What you are describing is what is known as "articulation work". To quote Suchman, "'Articulation work' names the continuous efforts required in order to bring together discontinuous elements - of organizations, of professional practices, of technologies - into working configurations". That makes it sound better than it is.
Ideally, your non-profit needs a decent webhost like Dreamhost that can transparently integrate with Google Mail and make the whole problem go away.
asmystiq wrote:
I configured Mail to use the work SMTP server to send messages from the Gmail account.
This is what is known as e-mail spoofing.
In the web Gmail interface, everything works smoothly.
Yes. Google is known for ignoring laws and facilitating any kind of network traffic, legitimate or not, in order to track activity and build value for its advertising business.
In Mail, even if the message was sent to workname@work.org, Mail replies show up with workname.work@gmail.com in the "From:" field
Yes. That is the way it is supposed to work.
I also set up a rule for redirecting Sent messages to Gmail and moving the original copies to Trash on the work account. In Lion, all was well and the replies indicated workname@work.org in the "From:" field and when I manually applied the rule to the Sent messages, they were sent to the Gmail account.
That's the "articulation work" in action.
I've looked at some of the discussion you linked (thank you for that) and found it enlighening, though I am not done reading all of it yet.
There are a number of different issues going on. Modern e-mail is extraordinarily complicated.
What I do now is not forward work email and keep the daily workflow focused on the Inbox of the workname@work.org account, which handles replies appropriately. I then set up a rule to redirect any mail from the work account that is over a day old to the Gmail account. I then organize it on the web interface (which is not optimal, but cuts down my time spent on the web interface from "always" to once daily or so).
You could probably improve that by creating folders in GMail from within Apple Mail. Once you move an old message from the work server to GMail where you have more room, you can have additional rules to move it around within GMail.
The only real, definitive solution is to have more room for e-mail. You should contact your system administrator and suggest switching to GMail or Microsoft's version. Everyone hates dealing with e-mail. That is why these transparent e-mail services are so popular. Once it gets setup, all the magic happens in the name servers and all anyone ever sees is "work.org". Plus, you will likely gain some additional functionality that Microsoft Exchange supports that older systems do not.
In the interim, the best solution is to show the "Reply-to:" field and put your "workname@work.org" address in there. Replies will be directed to that address but you will still have to move everything around after receipt. You should be able to configure your "work.org" e-mail system to automatically forward all you rmail to the GMail account. Combined with "Reply-to:", that is about as good as it is going to get.
If you need more clarification, let me know. Though I think that ML is behaving in a way that is not convenient and I don't see a way to create a hack to fix it. It seems like it would be an easy feature to add, but who knows what Apple folks are thinking...
What you have described is e-mail spoofing and Apple doesn't support that. No legitimate internet e-mail provider should support it. If Google does, then that is Google's problem. Most other e-mail servers would not allow that and that is why Apple doesn't support it. And, in general, Apple software is simply not very amenable to "hacks".
I have though about writing an Apple Mail plugin to automatically add a "Reply-to:" to certain e-mail messages. It will be a few months before I get time for that, so don't hold your breath.
