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Escape from Outlook 2011!

Oh, the sacrifices I make for our TidBITS readership. If I’d known what I was getting myself into, I would never have adopted Microsoft Outlook, from Office 2011, in order to review it (see “The Outlook for Microsoft Outlook,” 8 October 2010). Things got worse and worse as I continued to try to use the program. In addition to there being no formatting of quoting levels (Paste As Quotation, Increase Quote Level) there turned out to be no Resend command (so I couldn’t take an existing reply and send it again, to someone else or to the same person with the original reply quoted). For these and many other reasons, some of them appearing in the review, Outlook was turning out to be a horror. For the way I use mail, it was simply untenable.

So I decided to bite the bullet and migrate myself yet again into some other mail application. That’s when I discovered that Outlook 2011 lacks something else I require from any mail program—a way of exporting my mailboxes. You can save all your mail as a single .olm file, but no other application can read it, and in any case my attempt to do that failed (Outlook broke down in the middle of the operation). You can drag individual messages to the Finder, but this results in individual .eml files, which most other mail programs can’t import. What I needed was a way to export to “mbox” files, a more-or-less universal standard representing a mailbox and all its messages.

After some hours of banging around fruitlessly, I discovered that I already had the perfect mbox creation tool at hand. Not only that, but this was a tool that could reach right into Outlook 2011, grab all my selected messages, and assemble them into mbox files that Mail can import. That tool is EagleFiler, which I reviewed several months ago in “EagleFiler Turns a Finder Folder Into a Snippet Keeper” (24 February 2010).

As I said in my review, I was already using EagleFiler to slough off unneeded mail folders from Entourage. Using a mail client as a database over the long term has always seemed to me a confusion of categories in any case; certainly there needs to be fast searching of a small set of current or frequently needed messages from within the mail client, but in general it’s perfectly fine for me to archive most of my saved backlog to an application that really knows how to search the heck out of mail messages, and that’s exactly what EagleFiler knows how to do.

But would EagleFiler know how to talk to Outlook 2011? It turned out that developer Michael Tsai was right on top of things. He’s working on a beta version (1.5) that boasts a number of improvements, including better feedback in the main window when EagleFiler is busy indexing, more sprightly navigation and rearrangement of folders, indexing of email attachments, and much more. Most important, this version has the power to import from Outlook.

So, with the new version of EagleFiler in hand, I selected all my messages in Outlook and told EagleFiler to import them by pressing the F1 key, right there in Outlook. In less time than it took to make myself a fresh cup of cappuccino with my handy-dandy Pavoni Napolitana, EagleFiler had grabbed all my mail messages and assembled them into mbox files, each file having the name of the Outlook mailbox or mail “folder” from which its messages came. (The files do not have a literal .mbox file extension, but they are mbox files nonetheless.)

I tested a few of the resulting files by having Mail import them, and it worked perfectly. This, in case you’ve never tried it, is a two-step process. In Mail, you choose File > Import Mailboxes. This brings up a dialog where you specify the mailbox source type; in this instance, I selected the last option, “Files in mbox format.” This in turn summons an Open dialog in which I could select the mbox files created by EagleFiler and import them. Mail creates an Import folder and puts the imported messages into mailboxes within it, named after the mbox files on which they are based; you can move these mailboxes elsewhere in Mail’s On My Mac collection, but for now I’m just leaving them where they are.

I also took this opportunity to prune my email, by which I mean that I imported only a few mailboxes into Mail; the rest I simply left in the highly competent care of EagleFiler. If I discover later that I need the contents of a further mailbox accessible from within Mail, I can always import it then.

And that’s the end of the story. I have now migrated myself completely out of Microsoft Outlook and into Apple Mail. I’m not crazy about Mail as a long-term solution, but it has all the basic features I need, it’s sufficiently scriptable with AppleScript for my workflow purposes, and—most important—if I later decide to migrate out of it, I know that EagleFiler will be there to help me.


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Comments about Escape from Outlook 2011!
(Comments are closed.)

Michael Cohen  2010-10-26 10:45
Interesting as your EagleFiler solution to Outlook Prison is, I want to hear more about the Pavoni Napolitana!
uhuznaa  2010-10-26 12:17
After having made the transition to IMAP only mail servers all this is a thing of the past for me now.

Treat mail clients as what they are (clients) and let your server(s) handle the mail. Much better.
Matt Neuburg  An apple icon for a TidBITS Staffer 2010-10-26 12:44
Yeah, I didn't want to get into that in the article. For my main account, I like *one* of my clients on *one* machine to treat the account as POP and keep the messages, so that I have my database of saved messages even if I'm offline.
uhuznaa  2010-10-26 12:53
Well, can easily be configured to keep all Mails locally as offline copies even with IMAP. I think this is even the default.
Try the search tool, email disappear when viewed. Not too cool.
Steve Schifrin  An apple icon for a TidBITS Benefactor 2010-10-26 13:23
Thanks for the cautions. For a while, I've been using Softthing's EEAX to archive Entourage data, a program which still befuddles me a bit; but, the latest release boasts an 'export to Mbox' feature, as well as Outlook 2011 compatibility. I have not yet upgraded to 2011, so I can't verify the compatibility.
John McClung  2010-10-26 22:20
I'm about to leap from OS X TIger 10.9.11 to the latest system and a new Mac Mini; and from Entourage to Mail, unless someone recommends something else. I organize and keep almost all my business and personal emails. Should I use EagleFiler, or EEAX, to move everything to my new system? Thanks for advice.
Matt Neuburg  An apple icon for a TidBITS Staffer 2010-10-27 07:10
To move to the new machine, just use the built-in Migration Assistant. To migrate from Entourage to Mail (why?), just ask Mail to import your Entourage stuff.
kenstee  2010-11-01 12:51're on 10.9.11

And I'm just on 10.6.4. Impressive!
Frankns  2010-10-27 16:06
Exchange services are my "handcuffs." I've run Apple Mail fairly well and tried Outlook 2011 when it arrived, but was unimpressed. Were I on an true IMAP server, I'd try MailMate. It works well enough with Gmail that I'd consider it for my work correspondence.
Gary Kellogg  2010-10-27 18:58
Seems to me Outlook is proving to be Entourage with, ala' George Costanza, "shrinkage."
kenstee  2010-11-01 12:56
I guess this is one more argument for getting the "lite" version of Office 2011 that does not have Outlook - and save $70 or so to boot. That is if you "need" it. BTW, David Pogue of The New York Times had serious issue with Outlook as well
Huh. I was running Office 2004 on my PowerMac G5 all these years; when I finally bought a i7 iMac in September, I bought the upgrade to Office 2008 ($85 from Amazon), which entitled me to a free upgrade to 2011. I have it now, but held off upgrading. Glad I did, I think.
With there was a better alternative to Entourage--I *loathe* Mail--but guess I'll stick with Entourage 2008.
Doug Lerner  2010-11-01 17:27
I just wanted to add to the praises of EagleFiler. I am a former SOHO Notes user, who dabbled in Yojimbo but found all sorts of issues with it and then came across EagleFiler and have never looked back. EagleFiler, and Michael Tsai's support, are fantastic. I keep all my "snippets" of info in there.
Allerbe  2010-11-02 02:00
Bare Bones Software's Mailsmith may be 'abandonware' now, but for me it's still the email client of choice.
Kevin Grady  2010-11-02 15:49
I am a Mac Mail user, but I just had to setup Outlook 2011 for myself after reading this article.

I believe that Forwarding an email achieves the same result as Resend.

Then if you need to copy and paste a quote in another email, you can do this by using Forward with the desired text selected, and copy and paste this. There are other variations on this theme to the end which Matt gives a failing grade.

I think most Mac users in an Exchange environment will be quite satisfied with Office 2011. This seems to be Microsoft's aim.
Berkinet  2010-12-01 11:51
Forwarding does NOT achieve the same result as Resending. Resend manages the headers so the message appears to come from the original sender, and does not quote the contents. Forwarding shows "you" as the sender and quotes the entire message. SInce Outlook cannot change quote levels, you must do that part manually. Big pain.

As for "pasting quoted text," the Forward and copy trick works for existing mail messages. But, if you want to paste material from some other application, say a web browser, then it gets convoluted: Copy, paste, mail to your self, and forward and then copy again.

Sorry MS, Outlook is no more than a cosmetically updated LITE version of Entourage.
Berkinet  2010-12-01 12:17
Just found another Outlook annoyance... In Entourage if I sorted a mailbox so that newest messages were on top, I could position the cursor on the oldest (lowest) new message and press delete. The cursor would move upwards to the next message. Now the behavior is reversed. I must start with the newest new message and work down.

Another flaw from Entourage was maintained in Outlook: If you are deleting a series of messages by repeatedly pressing Delete, the cursor will automatically move to the next message. UNLESS that message has already been deleted. Then pressing Delete does nothing and the cursor does not move on.
Niren   2010-12-21 11:59
Thank you. EagleFiler worked like a charm. All my mail imported exactly as you described from Outlook 2011 to Mail.