How I Moved My Outlook email to Gmail and Retained the Best of Both Worlds

I’d been an Outlook user for many years – both corporately (using Exchange), and currently in my VA Practice. When you’re in the corporate world, Outlook is the client to use. But, during the past two years, a whole new world of education and exploration opened up while I went through my VA Training and the launch of my VA practice.

Class training emphasized collaboration with our clients was essential and we were urged to explore how to accomplish that–keeping in mind the technological comfort level of our clients.

I like to be sure something is going to function the way it says it will before implementing with a client, so I tried it out on myself! Last fall, Gmail came out with its highly anticipated IMAP feature. IMAP allows syncing of mail among multiple devices because the mail stays on the server. I read and heard a lot about it and I did a lot of studying and researching and then took the plunge.

Steps I Took

1. Before starting, I did a backup of my Outlook (you can’t be too careful). Then, I wanted some detailed instructions. I found them here with the How-To-Geek. He’s great. I followed these instructions and now I had my Gmail IMAP account in Outlook.

2. Then I started moving my outlook folders into Gmail. I used drag and drop to do this, although I’ve read since then that they should be copied, not dragged. I noticed that Gmail put annoying prefixes on each of my folders…the first three in the picture are before I edited the labels and the last two are after I edited the labels. It was more readable for me after I removed the prefix.

3. Then I went into my Outlook account settings (Tools>send/receive groups) and told Outlook not to check for mail in my Outook account, but to only check my Gmail IMAP account. I did this so I wouldn’t get duplicate messages – one set in my Outlook and one set in my Gmail.

4. Then I went into the Gmail Settings and under the ‘General’ tab, I added my email signature. Under the ‘Accounts’ tab, I told Gmail I wanted to send mail from my outlook address, not my gmail address (more about this later). I also tweaked the settings so I could ‘Get mail from Different Accounts’ and I added my Outlook account here. The ‘Labels’ tab contains the former Outlook folders, now renamed labels by Gmail. Here’s where you click on ‘edit’ and change the name of the label to whatever you wish. The next tab is the ‘Filters’ tab. Filters are like Rules in Outlook. They are insanely easy to set up and they work so much better than Outlook rules — ever have problems with Outlook rules??

What I Really Liked and What Really Works Well

I like, no love having email access from anywhere. Of course, everyone says that, but it is oh so true. Even when I’m at home and too lazy to walk upstairs to my office to see if some mail arrived, it’s wonderful because I can use a downstairs computer. When I’m at my sister’s house, I can check my mail – it feels great!

The filtering and spam catching abilities of Gmail are legendary — and true. The filters just work and Google is pretty good at catching only the spam.

Pretty much unlimited storage. Currently, I’m using only 1% of my storage – no worries there! I’ve read that many people move to Gmail because of the almost unlimited storage. Outlook warns not to go over 2-3GB in their mail accounts as it takes forever to load and can/does become unstable.

I can keep on using my Outlook 2007client. I’m familiar and comfortable with Outlook, how it works, what it does and what buttons to push. Gmail, with its threaded conversations is great, but it takes some getting used to (for me, anyway). The web Gmail interface doesn’t appeal to me that much — because I don’t have years of experience with it. I’m getting more comfortable with it after a week or so now. But I like knowing I can work in either.

What Isn’t Working and a Glitch with Google

Sometimes I get annoying pop-ups in Outlook regarding not being able to file a message, use default folder and a couple other annoying things. I don’t know why and haven’t researched it to see what it is.

With Gmail, there is an ‘All-Mail’ folder, and an ‘In-box’ folder. I also set up a separate folder for one account’s emails to go into. As a result, I get 3 copies of each incoming email in each folder. If I flag one of them, then all three will show up in my ‘tasks’ list. This is irritating and I haven’t decided what to do about this.

This could be the most irritating and I did research this one and as far as I know, no one has come up with a fix for this: I told the Gmail settings that I wanted all my replies to come from my default Outlook address–however, when I’m using my Outlook client to respond to mail sent to my Outlook email address and I hit reply, Gmail will make the return from my gmail account instead of my Outlook account. I have to remember to click the down arrow and switch accounts. This is quite exasperating. Now, this does NOT happen when I’m using the web Gmail – only when I’m using Outlook. Anybody know how to fix this?

correct setting

Overall, I’m very pleased with the migration to using Gmail’s IMAP service. I’d like to hear anyone else’s story or get some comments from others who have done this.

Next time, I’ll talk about how I moved one of my client’s mail from Outlook to Gmail!

Scroll to Top