Are you sure about port 25? AFAIK port 25 is rarely used these days.
What I would try if I understand your posting correctly is to set up a regular email account outside of FMP that uses your email server on AWS. Make sure that email works reliably every time. Then migrate those settings to FMP/S.
I've had good luck with FMP's SMTP email settings, but many of the problems posted here deal with Outlook so you're definitely not alone.
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We're having similar problems with Office365 at the moment. We've been using it with Dacons MailIt very successfully for years for SMTP and POP. However, MailIt is currently incompatible with FMP v16 and Dacons haven't responded to requests for help for over a month now. This is very disappointing, as they've been so good in the past. People elsewhere on this forum are asking whether they are still trading.
We're currently users of 360Works Scribe, so we have turned to them to use their Email plug-in. However, we can't currently get this to work, but are working with their tech support team. We've just made a test Office365 email account available for them to test with.
Our settings are: smtp.office365.com, port 587 with StartTLS encryption.
I'll update you here once 360Works have made progress (I only sent them the test account this morning).
Our attempt with 360works took a lot of time and didn't pan out. In looking at logs, the issues seemed to relate to java. I did notice that 360works has moved away from java with the fm16 compatable version. This may be more viable. side note: fmpa 15 is now crashing on open on my terminal services machine. This is what I see in the details:
Problem Event Name: APPCRASH Application Name: FileMaker Pro Advanced.exe Application Version: 188.8.131.525 Application Timestamp: 584785c3 Fault Module Name: 360Works_Email.fmx
I tried removing the 360 plugin and it's still crashing on open. fmp seems okay
I'll ask our IT guys if they can change the port # at MS. It would be fantastic if we could simply use the FM settings reliably.
Not arguing with anything you said.
Just wanted to say that I use the JavaMail API in several standalone and web applications with many email providers and all the apps experience zero email issues. Rock solid. I also use JavaMail in Windows utilities - on scheduled Tasks with zero issues.
I've also integrated JavaMail with FMP via a service. Again, zero issues.
I can't speak to 360 vs Java as I don't use any of their products, but I hope you get your issues resolved soon.
You can switch to MBS FileMaker Plug-in for sending emails.
Using SMTP via CURL functions. Check SendMail functions to build email with/without HTML, multiple attachments and properly encoded names & texts. Tutorial: Sending emails in FileMaker with MBS Plugin
We can even configure it for Outlook 365. No problem there.
Or if you like to send via Outlook, please check our new SendMail functions in 7.2 version of our plugin. They can send via Outlook, Thunderbird or other MAPI clients, independent of 32/64bit issues and with a few more options. see Send emails via Outlook
We had issues when we tried to use outlook 365 for SMTP, but have no troubles when we use exchange for SMTP. We don't use port 25, and the port may have something to do with it, but I think it may be more than that, and I think that the issue is with the outlook 365 SMTP.
You mention trying to use SES, and that works as an SMTP endpoint if you set that up. Nothing special about that, and you can use an IAM key and secret on port 25 if you like.
Another option, if you know some PHP, you could bypass SMTP altogether and send via the PHP SDK for AWS. Once set up, this is much quicker than SMTP anyway, since there is no ELHO handshake or anything, and you can insert an email directly into the sending queue. Bonus points for setting up your EC2 instance with a IAM Role that allows SES sending without needing additional credentials.
Then you can send to that script from FileMaker with an Insert from URL script step that uses wither httppost or curl options to send the data to PHP. Your PHP script can then just return the result, either an id or an error, that you can log in FM.
Many ISPs use port 25 to send mail From another server. It's very common. Some block it forcing the customer to use the isp's SMTP server. I use my own server and rely on port 25.