We are seeing a similar issue on emails with pdf attachments for some users 
using iOS (not for all though). We're sending them via Magnolia / JavaMail 
through a remote smtp server with authentication (not using localhost as smtp 
server).
Using Magnolia 5.4.3 CE. Email headers look fine as well, as far as I can see.

Some users (i.g. Gmail user) can see the pdf attachment on iOS / Apple Mail, 
while others with a non-Gmail-Account don't see the attachment, just the mail 
body (html).

-- 
Context is everything: 
http://forum.magnolia-cms.com/forum/thread.html?threadId=4f1c6b4c-b0a3-46bd-8016-e249e4bf8d16


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