Share your email problems and insight for an MPU episode

I’m using Apple Mail with Gmail accounts on iOS and Mac. It’s good enough for the throughout of emails I receive. It’s not great, but I’ve kind of given up on having an enjoyable email experience.


I use two different email applications: Airmail and Spark. I waffled back and forth between them for a while, then finally decided to go with both: one for work, and one for everything else.

I had several criteria for choosing an app:

  • It had to support GMail’s keyboard shortcuts. They’re real time-savers!
  • It had to support send later functionality. (I was exploring clients before GMail supported send later natively. I experimented with Boomerang and SaneBox, but those can get expensive quickly if you have more than one email account, and I have several.)
  • It had to support Exchange — really support it. I’ve groused more than once that an email client that says it supports Exchange, but supports it only if IMAP is enabled, does not, in fact, support Exchange.

I needed these apps so I could do two things: (1) Consolidate as much as possible, to minimize the number of places I need to check email. (2) Separate work and personal accounts so that I’m not tempted to go down the work rabbit-hole when I shouldn’t (academics are notoriously bad about taking time off).

So I use Airmail for my three work accounts (one assigned to me, one for the department I’ve been chairing, and one for an office that I’ve overseen for the past year), which are all GSuite accounts.

Spark is for everything else: a personal GMail account (I got it long enough ago that I had to get an invite for it), a grandfathered Google Apps for Your Domain account (if I ever end up doing anything serious with it I might upgrade to GSuite), and an Exchange account from an organization I’m associated with.

I tried Apple Mail a few times, but I was never satisfied with how it worked with the GMail accounts.

That Airmail and Spark are both available on iOS as well as MacOS provides some consistency across platforms, which I appreciate.

I need to say upfront that I hate web applications and so my email use has always been in the context of a dedicated client.

On macOS, I use Apple Mail for my personal accounts and Postbox for my (personal) business accounts. I was a Thunderbird devotee for years for two reasons: the Nostalgy plugin for keyboard shortcuts, and Thunderbird’s search-and-filter approach, which I found to be incredibly useful for quickly locating a message by winnowing down results. Over time, though, I got bored with the look and feel of Thunderbird and I switched over to Postbox to retain much of the functionality but with an interface facelift. Postbox has a similar set of keyboards shortcuts as Nostalgy for filing messages, copying messages, and jumping to folders, so I’ve been happy with that. I don’t find the search in Postbox to be as good as Thunderbird’s, and I’m not a fan of Postbox’s “focus pane” for filtering messages, but I no longer need to archive as much mail as I once did and so the search capabilities are not as important to me.

When I was able to use macOS at my previous job, I also used MailMate. I loved how granular it was, and I especially enjoyed being able to set different icon badge behaviors; I set one badge for messages from VIPs, one for an emergency list I had to monitor, and a third for priority requests. That really helped my workflow by allowing me to continue to process my email in scheduled sessions but with the flexibility of being immediately responsive if a critical issue was raised in my area. If I didn’t see one of those three badges from MailMate, I would ignore my email until the scheduled time, but if I saw a badge, I immediately knew the source and whether I would need to interrupt my work and respond.

On iOS, I use for my personal accounts and Outlook for my work account since we are a O365 shop. I do very little email on my phone—mostly just reading and the occasional response—so I have never felt the need to find a better alternative.

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Do you know that iCloud is not good as the only email? They are filtering emails and you don’t see them not even on junk spam or anything like that. It even happened to me with automators forum and chatted about this with Rosemary. I was trying to change my email to an iCloud one. I change this forum from @gmail to @iCloud. no issues, but on the automators forum I never received the email. If I tried another like @hotmail I get it with no issues. I did some research and it seems that in the past the Apple filtering is to strong and it can block you even some emails they think you should not receive it. I do not have rules or any third party application running that could block those emails.

Weird, would be great to know from all of you if you have problems with @iCloud. I want to get off the gmail wagon but with this, it got me thinking …

Work only allows Apple Mail on iOS. We have a few more options on macOS/Windows/Linux but the big three are Thunderbird (integrates via Lightning with our CalDAV calendar), Apple Mail (and Apple Calendar), and Outlook (no calendar integration though).

For personal email, I tend to stick with Apple Mail just because I can keep things simple. I use Fastmail so occasionally will switch to their iOS app or web client for Spam processing or basic work.

I also don’t like apps that store my email account credentials on their servers so most offering functionality beyond basic IMAP capabilities are non-starters for me.

I wrote about this recently, here. Apple started blocking email in iCloud as early as 2012.

I’ve written this elsewhere but I’m hoping to see solutions that don’t require MailTags as the developers always lag behind Mac updates and there’s still no iOS implementation available.

I’ve just used Apple Mail for about 15 years, all my time on a Mac. Before that I used Thunderbird.

I’ve got a Gmail, 6 POP, 2 IMAP, an iCloud and until recently an Exchange account. Mail handles them all just fine these days. I did have some problems with Gmail until I switched it off of POP. And there is some problems with rules, but not enough for me to look for something else. (I’ve got 19 rules). About 25,000 messages.

sharesheet, sharesheet, sharesheet, sharesheet & sharesheet…


I’m very happy to finally be very close to my dream email setup.

  • I use IMAP through Fastmail, to which I have transited after using Gmail for years. I have all my email archives, going back 25 years, when I first started getting on the Internet. I’m using my own email domains as aliases.
  • I am a Sanebox subscriber, using only the basic tier providing SaneLater filtering and the SaneBlackHole.

I use Airmail everywhere and I’m very, very happy with it. Despite their botched transition to subscription, the app has improved tremendously since they did, proving that subscriptions can bring durable revenue and help save the development of applications. Airmail has ironed out a lot of the issues I had with it and has been steadily developing new features. I love the feature parity between platforms (apart from rules, only available on Mac, but I’m filtering server-side anyway) and the fact that it pretty much does everything I would like: Send Later, customisable actions, Snooze, hugely customizables swipes on iOS…

I use the classical GTD model when dealing with email:

  • 2’ rule to deal with quick things
  • Make an OmniFocus task for everything longer (Airmail has always had stellar OmniFocus support, it’s even faster on the Mac than Apple Mail for this)
  • Make an OmniFocus task for waiting for reminders (I have Keyboard Maestro macros set on the Mac for this, such as a “Send, Archive, Add to OmniFocus” macro)

What I’m still missing is mainly Airmail features, but they are coming:

  • Send Later from email aliases (currently in beta)
  • TextExpander support on iOS (in development)

With that I think I will have my dream email setup.

I could add also that I’m devoting

  • 10-20’ per day in the morning to process my email inbox
  • 2h per week to deal with longer stuff

Despite being in a rush to finish a big project at the moment, my inbox never had more than 10 messages and my OmniFocus email list more than 10 tasks, and it has steadily remained like this for weeks. It’s the best I ever got at email in my whole life!

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I have lots of automations set up for Apple Mail that I cannot get any other email program to work with. My favorite is the excellent respondent auto-inserting script you posted a while back. I have this set up with a range of International greetings and this one automation saves me so much time. I work with many international students who have names that I’m not familiar with (and without automation I frequently misspell names which looks really bad). I use text replacement which means all my snippets work on Mail in iOS and MacOS.

I also have SaneBox and couldn’t live without the filtering, which puts all non-essential emails in a folder that I process once or twice a week. I find the Mail+Sanebox combination provides everything I need, and I actually enjoy using them. I’ve tried every other major client and none are as seamless and I find the interfaces get in the way of processing mail. It may be that I have got used to the keyboard shortcuts in Mail, any change feels like it slows my workflow significantly.

I know that similar features to the auto inserting of respondant (in the form of autocomplete) are available in Gmail, but I hate using a web app for accessing email as I frequently need to process my emails when traveling on long distance trains, when there is no cellular or Wifi connection.

I hate doing email on iOS in general, and only use Mail on iOS when I know I’m expecting an important message and I’m not at my Mac. I find processing email on iOS takes much longer as I don’t have the same level of automation tools available.

On the show, I’d like to hear your thoughts/insight into people who use multiple accounts for different tasks. E.g. a no-brainer would be work email is for work only. But to go one step further, I have an email address that I use only for genealogy research and correspondence.

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To each his or her own, but: I have greatly increased my own productivity when I stopped treating my email accounts as separate. I have aliases corresponding to different hats, but everything gets in the same place and processed all together. Then tasks are addressed appropriately depending on whether they’re work or other stuff (using dedicated time blocks).

Pound for pound, Apple Mail still does it for me. The ability to compose on the Watch, easily Archive, the ubiquity of the similar UI makes it a go-to, still.

I have one non-obvious address I use purely to register software. I have one just to register my domains. One linked specifically to all donations and political contributions. (Every year or so I need to nuke that one and make another, as that one gets shared or sold, sometimes quickly). One dedicated to Amazon and my Washington Post subscription (though now I just log in through Amazon). I have two personal email accounts and two business emails. And I make free use of temporary email addresses for registering with some sites/fora that I don’t care much about.

to expand: I’m totally happy with my current email setup (stock mail app only)
The only feature that’s missing is the sharesheet. Put that in, and I’m done.

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A few years ago I made the choice to use three different email apps for my three email accounts: Work. Personal. Newsletters/eCommerce.

This was not a technical decision at all. One of context and focus.

If I’m emailing my friends or family, I don’t want to be guilted by seeing unanswered work emails. When I’m working, I don’t want to see my personal emails. And I shouldn’t be checking my Newsletter account more than once a day. By having three different apps, I can have separate notification badge counts for work and personal, turn off work notifications on the weekend, and completely turn off all notifications for the Newsletter account.

This may seem overkill, but it allows me to stay focused on what I am focused on. Apps:

  1. Personal email - Airmail
  2. Work email - Outlook (we’re using Office365)
  3. Newsletters - Spark

FWIW, I probably would use Spark as my main email client, but it does not yet support VIP-only notifications, like Airmail (and Apple’s Mail app) do, which is another game changer for me.

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That’s an interesting tack, but if I did that I know I would only open the newsletters app :sweat_smile:

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Forgive me, but what follows is a bit of a James-Joyce-Stream-of-Consciousness post.

Like many of us, I spend a lot of time in e-mail. Unlike many of us, I really like email. I’ve tried experiments using tools like Yammer and Slack, but have always found that you still eventually end back up using e-mail. So what’s the point? E-mail is fast, convenient, easy, and exceedingly reliable (Outlook PST files to the contrary notwithstanding, and even those are mostly reliable).

With respect to e-mail clients, I have never adored one as much as Eudora, but I’ve been quite happy with Apple Mail. On desktop, it is all I use.

I, like @Helios, can’t abide web applications, so I’ve never found myself a fan of gmail or other web e-mail applications. I never interact with my gmail account on the web, unless I absolutely cannot avoid it.

My thoughts on clients follow, but I don’t believe that e-mail clients have much to do with what bothers people about e-mail. Its seems to me that the reason people get frustrated dealing with e-mail is less a function of the client they are using than it is their processes for managing email. Example, when I stopped treating my e-mail inbox as a to-do list and actually fully processed my e-mail (responding to the easy ones, filing the non-actionable ones, and adding the ones I needed to postpone for later into OmniFocus), e-mail became a non-problem for me.

Keyboard shortcuts, rules, and scripting make our time in e-mail more productive and efficient, and Apple Mail seems to handle those things mostly well. I find Apple Mail’s rules to be lacking and I’d like to see that tool improved–and taken out of the preferences pane where it seems like an afterthought. Here are some examples of where I have had trouble with rules. I have some rules that run multiple times on the same e-mail messages (I’ve disabled them). Some rules are only supposed to run on certain inboxes, but they run on all my inboxes no matter how they are configured. So, that should be fixed.

I do a lot of searching in my e-mail archives, and I’d like Apple mail to be better at that. It’s pretty good, but why can’t I search for a particular day (excluding particular days of the current month)? I would like search to be able to distinguish between emails that were sent “to” me, those that I was BCCd on, and those I was just copied on.

Where I see a client that is most in need of improvement, it’s Apple’s iOS Mail app. I access (or would access!) mail on iOS more than anywhere else, but there are annoying little problems that need to be improved. First, let me get this out of the way. Apple Mail on iOS has been very reliable for me (except during the iOS 13 beta period last summer, but I accepted that risk). I seldom have trouble sending, receiving, or filing emails. What I would like from iOS Mail is the ability to get my e-mail message OUT of e-mail. I can’t even move a message from one e-mail account to another on iOS the way I can on a desktop, and that comes in very handy. Also, on desktop, I use tools that archive my messages as PDFs in my file system. I would like to be able to do that or do other things to get a message out of my e-mail repository an into some other place. Printing to PDF is an acceptable workaround, but it’s not the most efficient solution to this problem.

The e-mail message attachment-size limit needs to be greatly increased. I send lots of attachments that (would) exceed the 10 or 20 MB limit.

Replying to an e-mail I’ve sent addresses the message back to me, instead of the other recipients. Sometimes I want to send a follow-up e-mail message to someone I’ve already emailed. So I reply from my sent message box. iOS Mail is not programmed to address the message to my original recipients, but instead addresses it back to me. Try this on Apple Mail on the desktop, it does it the right way.

I do not think Apple Mail on iOS gives you enough notice of emails that are stuck in our outbox or that failed to send. I haven’t been in the habit of checking an “outbox” in e-mail since I got away from dial-up Internet. But sometimes I only learn that an e-mail never was sent after I just happened to to a reset my iPhone and get a warning after the reset cycle or or the recipient calls me to let me know they never got a message I was sending them. This is a rare problem, no doubt, but it’s annoying when it occurs.

Search on iOS mail could be substantially improved along the same lines I mentioned for desktop. One particular improvement I would like is a better interface for the search bar. I often use at least three search facets when trying to narrow down a results-set, but the search bar is too short and there is often no way to get past the last facet to add additional ones. It’s not impossible but it’s not easy, either.

Lastly, I would welcome the ability to have rules in iOS, as well as Shortcuts support. Lots of Shortcuts scripting hooks would be great.


Server - Google hosted account (one of the grandfathered free ones)
iOS e-mail client - Spark (love it, I’ve tried all the clients, but it is the best IMHO)
iOS calendar client - (I’ve tried many others including fantastical & calendar5)
MacOS e-mail client - Spark
MacOS calendar client - Outlook &

Server - M365 (corporate provided)
iOS e-mail client - (sometimes, I’m getting more and more tempted to use)
iOS calendar client - (also tempting to to to
MacOS e-mail client - Outlook
MacOS calendar client - Outlook & Calendar.App

Other random points

1 - I like keeping work and private in different apps, makes sure I can setup very compartmentalised alerts and don’t fall into the “check my work email all the time” temptation.

2 - Spark is amazing, the smart inbox is great, the design/ux is very compelling, only thing is back ground re-fresh doesn’t work very well, but it’s not the end of the world. Also would be great to be able to re-map shortcuts (having to press command and delete to archive is a bit annoying).

3 - is still stuck in the dark ages, but getting better little bit by little bit. I’d love to say adding snooze should be a priority, but for me adding actions would be better so I could better integrate with things3 on iOS.

4 - Work is moving towards teams at a rapid rate, I’m using it more and more, and not enjoying the inability to find things. Both from a “where is it” point of view, but also the limited search capability in teams.

5 - Is the future web? I’ve needed to use my web browser to access my M365/Outlook a few times recently (mainly to search my deeper archive as I don’t sync last 12 months on Mac, and it has come a long way. I think I could almost get away with using browser at some point soon, and have a common experience with Google and M365 across my devices using web.