No solution here but I have some additional data that should help narrow the issue:
I have exactly the same problem running iTunes 12.5.3.17 on a PC running Windows 10pro 64 (build 14393). The problem is clearly intermittent and appears to be random. I have observed "unknown error 8392" over the past week or so after trying all of the following:
- "Update all Apps" occasionally works for some random number of apps and then fails completely while updating one particular app. "Update all" has only worked completely one time since this problem appeared.
- I have tried "Allow simultaneous downloads" both ON and OFF with the same result.
- Updating an individual app also randomly fails (more often than not).
- Rebooted system.
- Logged out and logged back in to iTunes.
- Deleted iTunes (and all other Apple software) and reinstalled.
- De-authorized and Reauthorized my computer.
I tried "Run Diagnostics" (under iTunes "Help" menu) with everything except "Network connectivity tests" turned OFF. The "Secure link to iTunes Store" test FAILED. Per the "Help" link, I cleared the DNS cache on my system which did not eliminate the problem. The log from this diagnostic test indicated that everything was normal and working with my network adapter and configuration. However, this log file also included the following:
Connection attempt to Apple web site was unsuccessful.
The network connection timed out.
Connection attempt to browsing iTunes Store was successful.
Connection attempt to purchasing from iTunes Store was successful.
Connection attempt to iPhone activation server was successful.
Connection attempt to firmware update server was successful.
Connection attempt to Gracenote server was successful.
The apps on my iPad (Gen4) and my iPhone 6s plus are successfully updating when I explicitly initiate the update. They don't seem to be updating automatically in the background.
My conclusion is that this problem has nothing to do with our computers, iTunes software settings, or devices. I suspect Apple has some problem with the inbound channels on their application update server.