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 I agree with you on auth part, especially given that signer apps can have special cases for file uploads like "sign uploads auths for this hash for any server for 5 minutes"

And I am in Spain too, beers sound nice  
 I would love to meet up. Although I'm cycling the Camino de Santiago right now so I'm not really in one spot for more than a day.
I just left Burgos this morning and I'll probably stop somewhere around Hornillos del Camino at noon

As for the auth event I agree it could work with NIP-98 and the signed could handle multiple events. However I dislike nostr apps asking for more than one signature for a single action.
The way I think about it, it is a single action. Your not signing to upload to a server. Your signing the hash + expiration so it can be uploaded to any server.
Again I'm thinking of it like nostr events. You sign once and publish to multiple relays 
 You are cycling and doing Nostr dev at the same time? 
 No development, I left my laptop at home. but I've been doing a lot of thinking 😀  
 And you are unicycling? Legendary 

I wanted to learn it when I saw the British YouTuber unicycling around the world years back. 
 Ohh that's way too far up to the North :(

Blossom servers should probably support both ways - "upload anywhere" and "upload only here", otherwise I'm forced to assume the server and app might reupload my file anywhere. Maybe nip98 needs a list of servers instead of just one. 

People had to invent "-" tag for events to prevent this permissionless rebroadcasting with relays, I'm sure the same question will rise with files. 
 Sorry to hear that, although maybe we will meet at nostriga?

The permissionless rebroadcasting is the point, that's how we get censorship resistance.
Blossom and NIP-96 are designed for public media, neither have the expectation that the media will be kept private.

I wouldn't be opposed to making my blossom-server implementation support NIP-96, however I don't think it would make sense to add it as a requirement to the protocol since supporting two event kinds would double the complexity 
 http authed webdav already does that use case anyway 
 Anyone can rebroadcast file permissionlessly by authing with their own keys. But ok, maybe delegating this to a server to save bandwidth is an added benefit. Will see how it develops  
 Haven't decided about nostriga yet 
 @hzrd149 I will get back to you shortly, sorry for the delay. I began to understand your approach with blossom. And how the files move through servers