I don't have an answer, but may be able to provide a clue: From other posts made here in the community, it appears that FMP 15 has added the ability to check and verify certificates which earlier versions did not do when sending out email via SMTP.
So I'd research SSL certificates to see if there might be a reason for the error you are getting.
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I came across this post because I was dealing with the same issue, and might have a solution now.
As philmodjunk suggested, this is an issue with Filemaker not accepting a SSL certificate installed on an email server. The key to working with that situation is how FM handles the process in a script:
If Set Error Capture is on, this step is treated as cancelled and will always fail to send.
If Set Error Capture is off, this step will warn the user, but allow to connect anyway (and remember this setting!). It will also tell you more about the certificate in question.
Since I want error capture on I did the following:
Set Error Capture (on)
Send Mail ()
If (get (lasterror) = 1634)
set error capture (off)
exit loop if (1)
set error capture (on)
This will return to the send mail step if it fails due to a certificate error, this time without error capturing. This will prompt the user to allow to connect anyway, exit the loop and continue with error capture on.
If sending the email fails anyway, the user will be warned, but it is not possible to account for it in the script I believe. BUT, once the user has done this once and checked the "remember" checkbox, this error will go away and errors can be trapped for.
Hope this helps whoever finds this!
Any Idea how to solve this Problem for Sending Mails by PSOS from iOS ?
ok, i made a compromise.
I turned SSL off, and changed the port to 25 with PlainPassword as Login method.
if you install FMP on the server, run the script with the above mentioned loop once, the OS might remember your consent to the certificate and PSOS will work.
I have not tried this, but its worth a try...