Fired from BATCH file. I know it should be a service, and I will make that happen soon. This server is still in development and I wanna see everything work before I harden security.
Ok so I put the Caddy output on one screen, then I pulled up Aurora (my file sharing site) on the other screen. Whenever I dropped a file into Aurora, Caddy output this:
Posting for posterity: I have solved this issue using the following IIS configuration -
IIS → Click the website in question → click Request Filtering → click the Headers tab → click Add Header → Configure this screen using the instructions below:
In the “Maximum allowed content length (Bytes)” field, enter this number, or something much larger than what is already in there:
2147483647
That fixed the upload size issue for me.
Some back story: When I originally posted this, I had ruled out IIS being the problem, stating that I had isolated the problem to Caddy - in fact, the large upload worked fine while no SSL was engaged. Once the SSL engaged, IIS began presenting this problem, and since I get my SSLs from Caddy, I wrongly assumed the problem was with Caddy.
Double edit: I think the maximum header size in IIS is 4294967295, which I think is dead-on 4 Gb, and works with my configuration. I just uploaded a 3.6 Gb CD image and it worked as expected.