How To Set Up Microsoft Outlook 365 with your Gmail Accounts Using POP3 in 2021

I just received my new Dell XPS 13, which meant that I needed to tackle one of my most dreaded tasks: Setting up Microsoft Outlook on a new Windows laptop.

It may not sound like much, but Outlook is the primary reason that I still use a Windows laptop (I have an M1 Macbook Air for my audio and video work). It’s a classic case of lock-in. I have been saving contacts and filing emails in Outlook since the late 1990s. I literally have 25 years of email saved up in my Outlook PSTs (of which I have several, because I long ago exceeded the maximum size limit). That packrat instinct has served me well, including when I was sued for $100 million (I won).

In addition, Outlook is a critical part of my workflow. I currently have eight different Google email accounts (from seven different organizations, plus my personal chrisyeh.com account) and Outlook allows me to gather all my new emails together in a single place, and deal with them there. If I had to manually switch between eight different email inboxes every day, I’d waste a lot of time.

But the problem is that Outlook is not designed to work with email accounts like mine. My oldest account dates back to the very first days of G-Suite (then known as Google Apps for your Domain) which means that I have a 15-year-old Gmail account with about 300,000 email messages in it. When I tried to set up Outlook, it nearly choked, despite running on a high-powered ultrabook with a new Tiger Lake processor and 32 GB of RAM. That’s because Outlook defaults to IMAP, which tries to synchronize local email with the server. That meant that as soon as I connected my first Google account, Outlook tried to synchronize 300,000 emails. And don’t forget, I needed to connect eight different such accounts.

While some of my newer accounts worked, the whole system was highly unsatisfactory. Each email account got its own .ost file, which meant that each had its own inbox. That defeated the entire purpose for my using Outlook!

At first, I tried to make things work with the IMAP setup. By creating a custom rule to move all new emails from all the other inboxes into the inbox of my primary email account, I figured I could still have a single inbox.

The only problem, of course, is that Outlook still couldn’t manage to synchronize that inbox, even after I let it run continuously overnight.

Even more frustrating, I couldn’t just replicate my existing Outlook account, which set up in 2015, the last time I changed laptops. In Outlook 2013, which I’ve been using for the past six years, I could manually set up my different email accounts to feed into a single .pst file, which gave me the unified inbox I wanted. But in the new version of Outlook, Microsoft didn’t provide the same access to low-level settings. All I could do if I wanted to set up a POP inbox is enter a password, and Outlook would automatically set up a new .pst file for each email account, once again preventing me from having a unified inbox.

At this point, I was getting pretty desperate. I looked up “depression” on WebMD, and found the following list of symptoms:

  • Trouble concentrating, remembering details, and making decisions
  • Fatigue
  • Feelings of guilt, worthlessness, and helplessness
  • Pessimism and hopelessness
  • Insomnia, early-morning wakefulness, or sleeping too much
  • Crankiness
  • Restlessness
  • Loss of interest in things once pleasurable, including sex
  • Overeating, or appetite loss
  • Aches, pains, headaches, or cramps that won’t go away
  • Digestive problems that don’t get better, even with treatment
  • Persistent sad, anxious, or “empty” feelings
  • Suicidal thoughts or suicide attempts

Aside from the suicidal thoughts, I had developed all 12 other symptoms within 16 hours of starting to set up Outlook. When I complained to my wife about it, she replied, “You’re complaining about having to suffer these symptoms for less than 24 hours? Most people are dealing with a good number of these every single day of their life!”

Point taken. But I was still miserable, and Googling for the answers was depressing me further. No one seemed to know what to do. The best answers I could get were that Microsoft Outlook sucked, and that maybe if I waited long enough, it would finally manage to synchronize.

That’s when I called in the reinforcements. Thomas Leavitt and I went to high school together (we both studied under the great Berkeley Blatz) and while I was busy at college, he dropped out and became the first of my friends to become an Internet millionaire when he sold his startup, WebCom (the world’s first commercial web hosting company). Since then, he’s been a senior technology guru throughout California. Back when we started a company together (his second, my first) he had a magical ability to get my computers to work properly.

Fortunately, Thomas still has that magic touch. We screen-shared and worked on my new laptop together, trying different approaches, Googling for new leads, and ultimately figured it out.

The key breakthrough was when Thomas figured out that there was a way to access the advanced email settings–if we set up a POP email account, checked the box for manual setup, and then deliberately provided an incorrect password, the troubleshooting mode allowed us access to the necessary settings. Crazy!

Given that the process took the combined efforts of two Internet pioneers who have been involved with dozens of technology companies, I figured it would be worth documenting here for anyone else who runs into the problem. So if you’ve been searching for a way to set up a unified Microsoft Outlook inbox with multiple Gmail accounts using POP3, you’ve come to the right place:

  1. If two-factor authentication is enabled, log into the desired account, and set up an app-specific password.
    1. Google Account > Security
  2. In Outlook, add a new account
    1. Check “add manually”
    2. Enter the wrong password
    3. Hit cancel on the password dialog
    4. Click “Change Account Settings”
    5. Incoming
      1. Pop.gmail.com
      2. Port 995
      3. This server requires an encrypted connection (SSL/TLS)
    6. Outgoing
      1. Smtp.gmail.com
      2. Port 587
      3. Encryption method: Auto
    7. Message delivery
      1. Use an existing data file (select the PST you want to concentrate the emails in)
    8. In POP Account Settings, enter the correct password
      1. If you are using 2FA, you will enter the app-specific password here
  3. Before you hit Send/Receive, go to Outlook Account Settings
    1. Set mail settings to Leave a copy of messages on the server, and uncheck “Remove from server after”
  4. You might have to hit Send/Receive a number of times for Outlook to make it all the way through the current mail.

Be sure to thank Thomas Leavitt!

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