the server could remove them when the send fails

That won't work. The send won't fail if the receiver stops receiving. You need some explicit disconnection mechanism.

• send doesn't wait for the datagram to be sent and acknowledged, so at best you'd know if a past send failed.
• There's no connection to keep track of a past send failures.
• There's no acknowledgment sent by the remote end to say it didn't fail.

The send will only fail if there's a local error (e.g. bad argument, no more resources, etc)

Kudos for IO::Socket::Multicast, though

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