Can I track a file upload and see where it fails?

Can Wireshark track a file upload over the internet and let me know where along the path the upload fails?

you can capture the upload and figure out what's causing the failure (RESET, timeout, packet loss, etc.) however there is no way to figure out where the error/problem occurs! The only thing you can say: It's somewhere between your client and the servers on the internet. Could be your network, could be the last mile to your home, could be your ISP, could be another ISP, your traffic has to cross, etc.

If not, is there anything that can?

No, there isn't.

If the problem is indeed your ISP, then you'd have to capture at several points within their network to find the bottleneck, but I guess that's not going to happen.

Windstream refuses to acknowledge any problem. Their stance is since I can get online and surf the internet there is no problem

well, what else do you expect to hear from their first line support ;-) There is never a problem on the ISP network :-)

BTW: If you have a work server (you mentioned it), you could capture at your client and at your server at the same time. In that capture file you should see packet loss. With that "evidence" you can try to talk to their support people again, but based on my experience, I'm telling you, that's going to lead nowhere (see a similar discussion with @Lucidcryotank)

So, what can you do?

• switch to a better ISP, even if it costs you more money!
• upload your files outside their "prime time"
• team up with @Lucidcryotank and file a FCC complaint if you're in the U.S. ;-))

Regards
Kurt