Mail won't deliver messages with an attachment

easternbitch

macrumors newbie
Original poster
May 27, 2013
4
0
London, UK
I've sent an email from my iCloud account using Mail with an attachment (a 25K word document) and it didn't get delivered. It's in the Sent folder but it didn't reach the addressee (and I cc'd my Gmail account as well - also no joy). I tried to send it with Gmail cc'ing iCloud account - still no joy. I removed and re-added the iCloud account to Mail, restarted Mail, restarted the whole MacBook. Nothing. I tried to send it from icloud.com - nothing. I checked that I have 'Always send Windows-friendly attachments' ticked on, but still nothing. Emails without attachments are going through fine. Emails with other attachments are sending ok. I'm completely lost here... Any advice would be greatly appreciated...
 

easternbitch

macrumors newbie
Original poster
May 27, 2013
4
0
London, UK
What if you zip that word document?
Tried. Still nothing. Sent it to my Gmail and it was thinking for a while (as in the fan wheel was going as if it was receiving something) but came up with nothing. Funny thing is that another random document from the same folder just went through. I've no idea...
 

justperry

macrumors G4
Aug 10, 2007
10,175
5,319
Home is everywhere and nowhere.
Tried. Still nothing. Sent it to my Gmail and it was thinking for a while (as in the fan wheel was going as if it was receiving something) but came up with nothing. Funny thing is that another random document from the same folder just went through. I've no idea...
Hm, I think I have an idea, are you sure you have rights on that file, like in permissions.
Get info on the file, see what happens.
But, now I think of it, you tried the zipped one, if you zipped that file it should have the right permissions.
 

desertman

macrumors 6502a
Jul 14, 2008
607
20
Arizona, USA

easternbitch

macrumors newbie
Original poster
May 27, 2013
4
0
London, UK
Apple, in its infinite wisdom, is censoring some emails sent through iCloud accounts in exactly this way: they don't arrive and the sender never knows about it unless the receiver complains. This might be the case also here, especially since other emails arrive.

See here: http://arstechnica.com/apple/2013/02/icloud-e-mail-censorship-thanks-to-overzealous-spam-filtering/

For me the main reason why I don't use iCloud email.
Thanks, that seems to be the only reasonable (kind of) explanation, since the document I'm sending is a review of an album I wrote myself, so rights and all that shouldn't be an issue... Everything else apart from that seems to be working...
 

justperry

macrumors G4
Aug 10, 2007
10,175
5,319
Home is everywhere and nowhere.
Apple, in its infinite wisdom, is censoring some emails sent through iCloud accounts in exactly this way: they don't arrive and the sender never knows about it unless the receiver complains. This might be the case also here, especially since other emails arrive.

See here: http://arstechnica.com/apple/2013/02/icloud-e-mail-censorship-thanks-to-overzealous-spam-filtering/

For me the main reason why I don't use iCloud email.
Wow, no provider anywhere should filter email, that is private, even if it contains porn or whatever.
 

easternbitch

macrumors newbie
Original poster
May 27, 2013
4
0
London, UK
Now I think about it - the document features quotes from a few generic spam messages... That's probably why it got 'censored'...

Thanks guys!!