How to use Mail Drop and Markup to send large emails in OS X Yosemite

Posted:
in macOS edited November 2014
With OS X Yosemite, Apple introduced a host of useful features for creating and sending emails, including Mail Drop and Markup, which allows users to send messages up to 5GB in size and annotate attached files before sending.



Mail Drop

With Mail Drop, Apple introduces a way to skirt the usual email size limitations by first processing and storing large attachments in iCloud, then adding a link to download the files in the original message. In practice, iCloud is acting as a go-between, with only the message text and iCloud link being sent across email service provider servers.




Using the feature is seamless to the Mail app experience. When creating a new email, simply click the paperclip icon to select files for attachment, drag-and-drop or right click on videos, images, ZIPs or other files to attach via share sheets. Sending multiple files is supported, but the combined total size must be below a 5GB threshold.

When a file is attached to a message, Mail displays total message size in an info row just below the "From" address line. The text dynamically changes from black to red if attachments go over the 5GB Mail Drop limit or, alternatively, the approximate limit for third-party providers.


Over-limit message sent from Gmail address.


On the receiving end, Mail Drop messages are displayed just like regular emails and will include links to download content from Apple's iCloud servers. If the recipient is also using OS X Mail, videos or pictures may be automatically downloaded and displayed in line with message text, depending on user settings.






Markup

In addition to sending large files, the new Mail app incorporates an annotation feature called Markup. Using this tool lets users add text, drawings, shapes and even signatures to image files and PDFs before sending. The feature is especially helpful when collaborating on documents or adding in quick notations to a picture or proposal without opening another app.


Markup pop-up menu button highlighted in red.


Markup is available directly from the email message window. When attaching images like the one above, a contextual extension pop-up button will appear in the top right corner. Selecting Markup from the menu will open the image in a separate window accompanied by a selection of tools. Alternatively, if you have other apps with extensions made available to Mail, they can also be selected at this time.

Apple's Markup includes range of tools from which to choose, like arrows, geometric shapes, loupes for zooming in on an image, text overlays and more. In many ways, the feature is akin to a stripped down image editor.




In the image above, we drew an arrow -- which is automatically recognized and morphed into a vector shape -- wrote "Want!" with the text entry tool and zoomed in on the iMac's screen with the loupe. Once added, shapes, text and other markings within the workspace can be resized, edited, moved or deleted.

Finally, Markup carries over the insert signature feature from Preview that lets users digitally sign documents. Users can create a signature by writing on a multitouch trackpad with their finger, or by taking a picture of a signed piece of paper with a Mac's FaceTime camera.

Comments

  • Reply 1 of 18
    Nice feature. Mail still seems crippled relative to Mailbox. It was nice to see Mail on iOS add better gestures for handling your InBox, but Mail is still a long way from convenient.
  • Reply 2 of 18
    lkrupplkrupp Posts: 10,557member
    Quote:
    Originally Posted by Minnesota_Steve View Post



    Nice feature. Mail still seems crippled relative to Mailbox. It was nice to see Mail on iOS add better gestures for handling your InBox, but Mail is still a long way from convenient.



    Mail is quite convenient. I’ve used it exclusively for many years and have tried alternatives like Mailbox.

  • Reply 3 of 18

    Sucks in which way?

  • Reply 4 of 18
    ibeamibeam Posts: 322member

    I wonder how long the Mail Drop link is good for. Personally, I keep mail forever on my Linux mail server. I think it goes back to before the year 2000. Somewhere around 25,000 emails, many with large attachments and it is lightning fast on the search too. I can't see Apple storing all that data forever.

  • Reply 5 of 18
    h2ph2p Posts: 329member

    Ahh, I was hopeful when I first heard about Mail Drop, that it would work regardless of mail provider because of the OS. Seems I'm wrong. Mail Drop works with Apple emails only, yes?

     

    EDIT: From the Yosimite page "When you’re signed in to iCloud, Mail Drop lets you send large files like videos, presentations, even a folder of images without having to worry about your service provider’s limitations." Sounds like, we CAN use Mail Drop from any service provider!

  • Reply 6 of 18
    ibeamibeam Posts: 322member
    Quote:
    Originally Posted by H2P View Post

     

    Ahh, I was hopeful when I first heard about Mail Drop, that it would work regardless of mail provider because of the OS. Seems I'm wrong. Mail Drop works with Apple emails only, yes?

     

    EDIT: From the Yosimite page "When you’re signed in to iCloud, Mail Drop lets you send large files like videos, presentations, even a folder of images without having to worry about your service provider’s limitations." Sounds like, we CAN use Mail Drop from any service provider!


    I think what the Mail app does is send the attachment to Apple via some protocol other than SMTP and then sends the email sans attachment, rewriting the email on the fly with a link it received back form Apple in the background. This should work with any service provider and with any third party email account. It is a feature of the Mail app and iCloud. 

     

    I'm not certain since I haven't tried it yet but that is how I think it should work. You can see in the image Mikey is using it with gmail

  • Reply 7 of 18

    Quick question: Does anyone know where mail you archive locally is stored in OS X?

     

    I knew I forgot to manually back up something before I installed Yosemite, so now I have to find the folder in my Time Machine backup.

     

    I know where the archive 'mailboxes' are, but they're empty of the actual messages.

  • Reply 8 of 18
    dacloodacloo Posts: 890member
    How do you set an expiration date for the linked files? Or does iCloud store your files for ever until the recipient (or all recipients) download the file?
  • Reply 9 of 18
    bugsnwbugsnw Posts: 717member

    It's so friggin' nice to have an email App that works again. Mavericks was driving me nuts with the erratic mail behavior. I learned several weird tricks to trigger a check for mail like checking for updated Apps in iTunes before opening Mail. Weird.

     

    All these extra features are just a huge bonus and very much needed. I'm curious about how long the attachments stay 'live' and whether we get an update that they were downloaded (optional).

     

    Yosemite is pretty awesome so far. Mail is a huge improvement. I'll even forgive the disappearance (for the most part) of the sidebar in iTunes.

  • Reply 10 of 18
    kkerstkkerst Posts: 330member

    Yikes. This isn't working at all for me. I attach say a 3G mp4 to an email, and it locks up my iMac forever. I have to force quit out of mail. I haven't been successful sending any mail drop email., and when mail starts responding, the message just sits there in my draft folder, never sends. Trip to the discussion.apple.com might help.   

  • Reply 11 of 18
    ibeamibeam Posts: 322member
    Quote:
    Originally Posted by Tallest Skil View Post

     

    Quick question: Does anyone know where mail you archive locally is stored in OS X?

     

    I knew I forgot to manually back up something before I installed Yosemite, so now I have to find the folder in my Time Machine backup.

     

    I know where the archive 'mailboxes' are, but they're empty of the actual messages.


    Go to folder...

     

    ~/Library/Mail/

     

    Look for subfolders for various accounts

     

    The messages are .emlx extension, unless you are using IMAP, in which case the messages are on the server.

  • Reply 12 of 18

    Ah, that's it. Had to open the e-mails individually and save them manually, but it works. Thanks a ton.

  • Reply 13 of 18

    Apple gives a default expire date of 1 month

  • Reply 14 of 18
    This was in the "What's new in mail" under help:

    You can use Mail Drop to send files that exceed the maximum size allowed by the provider of your email account. Mail Drop uploads the large attachments to iCloud, where they%u2019re encrypted and stored for up to 30 days.
  • Reply 15 of 18
    dacloodacloo Posts: 890member
    Apple gives a default expire date of 1 month

    That's cool, but dangerous. What if the sender didn't intend this? (since this process is all done automatically in the background)
  • Reply 16 of 18
    kantxkantx Posts: 22member
    Doesn't work.
    Mail Drop refuses to send message with 166 mb attachment.
  • Reply 17 of 18
    kantxkantx Posts: 22member
    Quote:

    Originally Posted by kkerst View Post

     

    Yikes. This isn't working at all for me. I attach say a 3G mp4 to an email, and it locks up my iMac forever. I have to force quit out of mail. I haven't been successful sending any mail drop email., and when mail starts responding, the message just sits there in my draft folder, never sends. Trip to the discussion.apple.com might help.   




    Same here.

  • Reply 18 of 18
    Nice guide! But did you consider using Filemail? They have a very simple web app that lets you transfer anything up to 30 GB to any e-mail for free. The speeds are great and the overall experience is very clean. It is the fastest way to move big files I have found so far.
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