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WinSCP log file does not include a header/start.

Which one is not complete and how would i make it more complete?

Complete log files please.

Forcing it to "off" results in a file with a bunch of questionmarks in the name, "on" behaves the same as "auto".

Log files attached.

Yep, Filezilla in SFTP mode can upload the file without issue.

It's also not related to total path length. Even uploading to / fails.

Re: "bad message" error on uploading certain filenames with SFTP

Can you upload those files using any other SFTP client?

"bad message" error on uploading certain filenames with SFTP

Tried to upload some files via SFTP and got the following error:

Bad message (badly formatted packet or protocol incompatibility).

Error code: 5
Error message from server: Bad message

This happens for example for this filename: "急上昇に載りました...朝通知きてびっくりして泣きながら録画しました...その一部始終をありのままに...視聴者さん、本当にありがとう。夢絶対叶えるよ私は。" It also happens with more characters in the name, but removing the r at the end allows it to be uploaded.

This does not happen with SCP.