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I'm curious what this icon represents. I imagine it's an ancient disk reader. Anyone know what is it?

enter image description here

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    Which version of Windows? – Nayuki May 12 at 20:10
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Looks like a Compact Flash to USB reader. Specifically, those finger grips on the side looks like an exact match for the Sandisk Imagemate (SDDR-09):

A pic of a Sandisk Imagemate (SDDR-09)

I believe the same form factor was used for the SanDisk USB SmartMedia Reader (SDDR-09-01) which used for the now obsoleted SmartMedia card format which were cards that were as flat as SD cards but a bit larger in size.

And there was even an older serial version with the model number SDDR-01; different data connection but same core form factor. But the size of that slot looks like a dead ringer for a Compact Flash card reader from ye olden days of about 15 years ago.

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