Mac Postbox Emails to Mac Outlook 2015 (ver 15)

Let me preface this with – I am NOT sure EXACTLY what Microsoft pegs this version of Outlook for Mac. It’s a monthly subscription and was just updated Mar 31, 2017. NO, this is NOT an April Fool’s joke. The path you are about to read is what I had to do to export and move to Outlook 2015 from Postbox.

Why Move?

Well, that is a good question. As a former Windows user, I was an entrenched MS Outlook user for years. Literally. I think I have/had used Outlooks for over 20 years. Outlook is incredibly comfortable for me to use. HOWEVER, when I moved to Mac, I discovered that Outlook does what it does on the PC – takes over calendars, contacts, email and all that. On the Mac platform, these items are often handled by different programs. Now, is that a bad thing? Or a good thing?  I don’t actually have a definitive answer. I can say if you LIKE all the Mac functions and are a solid Mac user, then by gosh, you’re probably going to be a lot more comfy with the more standard Mac apps – like Postbox, Apple/Mac mail, the standard events and contacts.  If, like me, you are trying to find a solution that works and are coming from the Windows world, the MS Outlook way of doing things might be very appealing.

However, when I went to the Mac about 6 months ago, I decided I wanted to follow a more Mac approach and less Window-ish method. I examined several email apps and ended up settling on Postbox. It was a bit ugly getting Outlook content into Postbox, but with a paid app and patience, cleanup, and all, it happened. But there were SO many new methods to get used to. Still have issues finding emails from Postbox. Havent’ figured out how to actually mark something as important so I can find it again across ALL folders – smart folders?? Have issues getting emails deleted properly – and not finding empty emails sitting in the trash. Just weird stuff. Nothing horrendous, it works as expected 99% of the time but it’s just… different.

How do you use email now?

I have a LOT of sorting and classifying of emails going on with ANY email application via rules, spam filters, etc. I have a lot of clients, a lot of services, invoices, billings, etc.  Leaving them in an inbox or a “Personal” and “Business” folder is just NOT sufficient. If a client pops up and says, “Hey, I sent you a logo image back when we started (a couple years ago).. Do you still have it?”  Well, if you have a monster folder with GIGABYTES and hundreds of thousands of stored emails going back years, this is NOT going to be easy unless you have these things rather weeded out. I keep a folder for each client. As clients have changed over the years, I archive them, but seldom actually delete them from my inbox. It’s a hoot to talk to someone and be able to reference an email conversation from a couple years ago. Love it.

Steps to Move from Mac Postbox to Mac Outlook 2015

There IS no way to go directly from the Postbox files to Outlook. Microsoft is not the most gracious in providing tools for the Mac side of things. MS still treats the Mac products like the red-headed stepchild. We will need to be using third party type stuff to make this work. The short version is Postbox to Stellar Mailbox converter to Outlook 2011 to Outlook 2015/2016.

Get Data From Postbox with Stellar Mailbox Converter

The method I followed uses Stellar Mailbox Converter. You can grab a copy here – The license for this version costs $39. Unfortunately, this does NOT leave a directly importable file. So it comes from the converter in RGE (Entourage) format. This software will suck in the Postbox data and present it to you for massage. So far so good.

In MY interim review of the converted mailboxes, I got some duplicated files/folders that had duplicated/cryptic names like Clients.sbd  and #PB#Clients as well as an actual folder name Clients. Some of these would HAVE content, others wouldn’t. The Clients.sbd folder had all the client subfolders below it, but the emails for the generic Clients were in the ORIGINAL Clients folder. If I had spent more time, I may have figured out what EXACTLY all this meant, but honestly, I was NOT looking for a 100% solution. There may be a few emails missing there, but when you literally have hundreds of thousands of emails, I really doubt that there will be that much critical. This mail move is NOT going to become a month long project wherein each email is carefully tracked and cross-referenced. If I get 90% of the emails over there, I can ALWAYS come back to Postbox if something is missing.

Nonetheless, I wanted it to be as neat as possible.  So, there was a lot of copying, pasting and moving. I pushed the subfolders from my Stellar output into a single toplevel folder. Postbox, and I’m sure other clients, created separate groupings for each server – Gmail, my Lizardwebs email server, another general webmaster account server, etc. SO, I didn’t really want them to all be separate over in Outlook as that is NOT the Outlook way of doing things. SO I combined them into a single top-level set maintaining the current structure as much as possible.

After all THAT, then it was time to export and save the new structured data into an RGE format.  With as many emails as I have, this is NOT an instant thing. So it took a bit. but it finally output an RGE file that I stashed away for the actual import.

Interim Import to Outlook 2011

This is an annoying but necessary step. There is NO method to import the Entourage format into the current Outlook versions. So, next, we’ll suck our RGE format file into Outlook 2011. Outlook 2011 is obviously an old version, but the only one capable of sucking in the RGE format. So, download even a trial version of Outlook/Office 2011 – I got mine at . It is named – MicrosoftOffice2011.dmg – and a little over a GB. I believe this version to be safe, but always trust your own judgement. IF you had a licensed version of it in the past, then you CAN download this version from Microsoft, but my license did NOT include 2011. So I had to get a trial version this way.

Once I installed it and chose the “Give me the trial version only” and customized the install (look for the “Customize” button on the bottom left in about the third screen) so it ONLY installed Outlook, then I popped it in. It tells you that it is a read-only version. You do NOT need to enter any licensing info, pay any money, etc. It’s just a vehicle for converting files.  When you start the Outlook 2011 up, go to the bottom, “Use Office 2011 to view my files for free” – that’s all you need.

Now, review your imported data. Hopefully all is well. I didn’t need to do any more work int here, but I believe you could move emails and folders around more if you needed to here.

NOW, you have a choice… You’ll either do an export from 2011 OR import the data directly from 2011. Your particular situation will be the determining factor. Read the next area before making your decision!

Finally import data into MS Outlook 2015

You can now proceed two different ways – Direct Import from Outlook 2011 OR Export to .OLM format and THEN import it.

If you want to import directly from Outlook 2011 into 2015/2016, you will need to import into a new clean profile. If you have an existing profile with some data in it, this is NOT going to be an option for you UNLESS you create a new profile! I’m personally a “I want to see a file” kind of guy, so I’m all about the OLM method. But for the sake of completeness, you DO have another option.

How to create a new Outlook 2015 profile

/Applications/Microsoft Profile – It’s sort of self-explanatory from there.

The Direct Import

Self-explanatory, but this is NOT the method I used and have already spent enough time detailing this. NOT going to go back and step through it.

The OLM method

Next, let’s Export – go to File => Export.  We’re going to export in the Outlook for Mac Data File (.olm) format.  I checked everything to be exported in the Export first screen. On the next screen, I also chose to delete all items after they are exported. I do NOT want multiple versions of these emails in multiple programs floating around when all is said and done. Having two versions of Outlook with possibly conflicting or duplicated content is not particularly tidy.  You can choose to leave it there if you wish (No, do not delete items), but I chose to.  Whichever way you go, at the end, you will have an OLM file.

Now, you can choose to import that file into an existing or a new profile as is most appropriate for your situation. I am personally attempting to pull the file into an existing profile – the one that I setup INITIALLY for my accounts. I have moved folders around in my Postbox setup, but I personally want to see if I can bring them all back together. SHOULD this fail, I very well may import it into a new profile.  As all of these operations are doing about 10 GB of data, they are pretty slow. Ugh.

OKAY – This is where I pull the plug…

Much as I really wanted to move over to Outlook… While Outlook is NOT a native Mac’ish type app and is more of a Windows thing, that deep down familiarity is a real pull.  But.  The more I work with this, the more I am beginning to feel that the overall benefits of being back into Outlook are going to be less than I really want. Postbox has caused me annoying issues here and there. The filters are occasionally flaky – global/non-global. Insistence on breaking down and bringing content in via server names in the back end. Thinking that maybe Outlook sort of hides that and dumps it all into one “Inbox” directly but not sure.

I wanted to pull the 6 months or so of missed emails in, but it appears now that there would be a lot of duplications. I have always used POP – nice old dependable technology and it kept my email from getting huge – relatively speaking of course. I still have probably 20 GB of email in the big scheme of things.  This all said…

NOW, if what I was after was to just move my data from Postbox to Outlook, I could have moved the content to a fresh profile and it would have been absolutely perfect. In my specific case though, it now is coming down to – “Is the effort worth what my outcome is going to be?” I carefully pruned and moved, categorized, etc all my emails and rules when I went to Postbox. There likely are a hundred or move rules that I have in place and ordered to make things happen properly in Postbox (for the most part). And I just do NOT feel like losing another couple of days on this.

Bearing in mind that I have always used POP and that particular technology has its’ best days in the past, it might be just time to setup an account as IMAP and push EVERYTHING up there and be able to use it like that going forward. But that’s for another day. Now, on to cleaning up a mess a webmaster left for one of my clients. Ugh.

SO. End of project. If you needed to know how to make the move from Postbox to Outlook, you have the steps above.


Author: Eric Erickson

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