I didn't really want to post across forums, and not really sure where this question belongs, so hopefully someone can help here. I am a C# .net developer, but I am dealing with a task that is a little outside of my wheelhouse. I'm not actually using Exchange Server (although I could, but would prefer not to at the moment), but I think this is more a general sort of question relating to SMTP setup within your domain. My messages for my test project are not reaching destinations in most commercial domains like Yahoo, Hotmail, etc. when I send from my SMTP. I am hoping to find a way to fix this that meets my objectives. More is explained below.
I am in the process of developing a pilot application that deals in part with workflows that trigger email messages to various stakeholders in the workflow. Right now, I have a commercial internet account set up with my ISP, and a static IP address. I have the A record and the PTR record for the static IP set up to point to my domain that I'm testing from, which is "test.feazell.net". I am running a server on my workstation called Lumisoft, which supports POP3 and SMTP (among other things). I have created an email account on this server called jane.doe@test.feazell.net.
The tests that I am conducting at this point are simple tests to ensure that my implementation of Lumisoft is working correctly and that I can successfully send and receive email messages to / from the test account. So I have sent out numerous different permutations of a test message to four email addresses: One to my Hotmail account, one to my wife's AOL account, one to my wife's Yahoo account, and one to another email address of a domain we own, which has email hosting from godaddy.
All external accounts are able to send TO Jane Doe, so I know the server is receiving inbound messages and my email client (Outlook) is successfully able to get them. When I send the test messages out to those four accounts however, I am able to receive them on our domain hosted by godaddy, but nobody else (meaning that Hotmail, Yahoo, and AOL all never receive the message). The message doesn't bounce, it just never gets received.
If I set up Lumisoft to relay through my Godaddy hosting domain, then the messages do get received by AOL and Yahoo, albeit in the spam folders. I know that some things, none of which seem to apply here, can get you filtered as spam and not delivered to end recipients, among them being: 1) You have a dynamic IP address (I don't), 2) Your PTR record doesn't match the domain of the sender (It does), and 3) Your message contains heuristics that make it look like spam (not likely, since I can send the same message from other domains or relay through godaddy and it least gets there (most of the time).
I never have these kinds of problems in my "real world" development, where our applications routinely send out email from our corporate domain. Of course, I'm not involved in the server configuration and setup there; I just write the software that interfaces with the SMTP server. Ultimately what my client does with the product and how they configure it will be their responsibility, but the pilot of course needs to work, look, and behave professionally.
I don't want to buy hosting for email accounts somewhere for a domain like this that is only a pilot, as it doesn't generate any revenue itself. There should be no reason, as far as I can tell, that this shouldn't work, in that I should not have to buy hostng somewhere else as long as my domain meets the requisites (static IP, valid PTR record, etc.) Is there something that I'm doing wrong or missing in the setup of my SMTP server? Would I be better off using Exchange? Are there options to relay my messages through another entity, but where the messages still reach the recipient appearing in all respects to come from me? (Meaning that the headers don't get munged up, for example the way they do when you relay through gmail, etc.)... Reply-to addresses work, and all that? Is there some sort of "white list" that (most) of the commercial email providers share that allows email from some sources to come through, while rejecting others? How do I get my domain (or a future client's domain) on that "whitelist"?
Godaddy will happily sell me Office 365 email accounts @ $29/year per email address, but that's not acceptable. There surely is a solution other than just throwing money at the problem.
Thank you for any assistance or advice you can provide!
--James