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Switching from Emailer to Eudora in Leaps and Bounds

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Earlier this year, I took a deep breath and changed my primary email application from Claris Emailer to Eudora. Normally, jumping from one application to another is no big deal. Most people have little trouble switching between Nisus Writer and Word, for example. However, when email is the backbone of your professional (and sometimes personal) life, the stakes run higher. The fact that the two programs' methods of storing and handling mail data differ widely made the jump seem more like a leap. Fortunately, a few outside tools and perseverance turned this email chasm into a minor canyon.

Shuffling Off Emailer's Coil -- Why did I switch, when Emailer is still a perfectly usable email program? Several factors convinced me it was time.

  • Although I could continue using Emailer (as many people do), it's clear there's no future for the program. The last update, version 2.0v3, was released at the beginning of 1998, but isn't currently available even from Apple's servers. I'm not concerned that there's no support for the program, but at some point in the future, something in an update to the Mac OS will break Emailer. The Mac OS's backward compatibility with older software is generally astounding - and plenty of TidBITS readers use older programs regularly - but my email is too important for me to risk. Quite simply, email has become my life. I use it to communicate with people, yes, but it's also my unofficial to-do list and archive of information.


  • Although there are many other email programs available (I was surprised at how robust Outlook Express appears to be), Eudora was really my only choice. In addition to its being a professional email client, I have direct access to help from Adam and Geoff, who have been using Eudora since its early days; Adam in particular is a well-known expert on the program, having written a pair of books about Eudora.


  • I was threatened with virtual harm by all of my fellow TidBITS editors, who relentlessly pushed Eudora's real and imagined benefits. (Adam: "You need to mow your lawn? I think there's an <x-eudora-setting> that will do the trick.") To be fair, we rely on email so heavily for the basic operation of TidBITS that Emailer's limitations occasionally caused significant annoyances or liabilities for everyone else in the organization.

Unlike upgrading to a new version of the same software, changing email programs required more work than I expected. On the surface, it's an easy task: I needed to move my existing mail to Eudora, and convert my address book without re-entering the addresses by hand. However, Emailer's method of storing both sets of data differs from Eudora's, and Eudora doesn't offer any method of converting or importing mail from other platforms. Outside help was required.

Passing the Mailbag -- The great thing about email is that it's a text-only medium. For the most part, a message sent from one email program can be read by any other email program. The problem lies in how the programs store and read the mail. Emailer stores all its messages in one large database file (with a companion index file that keeps track of the messages). Eudora, on the other hand, creates a separate file for each mailbox. Eudora mailboxes are plain text files; you can open them in a text editor or word processor and read all the messages if you want.

To extract mail from Emailer's database, I employed the "Export - Eudora" AppleScript script, part of the Import/Export 3.1 package found at Fog City's Emailer Utilities page (Fog City is the original developer of Emailer). To create a new Eudora mailbox, I selected all messages in an Emailer folder then chose Export - Eudora from the AppleScript menu. This script's advantage is that it creates a mailbox file that can be opened immediately in Eudora. However, converting thousands of messages was time-consuming, compounded by the fact that the script had a tendency to lock up my machine occasionally until it timed out.


Still, the process worked reliably, and it also gave me a chance to sort through my Emailer folders and determine which messages needed to go to Eudora or be stored as a long-term archive. Getting the new mailboxes into Eudora was simply a matter of moving the files into the Mail Folder located in the Eudora folder in the System folder, then launching Eudora.

Nicknames for Everyone -- Converting my email addresses was more of a one-shot event, though it required some initial setup. Although Emailer includes a command to export addresses to a tab-delimited file, getting them into Eudora is another matter. AppleScript again made my day. I consulted the eMailman Conversion page on the Web (which contains a variety of resources for converting between email programs - highly recommended) and found the script Emailer2Eudora, by Diana Cassady of VivaLaData.


Before running Emailer2Eudora, you need to download and install two other AppleScript components: the shareware Acme Script Widgets by Acme Technologies, and File I/O, available at ScriptWeb. These go into the Scripting Additions folder in your Extensions folder.


With the pieces in place, I exported my Emailer addresses to a tab-delimited text file and dropped the file onto the Emailer2Eudora program icon in the Finder. One problem I encountered at this stage turned out to be helpful: some of my addresses included older entries with garbled addresses, which caused Eudora to display a dialog box during the import process. To remove them after importing, I only had to scroll through the Address Book list in Eudora and delete the offending records.

The only other annoyance I ran into was that the nickname portion of each address, which is created based on the Name field in Emailer, ended up inverted. So, Geoff Duncan's nickname became "Duncan, Geoff." I'm sure there's an easy way to reverse these in the Eudora Nicknames file (which is just a text file, like everything else in Eudora) using a text editor and a good grep search, but I've coped by manually changing the nicknames as I come across them.

Miscellaneous Adjustments -- With my mail and addresses safely switched over, I was able to start adjusting to Eudora on a day-to-day basis. I had become used to Emailer's split-pane interface, which lists folders in the left pane and messages in the right pane. I like being able to access folders visually, so in Eudora I've displayed the Mailboxes window in a long column on the left side of my screen, with my In box to its immediate right.

However, I've never liked the split-pane approach to viewing messages, so my In box is strictly a window containing a standard tabular summary of messages; I prefer to open a message in its own window. The exception is when I'm searching through other mailboxes, where viewing the body of a message in a bottom pane makes it easier to scan.

Another adjustment required changing the way new messages are listed in the In box. In Emailer, my new mail appeared at the top of the list; Eudora's default is to list them at the bottom. Since I already feel like I'm buried under the weight of my email sometimes, I Option-clicked the Date column header to reorder the messages like Emailer (Option-clicking a mailbox's column header in Eudora sorts the contents of that mailbox in descending rather than ascending order).

And, although I generally dislike toolbars, being able to customize Eudora's toolbar has enabled me to create buttons that provide quick access to a handful of mailboxes and commands (such as the Settings dialog box and toggles for marking messages read and unread).

Overall, I haven't regretted the switch from Emailer: my mail is still easily accessible and I'm able to communicate as well as or better than before. There are several things about Eudora, though, that have truly streamlined or improved the way I work with email.

Breaking Up the Post Office -- At the top of the list is the way Eudora stores mail data. Emailer 2.0's single-file mail database was superior to Emailer 1.0's method of storing each message as a separate file, but it ended up being a large bull in a small china shop. Synchronizing Emailer's mail database to another computer or backing it up to DAT tape meant copying my entire 87 MB mail database, even if only a single message had changed. In Eudora, only changed mailboxes are copied, speeding up the process.

Emailer 2.0's single mail database file made searching faster than Emailer 1.0, but still didn't pass my coffee test when searching through all folders: I could start a search, go make coffee, and view the results (hopefully) by the time I returned. In Eudora, searches are blindingly fast, despite the fact that Eudora uses plain text files for storage and doesn't index the contents! I'm still amazed when it takes less than a minute to search through all of my active mailboxes.

Having multiple mailbox files also makes archiving old mail much easier. In Emailer, I'd set aside a block of time to run the "Export - Eudora" script on folders I wanted to archive, then delete those messages. Now, archiving a mailbox is as simple as quitting Eudora, moving the mailbox file to another location, and launching Eudora again. And since Eudora is fully Alias Manager-savvy, I can still have quick access to my archives without adding to the burden of the mail files in my Eudora Folder. If I put an alias to the archive in with the rest of the mailboxes, I've added only an entry in my Mailbox and Transfer menus.

I Respect Your Style -- I'll grudgingly admit that Eudora's capability to display styled email and inline images has been useful on occasion. As more email clients let their owners apply text styles like bold and italics (not to mention other HTML-based formatting), I'm glad that Eudora formats it properly so I don't have to wade through the HTML tags as I did in Emailer.

Even better, I can set Eudora to ignore specific styles in the Styled Text settings panel. I don't mind the occasional bold or underlined word, but I'd rather not put up with email that uses huge font sizes or ugly fonts - so I just told Eudora to ignore font and size styles in incoming messages.

Except on rare occasions (such as when I'm sending an inline image to someone whom I know also uses Eudora), I avoid sending styled mail entirely. Eudora helps my in my quest to keep my mail free of styles by asking if I want to send mail as plain text when I queue a message containing some sort of styles. And by selecting "Send plain text mail only" and the "Ask me each time" checkbox in the Styled Mail settings panel, Eudora's prompt when I queue a message with styled text comes up with Plain Only as the default so I can just hit Return to strip any styles automatically.

Added Touches -- Other details make Eudora a joy to use. I constantly Option-click portions of messages in their mailbox listing, which groups similar messages. For example, Option-clicking the sender field of a message summary in my TidBITS Talk mailbox groups and highlights all messages from that person. The same works for grouping subjects as well, of course, but it's not necessary in mailboxes that hold mailing lists, since for those I just use the Group Subjects option in the Special menu's hierarchical Sort submenu.

And although I don't use the feature often, scheduling outgoing messages has been helpful. If I've written a sane reply to a heated piece of flame mail, I can set the message to go out at the end of the day (or even the middle of the night) when my recipient hopefully has a cooler head.

What's Missing from Eudora -- I'm sticking with Eudora, no doubt about it, but several things continue to bug me. My number one wish list item is to be able to file messages using the keyboard. In Emailer, all you have to do is highlight a message, press Command-Option-F, then begin typing the name of the folder where you want the mail to be filed and hit Return. Eudora, on the other hand, is annoyingly menu- and mouse-dependent in this respect, requiring a trip to the Transfer menu (or to a toolbar button) to file each message. Although I'm sure workarounds could be built using utilities like OneClick or QuicKeys, an easier way to file mail without moving my fingers from the keyboard would be a welcome future feature.

Then there are smaller items that I bump against every day. I do more mail filtering now (though I can't tell if that's because Eudora's filters seem more flexible than Emailer's Mail Actions, or if it's because I'm more savvy about filtering my mail), and so I like Eudora's Filter Report window that tells me where filtered mail has been automatically filed. Eudora 4.3 added the capability to double-click the mailbox name in a filter report to open that mailbox, which is a nice touch. However, the window pops to the front after it's been updated, which is most annoying. When I'm in the middle of typing a new message and get an error telling me I can't enter text in the Filter Report window; swearing ensues.

For that matter, if I'm anywhere in the program and accidentally start typing in a window where new text isn't allowed (like an incoming message that doesn't have the editing pencil icon clicked), Eudora pops up a dialog box. I have to stop, click the OK button to dismiss the box, then return. A simple error beep would suffice.

Jumping for Joy -- I had expected a much more difficult time making the leap from Emailer to Eudora, though that was probably due to my overall reliance on email. Now that I'm becoming an entrenched Eudora user, will I ever be tempted to jump again to another program? For the near future, I don't think so. Eudora truly is the professional's choice of email programs. And besides, I think the other TidBITS editors would sooner nail my feet to the floor if it resulted in the loss of features we've come to expect in our internal email.


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