The Email Experiment: A Quick Check-In

Posted on October 3, 2018 by Paul Thurrott in Cloud, Google, Outlook.com with 42 Comments

I see fewer false-positives in Outlook.com than I do in G Suite/Gmail.

A few weeks back, I wrote about the first steps I’d taken in trying to find a suitable replacement for Google Inbox. I’m still researching and experimenting. But I learned something interesting that may impact how I handle email moving forward.

First of all, I did provide a short update to this work in the September 21 edition of Ask Paul as well. The short version is that, in addition to Outlook.com and Outlook Mobile, I’ve also experimented with Gmail (mostly by trying to clean up the UI), Outlook desktop for Windows (and Mac, though that doesn’t matter much to me), and various third-party email clients.

The thing is, I’ve really come to enjoy the new Outlook.com. And Outlook mobile on Android is almost identical to Inbox mobile. So I find myself somewhat inclined to stop looking.

But if you made sense of my convoluted description of forwarding email and sending email as if from another account in The Email Experiment: Outlook.com and Outlook Mobile, you know that I started my experiment there. First with my secondary Gmail account, which is now being forwarded to Outlook.com. Previously, I was forwarding both my Gmail and Outlook.com emails to Thurrott.com (which is a G Suite account).

What this means is that, for the past few weeks, I’ve been monitoring and using two email clients on the web/desktop: Outlook.com and Inbox (Thurrott.com). Using Outlook.com side-by-side with Inbox has been a nice test. I sort of like it better overall than Inbox, which is amazing. But I do miss Inbox’s in-place opening and closing of messages; with Outlook.com, it basically seems to refresh the page, and you go back and forth between the message and the inbox.

I can live with that. But the bigger, more interesting thing I learned is that in forwarding email from one account to another, I’m losing emails to multiple spam engines, none of which seem particularly intelligent to me. And while some of these emails are non-event mailing lists, some are emails I’d like to receive. And I’ve found no effective way to make that happen.

Google’s handling of spam, at least via G Suite, is perplexing. When I look at legitimate emails in the Spam folder, I’m told that they were marked because “It’s similar to messages that were detected by our spam filters.” Google flags some of its own emails this way, which is amazing. Plus email from Amazon, Apple, Microsoft, and others. Which is infuriating. And you can’t fix it, which is even more infuriating.

I should admit that I was at least vaguely aware this was happening. Some emails I was expecting were never forwarded correctly, and when I’ve looked in my Spam folder, I’ve always seen legit emails mixed in with the spam.

But it’s been interesting getting a lot of those emails again now that I’ve stopped forwarding my Outlook.com to G Suite. And I’m wondering if maybe forwarding email to a single central account isn’t the best approach, despite the simplicity.

What this means—and it’s a bitter pill for me to swallow—is that I might be better off keeping each email account separate, with no forwarding. And for simplicity’s sake, using an email client that will poll each account and optionally display the messages from each in a single view.

I fell in love with Inbox because of its simple design on both the web (desktop) and mobile. But in pushing all of my email through that one account, I’ve been losing messages. And this has me thinking about going in a completely different direction. Despite the fact that I had almost settled on just using Outlook.com.

A few possibilities.

Maybe forwarding email from Gmail/G Suite will result in fewer lost/inadvertent spam emails. I haven’t tried pushing my Thurrott.com/G Suite email through Outlook.com yet, but I can at least look at the spam folder in Outlook.com and see if it’s mishandled any normal Gmail email.

This is a long shot, but if I could disable spam filtering on the two forwarding accounts—so that each message was only subjected to a single spam filter—perhaps I’d see fewer false positives. Given the direction these services have gone—where spam isn’t particularly configurable—I doubt it.

Or maybe I just need to use an email application on Windows.

I’ll keep working on this, and experimenting with different things. But consider this a wrench in what I thought was turning into a plan.

 

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