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Ask YC: What do you use for outbound email sending?

54 points by terpua ↗ HN
I need to send out automated emails to users (e.g. invitations, share notices, etc.) and want to guarantee that recipients don't receive them in their spam folder.

I can minimize by utilizing SPF/DK/DKIM but it's not a guarantee. Services like Port25 that specialize in outbound MTA is quite expensive.

What do you guys use/suggest?

48 comments

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ComputerGuru
Depending on how much you're sending out and to how many people; Google Apps is a good choice.
bretthoerner
I realize you said it depends, but did they lesson the limit of 500 outgoing per account per day?

That's pretty low for any service, and a total hassle to create a bunch of fake user accounts and keep track of how much they've sent today while round robin-ing around "as many accounts as I hope I'll need today".

chaostheory
I think that's the for the free version. There's now a paid version. It's not cheap depending on how many email accounts you need for your startup ($50/year per email account), but it will give you a reliable email provider that gets you through a lot of spam bins

It's good to note to that you can do aliases for each account too

terpua
Guestimating around 100K+ per month initially. Google Apps Premier allows 2000 per day per user. Which isn't bad for $50/year. That is not a bad option but quite manual.

Authsmtp seems pricey in comparison.

ComputerGuru
I'm not sure what you mean by "quite manual?"

You just need to set up the Google Apps service manually; everything else (including creating accounts, new addresses, sending emails, creating email aliases, etc.) is fully "automatable" via their API; with wrappers available in Python, PHP, C++, Java, Ruby, Perl, and more....

terpua
I mean to say that if you need additional quota, you have to sign up/add a new account. It's one of those "you-wish-it-was-automated" thing.
evaneykelen
Try campaignmonitor.com. These guys rock (and no, I'm not affiliated with them).
terpua
CM focuses more on newsletter management, rather than automated emails like confirmations, invites, etc.
whycombo
Campaignmonitor seems to be "permission based", so you cannot send out Invites since invitees gave no permission. A current user deciding to invite another doesn't cut it as "permission".

If permission based is OK for your needs, AWeber is top of the line (www.aweber.com)

Here's a similar discussion: http://news.ycombinator.com/item?id=190633

plusbryan
I second this. Crazy expensive for large lists, but it worked like a charm.
epi0Bauqu
I would advise doing it yourself. It isn't that hard, and assuming email is an integral part of your service, I wouldn't trust anyone else with it.

In terms of specifics, I like qmail. In terms of spam management, there are lots of things to do. First and foremost, have daily monitors on all the major email providers. Get on all their feedback loops. I've found that contacting them with problems is annoying, but does work if you are following all their guidelines and are persistent about it.

metajack
Doing it yourself is hard, especially if you want any hope of getting past the major email providers spam filters. We deal with this every day.

Current stats say that our % of users who have signed up that make it through email confirmation step is about 22%.

Around 33% or so of our signups have yahoo.com addresses, and only about 12% of those manage email confirmation.

It is similarly bad for hotmail. GMail used to be quite good, but has slowly gotten worse over time.

I'd be very curious to know if others are measuring these things, and how you are doing. Feel free to contact me directly as well.

swombat
That sounds unreasonably low. You might have a different problem than just spam filters.

I've worked on several business that had to send confirmation emails (via our own servers), and the figures were never anywhere near as bad.

If there is any way that your users can benefit from signing up other users (e.g. if you run an MLM site), you might want to look into whether your stats are not being falsified by a few users submitting vast numbers of email addresses into your system.

metajack
I think it's unreasonably low too, but haven't figured out a way to solve it.

You can benefit by signing up other users, but this is not a very often used feature. It's not an MLM site, but a subscription chess service.

We track signups by ip and by browser cookies, so we're reasonable sure these are distinct people. Since we switched to the freemium model, there is little incentive for people to make duplicate accounts now, so I was hoping to see activation go up.

We do domainkeys and SPF and I have gone around the block with hotmail two times already.

We send approximately 25k emails a month, the bulk of which are sending out confirmation emails to people that signed up, and then a thank you for those that confirm. The rest are forgot password emails and invites.

epi0Bauqu
Following the above, I was relatively spam free for about 3 and half years. At the high point of my last company, I was sending about a million messages a day. There would be spam flare ups of course, but I would get them resolved through persistent contacting of support staff. Now that I have essentially no users in comparison :), I'm not sending hardly anything, but I'm still monitoring and am not having any spam problems.

In my new services, I did have issues originally, especially on Gmail. So there was an initial ramp up with spam issues on the majors. But like I said, after following all their rules and then persistently hounding their support staff to investigate, I've gotten past their filters.

SwellJoe
We've sent our own mailings out on a couple of occasions (to 4000 and 8000 users, respectively). And I've done it more often in the past, though for smaller numbers. I haven't had a bad experience doing it myself. A number of our customers are doing it regularly with phpList or poMMo.

There are a few things you have to get right (DNS including a PTR for your IP, SPF and now DKIM, RFC compliance in your server and configuration), but once that's done, bounce rate will be nearly as low as the quality of your list allows. Hitting the spam filters isn't all that bad either--assuming your message isn't spammy on other counts.

One other thing to be wary of: Sending to the same domain many times in rapid succession. Be sure you're not sending more than one or two messages at a time to Gmail or Yahoo or Hotmail (or any single server). So, randomize the list, and sleep for a second or two between each send, or something, to insure that there are pauses.

Oh, and at least Google's spam filters are reputation-based (and probably many others are, as well). The looser you play with the "opt in" requirement, the more likely you are to be flagged as spam by your recipients. It only takes a few to get your future mailings dumped into the spam folder. At that point your server itself is poisoned from sending to that destination for a while. So, make sure your recipients actually want what you're sending them.

fugue88
The default qmail install will accept and queue incoming messages for accounts that don't exist on the system, and bounce them later (usually to an unrelated, innocent address) if the account isn't created.

Did you do anything in your installations to address that problem? If so, what was it?

epi0Bauqu
Yes. Use the default alias to send all non-account email to /dev/null, and also set doublebounceto to /dev/null.
cmer
First of all, I'd advice NOT doing it yourself. (sorry epi0Bauqu).

Spammers ruined email and it can now be pretty hard to pass some spam filters. Of course, 95% of your emails will make it through if you do it yourself, but the last few % can be hard to get.

I recently started sending through Fastmail.fm for our website and it's been working fine. I simply setup sSmtp on our servers and everything that is sent through Sendmail is now relayed through Fastmail.

Another company I've considered is authsmtp.com. I haven't tried them, but their pricing seems to be very reasonable. The reason I didn't go with them is that I already had a Fastmail account (and I hate paying twice for the same thing ;-) )

We did Gmail before, but setuping Postfix to relay through them can be a major pain (mainly because of the way they authenticate). Fastmail (and I assume authsmtp) was a no-brainer.

Another thing that will help delivery tremendously is SPF. Make sure to set it properly (with hard fail if possible, ie: -all).

Good luck!

epi0Bauqu
No problem, I'm used to being contrarian.

Hard fail can send people who use email forwarding to their spam folders.

martian
+1 SPF. It helps a lot with the major email providers, and it's super easy to configure.
eng
My business relies heavily on e-mail (we send e-mail proposals on behalf of hotels to their customers), and we use AuthSMTP (http://authsmtp.com). $168/year buys you 10000 outbound e-mails per month.

That said, guaranteeing 100% success with the delivery of e-mail is pretty much impossible. You just can't control what the recipient has installed in terms of mail client, spam filtering software.

art_wells
I use SPF from a slicehost IP for membership confirmations, more-than daily mailings to most members, and occasional announcements. No reported failures yet and all my tests have worked. I figured hitting a large percentage was enough. When volumes get high enough, I'll worry about what could only be a very small percent of failures.
dcurtis
VerticalResponse.com works pretty well for sending out email campaigns.
josefresco
For newsletters, ConstantContact.com is THE standard and what I recommend to all my clients. They make sure that ISP's don't block your email, report on bounces, spam reports and provide statistics on opens, click-throughs etc.
andrewparker
Whatever provider you decide to use (and whether or not you decide to host it yourself or use an ESP), you should:

A) be sending from your own dedicated IP address (so that spammers sharing your IP address don't cause all your email to go to spam) and

B) work with a deliverability provider such as ReturnPath or Habeas.

AdamM
I'm working on an application where I need to send emails to 10,000+ users. The emails can be sent: multiple times per day, daily, weekly, or other. The content of EACH email is completely custom HTML (not swappable fields, but sort of like a custom RSS feed in an email.)

Can anyone suggest a solution that allows tracking of opens, bounce backs, and other standard metrics?

jaxn
EmailLabs has all of the traditional email marketing features (like the tracking that you want), but has a good API to allow your application to interact with them. I chose EmailLabs at an ecommerce company that I used to work with.
bprater
I've known the CEO of Aweber.com for years, and he strives to create a competitive service. They work very hard on deliverability and have connections to the big ISPs to deal with on-going issues. Good folks, check 'em out.
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cpr
I'd say get your own dedicated host with your own IP address, and use normal outgoing mail. (I use a colocated Xserve G5 with Postfix, which is a great system.)

As long as your SMTP server is reasonably secure (you can run simple blacklist tests on it from various sites), you shouldn't get caught by IP-based spam filters, and then it's just a question of whether your content looks spammy to your recipients' mail systems. That's unrelated to how you're delivering the email, so it's the same problem no matter what you're using to send.

lr
Why not use Google Apps for your domain (it includes email!)? I know they don't delete email, which is bad, but I'm willing to take that risk instead of running my own mail system. It is a piece of cake to set up, and they offer mailing lists, too!
scott_s
What makes you think you're not spending spam?

I'm not being glib. Really ask yourself if it's necessary to email this information to users. If I get email from a company and I don't want it, I don't like your company. If your company has information that you think is important to me, notify me next time I log in. Let me determine whether or not it's important.

terpua
It's information typically requested by a user (e.g. forgot password, register confirmation, etc.).
bayes
You must be running quite a big site if you're sending out 100k+ per month messages on forgotten passwords and registration confirmation.
terpua
Plus invitations, message notices, etc.
scott_s
Invitations and message notices are exactly what I was talking about.
jfornear
I was just trying to figure this out today myself. Very helpful discussion as usual. I love this site.
nbarr
Fastmail is an excellent service as has been suggested. Another you might consider is Rollernet.us.