Yosemite’s “Mail Drop,” with plain text emails, considered harmful.

Yosemite has a cool new feature “Mail Drop” which is really handy for sending large files without having to resort to file-sending websites or DropBox (or its non-Condoleezza-Rice competitors).  

If Apple Mail detects a giant attachment, it will offer to send it via Mail Drop, which means that the file is uploaded separately to a temporary iCloud URL.  It will stick around for 30 days.

The problem is that if you use this technique, it’s possible that any actual textual message might not be seen by the receiver of the email message.

If you send your email message as plain text — you might not even realize that you are sending a plain text message or a rich text message —or if the receiver’s email client shows them plain text instead of rich text — then ONLY the Mail Drop URL will be seen by the receiver.  Not your important message.

Here’s an example message I might compose.  (I use a monospaced font to display plain-text messages, but if you use a proportional font, it might be that obvious.)

The message transmitted doesn’t even contain the text; it only contains the Mail Drop URL:


Even if you commit to never sending a plain-text message with Mail Drop attachments, and you deselect Mail’s preference “Use the same mesage format at the original message”, you are not out of the woods yet.  If the receiver is using a mail client that prefers the plain-text portion of rich-text messages, then the problem happens there too.  That’s because the plain-text portion of the rich-text message lacks any text besides the Mail Drop link. Here’s an excerpt of a rich text message’s raw source — note the text/plain segment containing only the URL.

This is a real concern! For instance, we use FogBugz for tracking support cases, and while I want to encourage people to use Mail Drop for sending us large files when needed, we need to go through a lot of hoops just to determine if their message had any useful textual content in it.  Because all we see in a message that included a Mail Drop attachment is a big honking URL.

This isn’t just a rant; I’ve reported this to Apple (radar 18756471).  Hopefully they take it seriously!  If you, dear reader, know about Apple radars, feel free to file a duplicate if you think it’s sufficiently annoying.

© Dan Wood 2012-2016. My Comments Policy