plan3t: First off it looks like you can login fine. Assuming this was done via SSL/TLS this proves the cert is somewhat OK. Second, it looks like you are FXPing which introduces a bunch of other variables.
You obscured the IP addresses (which is good) but I just want to make sure they are actually valid and not 192.168.1.x or something else which is clearly incorrect and happens ALL THE TIME when people don't setup the HOST= option in ioftpd.ini and are behind NAT firewalls... When you say crash and then say you can't kick the user I'm a bit confused. The connection may be dropped, and/or the user stuck logged in or something but ioftpd didn't crash and completely exit.
John H: Error: Invalid issuer store location - that sounds like the cert isn't installed into the proper location or something else is wrong with it. Download certmgr.exe which should come with makecert.exe from MS (you'll need to search a bit as I'm not sure its released outside of the platform download now) so you can examine the certificate store...
Makecert in my experience makes AND installs the certificate. You don't need to click on the .cer file and install it.
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