It's usually a matter of some clients only supporting NIP-04, which all clients should have burned on the trash-heap by now, and other clients rightly defaulting to NIP-17.

Though, to be fair, I believe nostr:nprofile1qqs8eseg5zxak2hal8umuaa7laxgxjyll9uhyxp86c522shn9gj8crspz9mhxue69uhkummnw3ezuamfdejj7qgjwaehxw309ahx7um5wgerztnrdakj7qgkwaehxw309a3x2an09ehx7um5wgcjucm0d5hsvlnggv discovered some clients that have NIP-17 DMs that weren't being received by other clients that also have NIP-17 DMs.

Did you ever get to the bottom of what was going on with that nostr:nprofile1qqs8eseg5zxak2hal8umuaa7laxgxjyll9uhyxp86c522shn9gj8crspz9mhxue69uhkummnw3ezuamfdejj7qgjwaehxw309ahx7um5wgerztnrdakj7qgkwaehxw309a3x2an09ehx7um5wgcjucm0d5hsvlnggv?

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amber was making invalid sigs on the inside of the giftwraps sometimes, but not always

That's bizarre. Unfortunately I don't know if I can blame Coracle's flakiness on Amber. I think for me it's relay selections but my code is bad and hard to fix.

People DM with NIP-17 and never hear from people that only use NIP-04 clients and then end up using other clients or toggling odd NIP-17 to communicate. It's a horrible user experience.

100% agreed. NIP-04 should not be a thing anymore. NIP-17 should be the standard for all DMs on Nostr until we have something better.