Your questions answered: Why I switched from Outlook to Gmail

Your questions answered: Why I switched from Outlook to Gmail

Summary: We got a ton of reader comments and questions when David Gewirtz told us he was moving from Outlook to Gmail. In this article, he tries to answer most of them.

TOPICS: Cloud, Google, Microsoft, SMBs, DIY

A few days ago, I shared with you Why I bit the bullet and finally switched from Outlook to Gmail. To say that article generated letters would be an understatement. In addition to the comments from ZDNet readers in the article itself, I got a steady stream of email messages, Twitter comments, and Facebook opinions and questions.

Since there were so many different things discussed by all of you, I'm dedicating this article to addressing most of them (including those where you question my sanity). I expect to post some more detailed how-tos later on that go into specifics of what tools and solutions I'm using. But first, can we talk?

My mail system is better than your mail system

Are you saying you think Gmail is better than Outlook (client) or Outlook with Exchange?

Not at all. Outlook and Exchange are a brilliant team and I've benefited from using them for over a decade. However, as time has gone on, my daily usage patterns and workflow have changed, and the Outlook/Exchange combination may not be the best choice for me. I specifically documented some issues I had with rules, but it's also important to recognize that the organizations I work with are Google shops, so there's a natural fit there.

I still don’t understand why you switched to Gmail. Outlook is the Cadillac of emails, especially with Exchange.

Outlook is certainly a comprehensive package, but I don't think it's holding its place at the top of the heap anymore. For example, which Outlook are you talking about? Outlook on Windows is certainly excellent, but it's different from Outlook on the Mac. and Outlook Web Access could have been made by completely different companies. So, which Outlook is which? They're all workable, but that lack of cohesiveness has rough edges.

What about the Windows Phone? Isn’t Outlook and Exchange integration better?

This reader is commenting about my exploration of Windows Phone. In a perfect world, I probably would have finished my Windows Phone series before moving on to talk about email workflow. Here's the detail. After a few weeks of using Windows Phone, it's proving to be a fine environment.

That said, I have an Android Samsung Galaxy S4 on contract for nearly another year, and I'm probably not going to switch off of it, at least until the contract is up. As a product evaluator, I have to treat different systems as their own unique projects, and so while I'm using the Android phone as my daily driver (and it fits with the Google ecosystem), I am evaluating the Windows Phone environment.

I will give you one hint though: Windows Phone 8.1's integration of Outlook with Office 365 was... odd. You can't get to your email from the Office 365 icon. I'll discuss that more in a future article, but it's worth noting.

Desktop vs. Web client

So you basically moved from a desktop mail client to Web mail?

Mostly. I haven't completely given up on running a desktop client on one or more of my machines, but I'm finding the universal Web access extremely freeing. And it's really nice having a completely consistent UI for email no matter which machine I'm using at the time -- at least on PC-grade machines.

Why not use a local client, like Postbox or Thunderbird or Pegasus Mail?

I thought about Thunderbird, but the project is on hiatus, whatever that means. I've used Pegasus briefly in the past, and it's a heck of an email client, but I didn't find it as comfortable to use as I would have liked. It also feels kind of dated. The version update information lists Windows 2000, XP, Vista, and Windows 7, but makes no mention of Windows 8. It's certainly a viable client and if you like it, it's a solid choice. Just not for me.

As for Postbox, I was all ready to buy it (especially since it's based on Thunderbird, but with ongoing development support), but it doesn't do display scaling right on Windows 7. As a result, the text on my 1080p display is so small, it's unreadable. If anyone knows how to fix that, please post a note in the comments.

Gmail doesn’t work as well with non-Google devices since ActiveSync was disabled.

This is true. In fact, the Gmail app on my iPhone and iPad crashed trying to read my mail, while the native email app worked quite well. However, since I'm primarily using an Android phone, this isn't too much of an issue to me. I do wish, however, that Gmail would have continued to support ActiveSync fully. Interop is always a good thing -- at least for users.

Outlook techniques

Why not use both? You could use Google Apps for Outlook Sync, define rules in Google Apps, then read mail in Outlook

Yep, you could. I've done this sort of hoop jumping before. A lot. But I had this flash where I realized I was spending way too much time fiddling with coordinating accounts and keeping things all in sync. I wanted to simplify. One account. Simple.

Why wouldn’t you keep Outlook's signature files (which are local) on something like OneDrive so any device can look it up?

This pretty much tracks with the previous answer. Sure, I had a system that worked almost as well, using my daily backup syncs to move my sig files around. But who needs it? That's just more overhead and I'm at a stage where I just don't need that much overhead.

Signatures can be server based if defined as a rule with a template

Yep, that's a neat technique. Except I don't think it works. Inbound rules allow you to assign a template, but outbound rules don't. So you could do this if you were setting up an auto-responder, but not if you were composing a new message. Feature request for Microsoft: please add "assign a template" to outbound rules and allow users to replace or append the text.

Next up: Gmail vs., privacy issues, and your migration questions answered...

By the way, I'm doing more updates on Twitter and Facebook than ever before. Be sure to follow me on Twitter at @DavidGewirtz and on Facebook at

Topics: Cloud, Google, Microsoft, SMBs, DIY


David Gewirtz, Distinguished Lecturer at CBS Interactive, is an author, U.S. policy advisor, and computer scientist. He is featured in the History Channel special The President's Book of Secrets and is a member of the National Press Club.

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  • Switching

    I recently did a reverse switch from Gmail to My old phone was a Galaxy Nexus (no letters or numbers) so the email account I used was my gmail account. Because Android has hooks to all Google Services (*cough*). My home computer is a Windows 8+ laptop. So the email account for this machine is, of course, Outlook / Hotmail.
    Now, that I've finally got a Windows 8 phone, I could finally consolidate my email houses into one.
    Oh, by the bye, you could do well to get with your compadre Ed Bott regarding the Outlook 365 for business conundrum you've run across and he's previously documented; he may have a workaround, or three, for you to try!
    Crashin Chris
    • Yeah well

      If he does go back to Windows Phone, he won't have those Gmail contacts because the Sync feature is horribly broken!
  • Pointless justification, even an 8 year could do better. capabilities are unparalleled.

    You should think of getting trained in using modern email systems.
    • I am guessing you didn't really read the article

      As he goes over why was not going to do it for him - (a) he can't (he has Office 365), and (b) there are certain plugins he uses for Gmail that don't exist for

      Reading the article - always a good thing to do!
    • more troll nonsense

      You need to get trained in how not to be a self righteous dick then learn how to read then get your head out of your ass and learn t hat people have different needs Just because you prefer outlook and it works for you doesn't mean everyone else has to be the same.
      I don't know why you trolks even bother to come here as you just slagg off everyone else's opinion all the time.
      If you don't like other opinions then stop using the internet.
      Capt Frickin Obvious
      • Your comment will probably be removed soon

        Like the other 100 or so comments that were on this piece until today.
      • hey cap.

        fowlnet doesn't prefer outlook, he prefers microsoft, doesn't matter what it is.. if Microsoft are in a field.. they are fowlnet's choice.. before he considers or looks at any alternatives, then he tells everyone as if he knows about all of them and "chose" microsoft.

        If he was in high performance computing, he'd be pushing HPC windows, and it wouldn't matter that the worlds top 500 supercomputers only has 1 windows machine and it's nowhere near the top..

        It's just how he rolls, you get used to it after a while. it's actually kind of entertaining.
    • Even an 8-year old could... better comments than Owl:Net.
  • Good luck

    I'll give you a few months to discover all the shortcomings of Gmail and related services such as Google Contacts. I've had a Gmail account for many many years. So long that I'm one of the users who got grandfathered into the ActiveSync support. However, that didn't save Gmail and I migrated to a couple of years ago.

    The primary reason I migrated is the severely lacking Google Contacts. For example, Google Contacts cannot aggregate contacts from various sources such as Facebook, LinkedIn etc. and unify your entire universe of contacts. can aggregate all your contacts from all these services and even from Gmail btw, unify them and if it can't automatically unify a contact because one of your friends uses a different email address on Facebook vs LinkedIn for example, you can manually link those contact records together.

    The secondary reason is that the structure of how Gmail manages and stores emails really clashes with everything other than Android and the Gmail web interface. I'm not married to a single platform. I use PCs w/ the Outlook desktop client, I have a Mac and Windows Phone, several Windows tablets and many other devices that sync with my email, contacts and calendar. does it all w/o requiring an awkward mapping of the email structure. Gmail's conversation structure was unique when it came out, but over the years it has proven to be more of a headache unless you exclusively use Google products.

    Another great feature of is that it can use your SMTP server to send emails. I actually have my own personal email domain. Had it for years. I'm not running it myself, though. I never really wanted anyone to know my Gmail address. I wanted that my emails always come from With Gmail that doesn't work so well. While you can change the From in Gmail, the email header still contains the actual Gmail address and if a recipient uses Outlook they'll see the from as in behalf of Furthermore, when sending emails from a non-Android phone, the From address is the Gmail address. Not so with Because sends all emails through my domain's SMTP server, regardless if I send them from the Outlook desktop client, my phone or any other device they always originate from and the header shows that they came from my email domain so reverse lookup etc. works properly, so there is less of a risk that emails end up in people's spam folder, because they get interpreted as being spoofed.

    Don't get me wrong. Google has some great services. I use their search all the time. I love Google Maps and in fact all my emails still run through my Gmail account, but now get forwarded to my account. I keep Gmail as a middle man for several reasons. One reason I have to admit is that it has probably the best Spam filter ever. The other reason is that Google search can search my emails and inform me about upcoming flights, reservations, deliveries etc, but having everything aggregated in makes life with different devices so much more productive.
    • Most people work off of phones these days

      and your phone is already doing all that unification for you.

      In the gmail web client, gmail knows about every person you've ever emailed, or been emailed by. I can't think of anyone I've tried to reach in the last 4-5 years where it didn't just autocomplete whoever I was trying to email.

      So while your point is a valid one, there are a lot of factors that mitigate it to the point you'd never really notice the difference.
      • Missing my point

        If you indeed only use a single device (phone, tablet) than you have a point. However, I had an iPhone for many years and the contact unification in iOS at least up until iOS 4.x was pretty lackluster. The key feature it missed, maybe they added that by now, is to be able to manually link contacts if the automatic unification failed. I had many duplicate contacts for friends and colleagues who use different email addresses for different online services or used their middle initial in one service, but left it out in another service.

        Being able to unify my contacts in the cloud rather than on each device has the benefit that no matter what device I use to look at my contacts, they are always unified correctly.

        Maybe I am unique with all the many devices I use, but I doubt it. I have a job and need to do productive work, so I'm still using computers. I think Sean Foley is correct with his comment. I don't email much from my phone. It's a pretty bad experience trying to read longer emails on the small display and respond with more than a sentence or two, so the majority of my emails are read and written on a computer. When on the phone, I text, skype, whatsapp or call people.
    • Huh?

      I've had my Gmail from the Beta and there is no grand fathered active sync... Not anymore, they shut it off.
  • Rules on Outlook Web App

    I just want to point out an inaccuracy with your statement about rules in Outlook Web App that says "Outlook Web Access doesn't even let you set rules from the Web environment". This is not true. You said you were using office 365, so you can edit rules under the Settings Cog > Options > Organise My Email > Inbox Rules. To be honest, I use the desktop version of Outlook 2013 everyday and had a bit of snobbery about OWA due to previous versions, but we recently moved to Office 365 its surprisingly good. On top of that, they are doing some amazing work with Office web apps, OneDrive for Business, SharePoint Online & Yammer which is slowly starting to trickle through...
    • Rules on Outlook Web App

      You can't set rules at all using the light version of OWA. And the full version contains a limited set of rules, even if you enable the advanced set. I can't edit any of my 20 rules using either version of OWA.
  • Excellent responses

    I did chuckle at several of them.
  • The fact is

    He's contacts and people he works with, are Google, his phone is Android and he uses Mac. No real surprise here.
    Everybody chooses environment, that suits him best.
  • What about Thunderbird Hiatus?

    Hi, I'm a longtime Thunderbird user (on both Windows and Linux -- I use it to access the same mailboxes from many locations) and I don't understand the "hiatus".

    I've heard about Mozilla Foundation stopping funding Thunderbird development, but updates -- including many new features -- continue coming. I'm very satisfied with it and its vibrant plug-in ecossystem.

    I also had concerns about other mail clients, because they either don't deal very well with encrypted messages (specaillu PGP/GPG) and sometines they store the content unencrypted. Thunderbird + Enigmail was the only combo that passed without issues in mine (my customers) tests. Maybe Outlook improved so far, but at the time it was a disapointment. besides Gmail / looks like no way regarding crypto.
  • My Nexus + Gmail works great

    I drank the Google-aide many years ago (probably as a knee-jerk reaction to anything but M$). I have no problem doing everything I need to do on my phone as well as using a browser. I don't know of any scenario where what I have is insufficient to my needs.
    Roger Ramjet
  • What about digital signing and encryption?

    I've not see you address how you deal with email signing and encryption.
    These things are difficult to deal with when using a non local email client like like a web based gmail interface.
    How are you dealing with email signing and encryption?
    • I, too...

      ... am curious to this.