West Wind Internet and Client Tools
SMTP Server Options
Gravatar is a globally recognized avatar based on your email address. SMTP Server Options
  Michael Minahan
  All
  Feb 28, 2020 @ 09:28am

Hi Rick and All,

I have been using the WestWind Internet Tools library (for automated emails) for several years now with great success. But lately have had lots of SMTP username and password fails and other SMTP server related fails, which I have attributed to the fact that I have exceeded the user limits for my own personal email account (from Frontier.com, a Yahoo owned vendor) for ever increasing volumes of emails generated via WestWind SMTP forms that I integrated with my client apps.

This week, I setup an account with SMTP.com, and now integrated their SMTP Relay service with a customized Westwind SMTP form interface. All worked well at first, but now it appears that my emails with multiple email addresses in the recipient and CC fields are not being delivered (as they were in all my previous implementatons using smtp.frontier.com and a smtp server provided by Network Solutions

Note: I have always used a comma delimiter between multiple email addresses.

So far, SMTP.com has not been very helpful in helping me resolve this problem.

My question is: Can anyone recommend a reliable SMTP server that I can use with Westwind SMTP forms (provided in The Westwind Internet Tools library)?

And one that supports multiple email addresses on both the Recipient Line and the CC: Line?

Much obliged to anyone with some advice for me.

Mike Minahan FLoyds Knobs, IN

Gravatar is a globally recognized avatar based on your email address. re: SMTP Server Options
  Rick Strahl
  Michael Minahan
  Feb 28, 2020 @ 01:23pm

The problem isn't so much a reliable server, but rather a service that provides clean IP addresses that aren't blocked by SPAM blocker lists. This is harder than you might think, and even worse if you run your own server.

I went through this some time ago, when I was using my own SMTP server, which at some point got flagged for SPAM and resulting in almost no emails going through.

I now use a service (MailGun on a free plan) and that has been working better but it's also had issues with rejected emails from time to time. The problem is that on these services the low paid plans tend to share IP Addresses between a lot of accounts and if one of them gets flagged the IP Address is flagged and things start to bounce. Still MailGun has been way more reliable than my personal server ever was as the IP ratings that are 'new and clean' are automatically be assumed to be 'suspect'.

If it's important enough you can pay for more expensive accounts at these mail sending services which give you a dedicated IP address along with some guarantees that the IP is clean for mail sending SPAM lists as well as support if for some reason the IP gets compromised (as they tend to over time). But it's pretty pricey especially if your volume is low (as mine is).

I've basically come to the conclusion that email is no longer a guaranteed medium so you almost have to assume that it's not going to make it to a recipient. Which sucks because these days we pretty much have to validate all new accounts to ensure they are using real email addresses. And with that I can see that sometimes, these email validation messages just never make it which is frustrating as heck (especially as it means losing a sale in many cases).

I don't have a good answer to this. It might also be worthwhile to explore major mail services like GMail for their business accounts and options they have for sending emails. These services often rotate their IPs that are known to come from these big services and can often bypass the block lists (based on a number of other criteria). Reliable mail delivery these days is big pain in the ass and a complicated topic to deal with.

If you come up with a good solution please post back and let us know what you find.

+++ Rick ---

Gravatar is a globally recognized avatar based on your email address. re: SMTP Server Options
  Michael Minahan
  Rick Strahl
  Mar 3, 2020 @ 07:27am

Rick, Thanks for all the advice/issues regarding SMTP servers.

I think (maybe) I found a reliable one for my Client... SMTP.com ( an Ottawa, Canada outfit). They provide a minimum $5/month service for up to 2000 emails. With testing... Emails are being delivered via their SMTP server from the Westwind SMTP form that I have customized... But only works with only one address in the Recipient Line.
And if I put multiple addresses on the CC List neither of them are delivered.

Heretofore, using my own SMTP with Frontier.com I had no trouble using multiple addresses(with comma delimiters) on both the Recipient line and the CC line. But the Frontier. SMTP server has become very unreliable since last month which necessitated my finding a new service.

If I can't resolve the multiple address problem with SMTP.com, I will have to find another service.

Thanks again Mike

Gravatar is a globally recognized avatar based on your email address. re: SMTP Server Options
  Rick Strahl
  Michael Minahan
  Mar 3, 2020 @ 11:44am

Those are not issues of the client, but either of the server receiving them (most common) or potentially the service actually sending them.

wwSmtp definitely lets you use multiple recipients, cc's and bcc's.

Long CC lists are usually bumped by receiving servers. Short lists work (because that's common), but larger lists are considered SPAM and often rejected for that reason.

I use MailGun and most automated emails I send (including here from the message board with wwSmtp) have multiple addresses - it goes to the recipient and me and that works.

If you send larger lists you need to send them individually to improve your chances of the messages arriving.

+++ Rick ---

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