Technology & MSG

I use Mailman to provide mailing list services to friends, family, and non-profit groups in addition to running a few administrative lists. Doing so has recently exposed a problem with Gmail’s mail delivery.

I created a mailing list for Ben, who wants to try Mailman out for his church. I set him up as the administrator of the list using his Gmail address. He received the “your new mailing list” email from Mailman and changed the default password using the URL supplied in the email. He added a few subsribers to the list for testing, including his Gmail address. He sent out a test message to the list.

He never receives it. Weird. He calls me over and I try to help with the troubleshooting. We figured there were three possible issues; we would attempt to troubleshoot each.

1. Mailman
2. Postfix
3. Gmail

Mailman

We verify that “not metoo” is not set. It isn’t. If set, the flag would instruct Mailman not to send a copy of the email to the individual who sent it.

We check the archives. His test message is there. It is clear that Mailman received his email and processed it.

I check the Mailman logs. Nothing is out of the ordinary. I see his post in the post log. There’s nothing of substance in error, vette, smtp-failure, or any other log.

We enable the “ack” flag for his account. He sends another test message and receives the acknowledgement from Mailman, but not the post itself.

We change the administrator of the list to an alternate account. I’ve been the administrator and a subscriber of a list without problems before, but we figured we’d cover all the bases. It didn’t help; Ben still couldn’t receive list posts.

Postfix

I check the Postfix logs. For his initial email, I see Postfix receive the message and send it to Mailman. I see Mailman send a message to several recipients, including Ben’s Gmail account. I see Gmail accept the message without error.

So if Gmail accepts the message, where’d the email go?

Gmail

The missing messages aren’t in his Spam folder.

I have a Gmail account that has come in handy from time to time for testing and general use, but I certainly don’t depend on it for reliable mail delivery. That being said, I personally have never had a problem with my Gmail account. So we subscribe my Gmail account to his list. I receive welcome messages and list posts from his list.

Now, all list posts have the following header set.

Precedence: list

Welcome messages and such have the following headers set.

Precedence: bulk
X-List-Administrivia: yes

Now I’d say that his account (for some reason) is not accepting list traffic with the Precedence: list header set… but only for this list.

Here’s the rub. Ben is subscribed to one of my other lists that runs from the exact same server. My list is configured the same way as his, except that he receives posts from my list.

Closure?

Here’s the facts, all summarized in tidy fashion. Ben’s Gmail account:

• cannot receive list traffic from his mailing list
• can receive administrative traffic from his mailing list
• can receive list traffic from other lists served from the same host
• is not bouncing; Gmail servers are accepting email that my hosts sends to Ben

It’s important to note that my Gmail account is not affected in any work. All email traffic arrives and is accounted for.

There’s been news of late regarding Gmail losing email, but this seems to be a different problem. It’s not like the emails were delivered then lost; it’s likely that they aren’t being delivered at all.

Ben is going to email Google and inquire about this behavior. The bottom line is that Gmail — despite how people use it and how cool they think it is — is still a beta product and shouldn’t be handled as if it were production.

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