Outlook/Gmail Hack

Being a Mac OS person working in a Windows dominated office environment is not as seamless as one might hope. The software utilized on Windows machines does not always play nicely with Mac OS. In my office, we use Kerio Connect. It saves the organization money as an email service when compared to Microsoft’s Exchange, but with those savings come some big challenges.

One of the main challenges in the workplace is email storage space. We are given a downright meager 175mb of email storage. This makes searching old emails impossible. The bulk of emails I receive are stored on a machine that is inside of the office, hard wired on a closed network, and the archive is only searchable while on the machine at my desk. I could manually archive, create a .zip file of the archive, place it on a USB stick or perhaps in a Dropbox folder, and then copy that file to my Mac, but that is a lot of work to keep up with. Simply put, I want all of my email together in one place. I want it all to be searchable, and I want the storage quota my work’s email account to remain low. I want the comforts and convenience of using Gmail in the workplace while continuing to conform to what my IT Department sanctions as acceptable forms of email.

I needed a solution and this summer I found one. Outlook 2011 for Mac and a fresh Gmail account provided me with a decent solution.

Here’s how to create your own searchable archive of all your email.

On your Mac, open Outlook 2011. It will immediately prompt you to add an account.

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Click on ‘Exchange or Office 365’ and enter your work account’s information.

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Once your main email is installed, or if you have already have your work account activated, navigate to Outlook’s preferences.

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Once there, click ‘Accounts’ and then click on the small ‘+’ symbol in the lower right hand corner of the ‘Accounts’ window.

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Add your new Gmail account here. (I suggest a setting up fresh Gmail account, even if you already use Gmail. This insures the archive of messages you are about to create is separated from your personal emails. If you are a Gmail label and filter wizard, and want to combine, more power to you.)

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Here’s where the fun starts.

While in your work email’s Inbox, create a new folder called ‘Archive’. This is where you will place emails that you want to move out of your Inbox, but you want to keep searchable. This keeps your storage quota down but retains the functionality of all the email being there in your work’s email.

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Next, navigate to your work email’s Inbox and select all of the messages you’d like to archive.

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Drag those emails to the new ‘Archive’ folder to move them out of the main Inbox.

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This next step is where your personal email handling habits will come in to play. Personally, I like to keep a clean Inbox. If an email is in my Inbox, it needs to be acted upon. Once I’ve acted upon an email, I move it out of the Inbox and into a folder for keeping. Since I implemented this Outlook/Gmail partnership, I have moved nearly everything to the Archive folder and I now keep than 5 folders in my work account.

Once you are ready to see that magic happen, navigate to the ‘Archive’ folder, command-A for select-all, and drag all of that selected email to the Gmail Inbox.

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You’ll see this little window pop up.

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Immediately following you’ll see the window pop up that shows the upload process.

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Note: This upload process is very slow. It can take hours depending on the amount of email you are uploading and your connection speeds. For a frame of reference; I have 95mbps symmetrical at work and I’ve tried upload ~1500 emails and it took more than 6 hours. Your mileage may vary. I recommend having a cup of Aeropress prepared coffee while you wait.


When the upload process is complete, and you confirmed the emails are in the Gmail Inbox, delete the email from ‘Archive’ folder in your work email. Feel the sweet relief of a nearly empty email account.

I’ll write up how to set up this Gmail account on mobile devices in another post, but for now, if you follow these steps you’ll have all of your email searchable wherever you have your Mac and a connection to the internet.