Not getting Mail Drop prompt

Toby,

I think, I finally understand how it's working : it's more seamless that I was thinking.

Disable the "Send Large Attachments with Mail Drop" option :

1. try to attach a large document ( my test with a 55.8Mo file for exemple)

2. Information in Red : Message Size : 55.8Mo (Maximum 35.9Go ) (using a gmail account)

When the option "Send Large Attachments with Mail Drop" is ON :

1. try to attach the same document

2. Information in black : Message Size : 55.8Mo

3. Send is using the Mail Drop mechanism, and the receiver have a message with URL like "https://www.icloud.com/attachment/?u=http......" to get the attachement.

I was just disturbing that we don't have any information to know if Mail Drop is used or not !

http://appleinsider.com/articles/14/10/17/how-to-use-mail-drop-and-markup-to-sen d-large-emails-in-os-x-yosemite

Anyway, thanks for your helps, the advanced options help me to understand.

Mail Drop is only for files over a certain size, which I believe is 20MB IIRC. Anything less than that would be sent normally, anything more ought to prompt you to use Maildrop.

But when you try to send this 120mb attachement, to you see the message limit in red ? if not, you should be able to send it , and it will necessarily use the Mail Drop process. (There is no message, dialog box , alert or whatever who inform you , but if is accept this attachement larger than 35.9Go = it's using Mail Drop)

Well, i (mistakenly) tried to send a 91MB attachment from Mail using my IMAP'd gmail account -- afaik Mail Drop is using YOUR sending limit size to kick off Mail Drop. At first Mail gave me the Exclamation triangle icon as if there was a problem -- saying message is too large, but it eventually sent... Now, i had access to the receiving mailbox so i went and checked and it has an iCloud link in it! So it worked, but no prompt -- and i have the checkmark set to use Mail Drop (maybe that's why no prompt?). It wasn't pretty from my standpoint but it DID indeed work. the link began w/ this: https://ms-us-mtv-110-prod.digitalhub.com (which resolves to www.apple.com)

Interesting...

Seems it's supposed to be automatic.

http://support.apple.com/kb/HT6492

ok, so it was not the same trouble that me if you've still the message limit in red. ... Anyway I never seen pop up info to ask me if I want to activate Mail Drop so it's seems a strange behavior. I'll try to other computer (with fresh Yosemite install) and keep you inform.

So you can't attach and send the larger files? What error message are you getting, if any?