Using Markup and Mail Drop in the New Apple Mail

There are some great new features in Yosemite’s update of Mail, and the real stars are Markup and Mail Drop, but the seamless integration of these new tools may make it hard to find them if you don’t know where to look.
This tutorial will demonstrate how to access and use both of these new features to edit images, complete and sign PDF forms, and send attachments too large for email.

Using Markup

The tools available in Markup are, more or less, the tools I examined earlier in the Introduction to Preview tutorial, so it may seem like there’s not been many changes in Yosemite.
What makes Markup in Mail so special, though, is that many of those tools are available right in Mail without resorting to another app, and all changes made to image and PDF file attachments in Mail are discrete to that attachment and won’t affect the original file.
There’s no need to create a copy of a file to edit and send so that the original is preserved, because Mail takes care of that.

Edit an Image Attachment in Mail

Click the Compose New Message icon in the Mail toolbar. Attach an image to the new message, either by clicking the Attach a Document icon or by dragging the image into the new message window. Edit an image you’ve received via email by clicking the Reply to Sender icon.
Tip: If the received image does not appear in the Reply message window, click the Include Attachments From Original Message icon in the message toolbar.

Edit image and PDF attachments in Reply emails.

Hover over the attached image in the message window, click the icon that will appear in the upper right corner, and select Markup.

Use Markup to edit the image.

The image will open in a new Markup window. From here you can edit the image nearly as much as you would in Preview. Add annotations, such as arrows or loupes to call out important elements or text to illuminate details.
Even draw directly on the image with the Sketch tool without leaving Mail or opening the image in Preview.

Edit the image right in Mail.

Remember to select Done to save changes to the image attachment. The edited image will appear in the message window.

The edited image has replaced the original attachment.

Complete and Sign a PDF Form in Mail

As before, attach the PDF to a new or reply message, hover over the attached PDF and select Markup from the menu in the upper right.
Use the Text tool to complete PDF fields and edit how the text appears, including font face, size, and color, with the Text Style tool.

Add text to a PDF in Mail.

Click the Sign tool to add a signature to your PDF. Select a previously saved signature or create a new one with Markup. There are two ways to create a new signature: via the Trackpad or the Camera.

Add a signature to a PDF in Mail.

To create a new signature with the Trackpad, choose the Trackpad tab in the Sign tool and select Click Here To Begin. Use the trackpad to sign your name with your finger. When done, press any key.

Sign your name on the trackpad using your finger.

If the new signature is acceptable, click Done. Otherwise, choose Clear to try again.
The second option is to create a new signature with the Camera, allowing more control over how the final signature appears.
Sign a blank sheet of white paper ahead of time and have it at the ready. Choose the Camera tab in the Sign tool. Hold the sheet of paper with the signature in front of the Camera for a few moments. The Sign tool will recognize the signature and flip it on the display.

Hold a signed sheet of paper in front of the camera.

Once satisfied with the signature, click Done, or choose Clear for another shot.
After saving a new signature or deciding on a previously saved signature, select it from the Sign tool. The signature will appear in the PDF. Drag the signature to move it into place and grab the corners of the signature to resize it.

Select a signature and place it in the PDF.

When the PDF is completed and the signature is in place, click Done to save the changes to the attachment.

Troubleshooting Markup

If the menu to access Markup doesn’t appear when hovering over an image or PDF in Mail, don’t worry; the menu didn’t work for me out of the box, either. Luckily, Apple has released a fix and it’s dead simple.
Open the Terminal app, found in the Utilities folder within Applications, and paste the following command into the Terminal window:

1	/System/Library/Frameworks/CoreServices.framework/Versions/A/Frameworks/LaunchServices.framework/Versions/A/Support/lsregister -kill -seed

Press Return and wait for the prompt ending in $ to reappear. It will likely take several minutes and indeed took over half an hour on my older machine before I saw any activity.
Be patient.

Press Enter and wait for Terminal to do its job.

When Terminal displays the prompt ending in $, the operation has completed and you can close the Terminal application. If there’s no immediate change in Mail, relaunch the app.

It may take a while, but give the operation time to complete.

Using Mail Drop

Mail Drop is a new feature in Yosemite that allows the user to send file attachments that would normally have been too large for email. To do this, Mail uploads the attachment to iCloud and provides a unique URL to the file that is good for 30 days. Mail Drop can handle files up to 5 GB in size, so it should suffice for most attachments.

Sending Large Attachments With Mail Drop

Mail Drop is triggered automatically within Mail and doesn't require any additional effort. When attempting to send a large attachment, Mail will prompt the user to use Mail Drop, but the user may still attempt to send the large attachment via email if preferred.

Mail will prompt you to use Mail Drop for large file attachments.

The recipient will receive a download link via email, with a notice of the date the link will expire.

The recipient will receive an download link good for 30 days.

Click on the link provided in the email, and the download will begin automatically.

The download will start automatically.

Tip: Ensure you don’t exit Mail or shut down or restart the computer to allow the large file time to upload.

Conclusion

Apple has brought some great new features to the table with Mail in Yosemite, streamlining the process of sending attachments with the new Markup and Mail Drop features.
This tutorial demonstrated how to annotate images and complete and sign PDF forms using Markup, all without leaving Mail, and how to send files that would have previously been too large for conventional email. These new features look to make Mail a contender amongst popular third-party email applications.