The Email Experiment: A Quick Check-In

Posted on October 3, 2018 by Paul Thurrott in Cloud, Google, Outlook.com with 43 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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Comments (43)

43 responses to “The Email Experiment: A Quick Check-In”

  1. Avatar

    dcdevito

    Your timing on this article is impeccable. I removed all of (well as many as I could) Google's apps from my Pixel 2 XL and replaced them all with MS apps. I also installed Edge and will use it for a week to see if it can replace Brave.

    I started thinking about my email address itself, and whether I could switch to Outlook as I absolutely cannot stand Gmail, I love Inbox and need a replacement. But I'm thinking of switching to an Outlook address entirely, but I have a few domains wrapped up in my G Suite account. For now I'm going to just use Outlook's web app with my gmail address (not import) and see how it goes.

    • Avatar

      wolters

      In reply to dcdevito:

      I've considered doing this...and giving Cortana another shot (loved her Windows Phone and like it on desktop.) But I'm invested in Google Home so got to keep Google Calendar and Assistant going.

      • Avatar

        jprestig

        In reply to wolters:

        Google Calendar is a big part of why I stay so invested in Google apps. I can't convince the family to jump ship to the Outlook calendar. Also shared lists on Google Keep, shared albums on Google Photos, just further chains us to the Google train.

        • Avatar

          curtisspendlove

          In reply to jprestig:

          I just went through a major mail / calendar reorganization as well.


          The fam loves gmail / google calendar, so I don’t want to move them.


          But, I only need certain stuff, like shared appointments with the kids, Dr appointments, etc.


          So I created a separate “Family” calendar, told them if they wanted me somewhere it has to be set for that calendar, and moved the rest of my stuff out of Gmail.


          I’m actually forwarding to a personal business account with FastMail (I killed my G Suite account). But it should work fine to use a personal Outlook.com email address instead (I currently also forward my msn.com and outlook.com emails as well.


          The thing that drives me the most nuts about this, though is the spam issue. I have a reminder set every couple weeks to check all my spam folders on the forwarding accounts.


          I appreciate the tip in the comments to setup a mail action forward instead of the full account forwarding. That’s a good idea.


          I guess the the other option is to disable spam (as much as you can anyway) on the forwarding accounts.


          I feel that im still going to run into the case Paul points out where you can’t seem to truly, completely disable spam on gmail.

  2. Avatar

    Richardsona39

    Good timing as I've been hunting around for a better email also. Outlook.com is quite nice (I'm using the "coming soon" beta), but is missing 2 features from Inbox as well as Outlook Mobile: Unified inbox, and snoozing. Both are really important to me.


    The other thing that's maddening is that it doesn't seem that if I start a draft online or in the mobile app, the other doesn't know that it's there (something which Inbox did very well). So I can't start something on one device, and then pick it up on the other. Same limitations in the desktop version of Outlook.


    I also find it odd that it doesn't automatically pull in my contacts and calendar that are already associated with my MS account (via gmail…. maybe there's something I'm missing here)


    I've been using Mailspring, which is quite nice, and I like it's tracking of email opens/clicks. However I've found it a bit flaky and can lose emails. So am still searching for the best solution... I just can't stand the desktop UI of Gmail. And I do like to have a desktop version that downloads the emails, just for posterity (call me old fashioned).

  3. Avatar

    JerryH

    Paul, your post made me look in my Inbox spam folder for the first time in many months. Out of the 20 notes there, only one was legit (a note from a site about a breach and asking that you reset your account password - and it was a legit one). On the few occasions that I've checked my spam folder that is the first time I have found something I actually wanted in there. Google usually just kills it on spam so I usually don't need to check. Most of the other 19 on this occasion were political garbage "vote for me" type stuff. Yuck! Makes you feel unclean to even go into that spam folder.

  4. Avatar

    AnOldAmigaUser

    Today, Outlook.com started rolling out some new features under Compose and Reply:

    Suggested replies, which adds almost entirely inappropriate canned responses to emails you receive (it actually appears as part of the incoming email), and Joyful animations. Luckily, they can both be disabled.


    Thank goodness I was able to disable that second one before having to witness it. You never know what might push you over the edge.

  5. Avatar

    longhorn

    "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"


    That has always been the cleanest solution (on desktop). You get your email in one place, but you don't mix the services of different email providers.


    Windows Live Mail was great with Calendar and Contacts - I still miss it. I feel less confident in the new Windows 10 Mail app because it focuses on touch. I think you have access to the real Outlook client and it should handle everything you throw at it.


  6. Avatar

    wright_is

    I forward my personal domain to outlook.com and, what isn't removed as spam by my hosting provider is forwarded and Outlook and displayed "as-is", I have yet to see a single email that arrived in my provider account be marked as spam in Outlook.com

    What is interesting is, all LinkedIn email is marked as spam by outlook.com.

    I generally use Outlook 365 on the desktop and Outlook Mobile on Android. I very rarely go into the web interface.


  7. Avatar

    florianslezak

    Wondering if "linking inboxes" in Windows Mail (or Outlook) wouldn't solve your use case...

  8. Avatar

    BBoileau

    Forwarded gmail to Outlook has been working for me for many years. What I would like to see from Microsoft is the ability to open Outlook.com as either a PWA or some other sort of web login that allows several accounts, as it does on the Android app or in Outlook 365.

    • Avatar

      bassoprofundo

      In reply to BBoileau:

      They seriously need some sort of multiple account interface on Outlook.com. That's what keeps me tied to the desktop Outlook client for now (which, btw, still can't show a unified inbox).


      I have a personal domain which is still on WLD and my (primary) old Hotmail address as well as my gmail address. The Gmail forwards to the Hotmail, and I used to have the custom domain "redirect" (so it still shows as the original sender vs a forward where it shows as coming from my own address) everything to it as well. However, due to some fairly recent security related changes, redirecting from certain sender domains no longer works. As result, I now keep the custom and Hotmail accounts separate and need to either use a desktop client to show them in the same view or keep multiple outlook.com sessions open in separate browsers. Neither is a good solution...

  9. Avatar

    gabbrunner

    Ah, email. We used Newton for our organisation, with Office365 accounts, until they went out of business, and it was great. Since then we have switched to Missive, which is awesome, but it's costly and really aimed at teams. A write-up about Missive would be great, though, wonderful email application for small teams. For a personal, free email client, I can't think of any other worthy alternatives.

    Maybe if you really focused on spam and training the email filter for a week or so, the spam situation could improve? I remember you writing a post about such an experiment a while ago, dealing with junk and newsletters. Do you still receive a lot these days?

    We had a problem with false positives a while ago, basically potential customers asking for quotes that got flagged as spam because they were sent via contact forms. So what we've done is, we took a week or so to unsubscribe from every newsletter, and manually ask to be taken off email lists, and then we deactivated all spam filters. No it's down to one or two spam mails per day, which we manually have to eliminate.

    Not ideal, for sure!

  10. Avatar

    comchinc

    If you haven't try Hiri. I like the way it works.

  11. Avatar

    PcGuy8088

    Google's antics with respect to spam filtering does not surprise me at all. They have made decisions regarding Chrome over the years towards simplicity rather than allowing those of us which prefer to secure our login to gmail a bit more the options in Chrome to do so. The only reason Google is relenting their latest decision regarding auto logins via Chrome only because the large amount of press coverage it got.

  12. Avatar

    JeJoCo

    I use EM Client for people who still need an email client or who want a consistent interface. I have used it for years now, for an Exchange Online account and an Outlook.com account and it works well. I have also used it for clients who use other mail services, GMail, Yahoo etc. and they generally love the ease of use and simplicity. You can use 2 mail accounts in it for free to try it or buy it for around $50......definitely recommended!

  13. Avatar

    cjsacksteder

    FWIW, I've been using Outlook.com for 2.5 years but also Gmail when some vendor demands an email address and I know that means a lot of spam (NOT thurrott.com). It was flaky the first year but now is reliable. On a couple computers with the Windows Outlook client, I have the Gmail account configured as well as the Outlook one, instead of forwarding, so I can look at those messages once in a while. It is nice they are there but separate.


    Another nice thing about the Outlook Windows client is I can occasionally "mount" and old .pst file that contains 5GB of mail from my working days to find some old thread (then remove it, otherwise it gets indexed and backed up). The web interface is fine on a Chromebook or other system that doesn't have Office. On my Android phone, I keep trying the Outlook client, but still prefer the Samsung mail client and Gmail via the stock Android app.

  14. Avatar

    BFalcon1

    Ever think of using the Blackberry Hub? I think it is a great option.

  15. Avatar

    legend

    I have a dream... Outlook.com as web app that supports multiple accounts (Exchange, Gmail,...).


    But for now I'm stuck with the Windows 10 Mail app on my laptop. Maybe the new Outlook 365/2019 redesign will make me try it again.

    • Avatar

      Sprtfan

      In reply to legend:

      Maybe I'm misunderstanding, but you can configure Outlook.com to open different emails including Gmail and Exchange.

      • Avatar

        legend

        In reply to Sprtfan:


        Really? How does this work?


        For clarification: I want the mails separated and not in one account. Outlook.com should act as the mail client for multiple mail accounts (like Outlook Mobile on the Smartphone).

        • Avatar

          Sprtfan

          In reply to legend:

          When adding a 2nd email address to Outlook.com, it asks if you'd like to create a new folder or add to an existing one I think. This is how I set up mine and the the email from each address goes into a separate folder. I set mine up so all replies come from my Outlook.com address but it can be configured to send from the other email address as well.

          Once logged into Outlook.com, go to Settings, View all Outlook settings, Sync Email, the add an account. If you want to keep it separate, have it create a new folder during set up.

  16. Avatar

    RM

    Outlook on Android lets me have multiple email accounts added to it and I can display email from one account or all of the accounts easily. Unfortunately I cannot do this with outlook.com (at least I don't know of a way).

  17. Avatar

    jprestig

    I thought I was the only one that drove myself crazy with these things. Though it's not the same situation, I find myself bouncing between Outlook.com and Gmail more than I should admit. I have even tested the waters with iCloud.com email, which is downright terrible(it was a short lived test).


    I just can't seem to pry myself away from Gmail.

  18. Avatar

    dontbe evil

    outlook and outlook.com are millions of years ahead of gmail

  19. Avatar

    Illusive_Man

    I've never seen someone have so many issues with email. Just use Outlook.

  20. Avatar

    GilesBrule

    In the shot above that looks like a browser with the address bar missing, or like the google photos PWA. how did you get outlook.com like that?

  21. Avatar

    dave0

    I'm sticking with Inbox with the silly hope that Google will change their mind. The only other mail client I find usable is Outlook.

  22. Avatar

    Sprtfan

    I ran into a problem with losing emails a few years ago when I tried to "Push" email from an account instead of having it "Pulled". DMARC authentication policy can be set to reject emails that claim to come from a specific server but actually originate from someone else's servers in an attempt to stop fraudulent emails.

    I received the emails faster when forwarding but it was not worth missing emails that originated from Yahoo, Aol, emails from the school district , along with several others. I was able to get around this with setting up several rules when forwarding the email by my original email provider but they ended up wiping the rules out because it apparently causing problems on their end.

    This, in addition to emails getting lost in spam folder, lead me to just pulling the email instead of forwarding it.

  23. Avatar

    glenn8878

    You have complicated use scenarios. Decide on one email and just move all traffic to that email. This always helps to reduce spam and email subscriptions that you completely forgot about.


    It’s because of you Paul that I stopped using Yahoo in favor of Gmail for security. Maybe just move everything to Gmail.

  24. Avatar

    Daekar

    I had no idea things were anywhere near this complicated. Can't you just migrate all the nonsense attached to one of the accounts to the other and let the other lie fallow? That's what I did with my Gmail account. It gets practically no messages now, it all comes to my Outlook account now.

    • Avatar

      wright_is

      In reply to Daekar:

      I set up Gmail specifically for "junk" mail, site registrations, where I am not interested in anything they have to say by email. I then check the account once a month or so, which usually means deleting a couple of dozen "spam" messages.

  25. Avatar

    tiedemann

    I use SaneBox to train and pre-sort everything. Then it doesn’t matter if I’m using Windows 10 Mail or MacOS mail or their corresponding mobile apps. I haven’t lost any e-mails.

  26. Avatar

    sanjim77


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