This is irony, man. My last post talked about how entrenched in the Google empire I’ve become, and my disappointment when Gmail gets hung up, as it tends to do (from time to time). Every single thing in that post is true – including the part where I said that Gmail has changed the way I handle e-mail.

Gmail has an achilles heel.

I hate to say it, but I recently discovered this massive problem with Gmail, and it’s prompted me to go back to webmail roots…with Yahoo! Mail. Before I get into that, let me get into the nuts and bolts of this issue I’ve got with Gmail.

One of the things that I blogged about before was my need to send e-mail from multiple e-mail accounts, and Gmail provides this feature. You can add numerous e-mail accounts, and when you’re sending messages, choose one of those accounts to send “from.”

Thus, for the last several months, I’ve been using Gmail for ALL of my accounts – personal and work…and it’s been fantastic. Until I discovered that Gmail messages, when sent “from” an account other than Gmail, show up like this in the recipient’s inbox (especially in Outlook):

From: myusername@gmail.com on behalf of selectedaccount@workdomain.com

Unfortunately, this is a major problem when it comes to professionalism, and it’s a problem for those of us who don’t necessarily want our Gmail addresses being shared directly with recipients. Stupidly, I’ve been using this feature for months without realizing that it was appearing this way.

Yahoo! Mail offers to the same functionality, but apparently, without the whole “on behalf of” nightmare. So I’m giving Yahoo! Mail Beta a try for 30 days. If the transition doesn’t have me sleepless at night, dreaming labels, this could be my solution.

I’m extremely disappointed that Google has decided to implement this “feature,” and that it’s not as readily obvious as it should be. If you’re using Gmail in this way, beware.

I’ll keep the updates coming on my transition…