MY NEVER-ENDING QUEST FOR A PERFECT EMAIL APP

As usual, I’m going to take a little time to get to the point, but there are reasons.

First, a little more time has passed than I expected since my last column appeared. And, no, it has nothing to do with any illnesses. As with most of you, I am being careful nowadays, staying away from people except when it’s necessary, and washing my hands — a lot.

As I write this, Apple has closed all retail stores outside of China until March 27th, with no guarantee that they’ll reopen then. New products and services are expected to be at least a little late.

For now, I’m hoping that my gear will remain fully functional. After my iMac had its Fusion Drive replaced awhile back — both drives — I am mostly assured that it’s almost as good as new, but I’m not taking bets. I’ve just been trying to catch up on things that I had set aside.

One is the choice of email software. Other than the audio apps I need for my radio show, The Paracast, I rely on email and Internet visits. For the latter, I stick with Safari.

Yes, I know Chrome is number one in PC-land, but it has a few silly interface choices, such as having to hold the Command-Q for an extra second for the app to quit properly. It’s a design decision that just doesn’t make any sense. Thus Safari.

Now almost from the earliest days of macOS X, I stuck with Mail as my default email client of choice. tried other possibilities from time to time, but they never seemed as fluid. Microsoft Outlook would seem the logical alternative, but it has, until recently, been sluggish and buggy. It was too prone to just freeze at random, spinning cursor and all, when adding or modifying an account. I wasn’t happy with its ongoing lack of support for Apple’s Contacts, but that wasn’t the deal breaker.

In the days of the Classic Mac OS, I had settled upon Outlook Express, then offered as a free Mac app. It was compatible with System 8.1 through 9.x.

Prior to that, I was a loyal user of Claris Emailer, which had the added benefit of being compatible with AOL. I rather suspect it wasn’t a particularly successful product sales wise, and it was part of the slew of Apple products killed by Steve Jobs in the year after he took over as CEO.

When Emailer died, some of its developers went to Microsoft to work on Outlook Express for the Mac. I could see the influences, so I mostly stuck with that.

But when Apple released macOS X, I gave Mail a try. Barebones, but easy to use and mostly reliable.

When Microsoft added a mostly fully-functional version of Outlook to Office for the Mac, I periodically give it a try. It had a more professional veneer than Mail, but its performance issues never seemed to be resolved. In fairness, a major cause may well be that I have some very large accounts, with more than 100,000 messages strewn across several mailboxes. I should be culling out the 20-year-old messages I will never have any use for, but my present email host, PolarisMail, gives me more than enough space for a tiny price ($1.00 per mailbox for a “basic” 25GB account).

I might attempt a cleanup someday, but I always seem to find an excuse to keep at least some messages around, so I procrastinate.

In any case, since Microsoft began to frequently update Office 365 for Mac, and gave it almost equal status to the Windows version, Outlook has become speedier and a lot more reliable.

Last week, I decided to give Outlook a thorough trial, after allowing it sufficient time to update my accounts. Downloading IMAP messages from the servers appeared to occur faster than with Mail, though perhaps the visual effects of messages pouring into a mailbox enhanced that impression. It may be no different.

Now you might conclude that I finally found a version of Outlook that could replace Mail, but no so fast.

Things seemed to be alright for a while, until I tried to send some attachments to a client. The largest, just shy of 22MB before encoding, triggered an alert in Outlook that it couldn’t handle more than 25MB.

Now Apple’s iCloud mail system is limited to 20MB last I checked. But PolarisMail and Gmail offer 50MB. So what’s up with that?

Turns out that Outlook’s 25MB flag is a known bug, first reported in August 2017m and there’s no indication of when, if ever, it’ll be solved. For now, their workaround is to “use your Web mail when sending attachments that are larger than 25 MB.”

But it would seem, after nearly three years, that Microsoft ought to pay some attention to fixing this glitch.

What’s more, macOS Mail supports a nifty iCloud feature, Mail Drop, which allows you to send attachments of up to 5GB in size to pretty much any recipient. That’s not a misprint! What happens is that the file is uploaded to iCloud, and it is offered as a file download in email clients other than the macOS version of Mail.

It’s not that I routinely send large files, and I can always upload them to my server and share a link, or use the ownCloud feature of PolarisMail to share 5GB files. Either way, I don’t really have to depend on any specific email client. Except that Outlook would routinely warn me about messages with large attachments — and I’m not sure if they were being truncated due to my “transgression.”

In Microsoft’s efforts to simplify Outlook, they have also done some peculiar things, such as opening TextEdit if you want to check the source of a message. Keyboard shortcuts are even less intuitive than Mail, and examples are not important. If you really must know, you can check Microsoft’s support document on the subject.

As much as I like to try new things — or give old things a second look — I am content to abandon Outlook once again. If Microsoft does something major with it, I might revisit the app. But it’s not that there are some fancy email features that I crave. To many, email is a relic of the past. Texting and messaging on Facebook and Twitter have taken over for most of you.

At least until dictation becomes smart enough to make traditional keyboarding totally obsolete. It’s only partway there for now.

So I will now return to my usual topics, such as what Apple is up to, possible new product and service introductions. And don’t forget the possibility that future Macs will employ ARM-based processors. Some say that move is inevitable and may already be in the pipeline.

THE FINAL WORD

The Tech Night Owl Newsletter is a weekly information service of Making The Impossible.

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This article was posted on Sunday, March 15th, 2020 at 12:00 AM and is filed under Newsletter and tagged with: Apple, Chrome, Claris Emailer, Classic Mac Os, email, Fusion drive, Gmail, iCloud, iMac, IMAP, Mac, macOS, macOS X, Mail, Mail Drop, Microsoft, Office 365 for Mac, Outlook, Outlook Express, Outlook for Office for Mac, ownCloud, PC, PolarisMail, Safari, Steve Jobs, TextEdit.