OS X Yosemite Hidden Features Part 3

Continuing on with our series looking at features of OS X Yosemite that aren’t as well known or documented, Part 3 will focus on features in Apple’s Mail client.
Despite the graphical overhaul of OS X Yosemite, Mail as an app seems to function in similar way to how it was in OS X Mavericks and hasn’t experienced the relocating of settings and options as much as some other apps. So there is no real learning required to get to grips with it for existing Mac users.
There are, however, some rather nifty new features thrown in.  As I have mentioned previously, these may not necessarily be ‘hidden’ in the sense that you cannot ‘see’ them, instead the following features may not:

  • Be obvious as to where they are.
  • Be easy to understand on what they do.
  • Be as well documented by Apple.

New Feature 1:  Mail Markup
What is it?

  • Have you ever needed to fill in a form or sign a document that you have received as an email attachment?
  • Received a photo or map as an attachment and want to highlight or comment on it?

Normally, this would entail having to save the attachment, open it in an editing app, whether that be Preview, Photoshop etc, make your changes and save the edited file, then add the newly modified file back as an attachment in an email. Rather long-winded!
Enter ‘Markup’. This handy new feature allows you to annotate an image or PDF attachment easily while staying within the Mail app. How cool!
If you have ever used the ‘Annotate’ feature within the ‘Tools’ menu of Apple’s Preview app, then you will already know everything about this feature as ‘Markup’ is essentially offering you that ‘Annotate’ tool directly within Mail.
Below is a reminder of the Annotate features in Preview:
annotate feature os x preview
You can now sketch, add shapes, text, signatures, lines or arrows directly onto an enclosed image or PDF. Change the font and colours of these too!
Looking at it another way, instead of modifying an attachment that someone else has sent to you before re-sending it back to them. You can now even add an image into a new email, directly apply your annotation to it and then send it, all within Mail without having to modify the item before attaching it!
How does it work?
It is all rather simple. If you have received an email containing the attachment in question, just select to ‘Reply’ or ‘Forward’ the email containing the attachment as normal. If you wish to send someone else an email with an attachment but directly modify it, then again, just add the attachment to the email as normal.
Next, hover your mouse over the attachment and select the ‘down-facing chevron/arrow’ from the far right of the attachment as highlighted below by a red circle (using preview’s annotate features!):
annotating mail attachments
Once you have selected the ‘down-facing chevron/arrow’, select ‘Markup’ from the pull-down menu:
markup yosemite mail
The image or PDF then ‘zooms out’, offering an annotation toolbar at the top so you can now add your notations to the attachment with mouse, trackpad or keyboard!
markup annotations mail yosemite
Let’s now see it in action!
So now we know how to access Markup, what can you do with it?
I will work my way along the options of the annotation toolbar from left to right.
sketch osx yosemiteThe first option is the Sketch tool. With this option, you can use a pen tool so you can perform freehand drawing. Your mouse pointer will change to an ‘ink pen’ icon while you are hovering around the attachment, allowing you to click to select where you wish to start freehand drawing. Use the Shape Style, Border Color and Fill Color options to customise the size and color of your freehand drawing.
In the example below, I used the sketch tool to circle around the location of our Surrey office, the Sketch tool has then offered me some customisation options:
sketch tool yosemite
I can either keep to my ‘rough’ freehand circle, or select below to have it ‘tidied up’ :
tidied circle yosemite
I think the tidied up version is better than my freehand circle!
shapes os x yosemiteThe second option is the Shapes tool. As it implies, this tool can create shapes, but also insert speech bubbles or arrows onto your attachment, and even has a handy ‘highlight’ and ‘zoom’ option too:
shapes os x yosemite mail
I won’t demo all these shape options since most of them are similar and straight forward, but here’s how to create a custom arrow on an attachment:
Step 1: Select the ‘arrow’ option under the Shapes feature to add an arrow with the current Shape Style, Border Color and Fill Color settings.
Step 2: You can drag the arrow around with your mouse pointer, (a ‘hand’ icon replaces your mouse arrow). You can also use the ‘blue’ end point handles to change the length of the arrow or change the angle:
using shapes yosemite mail
Step 3: Drag the ‘green’ middle point handle to change the arrow from a straight arrow to a curved arrow:
shapes arrows yosemite mail
Step 4: Use the ‘Shape Style’ option to change the ‘thickness’ of the arrow, make it a dotted arrow or to add and remove the end points of the arrow:shape style option
shape style option expanded
Step 5: You can then use the ‘Border Color’ option  and ‘Fill Color’ option to change the colour of the border or to fill in the arrow with a different colour:
change shapes colour
(Choosing the first color  will allow you to have NO border or fill colour)shapes no fill
Let’s now look at how to add a custom highlight on to the attachment :
Step 1: Select the ‘highlight’ option at the bottom left of the Shapes feature shapes highlight option
Step 2: This should add a highlighted square on your attachment, allowing you to drag the blue resizing handles to select which part of the image you wish to highlight. The image below shows a red arrow pointing to the stations nearest the Amsys Surrey Training Centre and that area of the map is now highlighted too:
highlight attachments yosemite
Highlighting a block is quite nice, but the ‘magnifying glass/zoom’ feature is even nicer. I have re-selected the highlighted area and used the ‘backspace’ key to delete this element and will now add a ‘zoom’ element instead.
shapes magnifying glass
Step 1: Select the ‘magnifying glass/zoom’ option at the bottom right of the Shapes feature.
Step 2: Again, you can drag the zoom element around with your mouse pointer, (a ‘hand’ icon replaces your mouse arrow). You can also use the ‘blue’ handle to change the length of the zoom range:
change length zoom
Step 3: Drag the ‘green’ handle to change the amount of zoom required, I have used the green handle to zoom in further on the stations I wanted to highlight:
zoom in further
shape style optionStep 4: You can again use the ‘Shape Style’ option to change the ‘thickness’ of the zoom border, make it dotted or have a shadow.
The ‘Border Color’ option can also be used to change the colour of the border:border colour
add border map mail yosemite
Text text tool icon
The third option is the Text tool. As this implies, this can add a free text box onto your attachment.
Simply click on the Text option to add a free text box and again you can drag the Text box around with your mouse pointer, (a ‘hand’ icon replaces your mouse arrow) and also use the ‘blue’ handles to change the length of the Text box:
text overlay
Just like any free text box on a Mac, double-clicking inside the text box allows you to modify the text to be displayed.
With the text box highlighted, you can again use the Shape Style, Border Color and Fill Color options to customise the border thickness, color and background fill color and perhaps create something like this:
text annotation yosemite mail
With Text boxes, you can also use the Text Style option  to also modify the text’s font, color, font size, bold, italic and underlined options as well as alignment within the text box:
text font change
The end result can therefore look like this with change of font, text color with bold and italic added:
text font change result
Let’s combine those 3 elements together. The arrow shape, the zoomed shape and the text box:
combine elements yosemite mail
The fourth option, is the Sign tool. Just click the Sign dropdown arrow and select ‘Create Signature’, you can then select to create a signature with your finger if using a Trackpad, or with the use of your Mac’s camera which can take a photo of your signature on a piece of paper:add signature yosemite mail
adding your signature to email yosemite

When using the camera, it will ask you to sign your name on a piece of white paper and hold it up to the camera:
It will then capture the signature and reverse the image so that it is the right way round as shown below:
sign your name
With both options, simply select Clear to try again or Done to add the signature to your annotations:
add signature
You can now select the captured signature to add it to your attachment:
add signature to email yosemite
Again, you can drag the signature around with your mouse pointer, (a ‘hand’ icon replaces your mouse arrow). You can also use the ‘blue’  handle to change the size of the text box. The ‘Border Color’ option  can also be used to change the color of the signature text should you wish.border colour
Shape Style
The fifth option, is the Shape Style tool. As mentioned during the above steps when looking at adding shapes and text, this is used to change the ‘thickness’ of elements, make them dotted, blurred or shadowed and to add and remove end points to arrows:shape style option
shape style option expanded
Border Color  
The sixth option, is the Border Color tool. This was also mentioned during the above steps when looking at adding shapes and text and can be used to change the colour of any border of elements:
change shapes colour
(Remember that choosing the first colour will allow you to have NO border color)
Fill Color
The seventh option, is the Fill Color tool. I mentioned this during the above steps too when looking at adding shapes and text, this is used to change the ‘Fill’ color of any element, such as the filled in color of a shape or the background color behind text:fill colour apple mail
fill colour palette apple mail
Text Style text style apple mail
Lastly, the final option, is the Text Style tool. Also mentioned during the above steps when looking at adding shapes and text, this is used to modify the text’s font, color, font size, bold, italic and underlined options as well as alignment within the text box:
text font change
Right, I think we’ve finally sorted out the Markup feature in Mail!
So let’s see my end result PDF after using Markup:

final annotated pdf apple mail

This was created using the steps above, but also included using the ‘duplicate’ command (or ‘CMD’ + ‘D’ keys) to duplicate some existing annotate elements I had already created to save recreating them from scratch.

As you can see, by adding a generic London travel map PDF into Mail, I have managed to use the Markup feature to clearly highlight the best stations to travel to when visiting our Soho and Surrey offices. All without having to modify the PDF first before adding to Mail!
Useful Info about Markup
Finally, here’s some useful pieces of info about this Markup feature:

  • Markup Clean Up – As noted whilst i was creating a freehand circle, Mail can automatically ‘clean up’ or smooth out your drawings to make them look nice and tidy.
  • Markup File Formats – As great as this Markup feature is, it currently only works with images/photos and PDF files. So you cannot use Markup to annotate other types of files, for example a spreadsheet created in Numbers or Excel.

The Markup Extension –  Markup is in fact not just for Mail. It is part of the new ‘Extensions’ feature Apple built-in to OS X Yosemite and iOS 8. Extensions allows code from one application to be available inside another application. We have just experienced Apple’s Markup extension allowing me to use the annotation features offered within the Preview application directly within Mail.

So where is this Markup feature actually configured if not in Mail itself?
Well, OS X Yosemite offers a brand new System preference pane called ‘Extensions’ which offers the ability to provide ‘Extensions’ to apps and the Finder. Below you can see that the ‘Markup’ extension is enabled under the ‘Actions’ section to allow editing and viewing content across apps. (Preview to Mail in this example):
mark up extensions yosemite

Extensions, therefore, have the potential to completely change how Mac apps function. Hopefully Apple will incorporate more extensions into the file system and also allow developers to make their own or add to existing ones like Markup. Currently the Markup extension has limited availability, I’m hoping more apps will utilise it soon as it is such a useful tool.

For now, though, Markup has a perfect link between the Preview and Mail apps. So much so that if you have already created signatures using Preview, (Tools menu > Annotate > Signature, or visit this guide for earlier versions of OS X’s Preview app), these will automatically appear in a Markup enclosure in Mail when you select the Sign option! Cool!
New Feature 2:  Mail Drop
What is it?

Put simply, Mail Drop is a new OS X Yosemite feature integrated into the Mail app that lets you send large attachments in Mail without having to worry whether it is too big to send and then having to think about how you can get around email attachment limits if your email server rejects your email.
There are quite a few email systems that put a maximum size limit on email file attachments, meaning you are restricted on what you can attach to your emails.
This leads you into having to think of a way round this like trying to compress the files, crop/reduce the size of images, or even getting as desperate as having to upload your files a cloud-based storage solution and pasting in a link to this in your email.
Enter Mail Drop! With Mail Drop, you can now just drag a large file into a message as normal and click Send. Mail will execute Mail Drop to magically send the large attachment, (whether it be a presentation, video or just a folder of holiday photos) without any worry about size limits!
How does it work?

So, how does Mail Drop get around these email size limits?

As long as you have an iCloud account and are logged into this on your Mac, Mail can send the attachment by uploading the file to a temporary holding area on Apple’s servers where it is encrypted and held ready for download.
Just drag your attachments into an email message, Mail Drop can then take it from there. If the receiver of your email is also using Mail in OS X Yosemite, Mail can download the large file automatically so that they will receive the email with the download attachment as normal, as if it had been attached to the message.

However, If they use an earlier version of Mail, any another email app or even webmail, they will receive your email without the attachment, but the email will contain a link to download any attachments. A link that will remain available for 30 days before being deleted. The recipient will be notified in the email along with the link, the expiration date of the downloadable attachment.

The beauty of Mail Drop is that it costs NOTHING to use and the attachments stored in iCloud do NOT count towards your free 5GB of iCloud Drive storage either!
It doesn’t matter which email service you use either, whether it be iCloud itself or something like Microsoft Exchange, Gmail, Yahoo etc.

If you do have OS X Yosemite and are using Mail but don’t have an iCloud account, or you try to send an email without being logged into your iCloud account, Mail will just ask you whether you want to use Mail Drop or not.

Let’s now see it in action!

So now we know what Mail Drop is, let’s see how we can use it!
Sending the email:

Step 1: First of all, check you are logged into iCloud. Open System Preferences from the Apple menu and select ‘iCloud’. Sign in with your iCloud name and password if not already signed in. Check that iCloud Drive is enabled, then click on the iCloud Drive Options button and check that Mail is selected in the list of apps that store data in iCloud in order to activate Mail Drop:

mail drop yosemite

Step 2: Next, we need to check that Mail Drop is enabled for your email account. Open the Mail app and choose Mail > Preferences, click Accounts, then select your email account, click the Advanced tab, make sure ‘Send large attachments with Mail Drop’ is ticked:

enable mail drop yosemite

You can enable and disable Mail Drop here for each email account. So you can choose which accounts to use Mail Drop with.
If you are using Mail in OS X Yosemite and are logged into an iCloud account, Mail Drop should automatically kick in.

Step 3: Compose a new email message in Mail and drag in a large attachment:
send large files via apple mailStep 4: Mail may display the total message size just below the “From” address. This text should dynamically change to red if attachments go over the approximate limit for third-party email providers. (My above example screenshot used a gmail account). Click to Send the message and you’re done! (Remember that the attachment needs to be sent to Apple for hosting and, therefore, there maybe a waiting period before the email is actually sent).
Remember that the message size limit warning will trigger Mail Drop to create a link to the attachment instead of including the attachment in the email.
So what if you haven’t got an iCloud account or you are not logged in to it? Or perhaps you have disabled Mail Drop for your email account in Mail Preferences? Not to worry, you can still use Mail Drop but you will need to authorise this on sending the email.
Step 1: Compose a new email message in Mail and drag in a large attachment as mentioned above.
Step 2: On clicking Send, you will receive a notification from Mail asking you whether you want to use Mail Drop or not:

send large files apple mail step 2

Receiving the email:
Remember, if the recipient is using Mail in OS X Yosemite, they will receive the attachment within the email as normal. However, other mail client apps will receive the email with links to download any attachment from Apple’s iCloud servers and a notification of the expiry date of the download:

receiving large attachments from apple mail

Useful Info about Mail Drop

Tip! Remember to check that the email was sent before putting your Mac to sleep or shutting it down. If your attachments are large, they may still be uploading to Apple in the background. So check the Activity before closing Mail or putting your Mac to sleep or shutdown. (You can check your Mail Activity by selecting the Window menu in Mail and then selecting Activity). The next time you open Mail, you may find this error caused by you closing down Mail too soon:

useful infor about mail drop

This error can also occur if you have tried to send too many attachments using Mail Drop in a short period of time.

Mail Drop Limitations
Just as I mentioned for Markup, Mail Drop doesn’t suit all situations. Mail Drop may not activate properly even if both sender and receiver have an iCloud account. The reason for this is that Mail Drop is designed to work by using the sender’s file size limits for its trigger, NOT the receiver’s file size limits.
What does this mean?
Well, let’s say that you plan to send a friend a 15MB email, and your file size limit is 40MB. The email size is well within your attachment limit, but your friend’s maximum file size limit is only 10MB. Technically, the email cannot be sent at the current size, as even though it is smaller than your limit, it is larger than your recipient’s limit.
Since Mail Drop will only consider the senders’ file size limit, in this example, Mail Drop will not trigger an issue and, therefore, the email will send with the file received by your friend as a clickable link they can download from iCloud. As the sender, you will receive a reply notification that the recipient is unable to accept a message of this size.
Apple report that Mail Drop can only be used to send files if the email ‘exceeds the maximum size allowed by the provider of the sender’s email account’. In other words, as a sender, you cannot specify a custom file size threshold with which Mail Drop will trigger. So you cannot prevent situations like my example above.
Since Mail Drop is a new feature, we can but hope that in the future Apple releases a custom size control for Mail Drop to allow senders to ensure that their recipients receive attachments without having to receive a download link.
Mail Drop does support sending multiple attachments in the same message though, however the combined total size must be below the 5GB threshold.
In case you try and use Mail Drop but it fails to send, remember to open System Preferences and look at the settings in the iCloud preference pane. Ensure you are logged in correctly to your iCloud account. Check that iCloud Drive is enabled, then click on the iCloud Drive Options button and check that Mail is selected in the list of apps that store data in iCloud in order to activate Mail Drop.
New Feature 3:  Mail HandOff
Mail in OS X Yosemite also works with HandOff, so you can start to write an email on your iPhone or iPad, then switch over to your Mac to finish the email off. Perhaps you want to add a photo or another file to the email that’s stored on your Mac.
Refer to ‘New Feature 3: Handoff’  from Part 1 in this blog series for more info on this feature.
As well as these new features, searching for/within emails, previewing and Gmail & Microsoft Exchange integration seems to be more stable and efficient compared to OS X Mavericks.
Though not new features, it’s worth mentioning these as a benefit of using Mail in OS X Yosemite.
I hope you are enjoying this blog series and finding it useful. Please note though that the features and options I have mentioned are just a collection of the ones that I have discovered and found useful and it’s not a complete feature list.
Apple does has a good overview of the main new features of OS X Yosemite on their website.

Read part 1, and 2.
While the author has taken care to provide our readers with accurate information, please use your discretion before acting upon information based on the blog post. Amsys will not compensate you in any way whatsoever if you ever happen to suffer a loss/inconvenience/damage because of/while making use of information in this blog.
These features were tested using OS X Yosemite v10.10.2 and iOS v8.1.3 which were the latest Mac OS and iOS releases at the time of writing.