Thursday, June 22, 2006

The End of an Era - Migration from Eudora to Outlook

Warning: This is a *very* long entry so skip if it doesn't sound like a subject that is of interest to you :)

When I first started using the Internet, Eudora was the thing. In addition to Trumpet Winsock, for getting Windows 3.1 online, Eudora was there side by side with Netscape Navigator, pioneering the way people communicated and shared information.

From those days onwards, Eudora has always been my preferred Windows-based email client and pine is what I use when I'm in a UNIX shell.
I had absolutely no problem shelling out the money for Eudora Pro because it was just far more powerful than any other mail client I had used.
I think due to the nature of my open-source involvement the amount of emails I've been getting over the years has always been ridiculous, so I would definitely consider myself an email power user. My needs probably don't match everyone's out there.

Some of the most important features to me in Eudora where:

a) Extremely powerful filters. In the early days it could filter by arbritary header (e.g. Delivered-To:) when Outlook and other mail readers couldn't.

b) Eudora folders that receive new email will popup and tile on the screen. This makes it easier to keep track of which one of the dozens of folders actually
has new email. In Outlook you don't really know if you have unread messages lingering which is often the case with me.

c) The search is probably the best part of Eudora. It is unbelievably convenient and even with the improvements in Outlook 2003, the usability and strength
of Eudora's search leaves it in the dust.

d) You can Ctrl-left-click on any subject and it will group all the emails in the selected thread for convenient reading. The same also works on people's emails
if you are looking for prior emails from the person who's email address you are clicking on. This is extremely convenient and doesn't require you to sort
all the emails in the mailbox.

So why did I end up leaving Eudora? Well, over the years I had all sorts of issues. The issues always made me keep a close look out for other solutions, and specifically Outlook which I had been used to using in parallel for years in a corporate environment.

What were some of the issues I encountered:

a) Attachments, attachments, attachments. This was probably my #1 problem. Eudora decided to keep all attachments outside the mailboxes. Initially this sounds great. Attachments are accessible through Windows Explorer and mailboxes are smaller and more compact. This caused huge problems though. All these mails were kept in the same directory and every few months, the directory became so huge that it was slowing things down significantly.
What I had to do was empty the attachments directory by moving all attachments to a backup directory. This caused problems because when I wanted to actually open an old attachment, I'd have to find it in Eudora, and then as it had moved, I would have to go and find it manually in one of the backup directories. With 5 years of emails and over 4 gigabytes of attachments this meant numerous backup directories and was just a huge PITA.

b) The Search was definitely a huge advantage, however I was always hoping for Google Desktop Search to support Eudora so that I'd finally enjoy blazing fast search.
Last year this wish almost came true, when Eudora OEMed a search engine and provided fast indexed search. The excitement soon turned into dissapointement because this search was constantly out of sync and I had to resync it manually from time to time. It became so annoying that at some point I just turned it off and went back to the older slower but more reliable search.

c) I started getting a lot of crashes in Eudora's internal viewer, mainly when viewing certain spam mail. I was pretty convinced that moving to the Word viewer would resolve this problem as Outlook uses the same engine. However, for some weird reason I just couldn't get it to work. It would always show a blank page. After opening a support ticket, I was told that starting over with a new Eudora.ini file should solve the problem. I tried it and it worked, but I just couldn't be bothered to reconfigure everything so I stuck to the internal viewer and became more careful with spam mail.

The actual migration wasn't too painful although it took me a few days until I was absolutely comfortable in making the move. I started with a pilot migration, did some testing of the filters and the imported messages (remember this is about 6 gig of email all in all), and when I felt as comfortable as I could get, I repeated the process as I had recorded it.

A few annoying things popped up during the migration process:

a) For some stupid reason MS Outlook isn't good at importing Eudora. It apparently looses the message dates, so the recommended way is to import to Outlook Express, and then important that into MS Outlook. Does that makes sense? Definitely not, but every place I found on the Internet, recommended that, so I didn't take any risks. Microsoft - Fix your MS Outlook import and and let the world know you did!

b) Apparently I was still on the "old" PST file format which blew up on me when I reached 2gig of capacity. It took me a while to fix it because it didn't allow me to erase messages (I guess there wasn't enough room to do the operation), and that was even without moving stuff to the Recycle bin. At the end I found some tiny messages which I could erase, and then quickly things started moving.

c) When I added the new kind of PST folder to Outlook, I erased the old one, and renamed the new one. For that point on I was constantly getting the error message "The operation failed. An object could not be found.". Well that's just great. Maybe if I'm not supposed to rename a folder then I shouldn't be allowed to do so via Folder->Properties... I finally found KB 312354 (;en-us;312354) which has instructions on how to solve the problen.

I've been on Outlook for a few days already and there are various pros and cons to the move.

Here are a few early thoughs:

a) I already mentioned earlier, that when new email comes in, there's no way of knowing which mailboxes have that new email (if you tend to have unread email in those mailboxes.)

b) We use procmail Sanitizer at Zend which renames attachments so that they can't just be opened (renames THISISAWORM.TXT.EXE to THISISAWORM.TXT.12345DEFANGED-EXE). This becomes extremely annoying to open (You need to save and rename the files). Eudora in one of its latest versions added some magic where it was actually possible to click on those links and the right app would launch. Unfortunately in Outlook that isn't the case. However, the cool thing about Outlook is VBA and the ability to write
scripts that manipulate your messages. I actually wrote a script that goes over all my 6 gig of messages and renamed the attachments to get rid of the DEFANGED portion of the name.
I will write about that in a separate blog entry as I believe it will be useful to many. It's probably the biggest reason why the move worked out to be the right thing to do.

c) Auto-complete of email address is by far better in Outlook than Eudora. In Eudora it would constantly screw up by saving invalid address which were mistyped at some point, but it seems that Outlook actually parses them and doesn't save invalid email addresses(e.g. "Andi - note the missing "). This led to a lot of frustration with Eudora.

d) I prefer to use an English locale on my machine and not Hebrew. Eudora couldn't show Hebrew due to this, and I do get Hebrew messages from time to time. To workaround the issues I'd open the message in the Web browser. In Outlook it just magically works.
e) While you can mark messages for follow-up in Eudora, it isn't quite as nice as the support in Outlook, where you can mark messages for follow-up, and then they appear in a separate view folder. Very convenient.

Well if you've gotten this far you are probably thinking of migrating too. I hope this info helps you. I felt it was important to blog about it because it was a big step for me and I thought that if others are looking into it, some of this info would help. I'm sure I'll discover more pros/cons in the coming weeks, and I'll definitely miss Eudora's search capabilities, but for now, especially after having been able to get rid of a few years worth of DEFANGED attachments, it does seem I made the right choice.

Eudora, I'll always remember you though!



  1. I had the same trepidition some years back moving from Outlook Express to Mozilla Mail, it truly is frightening - I'm curious why you didn't choose Thunderbird though ;)

    I just recently moved from Thunderbird to Apple Mail - it was kindof a pain, but I found a tool (for Eudora of all things) that worked for Thunderbird and was able to transfer my mail with relative ease. Then... it just worked - though not being able to do sub-folders on my inbox sucks, as I like to put e-mail to different accounts in different sub folders :)

    - Davey

  2. A few reasons why I chose not to use Thunderbird:
    a) We had some problems here with Thunderbird users including loosing their whole Inbox on a crash.
    b) I use Outlook Calendar so it's convenient to have everything in the same place.
    c) I already used Outlook Mail for years so I am very used to it.
    d) I think Outlook is very mature, stable, feaure rich and has a decent scripting language. I'm not sure Thunderbird is there yet. I'm a big Firefox fan but those memory leaks...argh!...

  3. I would highly suggest, Aid4Mail to help with the e-mail conversion issues. I used it awhile back when I made a similar move, and it is fantastic. Definetly worth checking out.

  4. I quite like the look of Outlook, but as it's Windows only, I don't want to risk getting tied into a one-platform system.



  5. I beleive in outlook the default settings makes folders with unread mail bold and the number of unread messages beside it but I agree that if you have unread messages and then a new one comes it it can be a pain to find it among all the different folders.

    I have been using the 2007 Beta 2 for the last few weeks and I can say that it is quite good. The live search is the biggest improvement for me as well as flagged items appearing in the To Do list and calendar.

  6. I'd have to second that about thunderbird, I'm suprised about the problems you've heard of with thunderbird - we do PC support here, and the panic calls have dropped dramatically when we moved people from outlook to thunderbird.

    Although I guess we use IMAP servers throughout, so the loosing inbox's is not really going to be an issue.

    Interesting that calendaring seems to be a big requirement, we are seeing that here, as a justification for buying Exchange exploder.. ..oh well, more money for us on support ;)

  7. Andi, I recommend you to give a try for “The Bat!”
    45.00 dollars software works perfect for me over the last5 years. No problems at all. Size of all my mailboxes is more than 4G. Start up time is the same as you are using The Bat with empty mailbox.
    As far as I remember folks who used Outlook and had the same mail box size start Outlook and wait couple minutes to get Outlook started.

    Probably Outlook has a better calendar, but personally I value good and stable email client.

  8. I've had problems myself with both Eudora and Thunderbird.
    With Thurderbird I lost my whole Inbox in a crash, just like you described.
    With Eudora I've had problems when someone sent me an email with some weird chars and it messed up with all the other messages.
    I'm not sure about what really happened but I would tell that it is a pain when you lost all your important messages.
    I'll probably move to Outlook soon. The last version looks great!
    I specially love the new feature it has where you can leave it minimized in the tray and it pop up messages when new email arrives, just like gmail notifier does :D

  9. I found a workaround for Hebrew in Eudora. See the following thread:

    I agree with your comment about attachments, but I'm not sure that it matters so much. I suppose you could compress the directory or move it to a larger partition and/or use file links.


  10. Hi Andi,
    Small world, I googled for "Eudora hebrew" and saw your weblog entry...

    I am still using Eudora and will probably always use, the filters are amazing and work great with different personalities.

    I thought about moving, especially due to the lack of hebrew writing abilities (b-t-w, with the internal viewer hebrew shows just fine), but after ~11 years of archived eudora mail and the missing features of the other clients I always decide to stay.

    I actually run eudora with wine so I will be able to use it under my Slackware box as well...

    Yadid meha`avar (Army actually), Gil Disatnik
    gil [ ~ A%T ~ ]

  11. Ron Ellenbogen8/08/2006 07:29:00 AM

    Hi Andi,
    There is a way to know in Outlook about unread messages inside folders. In the folders inside inbox, you have "search folders". Inside there is an "Unread mail" folder which shows unread messages grouped by folder. You can drag it to the favorite folders section for quicker access. However, I'm not sure if this applies to several .pst files.

  12. I've been a big Outlook fan for years - like your colleagues, I was excited about Thunderbird last year but had the same problems with crashes and leaks.

    I finally lost patience with Outlook this week, though, and moved to GMail - I'm sure it wouldn't suit your needs by any stretch, since there's no sensible way to import old emails (yet), but so far I find it's far superior to Outlook for my relatively modest needs - especially since now I can easily access my mail from anywhere.

    Outlook served me well in it's time, though, I'm sure you'll be pleased with it. Good luck!

  13. I've been a big Outlook fan for years - like your colleagues, I was excited about Thunderbird last year but had the same problems with crashes and leaks.

    I finally lost patience with Outlook this week, though, and moved to GMail - I'm sure it wouldn't suit your needs by any stretch, since there's no sensible way to import old emails (yet), but so far I find it's far superior to Outlook for my relatively modest needs - especially since now I can easily access my mail from anywhere.

    Outlook served me well in it's time, though, I'm sure you'll be pleased with it. Good luck!

  14. I know one good tool-importing .ost files,which helped me in very difficult condition.Moreover software helped my friend too.It made it in seconds and free of cost.Utility demonstrated me how it read *.ost files and extract your mails, contacts, tasks and calendars.