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We're running into some trouble with our email being marked as spam. We are looking for a web service to provide the solution.

It seems that services like MailChimp & Campaign Monitor focus primarily on sending large amounts of similar marketing emails. The nature of our emails is different however: it's only being sent to people that we know personally and are paying us. An "unsubscribe" link is not applicable either, since there is no "list", the emails are sent on-demand by users.

Also, they seem to be focussed on marketing/design. We have the developers, we just want to outsource the delivery problem.

In addition, we have very few emails. However, they may contain sensitive data (password resets, invoices) and may be quite large per email (in the case of invoices). Being able to send attachments is also a requirement.

Can you recommend a service that fits these needs?

EDIT: added "web service" as per comments.

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migrated from superuser.com Jun 15 '11 at 11:16

This question came from our site for computer enthusiasts and power users.

    
Meh... all this segmentation in the Stack Exchange platforms feels completely unnatural to me. Anyway, I guess we should be on webapps.SE –  Klaas van Schelven Jun 15 '11 at 11:04
    
Don't worry, it was just a pointer. The thing is, the question is definitely not about computer hardware or software, and if you need a web service, please just add that to your question and flag for a moderator to migrate it. –  slhck Jun 15 '11 at 11:06
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4 Answers

up vote 3 down vote accepted

You have quite a few solutions at your disposal that all specialize (or at least focus on) transactional emails: the emails driven by user generated action on your web site or app.

For your needs specifically (email over TLS for security, able to add attachments, get your emails to the inbox) here are your choices:

As far as I know, most of these services will offer you what you are looking for. Specifically for PostageApp, we are in private testing of our delivery service (happy to bring you on board if you're pure transactional) and we utilize TLS for security and you can easily add attachments. In addition, we have an auto-flattening template editor that you can write in HTML and CSS (great for most devs) as well as a very well-designed backend.

Definitely let me know if you have questions about any of the services, happy to help point you in the right direction!

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+1 A good selection of available services. Also +1 for disclosure and the fact the your entire post isn't all about your product. –  Barry Jun 15 '11 at 17:37
    
I'll accept your answer as it gives a more or less full list. –  Klaas van Schelven Jun 16 '11 at 7:12
    
For good measure, there's also "critsend", though I'm not sure about it's maturity. –  Klaas van Schelven Jun 16 '11 at 7:12
    
In the past, I have included Critsend into the mix, but I haven't seen (first hand or second hand) anyone actually USE Critsend, nor do I know anyone who's gotten a beta account. So yeah, YMMV, but it's an option. –  JonLim Jun 16 '11 at 18:02
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Couple things you might want to have a look at first, before outsourcing, are:

Making sure that your email headers are properly formatted, including proper CRLF and Return-Path and Reply-To headers.

Make sure you send from a real email address through your SMTP server, rather than just from the sendmail program on your host.

Try some of these ideas.

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We went with

https://postmarkapp.com/

The keyword I was looking for is "transactional email", as opposed to bulk email, which they do not allow.

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This will take some development effort, but Amazon has a service and the first 10k emails a month are free, with the next 100,000 being $2 (hard to beat). Not sure it's exactly what you're looking for, but worth checking out.

Just to be clear, is it an email formatting issue, or are your servers getting black-listed? This may not solve your problem if it's a formatting issue. Amazon is going to send exactly what you ask it to.

http://aws.amazon.com/sns/

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