It turns out the weird behavior when I tried uploading multiple files at once (or big ones) was caused by nginx limiting the request body size (default is 1MB) so i set it to be 512MB on my nextcloud reverse proxy, very nice.
Symptoms were it would say uploading but nothing happened afterwards, logs didn’t say anything good either.
Here is the configuration i added:
# Adjust the max body size
client_max_body_size 512M;
# Adjust client timeouts
client_body_timeout 120s;
client_header_timeout 120s;
keepalive_timeout 120s;
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