Page last updated at 11:00 GMT, Monday, 6 June 2005 12:00 UK

Caught in the Windows to Mac rift

If the computing industry was genuinely competitive then switching suppliers would be easy, argues technology analyst Bill Thompson

Frustrated man, Eyewire
Moving to a new computer can be frustrating
I have fallen for the oldest trick in the computing book, and I am feeling like a fool.

Last month I bought a shiny new Apple PowerBook to replace an ageing Windows laptop. It is faster, has a clearer screen, does a lot more and has much better battery life.

But four weeks on I am still lugging the old computer to meetings, wrestling with the appallingly complicated Windows 2000 network settings when I need to use a wi-fi connection and having to remember exactly where I put the documents I am working on.

Messy messages

I am in this mess because six years ago I started using Microsoft Outlook to read my e-mail, and now I find that I am locked-in to it.

After four weeks of struggle I have not managed to get my old e-mail onto my new computer in a usable form.

Bill Thompson
If Microsoft thinks its software is simply better and more usable than everyone else's, they should have no reason to hold on to their customers by unfair means
It is my own fault, because I am a compulsive filer.

I have nearly two gigabytes of old e-mail messages, all carefully organised and categorised into several hundred folders, a rich and complicated hierarchy that reflects my work patterns, my friendships and my various commitments and engagements.

Because I use Outlook all of my precious e-mail is stored in what is called a PST file. It is a format that was created by Microsoft, is only understood properly by Microsoft, and is evidently carefully guarded by Microsoft.

In theory Thunderbird, the open source mail program, can read my old e-mail, but it consistently crashes when I try to do it.

There are third-party tools out there that may help, and I am about to start experimenting.

But the time I have available for this sort of administration is limited, and so the weeks drag on and the old laptop remains my constant companion.

Simple things

In a rational world Microsoft would provide me with a tool to do the conversion. And in fact it has released a program that will convert PST files into the format used by their new Macintosh mail program, Entourage.

Entourage is not so bad, and I could probably learn to live with it. Except that it will only read PST files that were originally created on a Mac, so it is no use for anyone like me who is trying to migrate from Windows.

Anyone with a suspicious mind would think that Microsoft wanted to make it hard for users to make the switch from Windows to Mac OS, and because they own the PST format they have decided to do this by failing to provide a migration tool.

Box shot of Microsoft Outlook, Microsoft
Bill has had problems with his e-mail program
Thunderbird and other tools have to work by reverse-engineering, figuring out how PST files work by examining them carefully, because the format is not published. And this makes it hard to get things to work.

Microsoft benefits, even if the reason for the lack of migration tools is simply that the PST files are too complicated and messy to be easily converted to industry-standard mail files that can be read by other programs.

I am technically literate, and yet I am finding it hard to get rid of my Windows laptop. Someone less confident than me would probably have given up by now, or simply been deterred by the prospect of having to mess around with migration tools.

The problems created by proprietary formats, and the ways customers can be locked-in to one supplier even when they would like to move, is the reason the European Commission is pushing Microsoft hard to provide details of its protocols and interfaces to its competitors.

Recently we have seen some evidence that the company is starting to change its approach.

The X files

Last week Microsoft announced it will be supporting industry-standard open file formats for the next release of Office, based around the eXtensible Markup Language, XML (and yes, it is an irritating way of capitalising the words!).

This is a major step forward, as it will allow word-processing, spreadsheet and presentation programs from any developer to work with Office files.

Unfortunately that does not help people like me, stuck with my valuable information in a file format that is obscure, complicated and inaccessible.

Let us hope that as part of their new commitment to openness the programmers at Microsoft start work on a comprehensive set of migration tools for older file formats.

After all, if Microsoft thinks its software is simply better and more usable than everyone else's, they should have no reason to hold on to their customers by unfair means.

Or am I missing something?

Do you have any advice for Bill? How have you found switching from one computer system to another? Let us know

Lovely idea, but you know you want to install Linux really! Mandrake 2005LE for PowerPC - install the OS and of course a nice free IMAP server from the CD to help you move all those emails over. Set your desktop right and it'll look just like MacOS anyway.
Jason, Nottingham

Where's the problem? E-mail the lot to a GMail account, then e-mail them all back to yourself and open them on your Mac. Do it one folder at a time and it should be fine. Personally though if you have 2GB of mail in the first place you would be in just as much trouble if your old laptop died tomorrow.
Darren Vine, Warwick

Call me cynical, but do I get a feeling that Bill is anti-Microsoft? I like reading his articles but I think it is unfair to criticise a company for keeping their designs confidential. Do Apple or Cisco make all of their information freely available?
Neil Small, Scotland

You can actually set up the IMAP server on your new Powerbook - Postfix Enabler from will allow you to do this. Once you have set up the server, connect to it from your all windows laptop, copy all the e-mail across, and hey presto, all your e-mail is in an IMAP served folder on your powerbook. Apple Mail, or Entourage will then both be able to access your old e-mail quite happily.
Alex, Bicester UK

Thunderbird has a maximum limit it can cope with. 2GB is too much to deal with in one pst file, but have you tried exporting your folders in segments, into 2 or 3 smaller pst's first, then trying to import/open them one by one? It might not crash if you do this. You may also want to consider clearing out old folders anyway, as 2 GB of data loading up into any program is bound to increase the risk of instability.
Andrew Gonoude, Crawley, UK

You're a brave man Bill! I constantly struggle with things like this but put it down to my own in ineptness, rather than taking a step back to think about the situation, and realise that it really should be much simpler. I guess this is the phenomenon that Alan Cooper refers to in his book The Inmates are Running the Asylum - technology that makes us feel stupid. Anyway your answer may lay here: Good luck! (from someone with a Bachelors and Masters in computing who suffers from computing problems ALL the time.)
Mark, Sheffield

Have you considered subscribing to a GB-sized IMAP email service, connect via OUTLOOK to that provider and migrate your local mail folders by dragging them within Outlook over to the IMAP folders? Having not used Outlook for a while (I too am on a Apple Powerbook but using Entourage) I am not in a position to actually trial this, but I believe it should be possible with a little (but not too much) elbow work to get your email onto the IMAP side. Once done, then import them into your Apple world using whatever e-mail client you wish.
Tim, London

Entourage has been around since 2000 - so it's hardly new as you say. If there is one thing you should be learning it is the Mac community's willingness to help one another. So try this solution. 1. Load Mozilla on your PC 2. Import Outlook Mail and Contacts into Mozilla 3. Mozilla Win uses the same file formats as Mail, Netscape, and Mozilla Mac, just do a straight directory copy. 4. If using Entourage just import from Mozilla after doing step 3
Jonathan, Penarth

I've haven't had to endure the problems you have encountered as I've always used a Mac but I do know that there are several software packages to help the transition one is called MoveToMac I think.Alternatively I found this article:
Adrian De Ath, Horsham, Uk

You just need to export to a comma-separated variable file (.CSV). I'm pretty sure that your new client will be able to import this format file.
Ian Wild, Ombersley Uk

I don't know about Outlook, but in Outlook Express, I can select multiple files, right-click, and then forward them to yourself as one message. With this method, you could turn each mail folder into one message with only a few clicks. It's a shame you used this problem as an excuse to promote Apple. For people who don't live in a cosy, smug bubble of Apple users (in other words, 95% of the world) the opposite problem of portability would occur.
Steve, Sussex, UK

Maybe this tool can provide a workaround. Have a look at: Success.
Patrick Debal, Laakdal, Belgium

My advice? Ditch your old e-mails. You only think you need them. Look objectively at why you're keeping them. If you have referred to them recently, examine the consequences of not having the information you referred to. If, and this is a stretch, if you really really need the information you have gathered over time, then take it out of your communications application and store it in a document retrieval system.
Matt, St. Albans, UK

I faced a similar problem when I switched a company's local mail accounts from Windows to Linux last year. The route was complicated, but it worked as follows. First import all messages from Outlook (pst) into Outlook Express. Evolution and Thunderbird can both import Outlook Express, although the received dates can get a bit stuffed. Alternatively, there are some java-based tools to do this part, but be aware, some of them lose attachments.
Paul, Hamburg, Germany

I think you are being a little harsh. Just imagine you are designing a computer program. You want to store information, and to do that you create a structure to do it. When you design this structure you design it to work well with your program. Why on earth would you design the structure in a way that is compatible with every other similar and competitive product. I appreciate the monopoly argument but think you can take it too far. If you had a business would you design every product to work with rival products?

At work we are encouraged to save our emails after a certain period as Text files, these will (i assume) transfer to a Mac with much more ease. It could be a bit of a large job to convert large numbers of emails contained in your .pst files to a .txt format, but I would hope that there exists a way to do via macro, or similar.
Paul Sewart, York, UK

Don't bother shifting your old e-mails. Just create another account on Mail on your PowerBook. If I'm not wrong, Mail should download the e-mails from the e-mail server you are connecting to. However, if you really want to see all your old e-mails, then you'll have to use Thunderbird or any other third-party tool. I don't know why Thunderbird crashes on your system. You could switch to Linux? Linspire, Mandrake,SUSE recommended
Mo Ham, Farnborough, Hants

I would find a friend with an Exchange server. Copy your mailbox onto the Exchange server. Then use your e-mail client on the MAC to download that e-mail. You have a number options but IMAP is probably your best. This will of course take a few hours for all of that e-mail to be copied around but I am sure it will work for you. I have a friend who uses my Exchange server over a VPN connection using his MAC.
Robert Chapple, Swindon, Uk

Your.pst files need to be converted into .mbox files so Entourage can import. See Mud

I would have thought that most people would have at least considered interoperability issues before changing between two radically different platforms. The simple fact of the matter is that if you had bought a newer laptop running Windows 2000 or XP you would have seen all the benefits of your PowerBook without the headaches of migrating messages. If your e-mail is so important then perhaps you should have considered this at the time rather than firefighting after the event and complaining that your assumptions were incorrect. Could it be that far from Microsoft being to blame, it is actually your fault for not asking the questions in advance?
Loz, Manchester, Uk.

I have since converted to a Mac Mini my self and had a lot of email in microsoft outlook. I found this really good e-mail converter program called Outlook2Mac the address is
Richard Tilford, Nottingham

One possible solution to your problem is to use Virtual PC. This creates an emulated Windows machine in your Mac, and allows you to switch back and forth between the Mac and the PC. Now, it doesn't work with all PC programs, but it works well with Microsoft programs (at least the ones I have used.) So this would allow you to have access to your old files, and move them to the Mac as needed. Good Luck!
Don Philip, Burlington, Ontario, Canada

I faced the same hassle last January (though I was moving my e-mail to Linux instead of Mac OS X) and the solution after a huge amount of research was to set up (even temporarily) an IMAP server on a Linux machine, move everything into the IMAP server, and then reread it from the target machine. As it turned out, I decided to keep the e-mail on my new Linux server with IMAP support since that way I wouldn't get locked into any e-mail program again. Now I can get to my e-mail anytime I want to from anywhere.
Neil Robinson, Cambridge, Uk

I had problems with large PST files and Thunderbird also. I used the import feature of Eudora to get my mail from Outlook and then exported from Eudora to Thunderbird. I can now use my mail store in Linux and Windows easily. It took a while, but was worth it, and I don't miss outlook, or the associated security risks
Liam, London

There is a little app, called Emailchemy you can get for the Mac, which will convert pretty much any mail format from one to the other, including Outlook for Windows. Should solve the e-mail problem. Not had much experience switching from Mac to PC, however, upgrading from Mac to Mac is an absolute dream these days. When you boot up the new Mac, it asks if your upgrading from an older Mac. Click yes, and it tells you to connect the old Mac with a firewire cable. Restart, and bingo! Copies all your files and setting over from the old Mac to your shiny new one! Boot the new Mac, and everything is there ready to use. Even has my old desktop picture! Pure genius! Now, if they could just integrate some PC to Mac transfer software into that, it'd be bang on perfect!
Dave Elliott, Birmingham, Uk

Perhaps the real value of this exercise is to highlight the dangers (to your sanity as well as to competition) of any proprietary data format. I started using server based IMAP/Webmail about five years ago. Nothing is ever stored on the client, so is always accessible - on Apple, Linux, mobile or even Windows , from anywhere in the world.
Philip, Reading, Uk

Bill Thompson is a regular commentator on the BBC World Service programme Go Digital.

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