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Okay, I see what you mean. We never paid attention to whether (1) was happening. I imagine Apple can tell based on the code that was running at the time. Even

Okay, I see what you mean. We never paid attention to whether (1) was happening. I imagine Apple can tell based on the code that was running at the time. Even in case (1), isn't it possible that Hide My Email bounces happen differently from regular @icloud.com bounces despite being on the same domain? We've also been wondering whether Hide My Email was ever responsible for generating the messages with meant-to-be-hidden addresses or whether it was only passing them along and failing to hide them. I don't think we have enough information to tell.

js2 3mo ago
> Even in case (1), isn't it possible that Hide My Email bounces happen differently from regular @icloud.com bounces despite being on the same domain? I don't think so because when I examine the headers of an HME delivered message to my real@icloud.com address there's only a single MTA involved. > We've also been wondering whether Hide My Email was ever responsible for generating the messages with meant-to-be-hidden addresses or whether it was only passing them along and failing to hide them. I don't think we have enough information to tell. The full headers of the bounce message will tell you.
- tjames7000 3mo ago
  We don't have full headers, unfortunately. I'm not very familiar with SMTP, but to test things out, we ended up running a minimal custom mail server with the nodejs 'net' module to have full control over responses. I think it'd be possible to set something similar up so that the same mail server handles Hide My Email and normal iCloud addresses differently. const net = require('net') const server = net.createServer((socket) => { socket.setEncoding('utf8') socket.write('220 ...') socket.on('data', (data) => { if (isHideMyEmail(data)) { // handle one way } else { // handle another way } }) ... }) server.listen(25, '0.0.0.0', () => { console.log(`Ready for incoming emails`) }); That being said, I have no idea how Hide My Email works technically. Maybe the headers would make it clearer.

js2 3mo ago

> Even in case (1), isn't it possible that Hide My Email bounces happen differently from regular @icloud.com bounces despite being on the same domain? I don't think so because when I examine the headers of an HME delivered message to my real@icloud.com address there's only a single MTA involved. > We've also been wondering whether Hide My Email was ever responsible for generating the messages with meant-to-be-hidden addresses or whether it was only passing them along and failing to hide them. I don't think we have enough information to tell. The full headers of the bounce message will tell you.

tjames7000 3mo ago
We don't have full headers, unfortunately. I'm not very familiar with SMTP, but to test things out, we ended up running a minimal custom mail server with the nodejs 'net' module to have full control over responses. I think it'd be possible to set something similar up so that the same mail server handles Hide My Email and normal iCloud addresses differently. const net = require('net') const server = net.createServer((socket) => { socket.setEncoding('utf8') socket.write('220 ...') socket.on('data', (data) => { if (isHideMyEmail(data)) { // handle one way } else { // handle another way } }) ... }) server.listen(25, '0.0.0.0', () => { console.log(`Ready for incoming emails`) }); That being said, I have no idea how Hide My Email works technically. Maybe the headers would make it clearer.