Playing embedded movies in Pocket IE has never been supported by default. It's just not part of the browser's coding. Microsoft did release a 'use at your own risk' plugin for Pocket IE under PPC2000, about 4 years ago I think, but it's been withdrawn or buried in their zoo of a website for a long, long time. Never really worked anyway. Had a video leak, so if a page miraculously managed to display video, then when switching to other applications (such as File Explorer or Inbox or Word, for instance) the video itself stayed on top, making multi-tasking unlikely. I tried it on a couple of devices but it just wasn't useful enough nor stable enough to keep trying.
If you have video content and need to distribute it in WMV format, I'd suggest first re-considering that choice. WMV and Pocket IE don't get along in another way besides display. If your MIME configuration on your server is not exactly right to suit PIE's strict expectations, a WMV (or ASF, or CAB, or TSK, or several other filetypes) will display as slow-loading raw code, gradually building the WMV file in the device's temporary folders somewhere where the average user is unlikely every to think to look for it. If you are capable of properly configuring your server to prevent this (and I still don't understand the particulars, so don't ask me), then by all means link to WMV files on your pages. Properly set up, these files should trigger the download dialogue in PIE.
Otherwise I'd suggest using MPEG and recommending Pocket TV, or using AVI (better, for quality and compressed scale) and recommending TCMCP, a great freeware which easily and beautifully plays DivX-encoded AVI and about a dozen other formats. Does MOV, WMV, ASF, MPEG, various audio stuff, just a ton of formats. Freeware, too.
Good luck. I hope there's better native video support for multiple formats on WM5.0, but doubt it. Seems it'll still be just WMP10, the mobile version, with no PIE tie-in, and no support for non-MS codecs. Not that I blame them really. Why try to support formats based on open source, when the boss man seems to think open source code is the devil's work?
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