Christopher Allan Webber at 2013-12-17T00:48:15Z
Found out that emails I'm sending from cwebber@dustycloud.org are hitting GMail users' spam folders. Not sure why, there's definitely a bunch of extra steps one can take to try to reduce the chance that gmail will blacklist your stuff, though it's kind of a black box as to why it happened. That's pretty frustrating.
This also makes me realize a few things:- email is an ancient, federated protocol, and email is not at all a new technology to free software, and deploying it right is hard. It's not just that new free network services are hard to deploy, these services are damned hard altogether.
- Gmail is a black box about this, as of course most Google servers are about everything. If this was a friend's server, I could ask them to show me what info they're getting from their spamassassin headers, or whatever, and I could use that to debug my mail setup. But since I'm only getting failures from GMail, I'm blind debugging.
- Once again, centralization begets centralization. I can't tell why GMail is spam-blocking my email, but I'm almost certain it wouldn't if I was sending it through GMail itself.
On the upside: I'm also convinced this is a solvable problem. We're seeing great strides on "easier deployment for sysadmins", and I really think we could build some layers on top of that. Not only could, but need to.
In the meanwhile, very stressful and depressing.Federico Bruni, pmate, Distopico, Claes Wallin (韋嘉誠) and 6 others likes this.
Claes Wallin (韋嘉誠) shared this.
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In the few mail hosting discussions recently we get these anecdotal polls on whether hosting is hard or easy.
$ nslookup -q=TXT dustycloud.org 8.8.4.4It's hard. I get it, and if you are reading this, there is a strong chance you get it, too. But when we get into the double-digit percentage of the population that can do an nslookup, I am going to gun for something else to focus on besides email.Christopher Allan Webber likes this.
I've had a similar problem in the past, now fixed.
Based on my experience, just an extra suggestion that I haven't seen mentioned thus far. Using DKIM signing might help as well --- as long as over time Google and other ISPs can learn that your signature is associated to a good reputation.
"apt-get install opendkim" is your friendStefano Zacchiroli at 2013-12-17T09:11:03Z
Christopher Allan Webber, sazius likes this.
You might want to add a SPF record to mediagoblin.org too - it hosts the mailing list after all :P
(Also, feel free to ping if you get stuck on anything. I love sysadmin stuff :D )
Matt Molyneaux at 2013-12-17T11:29:45Z
Christopher Allan Webber likes this.
@cwebber@identi.ca message headers on the Gmail side do include a line that indicates whether they think your MX records are set up properly. Not nearly as good as real debugging messages but it helps a little- email is an ancient, federated protocol, and email is not at all a new technology to free software, and deploying it right is hard. It's not just that new free network services are hard to deploy, these services are damned hard altogether.