importing email from Outlook for Mac 2011

I’m finally going to free myself from the clutches of Outlook, and move to a native OS mail client. (Am running a MacBook Pro from late 2011, 2.2 GHz, 8 Gigs DDR3.)

First I need to import all of my email archive into DTPO. My archive is just under 70,000 messages.

My questions are:

  1. Is this possible? (In a couple initial experiments, I’ve managed to hang both DTPO and Outlook, but perhaps I should be doing things differently, eg closing Outlook or the MS Database Daemon before starting?)

  2. If so, are there best practices for doing this the right way? My emails are important to me, and I want to minimize the risk of losing/corrupting some.

Any and all suggestions welcome - auch auf Deutsch wird ganz gut gehen!

This should be possible but I’d suggest to split the email archive into multiple smaller folders containing up to 5000 messages and to import one folder ofter another.

Thanks Christian.

Trouble is, the DTPO “import email” window hangs before I can even select a folder in Outlook from which to import emails. I remember now, this was one of the main reasons that I purchased DTPO 2+ years ago, when I bought my new Mac - to archive my Outlook emails. It didn’t work then, and 2+ years later, it’s still not working.

Is there any alternative way to import emails into DTPO from Outlook for Mac 2011, without launching the “import email” window? Or some way of avoiding freezing both DTPO and Outlook when I do?

All best,

Though I am not running Outlook, here’s something to consider…

As Christian suggested, split the mailbox into subgroups in Outlook, before trying the import in DEVONthink. This way you can select the groups individually to lessen the burden on DEVONthink.

Also (though it may not apply to Outlook (ie. I can’t test this), if you drag and drop from into DEVONthink then invoke File > Import > Email… DEVONthink will not list files that have already been imported.

With Outlook frontmost, click on your global Scripts menu button in the menubar. You should see two scripts for capture of one or multiple selected items to DEVONthink: one for selected mailbox(es)and one for selected message(s).

Jim - Unfortunately, I can’t get to a point where I’m actually able to select individual folders within Outlook. When I invoke File: Import: Email, the import email window appears, and both Outlook and DT freeze.

Bill - Many thanks, incredibly helpful. I’ve now successfully imported a few small mailboxes into DT, and will try bigger ones tomorrow. I’ll probably break up my massive archive (70k emails) into smaller, 5k chunks beforehand, as a previous commenter suggested.

One thing I’ve noticed: attachments to emails don’t seem to import reliably. Some appear as icons at the foot of the emails, and by double-clicking them, I can open them fine. Others – mostly pdfs and jpegs so far – appear as small-resolution images of the first page of the document, and I can’t find anything to click on to open the full document or full-resolution image. And some appear not to have come across at all.

Any idea where DTPO stashes attachments when it imports emails?

Many thanks again for your guidance!

The attachments should have come over properly in the messages. By default, the display uses Quick Look, in which attachments may not be immediately available. You can switch to display as rich text of a selected message by clicking on the Alternative Text button (in the navigation bar immediately above the pane in which the message is displayed).

Or open a selected message under Outlook by pressing Shift-Command-O.

Bill - yep, sure enough, I hit the Text Alternative button, and there the attachments are.

I can’t thank you enough for all your swift and accurate help. Your presence is a major competitive advantage for DEVONthink.

All best,

Hi again, Bill. Looks like I spoke too soon.

I tried to import a folder containing 6000 messages, using the procedure you outlined. Each of the headers imported correctly, but none of the email bodies made it - the log repeated, again and again for all 6000 messages, the same error message: “Couldn’t extract text from mail message.”

I’ll try cutting down the number of messages to import, but do you have any other suggestions?

All best,

DTPO failed with a folder containing 4000 messages as well. Same error message as above.


I don’t have a large store of email in Outlook 2011, but I am able to select messages in Outlook, drag them to a folder in Finder, and then import that folder into DEVONthink. When dragged from Outlook to that folder, they are .eml documents (as expected), with attachments intact. This method does not preserve conversation threads, if that matters.

Thanks, Korm. I tried your method, but for some reason, ended up with a lot of junk in the bodies of many emails.

I also suspect this approach would get pretty cumbersome, if used to import my 70,000+ emails.

However, at this point I’m ready for anything that works, down to importing 1 message at a time!

Just tried a mailbox of 1430 emails, and it seems to be going smoothly. Perhaps problems crop up above a certain size threshold…

Is it possible that your Outlook database is corrupt? Have you tried to rebuild it?

Outlook 2011 will export to .olm files, and there are 3rd party utilities available that will convert .olm to .mbox (UNIX mailbox). DEVONthink’s mail importer can import from .mbox mailboxes.

Korm - Thanks for the continued suggestions.

There seems to be no sign of database corruption - none of the symptoms listed in the link you gave appear in my Outlook. I may eventually give this a try, but sounds at this point like a massive outlay of time for a very small likelihood of positive return.

If I drag a folder from OUtlook onto my desktop, it becomes an MBOX archive (filename.mbox). From within DT I can then file:import:file to bring this .mbox file into DT. However, it comes in as an archive, not a folder full of easily accessible emails.

If I could find a way of unzipping this archive within DT, I’d be set.

Also, I’d use the DT file:import:email function, but when I do this, it defaults to Import from Outlook, and locks up both DT and Outlook. If there were some way not to default to Outlook for email import, I’d do that, but I don’t know what that way is.

Aha! :slight_smile: – I had not realized that dragging a folder from Outlook creates an .mbox. So, don’t import that using File > Import > Files and Folders…. Instead, import it using File > Import > Email… and choose the “UNIX Mailbox…” option:

When you click “UNIX Mailbox…” DEVONthink will prompt you for the location of the .mbox.

Just tested this with a Outlook 2011 folder, dragged to the desktop, and imported as above. Perfect results, over here. Conversations are threaded, attachments are attached.

(I agree on the Microsoft instructions for repairing Outlook 2011 – way too complicated.)

Hi Korm,

I’d already tried a work-around, by dragging Outlook folders to my desktop as described, then importing the resulting .mbox file into OS Mail, and finally using DT’s email importing window to pull the mails into DT. Your approach seems cleaner and I will adopt in the future.

W/ my import via Mail, everything ran smoothly, with no hangs, which is good for a start! However, the output in Mail, and also in DT, is full of junk - most emails start with garbage such as this (I’ve added ===== to set it off from my words):


st! (VPS 0649-1, 11/18/2006), Inbound message
X-Antivirus-Status: Clean


In-Reply-To: 000901c70a67$493619a0$8d1f1c97@IBMDE5586FAFE9

Mime-version: 1.0

Content-type: multipart/alternative;


X-OriginalArrivalTime: 17 Nov 2006 19:48:24.0580 (UTC) FILETIME=[57F0B440]

X-Antivirus: avast! (VPS 0649-0, 11/15/2006), Inbound message

X-Antivirus-Status: Clean

$Üìôü(=zÔì)a?aWaoawa©aÉaÑa÷aÿa%i ¨Úâ> š ì J




So perhaps your theory about a corrupted Outlook database has merit - I’ll try to rebuild.

Another QUESTION: when I try to re-import an mbox into DT that I had previously imported, I hit a snag. The DT import emails window appears not to want to import emails a second time form the same source, and I can’t find any way to re-set the .mbox file to “fresh”, ie make DT think they’ve never been imported before, and allow emails to appear in the import emails window without a little check mark in the DT column.

Any suggestions there?

Thanks again for all your brainstorming!

“Corrupted” messages – looks like you are using (or used at one time) Avast. Their forum might be a place to ask what’s up with the content of your email. DEVONthink just takes them as it finds them, so if there’s “corruption” due to something the anti-virus app does, there’'s probably nothing for DEVONthink to do about the situation.

DEVONthink prevents reimporting already imported mail on the assumption that duplication is not wanted by most users. To reimport a individual messages, conversations, folders, entire mail boxes, delete the thing you want to reimport from your database, empty the trash, and attempt a fresh import.

You’d need to delete the previously imported emails and empty the Trash or you could uncheck the option to hide imported messages and allow duplicates (depending on how much you don’t mind cleaning up).

The “Hide > Imported” checkbox only does what it says “hide imported”. It doesn’t “allow duplicates” :confused:

(At least, in the past 8 years it never has over here :slight_smile: )