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 I'm thinking, what was the point in Nostr if things can get blocked , taken down by relay hosts.  For which most people use the same few big ones.   Its better than twitter but only on par with mastadon (which is also more reliable ) 
 Nostr provides censorship resistance through replication. You use multiple relays. If stuff is taken off one of those relays you are not censored, you just have 1 fewer replication points. At that point you go add another relay to your relay list.

I am not suggesting censorship, nor am I promoting it.  I have no intention of sending anybody such a message. But I develop the chorus relay, and some operators will censor stuff, and I wanted to add code to make sure that when this does happen at least the person being censored finds out about it. 
 I am just wondering what is the best way to handle a large stack of DM messages to a friend list that should not be made public. do we giftwrap all of them or pick a select relay that is app specific for this stack of DMs?

the "right way" to do things on nostr feels like its moving and changing constantly so I am just asking 
 I'm not familiar enough with the DM chat NIPs to answer this with any confidence. @Vitor Pamplona and @hodlbod and @fiatjaf all know more than me about multi-party DM. 
 I don't know if I follow? Can't you just send each as a separate event? 
 You could but if a big stack of DMs goes to a large relay they can rate limit or block, as it can look like spam. 

cc: npub1ymt2j3n8tesrlr0yhaheem6yyqmmwrr7actslurw6annls6vnrcslapxnz 
 Just pick 2+ relays for your kind 10050 relay list and you should be good. Local backups are a good extra measure, either on a local relay or using a jsonl file. 
 Read this: nostr:nevent1qqsgn6ltu8c73r0d3pxkh5n05l5um6y9gd2sa74gts2e7v5luvuk9ssppemhxue69uhkummn9ekx7mp0qyfhwumn8ghj7mmxve3ksctfdch8qatz9ugzvqnd