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Second, the louder I am about this issue, the more attention is brought to it, and the more likely Apple is to actually do something about it and make the maintenance of their Windows software a priority. I would rather complain about it and see some positive change rather than continually handwave it and sweep the issue under the rug. If you’re all tired of hearing about it, you should be louder about it too!

I have provided feedback to Apple, many times, but this is a drum that needs to be beat on a bit more publicly. One person constantly bringing attention to a nonfunctional piece of software from the 3 trillion dollar tech company can only have so much of an influence.
Cool, what's your Feedback ID? I can try updating next time from my Mac mini in Bootcamp on Windows. That'd only be Windows 10, though. Keep in mind that you're dealing with a pretty niche situation here (ie: you updating with a cable on a Windows machine), so even my experience may still be different than yours. We're also not using the same cable :) so there's no way to be 100% sure...

Also, to your point about "being louder"... This is MacRumors, not the official Apple Forum. I assume you're posting there, too? First even? Apple employees will NEVER post something here stating they're an employee. That breaks Apple's own rules. So, sure.. yell about it super loud! But maybe just yell in the right direction?
 
Totally agree on Apple Mail, it really needs a lot of attention.

It does, but after seeing what Apple created (the Music app) as a replacement for iTunes, I'm not confident that any re-write won't just end up being worse than what we have now.

Loads of white-space, a third of the screen taken up with the word "Mail", another third with a generic icon showing the email sender, and then it failing to send to the right recipient half the time ...
 
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Cool, what's your Feedback ID? I can try updating next time from my Mac mini in Bootcamp on Windows. That'd only be Windows 10, though. Keep in mind that you're dealing with a pretty niche situation here (ie: you updating with a cable on a Windows machine), so even my experience may still be different than yours. We're also not using the same cable :) so there's no way to be 100% sure...

Also, to your point about "being louder"... This is MacRumors, not the official Apple Forum. I assume you're posting there, too? First even? Apple employees will NEVER post something here stating they're an employee. That breaks Apple's own rules. So, sure.. yell about it super loud! But maybe just yell in the right direction?
Hmmm. I’m not sure if I have a feedback ID! I’ve only provided feedback through phone/email or typically consumer-facing parts of Apple’s contact forms, not the developer portal. At least not in regards to Apple Devices, which is (at least as far as Apple is concerned) not in beta.
That said, I have no doubts that all sorts of Apple employees, officially or unofficially, are monitoring the MacRumors forums. and of course it is only due to a place like this that end users like us can coordinate and investigate/discuss these things for ourselves. I am sure my concerns are not falling entirely on deaf ears.
 
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