Just tried this on my 9.1 and 10.0(1) servers and it worked fine.
I went to the opening greeting call handler, selected the "error" greeting, set the greeting to play my personal greeting (it defaults to the system generated greeting), recording "hey, you dialed the wrong number" and then called in and during the opening greeting I dialed "88" - I heard "hey, you dialed the wrong number" and then it repeated the opening greeting recording as it should.
the default action after playing your custom greeting in this case is to "restart greeting" - which is why the opening greeting plays again.
Not sure what you did in your testing with the error greeting - check to make sure you have it set to play your personal greeting instead of the default system greeting - since you can't disable the error greeting there's not a lot of other items I can think of to check.
ah, that's a different scenario that only comes up with the option to "free dial" extensions on the handler - it's not an error (hence the error greeting is not activated) it's doing the dial and it failed and gets handed back - that message is hard coded (same as you would hear if you put an invalid number into a transfer string for a transfer rule).
the free dial option is special in that it's skipping any DB lookups to validate the number other than the restriction table check - the error greeting only comes into play if a DB check fails and that's taken off the table here.
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