Well, I think I’ll have to ditch GMail’s hosted email completely because of the way that GMail handles conversations (i.e. threads and mailing lists). After switching Inversoft and Pontarelli email to Google, I realized that GMail IMAP has a huge problem handling email sent to mailing lists. Apparently, if you send an email to a mailing list, the GMail MX server doesn’t place that email into your inbox when the mailing list sends it back to you. This is usually done by mailing lists programs like mailman and elmzm to allow you to track an email thread correctly. If you don’t have your own messages in a threaded view, you won’t be able to determine who is replying to you or what emails you have replied to.

The reason they do this is because rather than managing the GMail conversation view based on the emails in a folder, it instead manages it based on the emails in the folder and the emails you have sent. This is pretty obviously not following the KISS methodology and is probably best dropped completely in favor of a more traditional approach to threaded views. Thunderbird 2.0 provides a pretty decent threaded view of any folder and I’ve never had any issues. This is completely handled using only the emails in that folder and Thunderbird doesn’t rely on you sending emails from Thunderbird in order to handle threaded views. This is pretty smart since in many cases you can send email from an account via different SMTP servers and different programs or web applications.

Here’s the note I sent to GMail support about this issue:

This issue is known, but I wanted to let you know that it is really painful and would be a good thing to fix. The issue is that email I send to a mailing list via the GMail SMTP server or my companies SMTP server do not show up in my GMail inbox ever. The mailing list daemon is sending the email to GMail’s MX server, however, since the email was sent by the account that is receiving the email, it is never put into my inbox. Here’s an example:

1. Open Thunderbird
2. Write an email to dev@struts.apache.org
3. Send the message via SMTP server at newton.inversoft.com
4. Apache’s elmzm daemon sends the email to all the list members including brian@pontarelli.com
5. GMail’s MX server receives the email from Apache’s elmzm daemon addressed to brian@pontarelli.com from dev@struts.apache.org
6. GMail’s MX server drops the message and doesn’t deliver it because it is addressed to the account it is receiving the message for.

This is a huge issue with IMAP support and makes using GMail extremely difficult because I cannot manage threads correctly from Thunderbird since I cannot see my replies or the root message if I started the thread.

Please fix this problem because it makes the entire hosted GMail solution unusable for anyone that uses mailing lists regularly (90% of my mail comes from mailing lists).

If you need more information about the issue or help testing, please feel free to contact me. For now I will have to switch over to another email hosting provider until this is fixed.

I really hope they fix this soon because with the Google hosted business solutions this is going to cause MAJOR issues for businesses that use mailing lists for internal communication.