Phil, I may have a solution for you. Sorry that it won't be a short note, but the suggested solution should be quick for you to try. And yes, of course getting off cf11 would be best for so many reasons (including potentially devastating security vulns), to get you to either currently supported version, cf2023 or cf2021.
Until then, in your crippled state, let's see if we can get you going where you are. And you're right that updating Java should be the solution to your original mail deliver problem. Perhaps you've seen that I cover the topic in a post here.
1) But I suspect your problem is you went "too recent" in the java 8 updates, given your current OS. Let me explain: that subsequent error of "Can't find dependent libraries" for sunmscapi.dll seems to have started with 1.8.u251, especially if you are on an older Windows machine. (You didn't say what version you're on, but might it be as old as Windows 2003?) While updating your OS could be one solution, an easier solution may be just to not update the JVM "so far" as the 8u401 you went to.
As this problem started in 8u251, try 241 (one shy of that), and see if that gets you past the SMTP problem without the sunmscapi.dll problem. Granted, it's almost as bad for your JVM to be so old as that, but you're trying to get the ship back to land, not change out the engine while on a stormy sea. And no, you can't get that old 241 jvm version from Adobe, but you can from Oracle's jdk archive (the download itself will require a login, and an account is free).
And if anyone following might wonder if Java 8 is supported at all by cf11, it was, after its update 3 (and Phil said he is on update 19). For more, see my table mapping CF versions to supported Java versions.
Let's see if that gets you past whatever jvm limitation prevented your connecting to your smtp server. Before concluding, let me offer two more tips for you.
2) As for checking if the mail delivery "now works", as you may know you can try just copying a file from cf's mail/undelivr folder to the spool. Watch for it to disappear (per your cf admin mail spool interval). To know if it worked (assuming you can't see the mail delivered), you can certainly look in the undelivr folder, but beware that if it fails again, the mail file will be put there with the same name and date it had before. Look instead to the cf mail.log to see if an error occurred, or better look to the cf mailsent log of enabled.
3) Finally, as for your updating from Java 7 to 8, don't stop at "the mail delivery works", as there may be problems that would soon arise. Again, as you may know, in updating major Java versions underlying cf, it's also important to clear out the compiled Java files that CF created from your CFML over the years from your cfml. Those are in the cfusion/wwwroot/WEB-INF as cfclasses (NOT classes). I discuss this more in a post on solving common problems when updating the JVM. See specifically my point on clearing cfclasses there. (Then again, rather than DELETE those files of that cfclasses folder, I'd recommend you just rename it--while CF is down--so that it creates a new one. You may need to use that cfclasses folder to look for evidence of a vuln as I discuss in a very long post last March.)
Related to the last point, you have one more step when making a jump in major Java versions: see the next section of my post there, on removing also the related "stubs", "rest-skeletons", and "cfc-skeletons" files, related to other aspects of compilation of things in your past use of CF with Java 7.
Again, sorry for this long missive. It's clear you'd done your own homework (and perhaps you'd already seen some of these resources), but I hope I've connected the dots for you and given you enough to resolve things on your own. If not, while you could certainly ask follow-ups here, I'll just say that I can often help folks in your situation solve the problem quickly via direct remote assistance, discussed more on my consulting page.
/Charlie (troubleshooter, carehart.org)
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