Automators Ep. 2 – Email Automation


The latest episode of the Automators is up. This episode focusses on automating email. Should all of your emails be special snowflakes? No. You should automate that email so you can spend your time making things you love instead of answering email. So what are the tools?

Automating Email on the Mac


TextExpander is one of the best ways to get started with automation, and it is particularly suited to email. While there are plenty of text expansion apps, TextExpander is the only one that allows you to code in keyboard control and scripting

For example, using TextExpander, I can make a snippet that I activate in the subject line of an email that will create the subject line, press the tab key (jumping the cursor to the body of the email), type in the recipient's name, and finally write the body of the email. This goes way beyond basic text expansion and is a great way to handle repetitive emails quickly.

For bonus points, when I'm sending out emails for customer support, I will often have the snippet grab the contents of my clipboard which may contain a customer name or a discount code.

I know this is basic automation, but it’s something that everybody should know how to do. You can download the TextExpander snippet for your own use.

Adding a bit of AppleScript, you can also automate insertion of the recipient's name. Here's the snippet group and below is the video.




Automator is another vector toward automating email on your Mac. Automator includes a specific action to create and send an email. Unfortunately, you cannot insert variables for the recipient and other email fields. Instead, you either pre-populate in the script or you have it ask you when it runs. While this can be helpful, the way Workflow (and Siri shortcuts) let you populate these fields with automation generated text and contacts is the way to go. The below screenshot demonstrates the Automator actions available for email.

Click to enlarge.

Keyboard Maestro

Keyboard Maestro excels at email assembly and sending. Our best example of this is a Keyboard Maestro script that looks for the existence of a particular file. When Keyboard Maestro determines the file exists, Keyboard Maestro generates an email and attaches the file and then, if you're brave, sends the email for you.

Auto Sorting Email on the Mac

There are so many tools to sort your email. Apple Mail's built-in mail sorting rules are powerful. If you use Gmail, they have a lot of cloud-based rules to sort email for you.

If you use Apple Mail, check out Mail Act-On which lets you automatically file email.


AppleScript still has its use in email. I have an Apple Script I use (demonstrated above) that grabs the name of the email recipient from the email field and inserts it in the email. 

Automating Email on iOS

Often, automation for email on iOS comes down to the app you use. Rose uses Airmail and automates it often, as demonstrated by the below custom action screencast.

Dispatch is another good option for automating email. It automatically fills in the recipient name, it creates universal email links, and supports TextExpander. Drafts is another option for creating email. It’s a great app and allows you to write email without getting trapped in your inbox.

Workflow and Email

Workflow is one of the best tools for automating email on iOS. With Workflow you can truly create an iOS-based mail merge. Rose demonstrates this in a screencast. You can also download the Workflow and the Drafts action group.

Rose also mentioned a Workflow to automatically mail the most recent picture. Here it is.

Web-Based Automation

Google is the post child for powerful web-based email automation. There is almost no limit, so long as you are in the Google sandbox. Google's not the only option though. Microsoft also has web-based email automation. MPU sponsor SaneBox also supports the rest of us.

About the Automators

As you can see, our mission statement at Automators is that anybody can automate. I'm looking at you. If you like Mac Power Users, consider this show the other bookend. Listen to the show, download the samples, become a badass. Also please subscribe to the show, give it a review, and check out the Automators forum.

iOS Customer Preferences

9to5 Mac linked to this Creative Strategies report concerning App Store user preferences. There are a few points of note.

Many Users Rely on Google to Find Apps

Only 16% of the surveyed iOS users exclusively rely on the App Store to find new apps. I view this as an indictment of the App Store. For years it was terrible. I remember when I would search for "Tweetbot" by name and the app would return five twitter apps, none of which were Tweetbot.

I think Apple improved the App Store (a lot) last year with the new iOS App Store (and they look to do the same this year on the Mac). Nevertheless, the die has been cast. It's going to take a while for users to start trusting the App Store again. If you've given up on the iOS App Store, I recommend you give it a closer look. It's a lot better than it used to be.

Users Still Don't Like Subscriptions

54% of iOS users surveyed said they prefer a one-time payment over subscriptions. Frankly, I expected that number to be higher. While nobody is particularly happy about it, I do think users are coming to understand that there are instances where the subscription model makes sense. I'm also encouraged how some companies can avoid the subscription model and even achieve a sort-of upgrade pricing. The Omni group comes to mind. With the most recent version of OmniFocus, they did not require a subscription but instead, through some clever programming, give owners of the prior version a 50% discount. This is the closest thing I've seen to upgrade pricing on iOS, and I hope other developers consider it.

Fantastical 2.5 for Mac and New Video

Today Flexibits released Fantastical 2.5 for the Mac. There are several notable new features with the new version including integration and support for sending and receiving time proposals for meetings via Exchange, Google, and iCloud.

I run Fantastical on my 27" iMac in its own screen with 14 days displayed in week view. I think of it as my calendar control center. It's the only full-screen app I run on my 27" iMac and it's glorious. With version 2.5 they've added a bunch of great keyboard support to let you move and change events with just the keyboard. That is definitely my favorite feature in the new version. I demonstrate all of the new features in the video below. It's a free update if you already are a Fantastical for Mac user. 

Tame Winmail.dat Files with Letter Opener – Sponsor

Do you ever receive emails with winmail.dat files on your Mac? Windows users send them to me all the time. These files are windows formatted Microsoft Outlook email attachments and one of the rare file formats that your Mac has no idea how to handle. I get winmail.dat files too often, and I finally found the right app for dealing them with Letter Opener.

Letter Opener converts and displays the content of winmail.dat files automatically inside macOS Mail so that they appear just like any other email. With Letter Opener, you will never have to think about winmail.dat attachments again. Letter Opener is fully localized in Arabic, Cat, Chinese, Dutch, French, German, Hindi, Italian, Japanese, Korean, Portuguese, Russian, Spanish and Swedish.

I love Letter Opener because, since installing it, a long-time problem just went away. Now I'm barely even aware of receiving winmail.dat files because everything is taken care of right in Apple Mail. And for you mobile warriors, there’s also an iOS version. Go check out Letter Opener today and use the code "MACSPARKY" for 10% off.

Mac Power Users 439: On Our Desks ...

Katie and I share our home office setups on this week's MPU+ episode. We discuss all the gadgets in, on, and under our desks; what's connected to our Macs; and how we get work done.

This episode of Mac Power Users is sponsored by:

  • TextExpander from Smile: Type more with less effort! Expand short abbreviations into longer bits of text, even fill-ins, with TextExpander from Smile.
  • Fujitsu ScanSnap: ScanSnap helps you live a more productive, efficient, paperless life.
  • Anchor: The easiest way to make a podcast. Ever.
  • Gazelle: Sell your iPhone for cash at Gazelle!

Good Times in London

I had a lot of fun this week meeting with about 50 readers and listeners in London. As usual, I found most of the people in attendance are smarter than I am with Ph.D's, Scientists, Attorneys, Doctors, and generally smart people of all ages. If you ever have a chance to attend one of these geek meetups, I highly recommend. Just about everyone makes a new friend or two. The next one will be next weekend at the MacStock conference. I'll see you there.


Get Automating with TextExpander

I've heard a lot about automation this week as the Automators podcast gets launched. One of the easiest ways to get started with automation is by getting TextExpander installed on your Mac, iPad, and iPhone. TextExpander is a text replacement tool and so much more. With TextExpander, you can type a phrase like “ccell” and it will automatically fill in your cell phone number. But TextExpander is so much more than that.

Using TextExpander, you can have it automatically create the date and time. For example, when I talk with someone on the phone related to the day job and want to keep notes about the conversation, I just type “xdts” which, in my head, means date and time string. Then TextExpander automatically creates something like this, "2018-07-13 13:23". If I need to put the full date in a letter, I just type “fdate” and TextExpander puts in the current date, like this, "July 13, 2018".

But TextExpander goes much deeper. It can use the contents of your clipboard to auto-fill in snippets. It can press keyboard keys, like the tab key, to automate filling in forms on the web or creating an email. You can get it for yourself and your team members so you can share snippets with your team members. 

I’ve done so much with TextExpander over the years that I even have a page of snippets I’ve created that you can download ranging from movie to reviews to conference calls. To learn more, head over to and let them know you heard about it at MacSparky in the “Where did you hear about us” field.

Free Agents 51: Freedom Frogs

On this week's episode of Free Agents, Mike and I talk about why “eating your frog” is an important free agent survival skill. I talk through a pivot in my approach to book publishing, and Mike shares his struggles with “Imposter Syndrome” and how he overcomes it.

This episode of Free Agents is sponsored by:

  • Squarespace: Make your next move. Enter offer code FREEAGENTS at checkout to get 10% off your first purchase.
  • FreshBooks: Online invoicing made easy.

Mac Power Users 438: Workflows with Matt Gemmell

Matt Gemmell joins us on this week's MPU+ episode to discuss life as a software engineer-turned-writer, his evolution from Mac to iOS, his passion for fitness, and being an independent worker.

This episode of Mac Power Users is sponsored by:

  • Squarespace: Make your next move. Enter offer code MPU at checkout to get 10% off your first purchase.
  • Timing: The automatic time-tracking app for macOS. Use this link to save 10% on your purchase.
  • The Omni Group: We're passionate about productivity for Mac, iPhone and iPad.

Home Screens - Zac Hall

Zac Hall headshot.jpeg

This weeks home screen features Zac Hall (Twitter)(Website). Zac is the lead editor and one of the prolific gang of writers over at 9to5 Mac. Zac and I recently met for the first time and found ourselves in a mutual admiration society. So Zac, show us your home screen.

Home screen 1.png

What are some of your favorite apps?

Streaks by Quentin Zervaas at Crunchy Bagel. I use it to remind myself to track my weight with my smart scale, close my Activity rings with my Apple Watch, and use the Breathe app on my Apple Watch daily. The app talks to HealthKit, too, so marking an item as done and continuing the streak is automatic.

Tweetbot by Tapbots. I try all the Twitter clients and nothing else feels as fast to me. Given my job, I just don’t feel “at work” without my timeline streaming. Twitter is both my primary way to track breaking news and the “water cooler” where I talk with friends.

Fantastical from Flexibits. I tend to prefer Apple’s built-in apps over learning other apps, but Fantastical has always just been light years ahead of Apple’s calendar app for me. Natural language input makes scheduling events on the right calendar super easy, and the simple list view just clicks with how I process my calendar. Fantastical also has a really great month view widget that I keep turned on.

Nike+ Run Club. I track all my runs with NRC. The built-in Workout app on the Apple Watch is great and getting better all the time, but Nike+ Run Club does a great job of showing how many data points that Apple’s Activity app doesn’t highlight. Data like how many miles I’ve ran per month, how many miles I’ve ran in total, and my fastest mile, 5K, 10K, and half marathon. I’m pretty locked in for now.

Apollo, a Reddit client. I only follow a few subreddits, each Apple related, and it helps expose me to points-of-view I may not be seeing on Twitter based on who I follow. I really like how this app takes advantage of the ability to offer a variety of app icons too.

Reeder for RSS. I've used David Smith’s Feed Wrangler subscription RSS service since it launched a few years ago, and it works great with Reeder on iOS and the Mac.

Instagram. I love the stripped down view of the world with a photo and a caption. After reading all day, an image is just so refreshing to process. Instagram recently added the ability to follow search terms and hashtags too, and I use this for one group: #CloseYourRings. This puts people using their Apple Watch to workout in my feed which motivates me to do the same. I wish it wasn’t owned by Facebook and I really wish there was an Instagram for iPad, but I like the community on iPhone.

These aren’t necessarily on my Home screen at all times, but a few are. App launching for me is a combination of widgets in the Today View, Spotlight search, notifications, and apps categorized in folders alphabetically on my second Home screen. My primary Home screen is just one part of that approach.

Which app is your guilty pleasure?

Pokémon GO. So much that I’ve recently uninstalled it — for now at least. For a while, it motivated me to go new places and explore, but I started to get a little too obsessed with advancing in the game.

When I noticed I was less present in the real world (and spend real world money to keep playing), I knew I needed a break.

What app makes you most productive?

Things! I’m fortunate to be able to work remotely and have a lot of agency over what I work on day to day, but that means I need to be my own manager a lot of the time.

My approach to task management with Things is thinking of myself as my own employee. When I’m populating Things with tasks ahead of time, I think about the process as what I want my one employee to do.

Then I use it as a reference point for what an ambitious version of me from the past has assigned the current, slightly less focused version of myself to do. It’s a total brain hack but it works for me, and I feel a lot more accomplished at the end of the day.

What app do you know you're underutilizing?

Workflow! I’m really looking forward to Siri Shortcuts in iOS 12 and I’m really into home automation through HomeKit, but I’ve never really unlocked the potential to Workflow and other forms of automation on iOS. I can’t wait to dive in again when the new Shortcuts app debuts in iOS 12.

What is the app you are still missing?

Audiobooks from iBooks (or Apple Books starting in the fall) on Apple Watch. The redesigned Apple Books app looks terrific on iPhone and I enjoy listening to audiobooks in the app, but I would love to be able to see my audiobook library and stream it from the watch.

Apple Music and Podcasts streaming on watchOS 5 is really great on my Apple Watch Series 3 — especially over LTE when I’m away from my iPhone — and audiobook streaming is the last streaming media source I’m missing.

How many times a day do you use your iPhone/iPad?

Moment of truth… Prior to iOS 12, I could honestly give a low ball, double digit guess and believe it, but now we have Screen Time and the data doesn’t lie.

According to Screen Time in iOS 12, I’ve picked up my iPhone 340 times today, or 15 times per hour and once every three minutes. Tweetbot and Messages are my go to apps, and I’ve logged 3 hours 31 minutes of usage.

In reality, I could try to game those numbers down a lot on typical work days like today when I’m working primarily from my Mac and anything on the iPhone is mainly checking in.

If Screen Time comes to the Mac, my numbers will really rocket.

What Today View widgets are you using and why?

I love widgets that are so glanceable I rarely need to open the app. I keep Weather, Activity, and Streaks at the top for this reason. I count calories when dieting or trying to maintain a weight with MyFitnessPal. The widget is both a reference point for me and an app launcher.

Things and Fantastical give me an idea of what tasks are on my radar and what’s coming. Photos for recommending Memories, Music and Podcasts for starting audio, and Apple News for glancing at headlines.

Finally, I keep the Batteries widget at the bottom for seeing iPhone, Apple Watch, and AirPods battery status at a glance.

What is your favorite feature of the iPhone/iPad?

iCloud Photo Library. It gets a bad wrap sometimes, but the experience has been rock solid for me since I started using it in beta.

I currently have 21,687 photos and 1,921 videos and counting that are all instantly accessible on my iPhone and iPad — regardless of how much local storage my device has. That’s every photo I’ve ever taken (and kept) from any camera viewable on all my devices.

And unlike Google Photos, iCloud Photo Library has a solid Mac app in Photos — I would pay for iCloud storage if the only thing it did was unlock iCloud Photo Library.

If you were in charge at Apple, what would you add or change?

My first answer is sharing the full Mac roadmap with customers. I think previewing the iMac Pro months in advance and confirming the redesigned Mac Pro years in advance has served Apple well. I would like to see a similar openness with other Macs in Apple’s lineup, like every MacBook and the Mac mini. But that response is probably motivated for my desire to upgrade to a newer MacBook Pro as soon as something new is ready.

Separately, I would love to see Apple continue to advance its focus on helping customers live a better day through health and fitness. I love capturing data in the Health app, but it’s not always clear what to make of the information. I think Apple could do more to make this information actionable through education.

The Apple Watch also does a great job of pushing you to be more active with Activity rings and the Workout app, but I think there is an opportunity for a more structured digital fitness trainer. That could be in the form of a first-party fitness coaching app or even workout videos from Apple’s fitness experts.

I always get really pumped up from the Apple Watch ads showing people being active in different ways, but my comfort zone is currently limited to the treadmill, elliptical, and outdoor running.

Do you have an Apple Watch? Show us your watch face tell us about it.

Absolutely! I adore the Apple Watch, and I love seeing it get more powerful and capable every year. Workout tracking and the Activity rings motivated me to diet and exercise to improve my health a few years ago, and the Activity Digital face was my top choice.

watchOS 4.3 added Activity rings as a data source on the Siri watch face, however, and I’ve been using it since then. I’m really looking forward to third-party data sources coming to the Siri watch face in watchOS 5 this fall.

The trick to the Siri watch face for me has been turning off data sources in the Watch app on iPhone that you don’t want to see on your watch face (like Apple News and Stocks in my case).

Once you tune the Siri watch face to your liking, it can be the most dynamic interface on the watch.

I always want to see the current temperature and date so I use those as complications, then other data sources appear on the timeline: Activity rings, personalized Apple Music playlists, HomeKit scenes based on time and location, and timers but only if they’re running.

I love how contextual it can be compared to the other watch faces.

What's your wallpaper and why?

A photo of my son Rory! He was born August 2017 and he’s changing all the time — and so is my wallpaper but it’s always him.

I really like using Live Photos when I capture a good shot because it animates when I press the lock screen firmly, but the current photo is one captured on my Sony a6500. Every few weeks, I like to take out my good camera and just crawl around with him and take a ton of photos with him.

The iPhone is fantastic as a camera and captures almost all of my photos, but sometimes dedicated cameras just do a better job with indoor lighting.

Anything else you'd like to share?

Sure! For anyone with a free slot on their Home screen, check out the 9to5Mac iOS app. We don’t promote it a whole lot, but my 9to5Mac Happy Hour podcast co-host Benjamin Mayo develops it and recently shipped a big update to how notifications for breaking news works. Try it out!

London Meetup Today

If you're in London today, we're having an MPU meet up in London on July 9th, at 6PM London time at the Wetherspoons just outside of Victoria station 5. Weatherspoons is a basic pub where we can walk around and converse. There’s no dress code. Just come ready to have some fun. Hopefully a few other friends from Relay.FM will be in attendence. Rose Orchard is even flying over from Vienna.

Your nearest Apple Store will be Regent Street which has been refurbished to be a flagship store. Also, if you come, make sure to ask me for some stickers!

Automators Episode 1 - Calendar Automation

I'm so happy to see Automators #1 get released. The Automators is really a great experience for listeners. We talk through how to automate your life and share the downloadable scripts (and screencast a bunch of it) so you can take our work and use for yourself as a completed automation script or build upon it. Rose and I will take turns making the detailed post for each episode. Rose gets odd. I get even. So this time you'll find all of the details on Rose's post. Just to give you an idea, below are my screencasts for my Travel Time and Hyperscheduling  scripts. Finally, don't forget to check out the detailed show notes.

Timing Adds Multi-Mac Synchronization

A lot of people are getting religion about time tracking lately, myself included. Working in a law firm for all those years I got used to tracking time I spend on client matters. However, what I missed was the idea of productivity-based time tracking. Sync

Timing (a sometimes sponsor of my podcast) brings that to your Mac. It’s a great app that sits in the background and keeps track of your what you’re doing on your Mac and gives you a nice report, even grades your productivity.

For me, it’s been a great way to find (and plug) those rabbit holes in my productivity.

Today Timing released a new version that gives you all of those features and also now syncs that data between multiple Macs. So if you’re working on desktop and laptop machines, your data just got a lot better. This also gives you an off-site backup for your data so you don’t lose Timing data regardless of how many Macs you use. The new sync is an an important addition, done elegantly. The update is free for existing customers. You can get the app directly from the developer or as part of your SetApp subscription


Mac Power Users 437: The iPhone as a Communicator

Mac Power Users Artwork.png

Speakding of podcasats, of all the things an iPhone can do, we sometimes forget it is a great device for communication. In this episode, we dig deep on how to use the iPhone as a communicationd tool.

This episode of Mac Power Users is sponsored by:

  • PDFpen from Smile: With powerful PDF editing tools, available for Mac, iPad, and iPhone, PDFpen from Smile makes you a Mac Power User.
  • 1Password: Have you ever forgotten a password? Now you don't have to worry about that anymore. Save up to 20% using this link.
  • Casper: The Internet’s favorite mattress. Take advantage of Casper’s limited time Fourth of July offer.
  • Pixelmator: The world’s most innovative image-editing app.

​MPU T-Shirts and Hoodies Available for Limited Time

There’s a big promotion at Cotton Bureau that ends tomorrow. As part of the promotion, we agreed to put some of our MPU merchandise back up for sale. We really weren’t planning on selling these again but the folks at Cotton Bureau asked and it looked kind of fun so we agreed.

So if you’d like an MPU hoodie or t-shirt, now’s the time. They are also giving away some pretty cool technology so you may end up with a lot more than a t-shirt.

Manage Cloud Storage on Your Mac with CloudMounter

Like everyone else, I have files distributed across a collection of cloud storage services. As a result, I'm always juggling how to keep track of that data on my laptop with limited SSD storage.

Screen Shot 2018-06-24 at 10.41.38 AM.png

Recently, I picked up a copy of CloudMounter. CloudMounter is a Mac utility for precisely the above-described problem. Specifically, it runs in the Mac's menubar and lets you attach various cloud storage solutions. They’ve got the usual suspects, like Dropbox, Google, Microsoft OneDrive, and Amazon S3. They also have more unexpected providers like Backblaze and various flavors of FTP.

I've been happy with CloudMounter. It gets out of the way but still gives me access to my cloud storage without filling up my SSD. The application integrates with the Mac's Finder, so you see the mounted cloud storage as just another volume in the Finder. Even though those files show up in the Finder, Cloudmounter doesn't download the files to your hard drive which is the trick that saves you so much space.

There’s also an option to encrypt your cloud data through CloudMounter, that gables the cloud files if they are accessed from a different device. Because I use multiple devices and platforms, I did not enable this.

Even on my desktop Mac, I have limited SSD storage. As a result, there are pieces of Dropbox that I never automatically download. Instead, I have to fiddle with the application settings or go on to the web service if I want to get access to those files. Using CloudMounter, I'm able to get to them much faster.

If, like me, you've got a lot of data stored in the cloud, CloudMounter may be the solution you're looking for on your Mac.