Now from home

A few weeks ago, I posted my intention to move to Gmail all my email accounts. However, there was a problem when sending emails from a non-Gmail domain. Some email clients, like Outlook, add the “on behalf of’” string to those emails.

Fortunately, the Gmail dev team have added the possibility to send those emails using their own SMTP server, so the problem is gone now.

So today I’m moving all my email to Gmail. The process is really simple:

• Sign up into Google Apps for your domain
• Create your email addresses in Google Apps
• Change the MX records for email (Dreamhost even has a button to update them for you)

Because I plan to not use Outlook at all, I need to upload all my existing email messages to Gmail. Google has a tool called Google Email Uploader to do so. It can take a while to upload the email.

Also note that emails bigger than 16 MB are not uploaded.

Everything is going just fine so far.

Because I plan to upgrade to Windows 7 as soon as possible, I’ve thought that maybe it’s time to finally leave Outlook behind and move to Gmail. I’m not totally convinced as there are many features in Outlook that I use extensively. All of them exists on the “Google online only” world but I want to be sure that they will fit perfectly in my workflow before doing a definitive move.

For example, there’s an issue when sending emails from different (not Google) accounts in Gmail.

Gmail allows you to receive emails from multiple POP3 accounts and you can also select from which account you send emails; but there’s a gotcha. When someone receives an email sent by Gmail using a different account, not the Gmail one, they receive something like this in the sender field:

account@gmail.com; on behalf of; Jose [jose@otherdomain.com]

This of course is not what I expect. Google is aware of this situation and they’re trying to fix the issue by sending the email through the original SMTP server instead of using their own. It seems that if they use their SMTP server using an email address from another domain, most emails will end up on the spam folders.

I know it’s annoying, and we’re working to fix this "On Behalf Of"

behavior as soon as we can. As we’ve mentioned in our Help Center [1],

the reason we include your address in the headers at all is to help

prevent your mail from being flagged as spam by your recipients’ email

services. For those who want the technical details, we use the

‘Sender’ field to be consistent with DomainKeys [2], a commonly used

email authentication mechanism. If we didn’t do this, your messages

may get sent to your recipients’ spam folders, which would be worse

than the annoyance the current implementation is causing.

The ideal (but non-trivial) fix is to enable you to send mail through

your own ISP, while still allowing you to use the Gmail user

interface. This is the feature I mentioned above, and the one we’re

working on now.

I’m looking forward to see this problem fixed. I’d really love to manage all my email accounts from a single “online” place.