Well looks like it is something messed up in the actual update process. I installed FMS with my Dev License on another machine and I was able to get everything working perfectly.
Must be some problem with using the FMS updater vs removing completely removing and installing with the latest version. I do wish things would just work like they are supposed to.
So that was not the fix actually. Wiping the entire machine and starting over. Hope that works.
Did the wipe and reinstall work? Seems rather draconian.
We had exactly the same problem after installing the 14.0.4a Update. fmsadmin command and Webdirect didn't work. SSLPassPhraseDialog: file '/usr/bin/fmsgetpasskey' does not exist. On the machine on which I got this error, there was no /usr/local/bin folder neither a /usr/bin/fmsgetpasskey file.
Fortunately I have another machine on which the installation worked fine. So I copied the whole /usr/local/bin (contains the following links: fmsadmin, fmserver_helperd, fmserverd, fmsgetpasskey) folder of the working machine to the defect one.
Then I changed the following line in /Library/FileMaker\ Server/HTTPServer/conf/extra/httpd-ssl.conf
Afterwards I started webdirect again using:
sudo /Library/Filemaker\ Server/HTTPServer/bin/httpdctl graceful
Webdirect now works like a charm.
dkb: "Did the wipe and reinstall work? Seems rather draconian."
Is that why they call the engine "Draco?"