you that the new company beach balls are in. If the entire domain is blocked, the entire domain is blocked, right?

Not really. If you block an entire domain from sending e-mail by listing the domain in the Blocked Senders list, individuals within the domain can still receive e-mails if they are specified on the Safe Senders list. The Safe Senders list has priority over the Blocked Senders list, enabling just this very thing.

Before leaving the Safe Senders and Blocked Senders tabs, let’s look at one more set of options found only on the Safe Senders tab, the auto-trust features.

At the bottom of the Safe Senders tab (see Figure 8.22) are two options for adding users to the Safe Senders list automatically. By default, anyone in your Windows Contacts is allowed to send mail to you. They are “trusted,” but not actually on your Safe Senders list. This means the list can be disposed of and their ability to e-mail you will remain. In fact, their names and e-mail addresses will never appear on the Safe Senders list.

The Junk E-Mail Safe Senders Page

The “Automatically add people I e-mail to the Safe Senders list” option is different in that entries for every e-mail address you send to from Windows Mail is added to the Safe Senders list when this option is checked. A message does not have to be successfully delivered or even have to leave the Outbox for this entry; it is added as soon as you click Send.

Now, if we consider the settings available to us for junk e-mail filtering given this information about the Safe Senders and Blocked Senders lists, we can make more informed decisions. Let’s review our options again:

No Automatic Filtering Mail from blocked senders is still moved to the Junk E-mail folder.

Low The most obvious junk e-mail is moved to the Junk E-mail folder. • High Most junk e-mail is caught, but some regular mail may be caught as well. Check your Junk E-mail folder often.

Safe List Only Only mail from people or domains on your Safe Senders list will be delivered to your Inbox.

If a sender’s address is on the Blocked Senders list and the option for No Automatic Filtering is selected, any message he sends will be received and compared to the Blocked Senders list (which is essentially a local blacklist) and, when his address is matched, moved to the Junk E-mail folder. The true junk e-mail filters are never put into practice. Consequently, mail from any and all other sending addresses, no matter how obviously spam, will be delivered to the Inbox.

If a sender’s address is on the Safe Senders list and the Safe List Only setting is chosen, all mail from that sender, and that sender only, will be accepted. Obviously, no further filtering is applied or even required. Although this is a highly secure setting, it is one that places a great deal of administrative burden on the user because enabling any sort of e-mail communication from a new contact requires that the Windows Mail user take action to update the Safe Senders list.

A last option remains on the first tab of the Junk E-mail Options window, and that is to “Permanently delete suspected junk e-mail instead of moving it to the Junk E-mail folder”. Although this may sound like a fairly reasonable choice, keep in mind that “suspected” junk e-mail is just that. In addition, the level of suspicion is adjustable based on the Low/High options, which means legitimate mail can be moved and deleted without your consent.

Working with Junk Mail

When a message is detected as junk e-mail, it is placed within the Windows Mail Junk E-mail folder. This means the message is in the Windows Vista file system and is still very much accessible. By clicking on the Junk E-mail folder, you can actually see the message which, depending on its content, has been filtered or blocked from full display

In this particular example, Windows Mail detected both the potential for a spam advertisement and the presence of images. As a measure of protection, the images have been blocked, as is described in the warning banner posted within the header information bar.

From here, you have several options. From the messaging toolbar, you may delete the message or mark the message as “Not Junk.”

Although choosing to delete the message rids your Junk E-mail folder of the suspect message, marking the message as “Not Junk” automatically moves the message into the Inbox. This is a one-step process that allows you to quickly recover any message erroneously identified as spam.

In addition to the toolbar, you may simply right-click a message in the Junk E-mail folder and select any one of the five options available to you.

Junk E-Mail Options at the Message Drop-Down Menu

From the right-click message menu, you may add either the sender or the sending domain to the Safe Senders list or to the Blocked Senders list. In addition, you may also mark the e-mail as “Not Junk” here. You cannot, from this menu, delete the message.

As with the Phishing Filter, some messages that are truly junk in their core will arrive unscathed through our Junk E-mail filter. Although this is a nuisance, it is not the end of the world. And although not quite a one-click process as was deleting or releasing a message from the Junk E-mail folder, the steps for marking an e-mail as junk are still familiar. To mark an e-mail as junk, simply right-click the message, navigate to the Junk E-mail menu item we saw earlier, and choose again from the options presented (this time there are only four, because “Mark as Not Junk” is unavailable to us for messages already in the Inbox).

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