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.