Nicholas Skinner

Freelance website and web application developer

Switching to GMail – GMail Pros and Cons

Outlook / GMail LogosI have been growing increasing frustrated with Microsoft Outlook which I have been using as my primary email client since around 2000.

  • Often crashes, especially if used with IMAP accounts.
  • Never shuts down properly (.pst files are ~2.5GB).
  • Searching is very poor / slow.
  • Generally does not seem to be very fast.

Switching to another application was therefore not a decision I took lightly, especially since with a number of different accounts (I am involved in a number of different businesses), it is handy managing them all in one place. Another reason for switching however was that they are mostly all POP3 accounts, and I recently purchased an iPhone which works better with IMAP than POP3.

I considered Zimbra however although there are hosted solutions available for individual users it does not seem to be primarily aimed at that market. I therefore decided to go with Google Apps. Google Apps supports using your own domain name e.g. “” rather than “”, along with calendar, and contact syncing to the iPhone. To set it up you just need to signup and switch over your MX records to Googles servers / verify you own the domain with Google (either setup a CNAME record or put a text file on your web server).

I am still in the process of moving over accounts to GMail and have moved 4 so far. I was hoping to just have a single GMail account however in the end this has not worked out. GMail does allow you to add multiple addresses to “Send mail as” and has a “Reply from the same address to which the message was sent” feature however some email clients such as Outlook 2007 will show “From on behalf of” which does not look particularly professional. The other issue is that the iPhone does not seem to allow setting up multiple senders.

I have therefore currently setup two Google Apps accounts, one for my main email and 1 for my other 3 businesses. They are all liked in some way therefore it is not too much of an issue for mail to show the “on behalf of” line.

Setting up multiple Google Apps accounts I was expecting that cookies may prove to be an issue i.e. I might have to keep signing in/out of different accounts (or use the Firefox Profiles workaround) as you would if you have multiple regular Google Accounts, however it turns out this is not the case as cookies are handled on a path level / you login at e.g. “”

Setting up multiple GMail accounts however then leads to another problem, GMail Notifier only supports a single account. I am therefore planning on setting these account up in Thunderbird and running it just to get the desktop notifications (i.e. I will see the notification then login to webmail to take advantage of conversation view / searching etc).

I have been using GMail for a few weeks now and on the whole am very happy with it however there are a few issues I have experienced regarding sending executable program files via email, and backing up email.

GMail does not support sending or receiving .exe files via email, even in .zip files therefore I have resorted to setting up a send only account in Outlook for sending messages although have not yet found a way around the receiving issue (luckily however I generally do not receive many .exe attachments via email).

In terms of backups I looked into a few options however am not sure there is a perfect solution available at the moment. A common solution seems to be running Thunderbird and using the Work Offline Synchronise feature but this did not seem too elegant to me. I therefore looked into a few software applications.

  • MailStore – Looks like the best however does not support automatic backups (scheduling) in the free version (paid version is 349 USD).
  • Forwarding messages to another POP3 account, or using e.g. Fetchmail to retrieve them via POP3 is a possibility however does not preserve labels or sent items.
  • g-archiver – A viable option however after their recent issue with sending peoples passwords to one of their developers I thought it was best to avoid.
  • GMail Backup – I chose to use this in the end. It can be used from the command line and therefore easily scheduled however does seem to store messages with long names (as separate files) in a single folder which is not particularly ideal as I now have a folder with +6,000 files (mail for around 1 year as when switching to GMail I imported mail from Outlook) that is not great from a performance point of view.

One Response to “Switching to GMail – GMail Pros and Cons”

  1. Backing Up Gmail Accounts (Part 2) - Nicholas Skinner’s Blog Says:

    […] to Gmail in 2009 I have been trying to find a reliable long term backup solution. First I used GMail Backup (but it had problems with large folders, and setting messages as read), then switched to Gmail […]

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