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Reluctantly Switching from Eudora to Apple Mail

After months of hemming and hawing, I recently took the plunge and switched from Eudora to Apple Mail. I had thought that – as Eudora users go – I was a relative lightweight, but now I’m not so sure. I followed Adam’s wake into Eudora, letting him set the software up for me and then serving as his editor for “Eudora 4.2: Visual QuickStart Guide” from Peachpit Press. However, I seem to have picked up more power-user procedures along the way than I had realized, and I’ve found that Mail thinks about filtering in exactly the opposite of how I’d set up Eudora, and that it requires far more effort for complex searches, which it turns out that I do often.

On the plus side, I’m liking Mail’s spam filtering, I’m ending up with far fewer email windows open at once, and I do enjoy some of Mail’s “trendy 3-D junk.”

Based on plaintive email I’m receiving, it seems that many people are reluctantly contemplating a switch away from Eudora to an email client that’s more actively supported or that has a more modern interface. I wrote this article to share my difficulties in making the switch in hopes of improving the experience for those who may follow (or choose not to follow) in my path.

Clean Up First — The standard geek advice on the switch is that you shouldn’t use Mail’s tools to import your old data from Eudora. Instead, you should use Andreas Amamn’s donationware Eudora Mailbox Cleaner. To be fair, one geek I know, John Baxter, suggested via Twitter that I just start afresh, and that might, frankly, have been simpler.

My first step was to clean and organize my Eudora mailboxes and delete some old mail I didn’t need. I should have taken this step further, and especially concatenated older mailboxes that no longer needed to be individual, since Mail works better with fewer mailboxes and a more shallow hierarchy. I next made a copy of ~/Documents/Eudora Folder, just in case. I also sorted my ~/Documents/Eudora Folder/Attachments Folder by size and removed all attachments that looked like I didn’t want them and were over 5 MB in size. [Editor’s note: Also, either delete the contents of your Junk folder in Eudora, or create a manually activated filter to move to the Trash attachments for all messages, select the contents of Junk, and choose Special >
Filter Messages. -Adam]

Running Eudora Mailbox Cleaner is a simple matter of dropping your Eudora Folder on the Eudora Mailbox Cleaner icon and then indicating what you want converted: email messages and mailboxes, nicknames, and filters. I selected all three. I mistakenly thought that Eudora Mailbox Cleaner would run through my Eudora data and then, when it finished, give me some sort of “Import to Mail” option, or give me a file that I would then import into Mail. Big mistake.

In fact, Eudora Mailbox Cleaner whacks your data right into Mail and into Address Book. Your messages and mailboxes go into Mail, your filters go into Mail as rules, and your nicknames (and nickname groups) pop into Address Book. Automatically moving Eudora stuff into Mail and Address Book isn’t a bad thing, if Eudora Mailbox Cleaner works on the first try. However, it took me four tries before it worked properly. Each time Eudora Mailbox Cleaner got stuck, I used the status info shown above its progress bar to delete the problematic nickname or mailbox from Eudora. Nothing that I deleted was particularly important. (On the final pass, Eudora Mailbox Cleaner took about 45 minutes on my 2 GHz Intel Core 2 Duo MacBook Pro to convert my 2
GB Eudora Folder.)

I thus ended up with four copies of mailboxes and rules in Mail, plus four copies of every Eudora nickname in Address Book. Sigh. It was easy to delete the extra imported mailboxes, and easy to delete the extra rules, except that – and I realized this later – I retained the wrong set of rules, so they didn’t match my retained mailboxes. This led to Mail creating new duplicate mailboxes on the fly and some late-night begging on my part to Adam to make my email work. I found it extremely unsettling to be without email not because I’d chosen to go offline, or because a server is flaking out, but because I, myself, had made a user error. Had I realized that Eudora Mailbox Cleaner worked this way, I would have deleted everything from Mail
after each of the first three failed imports. I also might have tried exporting my nicknames to vCard format first and then imported them into Address Book, using Eudora vCard Export, also by Andreas Amann.

Next, I had to rebuild each mailbox in Mail to make its messages appear. I found that I couldn’t select multiple mailboxes to apply the Mailbox > Rebuild command: each one had to be selected individually, although I could start rebuilding one before the previous one finished. You could make a keyboard shortcut to speed this up, as I did, but fortunately, Eudora Mailbox Cleaner comes with a script that automates this task, and learning about this script is just one of the many reasons why, ahem, I wish I had read all of the somewhat lengthy Read Me first and more fully thought out my switching procedure before I jumped in.

My advice is this: if you need to get a few mailboxes working, rebuild them by hand. Otherwise, let the script run while you go out for a meal or even overnight. The script frequently switches Mail to be the active application, so it’s not practical to work on your Mac while it runs. As a point of reference, it took about 15 minutes for Eudora Mailbox Cleaner to rebuild the 166 mailboxes that I did not rebuild by hand. Once your mailboxes are rebuilt, note that you have In and Out boxes from Eudora that are separate from Mail’s In, Draft, and Sent boxes.

It was also easy to delete the extra Address Book entries; Address Book has a command for removing duplicates. But because I hadn’t cleaned up my nicknames first, I now have a number of wacky Address Book entries, including some remnants of what I think is Eudora’s recently used addresses feature. Fortunately, I hadn’t much used Address Book before (I currently use Now Contact), so I can slowly weed these out as Mail suggests odd options for auto-filling email addresses. In fact, avoiding Address Book as my primary contact manager is now especially appealing, since I can use it only for desired Mail nicknames. If I used it for everyone I know, it would offer too many unwanted options when autofilling an email address in Mail. This seems
like a misstep on Apple’s part.

Work Flow — The next big problem is that I had set up Eudora to show me only the new messages I wanted to read. This technique, known as a “saved search” in Eudora, has prolonged Eudora’s life for me and many others, since it is so handy (Adam first promoted this technique in “A New Way to Use Eudora,” 2004-12-20). To accomplish this, I created a filter for each person (and mailing list) from whom I routinely receive mail – about 100 filters all told. In each case, the filter puts matching messages into a mailbox associated with that person (or mailing list). I then put each of those mailboxes into one of three folders – People (who I work with), Family, or
Friends. Next, I set up a saved search that would show me unread mail from mailboxes in those three folders, and depending on my available time, I’d sometimes change the criteria to concentrate on mail from colleagues in the past 5 days, or if it was the weekend, I could see only mail from family and friends. An advantage to this strategy was that after I’d read a message, if I wanted to keep it, it was likely already filed into an appropriate mailbox, so I didn’t have to take any further action.

I also made a point of checking my raw In mailbox regularly for messages from strangers, and to delete wayward spam that made it past the two spam filters – our server-side Postini filter and Eudora’s local SpamWatch filter. These two filters were working increasingly poorly, and the spam I was receiving was increasingly crude and upsetting. Although I know I could have solved that problem in other ways, this awful spam was the final straw that caused me to decide to switch. So far, Mail’s spam filter is working far better than Eudora’s was.

Unfortunately, Mail’s rules and smart mailboxes assume a different approach, and it has taken me about a week of working with Mail to get my head around it. If Mail supported searching on “folders” that hold groups of mailboxes, I could stick with my current strategy, but since Mail doesn’t offer this feature, I had to reconfigure everything. In Mail, if you want to go with the flow, you let everything pour into your Inbox, filtering out only mailing lists whose messages you wouldn’t want to mix in with others in a smart mailbox. You then use smart mailboxes to look at different groups’ messages in your Inbox.

That sounds pretty easy to set up, and it took only one session in Address Book to make reasonably good groups and get those smart mailboxes working – I ended up with four mailboxes for four discrete groups of people who I frequently exchange email with. However, I was then faced with the problem that after I read my messages in my smart mailbox, they were still, in fact, in my Inbox. If I wanted to file them for archival purposes or to indicate some future action that I should take, I had to move them manually in some way to another location. For a while, I thought I’d try Mail Act-On 1.3.3, which is intended to help with this problem, but whose Leopard compatibility is still in

However, I felt reluctant to base my entire email strategy on third-party software that might make it difficult to upgrade to the next major version of Mail as quickly as I might need to.

So, I tried enabling my rules (from the old filters that came in from Eudora) that filter incoming email from individual people into their individual mailboxes, instead of into the Inbox, which takes care of a lot of my post-reading filing. The messages still show up in my smart mailboxes, but when I consider them read, I can either delete them or do nothing, and if I do nothing, they remain in their appropriate person-specific mailbox. I know that some people are comfortable with a huge Inbox of read messages that are unfiled, but I prefer a more finely grained organizational system.

I’ve found it valuable to check each rule to be sure it does what I want, so I turn on five or so in a session, reconfiguring them as needed, and then watch what comes in to see if it’s going to the right place. This didn’t work well when I had Mail set to check for messages every 5 minutes and I was getting a high volume of messages, because Mail didn’t like having to display messages in my smart mailboxes while it was checking and filtering. This is akin to Eudora, where sometimes incoming messages would appear shortly after it would seem that they should have, but Eudora would let me continue working without a fuss. [Editor’s note: In Eudora, bring the Task Progress window to the front to make it filter right away; otherwise it waits
until it senses idle time. -Adam] I recently set Mail to check for new email every 30 minutes, and that seems to help, since I’m less likely to be trying to work with a smart mailbox when Mail is also trying to work with it. However, my email volume has been light recently, so the jury is still out on how well all this will work.

Manual filing is still more difficult in Mail than it was in Eudora. The contextual menu is awkward to use, and the dragging method is hard because I have so many mailboxes to use as potential targets. I have been slowly reorganizing my mailboxes to put frequent targets at the top. Mail insists on alphabetizing mailboxes, so I renamed some mailboxes to begin with an asterisk in order to group them at the top without nesting them. I expect that my entire mailbox organization strategy will evolve over time so that the strongest organizational criterion becomes frequency of use instead of topics or relationships.

What I know now, after a week of using Mail, is that some of my initial troubles with filing related to my overall mousing speed and my lack of having scheduled enough time to settle into Mail. For example, it took me a few days to realize that, when dragging a message out of the viewing pane and into a different mailbox to file it manually, I was dragging downward too much and not enough to the left toward the sidebar. Dragging more slowly and making an effort to drag to the left helped enormously. If you drag down too quickly, Mail thinks you want to select multiple messages in the viewing pane. I still mis-drag about 20 percent of the time. Another problem directly related to my impatience was that I never hovered over a top-level
mailbox long enough to realize that it was spring loaded, so I was often adjusting my sidebar before I filed a message just to bring the target mailbox into view. It is much easier to just wait a moment for a spring-loaded mailbox to pop open!

I’m still having trouble with ad-hoc searching in Mail. The basic search functionality is easy to use, but doesn’t allow the kind of boolean searching I do often. Nested smart mailboxes can help with this, but they perform slowly on my system and are annoying to set up for a quick ad-hoc search. And, I miss Eudora’s Option-click feature where you could Option-click any bit of metadata on a message – such as the Sender or the Subject – in a mailbox listing, and immediately see all other messages with that metadata grouped together. Joe Kissell, author of various editions of “Take Control of Apple Mail” (the Leopard edition is slated for early May; I’m acting as guinea
pig and editor), suggested that I learn how to type important bits of search syntax directly, that I search in Spotlight in the Finder, or that I look into the $29.95 MailTags plug-in.

Two Specific Fixes — My first few days in Mail were especially disconcerting due to a few special problems that I encountered. You might run into similar ones, so I’ve noted them here.

The first problem was that each time I launched Mail, I had to enter two passwords for my incoming email accounts and two passwords for those same accounts’ outgoing servers. My keychain seemingly could not remember them. This was a drag, but, again, Joe’s draft came to the rescue, advising me to launch Keychain Access, choose Keychain Access > Keychain First Aid, and then repair my keychain (honestly, if I didn’t edit these ebooks, I’d never be able to get my Mac to do anything).

The second problem that I had to figure out on my own was that Mail wouldn’t let me move messages out of one of my inboxes – the messages kept bouncing back as though the destination mailboxes were locked, or radioactive, or something. The fix related to a setting for the account where I was having messages also kept on the server for a week after delivery. Apparently that was a no-no.

Change can be painful, and changing to Mail so far has been more time-consuming and more frustrating than I’d anticipated. My biggest mistakes were not preparing enough in advance and not giving myself more time to get comfortable before I needed to be up and running effectively. Although I’m starting to settle in, I sense that I am pushing Mail with the volume of email that I receive and the amount of work that I want it to do for me, so although I don’t think I’m moving back to Eudora, I’ll be keeping my eye out for other options, such as the new Outspring Mail, covered in “Outspring Mail Promises Intelligent
” (2008-03-31).

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