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The company's decision to introduce its own portable media player with accompanying software and online digital music store was thought to have been prompted in part by its disappointment with the failure of Apple's rivals to significantly dent the iPod's dominant market share.

The extent of Microsoft's dissatisfaction has now been revealed in an extract from an email conversation between the company's media software executive Amir Majidimehr and Jim Allchin, the co-president of the company's Platform Products and Services Group, in which Allchin raises the possibility of having to talk to Apple CEO Steve Jobs about providing iPod support for Windows Media Player (WMP).

'I think I should talk with Jobs,' he wrote. 'Right now, I think I should open up a dialog for support of the iPOD [his capitals]. Unless something changes, the iPOD will drive people away from WMP.'

Majidimehr's reply expresses his dismay with the efforts of Apple's rivals, and their preference for their own software over WMP.

'We have been unsuccessful in the past to convince these vendors to open their eyes and accept that there is better software out there than what they ship with these things,' he wrote. 'Of course, some are better than others but none are a match for Apple. For good or bad, the message is finally getting through (with retailers threatening to sell iPod) but we are not waiting for that. Tomorrow, we have an entire crew descending on Creative

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and after that, Samsung and Rio to get them motivated to build the "right" device.'

If they do not listen, he added, 'then it is time for us to roll up our sleeves and do our own hardware.'

In his reply email, Allchin describes his experience with one player, Creative's Nomad Jukebox Zen Xtra, as 'really terrible'.

'The physical device is not even in the same league as the iPOD,' he wrote. 'I mean it is ugly, not smooth to the touch (hard edges and uncomfortable to hold, etc.), fragile (easy to break), the controls are difficult and they hurt your finger if you use the "jog" dial much at all, etc.'

And the software was not much better, largely because Creative preferred its own to Microsoft's Windows Media Player (WMP), although that is where most Windows users will have ripped any music that they already have on their computer.

'The installation encourages you to use theirs over WMP,' he wrote. 'Setting up a relationship to copy all the music from WMP is very unintuitive. Copying the contents of a playlist isn't too bad, but doing everything is very strange. ... The actual Playlists themselves are not copied over to the device. So you just lose that capability on transfer. ... There is no synchronization as you know. You copy it across and the next time, you have to copy it ALL across again. ... One of the worse problems I had is that it appears NONE of the metadata that you put in the WMP library is carried over.'

At the time Allchin pinned his hopes on the forthcoming WMP 9.1 release.

'I am REALLY counting on wm9.1 to fix this terrible experience,' he wrote. 'Apple is just so far ahead.'

The email was submitted as evidence in the Iowa antirust lawsuit against Microsoft, where plaintiffs are trying to demonstrate that Microsoft overcharged consumers for its software, and is the second Allchin missive to have come under scrutiny. The first gained widespread publicity after Allchin said that were he not working for Microsoft, he would buy a Mac, a remark he later said had been taken out of context.