The Ultimate Guide to Synchronizing Gmail and Outlook

Synchronized Swimming

Synchronized Swimming

I love Gmail and I love outlook. While I suspect in the end I’ll be able to use just Gmail web-based interface there are still huge productivity gains for outlook.

What I really want is the ability to use both at the same time when all my data is in sync, including folders, contacts etc.

The problem is that both companies don’t have any interest in making the combo work well. Microsoft wants to sell expensive exchange servers and Google wants every one to move into Chrome\ChromeOS world.

In theory one can use either IMAP, POP3 or Google Apps Sync to get this task done. I have tried all of them, but now I think I found the holly grail.

1. POP3 + SMTP

Using POP3 to get all the messages form google works pretty well in terms of performance. the problem is that the synchronization is only one way from Gmail to Outlook.  Moreover, Gmail ignores POP3 instructions to delete the emails that ere downloaded. It always keeps ALL the emails in Gmail, even if they have been downloaded. This configuration works well if you want to

  • Gmail is backup for Outlook
  • Do fast searches in Gmail
  • Use Gmail web-based interface when your own laptop is not available

However, Gmail can’t be my main client, because I’m a heavy folders user (300 now) and my Inbox is only for open items ( less than 200 on most days).

Another problem is that contacts and calendar are not synchronized. while Gmail support iCal format, it is a one way sync again.

Also notice that if you do send items from Gmail, they appear in your outlook Inbox folder, and not in your Sent Items folder. So in this scenario Outlook is my productivity tool and Gmail is backup. BTW, Gmail actually works with POP3S and SMTPS , which is a nice touch of security.

2. IMAP + Google – Since IMAP

Allows synchronizing folders it should have been the final solution. Unfortunately there are two huge problems:

  • IMAP is just a bad protocol, lots of bandwidth usage among other problems.
  • Microsoft support for IMAP in Outlook 2003 was probably given to the worst programmers in the company. They did such a horrible job, that one suspects  Microsoft decided to keep the code unchanged for 2007 :). Seriously, it seems that Microsoft did IMAP support just for the record. Crashes and slowness are the common symptoms.  It is no wonder as the big money is from Exchange servers. I guess this is also why they killed Outlook Express.

3. The Solution that works for me

Google Apps Sync + Better Gmail 2.0 Plugin +  Windows Desktop Search + some configuration tweaks.

Google Apps Sync for Outlook is a client side application that google wrote that uses a proprietary protocol instead of IMAP. The result is a very smooth synchronized operation and an almost flawless migration process of 7GB account with 16,00 items in the biggest folder.

With better Gmail 2.0 one can make the folders show up in a tree structure (but drag-and-drop is lost). The other option is to add “Go to label” from Google Labs, which is a must have if one has 300 folders.

Under Gmail->Settings Turn “No snippets” On, so the inbox looks cleaner, like in Outlook.

The pros:

  • It uses a separate Outlook profile, so it is possible to get back to the old one.
  • Mail, folders, Contacts and Calender are all synchronized both ways.
  • Performance is pretty good and there is little CPU consumption on the client.
  • If one changes his mind , he can continue with either option at any time.
  • Seems like Google are updating the tool, the last version is better than earlier ones.

The cons:

  • Google Apps requires  Premier Edition. This basically means $50 per year per user.
  • Despite the $50 per user Google hates to give support. If something goes wrong, It is praying and debugging time.
  • Although my Migration progressed really well for three days. I had a horrible experience in the end. My client CPU kept going up to %100. The Google App Sync has almost no UI, so it is next to impossible to understand the problem or fix it.  Google almost refuses to let customers intact with human and keep pushing to the web-based support which was not helpful. Even after I finally got a human response, it was very slow and clueless. For seven days my email productivity was very low. As a result, I was forced to use Gmail on FireFox instead of outlook, which led to some pretty wild conspiracy theories. In the end I found the solution. It turns out Gmail App Sync can not migrate messages over 20MB, once I deleted those everything seems to be in order.
  • Since GAS created a new profile one needs to redefine filtering rules, preferences, signatures and similar configurations.
  • In Solution #2 Deleted messages are never really deleted , as Gmail acts as super backup. In this solution they are really deleted in both sides.
  • Google recommends to synchronize only 1GB of data. I’m still not sure exactly what it means.

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3 Responses to “The Ultimate Guide to Synchronizing Gmail and Outlook”

  1. Free Malware Removal Support Says:

    Just like, I love Gmail and I love outlook too. Thanks for this post, its very useful and it provides valuable information about outlook, gmail, pop3 etc.

  2. Matt Says:

    Hi there,

    Trying to implement Gmail/google apps in our office, would love to pick your brain a little further over your experience….

    Right now I’ve got some high level (lots of folders) users utilizing IMAP/GMAIL …. unfortunately its not GASMO …. would love to implement premier but getting some puch back to do to the issues created by imap and outlook and gmail *shakes fist*.

    So yes … would love to correspond a bit if you have the chance.



  3. Simon Cross Says:

    I have an office gmail account for email but always use outlook (2003). My problem is when I move an email from either my inbox or sent bos to a specific subject folder the contents does not show in the new folder until I separately go to the folder and highlight it – it then takes a few moments to what I can only assume is to download to the new location. Help please. (the email which does not have these problems)

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