Gmail woes

I am so pissed off right now. I decided to take on a little experiment, eschewing Outlook in favor of routing all of my e-mail through Gmail. Combined with auto forwarding, POP3 checking and the “send mail as” feature, this should have been a no-brainer. I should have been able to use Gmail as my mail hub without difficulty.

Should is the operative word here. The endeavor met with great difficulty.

As it turns out – and I’m certainly not the first to discover this – whenever you send via Gmail’s smtp server, it adds your Gmail address in the “sender” field of the e-mail header. Normally, this wouldn’t be a problem since the “from” field of the header would display the e-mail address you think you’re replying from.

For example, if I allow Gmail to send mail from my hypercrit.net address, the messages will come through with me@gmail.com in the “sender” field and me@hypercrit.net in the “from” field. Most e-mail programs display only the “from” field by default, keeping the “sender” field hidden, for the most part.

But as it turns out, Outlook has another way of doing things. Outlook displays any message I send via Gmail’s smtp server as “From me@gmail.com on behalf of me@hypercrit.net.” Apart from looking unprofessional, some people are now responding to my Gmail address rather than my hypercrit address.

(Oh, and of course most of the people I e-mail on a given day are using Outlook. Heck, most of the business world uses Outlook, so they’re all seeing my unprofessional address.)

This feature is well-documented and has been complained about for years. It’s in place to prevent spam from being marked with Gmail headers and therefore earning the trust of your e-mail program. But this feature also – almost with no warning – gives your private Gmail address to people. Not cool.

The only warning I could find from Google is on the help page related to the “send mail from” feature, where the note about “on behalf of” is relegated to the last paragraph.

I know that Gmail will not get rid of this feature; the service says it’s obeying some arcane industry standard e-mail regulation (one that no other major service adheres to – them’s principles for you), and I’m sure it really does reduce the amount of spam sent via Gmail and forged headers.

Tell you what I’d like to see: A bit of text that warns you of this possibility when you elect to add a “send mail from” address to Gmail in the first place. It would save a lot of people a lot of headaches.

Meanwhile, I must continue to use Outlook to manage my mail, which sucks. Really sucks. Or I could generate a Gmail account for each of the addresses I want to send from and then add them all to a desktop client. (Do you have any idea how hard it is to get a professional-looking Gmail username these days?) (Oh, and since one of my e-mail accounts is on an Exchange server, it makes using any e-mail program other than Outlook mighty difficult.)

Considering that my whole point here was to avoid having to use a desktop client in the first place, I’d call this little experiment a total and utter failure. I am chained to Outlook it seems, at least until my business makes the switch to Gmail later this year.

I’m counting the days, but inwardly, I know I’ll still wind up checking everything through a desktop client anyhow. Sigh.

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