Could it possibly not be FileMaker's fault and maybe it it your mail server's fault? For example, you say you're using SSL. That means you either have an authorized or self-signed certificate. Could it be that your certificate expired and you didn't renew it? They expire every year and I find lots of people forget to renew them. FYI, what kind of software is running your SMTP service and do you have access to change its configurations? Are you using a mail client to send or directly to the SMTP server? Since it seems to only be a problem when you send the attachment, could it be that the mail server has an attachment file size limit? Try sending something from the server that is bigger? Try it using a mail client and what are those results. Have you tried sending it from another computer and do you get the same result? Or you can do like I do for most of my clients and turn on mail services on the FileMaker server for sending mail only and FileMaker only has to send to itself (Localhost or 127.0.0.1) and set no limits on it. In fact, I often set them up to only allow emails from itself, but turn on open relay so you don't have to authenticate because no real need to authenticate between services on the same machine. Anyway, there probably are several other possibilities and suggested solutions. These are just a few to look into.
Thanks for the suggestions. I've forwarded your reply to my client's techie, who's responsible for not-Filemaker issues. Will let you know!
Here's some more information. Unfortunately, nothing he discovered helps to solve the mystery:
They're using gMail's server as their smtp server.
"We are using SSL but it would be google's SSL certificate I believe, though I double-checked and the PACE SSL cert is good till August 2014.
Gmail's attachment size limit far exceeds the few hundred kilobyte attachment we are sending."
Also: can you please explain "Turning on mail services on the Filemaker server?" Haven't ever done that. What are the advantages? What does that let users do that they couldn't do by sending mail via an smtp server?
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Ahhhh.... but Google has all kinds of algorythms to make sure people are not inappropriately using their SMTP servers. I have seen this several times when using Google, which usually happens after trying to send a lot of emails from the same IP. You might get it to work for a while, but then things change. You do not run the Google mail so can't speak to how it works. But the price is right for when it does work. Have you tried another SMTP server? That is what I would do first. My normal setup for clients has always been to turn on the mail on the server that is running FileMaker Server and allow auto-replay from 127.0.0.1 so that you don't have to authenticate. It makes life much easier.
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Taylor has just gently made a very strong point. "But the price is right for when it does work. Have you tried another SMTP server?"
If this is a commercial customer you should consider using a list server company. It's very inexpensive and more importantly you get a partner who has tech support and wants you to succeed. There are other benefits, too. You get reports and you avoid the possibility of getting your customer blacklisted. Nothing causes more discontent than that.