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Thanks for sharing your solution.
I have tried WinSCP against Paramiko server with the same setup (same paths and transfer settings). But with vanilla Paramiko code, I could not reproduce the problem. Maybe they have customized (and broken) Paramiko code somehow.

I wanted to update this topic to relay that I've gotten it to work by adding -resumesupport="off" to the put command.

Yessir. The FTP host is an endpoint for Apple School Manager, an education product that Apple offers and we subscribe to.

Re: Thank you for your response Martin

Ok, you are right. It seems like a server-side problem then. Is it some official Apple SFTP server? They are using Paramiko implementation. I'll try to setup similar test server.

Thank you for your response Martin

"Optimize connection buffer size" was already unchecked
I have attached the Filezilla log (Verbose) as requested.

I appreciate your help

Unable to upload file SFTP

Good day all,
I am having a challenge uploading a single zip file to a remote host using SFTP.
I have no issues connecting to the host, only transferring.
The transfer times out with 0 bytes sent.
I have attempted the transfer using both command-line and GUI methods of WinSCP.
FileZilla does not have an issue but this is not an option since it's a manual operation.
I have attached the most recent .log file with credentials/internal information redacted.

Thank you for any suggestions!