I am using a MacBook Pro with macOS High Sierra 10.13.1. Using MS Word for Mac 2008, 12.3.6, the Compress option barely compresses my large files which contain lots of photos. Can you recommend a different approach?
There is a newer version of High Sierra, OS 10.13.2, that was released a couple of weeks ago. Not sure it will help, but you can get the OS 10.13.2 Combo Updater form here:
Don't know if it will resolve your issue. I use Office 2016/Word 2016 (and 2 other modules), but I have tried what you are doing. I do see where you have the latest version of Office 2008, and according to this:
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