Outgoing Mail from the Web server

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The web-server needs to send mail to provide acknowledgements and notifications related to registrations, to send lost usernames and passwords and to send newsletters.

Sending mail reliably has becoming more challenging in recent years with recipients aggressively blocking perceived SPAM, so NeatClubs has needed to evolve accordingly.

The sections that follow explain the issues involved in sending bulk-mail and offer solutions contrasting the "pros and cons" of each.

1. What is the issue? Why is this so complicated?

2. What are my choices and what are the "pros and cons"

3. Once I've decided on an approach, how to I setup my mail?

 

1. What's the issue? Why is this so complicated?

In the early days of the internet, mail protocols were designed such that senders were "trusted".

It was common to have people relaying mail through internet hosts with no need for usernames or passwords.

With the commercialization of the internet however, policies have needed to be tightened considerably. Part of what makes the problem complex is the need to maintain backward compatibility with existing internet software and services.

SPAM has emerged as a major challenge for all commercial internet service providers (ISP).  While policies vary, most have changed their practices in recent years to combat SPAM. Among the steps that providers take are:

1.Protecting their mail-servers with firewalls to make sure that only people connecting from their own network can access mail servers (ISPs commonly block port 25 for example, used by SMTP to those outside their network)
2.Providers increasingly require that connections be "authenticated" with strong usernames and passwords.
3.Providers may use SPAM filtering software to intelligently filter e-mail.
4.They may use external service providers offering RBL services (reputation based lists) and refuse to accept connections from mailers that 3rd parties view as unreliable.
5.Large mail providers often provide tools that allow their users to classify mail as SPAM, and if enough users tag a sender as a suspected spammer, the ISP may refuse to deliver mail too all recipients on their network from a suspect bad sender.
6.Large mail receivers use a variety of other techniques such as performing reverse DNS lookups to decide whether the sender is "big" and more likely to have proper security measures in place and be trustworthy. They may also look for the frequency of invalid e-mail addresses coming from a sender, and if they see multiple messages to non-existing mailboxes, they may assume that a sender is attempting to guess mail names, making the sender look like a spammer and be likely to be blocked.

Because of the issues above, unless every customer is setup on their own unique IP address with their own unique mail-server, it becomes virtually impossible to guarantee reliable mail.

If "customer A" on a server sends a newsletter to an address list that contains a dozen or so no longer valid aol.com accounts (as a real example), AOL are likely to ban the originating IP from sending e-mail thereby affecting all other customers with a hosted web-site on the same machine. As a result, poor practices on the part of one customer on a shared service can effect others.

If "customer B" sends what they think is an appropriate e-mail, but some receivers view it as "spammy", an ISP or RBL provider may decide that the sender is to be temporarily blacklisted, also affecting delivery for everyone.

Finally - some ISPs will tolerate a limited volume of e-mail from a sender, but if the volume becomes large, they become more rigorous in their requirements, sometimes performing reverse look-ups on IP address and refusing to accept mail from senders where the "from" addresses does not match the reverse DNS lookup.  In the case of a NeatClubs.COM customer running "myclub.com" a reverse DNS lookup will yield an address like "neatworx.com". ISPs generally create exceptions to these rules for large, established bulk-mailers whom they view as more trustworthy.

You get the picture! These issues and more affect mail delivery and they are changing all the time and vary for ever receiver of mail.

2. What are my choices and what are the "pros and cons"

Fortunately there are choices. The NeatClubs.COM software has been designed to be flexible in how mail is configured. The table below explains the different options for sending mail from the web-server, cost implications, and their pros and cons. It should be noted that people using Outlook e-mail clients (or those on devices like Android based devices or iPhones/iPads) will face the similar technical challenges, but for most outlook users it will be more feasible for users to use the SMTP server belonging to their own ISP. Also - sending individual e-mail messages are much less likely to trigger a defensive reaction from an ISP so individual e-mail tends to be less problematic.

Approach

Description

Pros

Cons

Cost Implications

Recommended?

1. Originate mail from the web-server (default)

This is how most NeatClubs.COM sites are deployed. Mail recipients will see mail originating from the IP address of a shared web server that hosts multiple customer domains.

Simple and inexpensive
Prone to mail being blocked for any of the reasons described above.
No "bounce management" means there is no easy way to purge newsletter mail lists containing invalid email addresses making sending newsletters using this approach more problematic over time.

No additional cost - included in the service.

 

Depends on requirements.

2. Relay mail through your own ISP mail account

In this scenario NeatClubs.COM is configured to connect directly to an ISPs mail-server. This may or may not be permitted by the ISP depending on their security policies. (Remember, even though an internet user may be able to connect to a mail-server from their own internet location, the NeatClubs.COM hosted web-server will be outside of the providers network)

Fairly simple - involves minor customization to the NeatClubs system setup
ISPs may not permit this. Even if do they now, it is possible that their policies will change over time, or they may introduce new restrictions or added fees.
Different ISPs handle the problem of sending mail "on behalf of" foreign domains differently. It may be visible to your customers that you are using a personal ISP account for purposes of sending e-mail. (not regarded as professional)
ISPs usually place restrictions on the amount of mail they will accept in a short time period, so this approach is incompatible with sending newsletters to large numbers of recipients for most customers.

No additional cost - included in most internet services (although providers may intentionally disallow this)

No - mainly because it is difficult to administer, and ISPs are frequently changing policies and practices possibly making this a temporary "fix".

3. Relay mail through a reputable bulk mailing service like authsmtp.com

In this case a customer purchases their own bulk-mail account from a provider like authsmtp.com. Mail must originate from an address that a human is able to respond to as a requirement for using their service.

After registering a sending e-mail address with them, they will provide an SMTP server, username, password and several ports that can be used to send reliable outgoing mail without any restriction.

They will send "bounces" back to the originating e-mail address and will consolidated reports related to SPAM for the sender to take action on.

Improves mail reliability
Notifies the sender of any "bounces" so that they can keep their member directory accurate and up to date
Mail is delivered much more quickly
Administration tools available via authsmtp.com's control panel provide sites with an audit trail of all outgoing e-mail.
Requires some additional configuration work. The service must be monitored to ensure that threshold limits are not exceeded
Domain SPF records should be modified to authorize the AuthSMTP servers as designated senders for the domain to ensure optimal reliability.

Relatively inexpensive.

Approximately $100.00 per year will purchase up to 5,000 outgoing mail messages per month - more than adequate for most smaller organizations.

Yes

4. Have NeatWorx take responsibility for setting up a bulk-mail account for you

In this case, a customer can "piggy back" on our own high-volume mail contract, and we will include the customer as an authorized sender.

This is not intended to be a "revenue grab" by any means - we are attempting to price this service just in a way that allows us to re-coup our increase in administration effort.

Customers who have access to someone with technical skills will have no trouble setting this up on their own (option "3" in the row above)

Improves mail reliability
Notifies the sender of any "bounces" so that they can keep their member directory accurate and up to date
Mail is delivered much more quickly
Customer does not need to worry about any setup work
Domain SPF records should be modified to authorize the AuthSMTP servers as designated senders for the domain.
This will be more costly than purchasing and configuring your own bulk-mail package.
This is slightly less flexible than option "3" above because while customers will be advised by e-mail of any issues without outgoing mail, they will not have access to a shared control panel for security reasons.

Slightly more expensive owing to our added administration effort.

Budget an additional $25.00 per month or $300.00 per year for a managed service to handle outgoing mail.

Yes

5. Originate newsletters from a 3rd party commercial newsletter service like Constant Contact or MailChimp

For those focused on Electronic Newsletters this approach has many benefits.

It provides many features that do not exist in the NeatClubs.COM  software including newsletter templates, campaign management, tracking and reporting. It is a newsletter only service however that does not integrate fully with NeatClubs, so excellent for newsletters, it does not solve the problem of ensuring reliable mail from the web-server. Customers choosing this option will likely need to do so in combination with one of the other options above for optimal results.

Provides an excellent infrastructure for sending high quality newsletters
Solves problems related to bounce management and SPAM (for newsletters only)
Provides newsletter specific capabilities that none of the other solutions offer.
Ensures that your newsletter sending activities will not result in your regular mail service (or that of our other customers) being compromised due to your activities.
Not integrated with the Member Database in NeatClubs. (although we are working on a partial integration with Mail Chimp presently)
More costly than other options.
Does not solve the "entire" mail problem - deals with the newsletter part of the problem only.

Relatively expensive

Maintaining a database in Constant Contact of more than 2500 e-mails (common for even small clubs considering past membership) will cost a minimum of $50.00 / month.

While a good solution for those who see high value in Newsletters, it may become expensive over time for clubs.

Depends on requirements

 

3. Once I've decided on an approach, how to I setup my mail?

If you are using the web-server to send mail (the default solution), there is really no setup to be done - just be aware that there are issues, particularly when sending newsletters and ensuring reliable delivery of registration confirmations.

You can define system-wide e-mail setup preferences under  "System Setup" / "Preferences" / "E-mail" when logged in as an administrator into NeatClubs.

The "From" address should be a real address so you are made aware of bounces from invalid e-mail addresses (although we do not strictly enforce this).

We will become aware of all your bounced e-mail however of you provide an invalid "From" address.

This is because when e-mail bounces, the "bounce will also bounce" if it is originated from an e-mail address that does not exist.

In this case we will deliver mail to the "postmaster" account that we monitor for all domains. (this account and an "abuse" account are required to comply with internet standards related to e-mail)

 

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As shown above, to use our web-server to originate outgoing mail simple make sure that "Use an external SMTP server to send e-mail" is set to "No"

The rest of the configuration will be automatic.

If you are using AuthSMTP as your mailer, learn how to configure it here.