Solution May Take Patience

June 17, 2008 12:44 PM

Our company has been using Gmail’s SMTP servers without issue for the last couple years for sending our ecommerce clients emails that read “A customer has placed an online order on your web site. To access it go to https://www.sometime.com/.” - Well, this week Gmail started blocking our outgoing messages as spam.

Every time we send one of these emails, or anything similar to it, we get the following response from Gmail:
This is an automatically generated Delivery Status Notification

Delivery to the following recipient failed permanently:

[e-mail]

Technical details of permanent failure:
PERM_FAILURE: Message rejected. See http://mail.google.com/support/bin/answer.py?answer=69585 for more information.

This has been an issue for a lot of people as of late. We don’t have time to hope Gmail fixes their false positives issue, and need another solution ASAP. We send roughly 200 to 250 emails a day, to one recipient per email. We need a solution that isn’t going to blacklist us as spam before the message even leaves (Gmail) and isn’t going to be hit as spam when it hits the client’s inbox.

We have started looking into other solutions like Send Blaster and
Secure SMTP - any thoughts on these services, or perhaps a better service?

Ideas? Suggestions? Anything useful that may help us? Thank you in advanced.

posted by B(oYo)BIES to computers & internet (9 answers total)

Doesn't your website hosting provider provide some sort of email service?
posted by bitdamaged at 12:59 PM on June 17, 2008

Why are you sending these through gmail? You have absolutely no comeback because it's a free service.

Why not just use your own ISP's mail server? You shouldn't have any problem sending that kind of volume of mail, particularly if you talk to them about it first.

If that's not an option, why not set up your own mail server?
posted by standbythree at 1:02 PM on June 17, 2008 [1 favorite]

You are misunderstanding e-mail and how it should work. Do you have a technical contact? Someone who handles your network? Your internet provider? Contact that person and find out what SMTP server you can officially use, or set up your own.
posted by odinsdream at 1:08 PM on June 17, 2008

We use fastmail.fm for the sending of emails and despite sending quite a few emails out & despite the form-like nature of those emails, we get no spam related bounces from fastmail and very few spam-bounces in total. There's a minor cost, but given the quantities of email you send out, it's negligible.

odinsdream: Don't want to criticise too much, but wanting to use an external SMTP provider isn't such a stretch. We don't use our ISP's SMTP server because it's been blacklised by some mail providers & we haven't set up our own SMTP server because (a) it's outside our technical comfort zone and (b) a lot of people blacklist SMTP servers that exist in cable/adsl/etc IP blocks.
posted by seanyboy at 1:26 PM on June 17, 2008

seanyboy; perhaps I should have been clearer - you should use an SMTP server that you're authorized to use, not just one that happens to accept your mail for delivery, as Gmail apparently was doing for a time.

The first problem is that there's apparently little understanding that this was not the correct way to send mail; indicated by the tone of the question.

Second to that is choosing an SMTP server - which means either running your own or using one you pay for. One you pay for can either be the ISP's server provided for their customers' use, or a third-party mail service that you've also paid for.

Making these decisions is non-trivial, though, which is why I recommended that the questioner get in touch with someone more technical who can assist, preferably someone who's already assisting them with their inbound e-mail.
posted by odinsdream at 1:45 PM on June 17, 2008

POBox.com and listbox.com offer various hosted email services. If these responses are important to your business, it's probably a good idea to have a contractual relationship to support it (and the listbox rates look like they are in the $15 - $30 / month range)
posted by jenkinsEar at 2:34 PM on June 17, 2008

Setting and running up a full-blown mailserver is a huge PITA. But if it is just for outgoing mail, it's quite easy.

For example, on a linux distro with the 'yum' package manager you do:

yum install exim

Then make sure that reverse DNS works correctly. Usually this involves adding the fully qualified domain name (FQDN) to /etc/hosts.

Assuming your domain is: store.com and the server is: order1

127.0.0.1 order1.store.com order1


Type:

hostname -f

...and you should see a fully qualified name.

Then you can watch mail going out on /var/log/exim/main.log to see if anything is rejected.
posted by kamelhoecker at 3:02 PM on June 17, 2008

odinsdream I think you're making an assumption of facts not in evidence.

While I my domains are hosted elsewhere, I use Google for Mail (great web interface and pretty damn good spam blocking). I'm assuming that the OP is doing something same. Last I checked the Google SMTP server required a login for use.
posted by bitdamaged at 4:50 PM on June 17, 2008

I think the question is about an authorized GMail user -- maybe even a paid one -- having their messages rejected, which is definitely something Google should be fixing for its users.
posted by rokusan at 6:56 PM on June 17, 2008