Share your email problems and insight for an MPU episode

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.

Is incredible they do that. I planned to go full Apple since they have 3 free aliases and was working fine, but I am nervous they block important emails. Nice research and thank you for pointing me to it.

I use Apple Mail to collect some receipts, and I use the share sheet in iOS to send myself links/notes at other email accounts I have. As far as I can tell with my light iCloud Mail use I’ve never had mail I wanted fail to get to me, nor has any mail I’ve sent out fail to get to intended recipients.

On the other hand, so far this year I’m pretty sure I only received this one piece of spam in my iCloud Junk folder, which (a) I’m not sure was actually spam and (b) seems like a ridiculously insufficient amount of spam for five months.

I have to conclude that Apple is holding back spam from reaching my Spam folder, which frankly I find annoying and, if they get it wrong, potentially problematic.

I hear people talk about their difficulties with email in terms that seem to indicate that they consider email to be somehow expendable or extra or an added, unwanted burden that they believe they can strive to eliminate.

I have no problems with email. I really like email, actually.

I guess one insight I can offer is that, to me, email is no different from any other input in my life. It’s unavoidable, if not essential. It has been the primary communications tool at every job I’ve had for the past 25 or 30 years. It’s never been optional or extra, and I certainly don’t see it losing its value or importance in my workplace anytime soon.

I’ve heard of people who declare email bankruptcy or who just end up accumulating so much unread mail that they delete everything, assuming that anything that was important enough or urgent enough will somehow resurface some other way. I’ve never had a job that would allow me to do that — at least not without serious consequences.

Maybe this qualifies as an insight: The one way email differs from other inputs in my life is that it has the benefit of being self-documenting. Most other inputs ultimately require some amount of note-taking on my part — even if it’s just a mental note — and then those notes get processed into actions and are either filed or discarded. With email, the incoming message is the note, already written for me. I just have to decide what to do with it. I like that.

I use a GTD approach, and I can do that in any client that permits me to create an Action folder, an Archive folder, and a Trash folder. I use Mail for personal email and Outlook for Mac for work email (because I have to; otherwise I’d use Mail).

Generally, every message that lands in the inbox gets replied to and/or goes to Action, Archive, or Trash before the end of the day. No message spends very much time in my inbox, and no message spends more than a week in the Action folder, because that gets cleared during every weekly review.

The nature of my work as a writer and editor is such that I can rarely ignore my inbox for more than 20 minutes or so. While I’m always working on longer-term projects, I still get requests to handle smaller projects that need to be turned around quickly. This is not constant, but it’s frequent enough that limiting my exposure to email or turning off notifications or quitting the app for long periods would only work against me.

My department does most of its project management in Jira, and the only reliable notification system in Jira is email, so in addition to normal messages, I get a lot of Jira notifications that need to be processed throughout the day.

Even if all of that weren’t true about my job, I’d be happy to jump in and process most emails as they arrive, simply because I don’t like not knowing what’s waiting to blow up on me because I ignored it.


Apple Mail used to be perfectly fine and reliable, but over the last year – it has developed quirks that are highly annoying.
Not sure if it is necessarily Catalina, since it was present from Mojave, and possibly earlier.

In effect, Mail does not fetch emails in the background anymore.
When jumping back into Mail, many of my gmail accounts (I have several) are “offline”.
Trying either “take all mailboxes offline/online”, or “synchronize all accounts” sometimes works – but more frequently, it is quicker to ship Quit/Restart the Mail app.

And then – its always a case of having to wait for it to first download the 50/100/150/200 messages that haven’t come in.

All that said – since all of my Gmail accounts are personal, and I seldom to ever actually receive anything important via email to these accounts (or alternatively, I am expecting something, which sees me go and actively find it) – in a bizarre way, this ‘broken’ approach actually suits me.
It would not were I to use it as my primary email client (use Outlook for that).
I dabbled with the other third party clients on the Mac several years back – and for my needs, didn’t need anything more than That appears to still be the case today.

So, figured I would share one perspective of a macOS user, who has some issues with the built-in mail client provided by Apple.

Over on iOS – I, like @MacSparky, spent every couple of months jumping through my email clients, before always returning to
If someone asks what my take is on both, the appropriate response that pretty much covers my feelings is: “It’s fine for what I need”.
Again, had it not been for the fact that Outlook handles my business-world emails, the above would most likely be far more of a rant about where things are at.
Clearly, I needed to get this off my chest – since cannot see it adding that much value to what has already been said above! :sunglasses:

This is great. After reading that I thought “I really like a well written email” for this very reason.

I use Spark for my two personal, school (as a teacher), and church accounts. The two personal accounts are Gmail and I have no problems using them in the web. In fact I really enjoy the filtering/sorting they do (a big reason I like Spark). School uses outlook and I find the web app to be busy. I don’t really like it, but it is what I use to do stuff like creating meetings. Our church uses register for its email and I think it’s hot garbage.

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I admire this especially as it relates to the concept of Deep Work. I’d imagine there’s an expectation to call or text you if more urgent?

I’ve been a Spark user for the past couple of years. The things I dislike about it is the lack of external archiving abilities to something like DevonThink for example and I’ve had issues with syncing lately. I’ve started going back to the Apple Mail app lately but honestly am displeased with it as I make use of the Snooze feature in Spark and sending emails scheduled at a later time. Right now since I’m looking for jobs unfortunately my life is run by email. In past jobs it was always stuff I had to pay attention to (teacher). I’ve dreamed of having email off my phone or checking it once a day but honestly that doesn’t seem very realistic right now. Maybe just maybe in the future but truly might not happen until I’d retire (I’m 26 now). Email has been that ever looking thing in the background of my life. I’m not as hung up on Inbox Zero but have a pretty good process and Sanebox has helped filter stuff out for later too.

I generally agree. I get a LOT of email but I’ve never found it hard to manage and I agree it has many benefits as you have noted. I also process my email religiously. As of this morning I have only 5 unprocessed emails in my inbox. I am rigorous about marking emails as spam and I have approx. 30 server side rules for processing emails. I also use a “junk” email address for all vendors, publications, etc., and have rules to forward emails from selected sources to my “real” work or personal accounts.

Where I differ from your process is that as a rule—a rule I sometimes break—I batch process my email twice a day so that I can remain focused. In simple terms, My day starts at 6:00am and I spend from that time to 9:30 in mostly uninterrupted focused project work. The rest of the day and most evenings are spent in meetings or at events.

I have struggled with finding the right client. I have defaulted to Apple Mail and I never have problems with it but it lacks features that would make batch processing emails better and faster. I would default to Spark except every time I try I run into some issue.

Airmail might be exactly what you need; it’s subscription-based, but very cheap ($10/y). Worth using the trial at least.

Good point. It didn’t occur to me to include doing that, probably because it has become second nature, but, yes, that’s absolutely a part of what I’ve done over the years to optimize the signal-to-noise ratio in my inbox. I only have a few rules. Fastmail’s spam management seems to do the bulk of the work for me.

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Indeed. Many of my rules are not specific to spam, they are rules to process and file emails. It may take a few minutes on the front end to create the rules but in the long term they save a lot of time and lower the noise. :slight_smile:

A few recurring topics/issues for me:

1. Organizing and Storing Emails. I sort my emails into folders by topic/client. One of the most important things to me is that filing an email be made easy. I’ve used Mail Act-On and Mailhub to make this fast on the Mac. But I’d prefer a built-in solution for mail. On iOS, Apple does an ok job of guessing the right folder. But it would be better if Apple gave you it’s top 3 or four guesses, and let you pick. Even better would be keyboard shortcuts for filing on iPadOS. The only other client that seems to do this right is Spark. (But I found Spark flakey and don’t really trust it anymore.)

2. Sharing on iOS. I can drag and drop an email on iPadOS. Just let me do the same via a share button.

3. Smart Folders on iOS. (Although I note that the token searches are actually pretty powerful on iOS. I don’t think most people use them to their potential. I just wish I could save them.)

4. Rules on iOS (in the cloud for .mac/.me/.icloud).

5. Display of attachments. Apple, please stop displaying all single-page .pdfs attachments as though they were images pasted in-line. I know I can right-click and choose to “view as icon.” But that should be the default for .pdfs. (Or there should be a global setting at least.) While you’re at it, please consider having an “Attachments” section at the top of email messages. It makes them easy to see so I don’t have to scroll to the very bottom, or hunt around in the middle of an email to find the attachments.


Apple is the one that works and doesn’t do weird things with emails out of my control. I also like that I can access the data trough the backend to save or store emails.

Either way anything but MS Outlook!

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I use Apple’s mail apps to access all of my email accounts (gmail for personal, Exchange for work). It’s fine.

The bigger problem with email for me is that it exists at all. The volume of important messages coming my way is so great that any individual message has very little chance of catching my attention. I’m not sure what the answer to this is though.

Email, for me, maps pretty closely to the Eisenhower quadrants popularized by Covey (realizing most have seen this, so just sharing so it’s in the thread.)

Too much quadrant 1 email will burn you out, but the email you get is just a symptom of the structures of the organizations you participate in and your commitments. The problem needs to be resolved by changing what you’re responsible for, I think.

Quadrant 3 email I try to turn into something ephemeral. E.g., in my role, I only set downtime alerts to Slack messages so I don’t have to lift a finger if the service comes back on its own. (Chat notifications are their own issue, so on-call is the next step as our organization grows.)

Quadrant 2 email I love to receive. I just love writing and receiving thoughtful, change-producing emails about improving and enjoying our company, family, city, personal lives, etc. If you’re overwhelmed by those, you’re blessed! :slight_smile:

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I use both Apple Mail and the Google Mail app on my iPhone to access both gmail and other email providers. Google Mail gives a notification if I receive an email, which Apple Mail can’t do with Gmail due to gmail’s slight lack of standards compliance as I understand it. Otheriwse I mostly use the Apple Mail app on iOS.
You can have more than one app installed, and use each for whatever it’s best at.

I like a lot of what has been said in this thread. I’m looking at moving away from (either to another client, or from the service entirely), and the issue that keeps me up at night is no one seems to manage threads as well as the Gmail client. Reading Gmail threads before I reply is such a help to me. Every time I manage my Gmail email in a more traditional client like Mail, archiving starts separating the threads and it really annoys me. Is there a good solution to this problem?

I’m also interested in better ways to get email search speed and power approaching Gmail’s, without using their web client or when using another email service. Auto-import to DevonThink seems most promising but I would love to discover a better solution, possibly one that automatically updates itself with IMAP (and is secure and responsible with my email archive.)

P.S. I’m excited to try the beta (from Basecamp) and I hope it succeeds on what its marketing page is hinting at accomplishing. Would be interested to hear your brief thoughts on it.