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A while ago, I'd tested this by sending myself an email with a file attached, then opening it in a web-based client. What I saw was a blank message with a single smime.p7m attachment. I assumed this must contain the body of the message and the attachment, both encrypted.

Recently, though, I got a nasty surprise from iMessage—it apparently doesn't encrypt files you send. This lead me to be suspicious about pretty much everything that transfers files and claims to be secure.

Are attachments sent using Mail really encrypted with the body of the message, or are they just sent insecurely alongside it?

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This depends on the client: what are you using? – Matteo Dec 31 '12 at 13:45
@Matteo It does? O.o I would think it would be a standard that all clients follow. I use Apple Mail, in any case. – Blacklight Shining Dec 31 '12 at 13:51
@EricDANNIELOU The mac tag is for hardware; osx is for Mac software. See the tag wikis. :) – Blacklight Shining Dec 31 '12 at 14:20
iMessage claims to be secure? – Daniel Beck Dec 31 '12 at 14:37
@DanielBeck With end-to-end encryption, your messages stay safe and private. – Blacklight Shining Dec 31 '12 at 14:48

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