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.

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


In addition to hosting the ZDNet Government and ZDNet DIY-IT blogs, CBS Interactive's Distinguished Lecturer David Gewirtz is an author, U.S. policy advisor and computer scientist. He is featured in The History Channel special The President's Book of Secrets, is one of America's foremost cyber-security experts, and is a top expert on savi... Full Bio

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