However if I copy and paste this into Google Chrome on the same machine, I get a download of a 2.9 GB file. Get this, using Fiddler4 to analyze what traffic the Windows Media Creation Tool is trying to get to shows a session terminated by remote server to: I'll see if this forum lets me attach the whole putty log but if you have any ideas before I open a ticket with Cisco, please let me know what you did to allow this tool to download Windows 10 iso (or usb stick image or in place pc upgrade). I then ran another logging session and the tool still errors out. I tried putting some Regex's into our allowed domains whitelist (Custom URL Categories) but its still blocking. I then opened this putty.log in Notepad++ and found all occurrences of denied.

I had Putty log all output to a text file and then run the Media Creation tool to download a Windows 10 ISO file.

So I used PUTTY and logged into our S170 and did grep, access logs and put in the IP address of my test machine. I'd rather put the appropriate URL's in to allow this tool to work. I'd rather not mess with bypass lists because you can forget an IP is in there, plus its messy and unwieldy to maintain. If I put a machine's IP address into the BYPASS list, these tools work great. If I use the Windows 10 upgrade tool or the Media Creation tool, I always get an error that coincides with an issue downloading the data.

Windows 11 download media creation tool