Phil
In my experience (20+ years, including a couple of stints as postmaster) the answer to "is there an e-mail system that does X?" is always "yes", no matter how insane a behaviour "X" appears to be. If it matters to know that an e-mail and attachment arrived, ask the recipient human to confirm positively that they got it (don’t get me started on automatic read-receipts...). And keep a copy yourself until they do, so you can keep trying different routes.
And there are so many ways and places that email content gets modified that it's impossible to give a general answer to the question about whether mails are recoverable given sufficient chocolate. Attachments may be vanished anywhere from the sender's own outbound service (I know of places where encrypted attachments are stripped on the way out because they can't be checked for unauthorised information leaks) to the recipient's own device trying to be "helpful" and classing them as "spam", "junk", "clutter" or whatever the marketing-term-du-jour is. They all just increase the number of folders where you have to look for lost plane tickets :(
Sadly, e-mail long since ceased to be a reliable delivery mechanism, largely thanks to the systems we implemented to defend against widespread abuse of it :(
Andrew
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Andrew Cormack
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> -----Original Message-----
> From: This list is for those interested in Data Protection issues [mailto:data-
> [log in to unmask]] On Behalf Of Phil Bradshaw
> Sent: 11 August 2015 17:20
> To: [log in to unmask]
> Subject: Encrypted attachments on encrypted mail
>
> Hi All
>
> Wonder if someone can clarify something for me.
>
> It is well known that some encypted mail systems (e.g. CJSM last time I
> worked with it) will reject encrypted attachments sometimes stripping them
> 'silently' from the message.
>
> In such cases can a recipient actually recover the attachment by talking
> niceley to their IT people or must they ask sender to resend either
> unencrypted or via a different channel ?
>
> Are there systems where the recipient does not even get the email or a
> notification of it? If so does the sender get an undelivered bounce back?
>
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