This article originally appeared in TidBITS on 2000-09-11 at 12:00 p.m.
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Eudora 5.0 Reads Your Mind

by Adam C. Engst

With today's release of Eudora 5.0, Qualcomm has at once shored up some weak spots in their popular email program and raised the bar with innovative new features. Foremost among the new features are Eudora Sharing Protocol (ESP), a plug-in that enables Eudora users to maintain the contents of shared folders automatically via email, and MoodWatch, a new technology that gives some indication of the "spiciness" of a message. But let's start with the "it's about time" features.


Basic I/O Functions -- Many have complained about Eudora's inability to import messages from the proprietary database formats of other common email programs. Eudora 5.0 finally adds the capability to import mail from Claris Emailer 2.0 and Outlook Express 5.0, and although the feature won't interest existing Eudora users much, it should make converting to Eudora easier. Unlike most other importers, Eudora doesn't rely on a slow Apple event-based approach, and in my testing, imports of a few hundred messages moved along quickly.

Those who have mail that was originally received by Claris Emailer 1.x may experience some problems though, since older messages that displayed fine in Emailer 2.0 don't always import properly into Eudora. Running the messages through Outlook Express didn't seem to help either, though the results were different. Messages created in Emailer 2.0 or Outlook Express 5.0 posed fewer problems, although it's still a good idea to rebuild your email database before attempting an import (launch those programs with the Option key held down; in Emailer, perform an Advanced Rebuild). And of course, if all else fails, you can fall back on the AppleScript scripts that have worked in the past (for details, see "Switching from Emailer to Eudora in Leaps and Bounds" in TidBITS-528). Qualcomm has been made aware of the problem and is aiming for a fix in 5.0.1.


Little Black Book -- Qualcomm is slowly updating various large sections of Eudora, such as Eudora Pro 4.2's radically improved Search functionality that we discussed in "Eudora Pro 4.2 Continues to Deliver" in TidBITS-488. In 5.0, the Address Book receives some attention, though the results are nowhere near as compelling as 4.2's new Search. Essentially, the Address Book gains an interface similar to the Mailboxes window with small icons for address books, individuals, and groups, and it also now stores more information, thanks to the addition of Home, Work, Other, and Notes tabs.


Although there's nothing particularly wrong with the new Address Book, there's nothing particularly interesting about it either. It's the old Address Book with additional fields. When asked, Steve Dorner (Eudora's primary author) said that the Eudora 5.0 Address Book was mostly laying the foundation for future features, such as Palm synchronization and integration of contacts with email messages. Clearly, Qualcomm is trying to match Outlook Express 5.0 on a feature checklist basis, and an improved Address Book was necessary for that goal.

For people with any kind of serious needs from their contact managers, Eudora 5.0's Address Book is just a tease, much like the same feature in Outlook Express. I don't even want to see Eudora's Address Book replace my copy of Now Contact, though I'd appreciate some synchronization between the two. I'd prefer to see Eudora's Address Book concentrate on email-specific features. How about a fast search for all mail from or to selected contacts? Or perhaps Eudora could include contact information in headers that other copies of Eudora could use to populate the automatically generated nicknames in the History List more completely?

Scripts on the Menu -- Another small feature that many advanced Eudora users will appreciate is the addition of a Scripts menu that provides fast access to AppleScript scripts stored in the Scripts Folder (inside the Eudora Stuff folder in Eudora's application folder). The first item in that menu is Open Scripts Folder; after the Scripts Folder opens in the Finder, you can drop any scripts you use into it and execute them by choosing them from the Scripts menu. It's a nice touch, and it also enables you to attach scripts to toolbar buttons by Command-clicking an empty spot on the toolbar and choosing a script.

Lies, Damned Lies, and Statistics -- With this next feature, statistics on your email usage, Eudora starts to raise the bar for email once again. The feature itself is mostly for fun, but it's unusual and provides information that we all bandy about as evidence of email machismo. How many email messages do you get every day? Thanks to Eudora's new statistics window, accessible from the Window menu, I know that my estimates of 150 messages per day were spot on. In the two months I've been using beta versions of Eudora 5.0, I've received an average of 148 messages per day, 1,039 messages per week, and 4,519 messages per month. Similarly, I send an average of 41 messages per day, 288 per week, and 1,255 per month. Even more interesting, Eudora tells me that I spend an average of 1.8 hours per day using Eudora, 12 hours per week, and 55 hours per month. That's actual activity in Eudora, not just the time the application is open. Eudora happily displays all these statistics for the year as well.

< mailstats.html>

If you click the More statistics checkbox, you can learn how your activities break down. I see that I spend 29 percent of my time reading mail, 61 percent composing, and 10 percent mucking about with other things. With sent mail, I can see how my outgoing mail breaks down by forwarded messages, replied to messages, redirected messages, and attachments sent. For incoming mail, I can tell how many attachments I've received and what percentage of my incoming mail I've read.

Along with the raw numbers, Eudora draws graphs that clarify your patterns of sending mail, receiving mail, and using Eudora. The graphs also showed me that Eudora considers importing mail the same as receiving mail, and some tests I'd done had resulted in importing 1,800 messages. Since the dates on the Emailer 1.x messages I was importing were screwed up, Eudora counted them as arriving the day I did the import. I didn't want to skew my numbers that radically, but since Eudora actually stores the statistics in a straight-text XML file in the Eudora Folder, I was able to edit out the spike by changing some numbers.

Mood Rings -- Remember those mood rings from long ago that claimed to report your mood by changing color? I presume they worked on temperature - the hotter you got, the more uptight the mood ring claimed you were. New in Eudora 5.0 is a superficially similar feature called MoodWatch, which is based on work done by David Kaufer, chairman of the English department at Carnegie Mellon University. Qualcomm implemented David Kaufer's work in a fast algorithm that examines every message to identify words or phrases that some people might find offensive. The basic idea is to determine if what you're writing might be construed as a flame, or as a heads-up that an incoming message might be a flame before you start reading.

< moodwatch.html>

MoodWatch works both on incoming messages and messages you write, assigning every message between zero and three chili peppers to indicate the level of "spiciness." Chilies appear in a new mailbox column, and for outgoing messages, on the right side of the window toolbar (for zero chilies, outgoing messages display an icon that could be interpreted as an ice cube to indicate you're cool).

I was initially dubious about MoodWatch, but I seldom find myself disagreeing with it, although why a message receives chilies is occasionally confusing. For instance, ListSTAR sends me daily logs that often have chili ratings, which befuddled me until I realized that they were generally related to the subjects or senders of spam messages directed at my auto-replies.

MoodWatch is mostly informational, but it does offer some interactivity. In the MoodWatch settings panel, you can decide if you want it to warn you when sending messages with a certain chili rating. You can also Option-click on a message's chili rating in a mailbox window to select all messages with the same rating. However, you cannot search or filter on chili ratings, because the entire system is sufficiently subjective that searches or filters could easily produce undesirable results.

I mostly like seeing the chili ratings on the messages I'm writing, and just last week I reworded a hastily composed paragraph in a message that simply didn't need the expression that generated a pair of chilies. I'm a strong believer in using language appropriately, and if that means a message needs to go out with a full three-chili rating, so be it. But having Eudora warn me about inadvertent mistakes when I'm not paying attention is welcome.

A few notes about MoodWatch: It's specific to English (and probably American English at that), so your results may vary when using other languages. It's also entirely internal to your copy of Eudora, so no one using other email programs will see the chili ratings in any way. And of course, you can always turn it off.

ESP: Not What You're Thinking -- Eudora 5.0's most innovative feature is ESP, a plug-in whose name expands to Eudora Sharing Protocol. At its heart, ESP is simple - it enables everyone in a group of Eudora users to maintain a folder whose contents are identical on each person's machine, with ESP automatically sending and receiving updates from the members of the group. It all happens via standard email, but without bothering you with the automatic messages.


For the most part, you don't do anything in ESP itself; it just works in the background, occasionally prompting you with dialogs when necessary. But to create or configure groups, you work within the plug-in's interface, accessible by choosing ESP Groups from the Special menu (if that item isn't present, the ESP plug-in isn't installed where Eudora can find it, preferably in your Eudora Stuff folder).

An ESP group has several parts, including the shared folder itself (created by default in an ESP Groups folder in your Documents folder), a Eudora mailbox to store messages from the group, and the Eudora personality to apply to your outgoing messages to the group. An ESP group also contains a list of users, each of whom can play one of four roles: full member (send and receive updates), broadcasting member (send updates only), receiving member (receive updates only), and custom member (obey a set of custom actions regarding new, updated, and deleted items in the shared folder). The group creator uses ESP itself to invite users; it creates customized messages with a special attachment that the invitee's copy of ESP uses to configure itself to participate in the new group. Although the group creator can set an initial role for each invitee and even set a warning to appear if that person tries to change his or her role, control ultimately lies with each individual.

When anything changes in one copy of the shared folder, ESP packages up the necessary files along with instructions to the remote copies of ESP about what actions to perform and sends the message out. The receiving copies of ESP then unpack the files, look at the instructions, and perform the necessary actions to keep everyone's shared folder synchronized.

It's hard to predict exactly how people will use ESP because although ESP is good at maintaining multiple backups of updated and deleted documents, the disconnected nature of email means that it is possible for two people to modify the same file at the same time. Put simply, if you already have and rely on a single shared folder on a centralized server, you'll find switching to a distributed shared folder maintained by ESP frustrating, since you never know who's working on a file or if your folder has all the latest changes. My feeling is that ESP is not ideal for sharing documents that multiple people change frequently.

Where ESP's brilliance shines through is in easing email file distribution among a group. For instance, I'm creating and editing content for a Web site right now, and I'm constantly mailing drafts and final copies all over the place. Worse, whenever I receive an edited version, it's a totally new document whose changes I have to merge manually. If we were using ESP, I'd only have to worry about the current version of the document in the shared folder, and I could set the number of backup versions to retain in case of trouble. Another use of ESP might come in maintaining a shared folder of family photographs, where each member of the family could simply drop pictures into the folder to send them out the entire family.

Overall, I find ESP fascinating because it introduces intelligence into the process of sharing files via email, something we all do these days. Although you would set up ESP only if you anticipated an ongoing need to share files with a group, the functionality is sufficiently compelling that even people who must rely on other email programs might consider setting up a special POP email address (such as one via Apple's iTools or at Yahoo Mail) and running Eudora purely for ESP's file synchronization features. Luckily, ESP is cross-platform, so people using Eudora 5.0 for Windows can also participate in ESP groups.


Upgrade Details -- Eudora 5.0 is the first upgrade Qualcomm has released since Eudora Pro 4.0 back in January of 1998 that requires payment from some users. Whether or not you have to pay depends not on what version of Eudora you're currently using, but which version you last purchased. If you bought Eudora Pro 4.0 or 4.2 (whether or not you've subsequently taken advantage of the free upgrade to 4.3), the upgrade costs $30. If, however, you bought Eudora 4.3 to switch from Sponsored or Light mode into Paid mode, the upgrade to 5.0 is free.


If you're currently running Eudora 4.3, you can verify your situation and download Eudora 5.0 by first choosing Payment & Registration from the Help menu, and then clicking the "Find the Latest Update to Eudora" button (you must be connected to the Internet). A moment or two later, Eudora will display a window telling you that 5.0 is available, and if you're running in Paid mode, whether or not you have to pay to run 5.0 in Paid mode. It's a 4.7 MB download. If you have to upgrade, the first time you run Eudora 5.0, it will tell you that you have to pay to keep running in Paid mode and provide a link to pay on Qualcomm's Web site. Eudora will then continue to run in Paid mode for an hour to provide time for the transaction to be completed and so you can receive the registration code Qualcomm's servers will mail back to you.

If you haven't already upgraded from 4.0 or 4.2 to 4.3, you must first upgrade to 4.3 and then follow the procedure above. If you're still using a version of Eudora prior to 4.0, you'll have to pay the full amount, which is $50.

Of course, if you wish to use Eudora 5.0 for free, you can still do so in Light mode (which lacks many of Eudora's advanced features, including most of those mentioned above) or in Sponsored mode (which provides all of Eudora's features but requires you view ads).

As with any upgrade, the question is whether or not the new version is worth the effort and cost of upgrading. With Eudora 5.0, the answer depends significantly on your situation:

It's hard to see quite why Qualcomm chose to call this Eudora 5.0, rather than something like 4.5. The version number bump was probably influenced by the competition with Microsoft's Outlook Express 5.0, whose version number was artificially increased to be comparable with Internet Explorer 5.0.

But more to the point, although MoodWatch and ESP are fairly major features, they're less compelling than the inline spelling checker and search functionality that appeared in Eudora Pro 4.2. And although Eudora 4.3's changes mostly revolved around the move to Light, Sponsored, and Paid modes, in some ways that change would have made more sense as the event to trigger an integer upgrade. As it is, the upgrade is most understandable by the length of time you've received new features from Qualcomm for free, with only Eudora 4.3 purchasers qualifying for a free upgrade. That turns out be the key - from now on, upgrades for those who have paid for Eudora will be free for a period of a year after you paid.

No matter what the specifics of your situation may be, Eudora 5.0 is a credible upgrade in multiple ways, and even if it doesn't address all of the program's remaining shortcomings (the entire filter architecture is aching for an update, for instance), it's worth serious consideration both as an upgrade and as a replacement for other email programs.