Switching camps from Outlook to Gmail

Today we review something you probably already use: Gmail, but in a specific context. Let me explain.

I have active Gmail, Yahoo and Outlook accounts as well as three IMAP accounts from my start-ups. If you’re an entrepreneur, you probably have a similar set-up. I used Outlook to manage all these inboxes.

The problem was that spam became uncontrollable, specifically for my three IMAP accounts and for Yahoo. I tried putting spam assassins on the server level; local filters on the local level; all for naught. I continued to get abused by Viagra pills, Nigerian despots, lonely women and all the other clever variations spammers use. It was overwhelming.

I always thought Gmail was amazing at beating spam. So I decided to route everything through Gmail so Google can filter out spam for all my accounts. I can then continue to use Outlook to manage this cleansed mail.

Here’s what I did:


Imported all the accounts into gmail.com via Settings > Accounts and Imports.

Created a label for each so they appear as their own mailbox on Outlook. The method to do that is Settings > Filter > Create new filter. For example, for all emails with yahoo.com in the to: field, direct into the corresponding label.

Kept the default Gmail setup for different tabs: Primary, Social, Promotions, Updates and Forum. These tabs work really well, and after importing all my emails they in turn were automatically organized around those tabs.

In case you’re not familiar, Gmail analyzes whether an email is from a social network or forum, an ad, or spam, and then categorizes them accordingly into these tabs. This isolates the mail that are important (i.e. Primary) and you can glance through the rest whenever you want. This system works superbly.


The problem however is that mail clients like Outlook don’t support Gmail tabs, and thus I wouldn’t be able to access the Primary tab. Without it, the inbox I get on Outlook contains everything, including for example the ads already categorized under Promotions. This defeats the purpose of the whole exercise!

Fortunately, there’s a hack around it: create a label to mirror the Primary tab. Filter all emails that match Category:Primary and direct to the new label. Via this label, I can now effectively access the Primary tab from any mail client.

Gmail takes its sweet time to import mail. Presumably, because Google has to scan emails so they can categorize them correctly (and figure out what ads to display, but whatever).

outlook3On clients like Outlook, Gmail is the only account needed. All the other emails you’ve imported with their corresponding labels will appear through it. On mobile, I can now actually use the native Gmail app, which of course does support tabs.

After a week of use, I’m happy to report that spam is mostly eradicated. I say mostly because Gmail does not do a complete job detecting spam of Chinese origins.

Switching to Gmail made a huge difference on mobile. Now, when I get an email notification I’m more likely to check it, and it’s far easier to keep track of what I need to read now that my inbox is not flooded by spam.

There are important drawbacks, however. The biggest is that Gmail doesn’t play well with Outlook. Three problems:

1) Outlook is slow at indexing and displaying Gmail;

2) Mail sorted by time is actually time received, which is the time you imported all those emails into Gmail and not the time they were actually received. You can fix this by sorting by time sent, but then you can’t group emails by conversation on Outlook;

3) When you send email from Outlook, you have to always specify who it’s from unless you’re comfortable with the default.

I suspect all local clients, not just Outlook, have these three annoying problems. I actually gave up using Outlook on an older PC because it was too slow and just used gmail.com instead.

If you’re an Outlook addict, you may not want to follow in my footsteps.

The other drawback is that Yahoo also doesn’t work well with Gmail. Fetching Yahoo mail is rife with errors and delays. Gmail will often say it encountered server or authentication errors when it tries to fetch from Yahoo. So Yahoo mail that I received yesterday may only appear today on Gmail. I’m OK with this as my Yahoo mail is typically used to register for apps and websites, but your situation may be different.


Overall, I’m happy with the switch. I’m disappointed I stopped using Outlook – it’s more fully featured than Gmail, and the calendar integration is leaps ahead – but defeating spam is worth the price.

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