Well, that leaves one or more of:
1) the bundle path (which you say is good, but it might be worth double checking),
2) the actual file executable content,
3) missing libraries, or
4) corrupted download of the plugin.

For (2), try using the "file" command on the actual executable file of the SSL plugin and on the executable of a known good plugin - this will look at the first few bytes of the file to see what type the loader is going to think it is.  You'd expect them to be the same type :).

For (3), there's a tool to get a list of libraries used by the executable.  Use "otool -L" for 10.5, and possibly "dyldinfo" for 10.6.  I haven't used them recently, so my memory is pretty vague, but the idea is to get a list of required libs, then go around looking to see that you have them.
Sometimes it can be as simple as a missing symbolic link for a a general name (e.g. "libfoo" -> "libfoo.1.2.3").

For (4), I guess you download a second time and compare the resulting bundles.  You might have to cobble something together with "find" and "cmp".

If none of the above work, I'm out of ideas :).

On 2010-Oct-4, at 19:56, Lawson English wrote:

> There WAS a quarantine bit, but I removed it by doing xattr -rd "com.apple.quarantine" SqueakSSL.bundle/  which removed the flag all the way down but I still get the same error. :-/
> 
> 
> 
> On 10/4/10 6:12 PM, Tom Rushworth wrote:
>> The '@' means there is an extended attribute set on the file.  Use "ls -l at ed" to see what it is.  If it is the "quarantine" bit, it won't execute unless you answer a popup dialog saying it is OK to do so.  You can use the "xattr" command to remove it.  There is no man page for xattr, but "xattr -?" gives an almost usable usage message :).
>> 
>> On 2010-Oct-4, at 13:41, Lawson English wrote:
>> 
>>> The bundle is in the right place and all the permissions seem to be correct. There IS a difference between this and other plugins though:
>>> 
>>> the bundle has permissions drwxr-xr-x@ 4   vs   drwxr-xr-x  4  for other bundles.
>>> the executable has permissions -rwxr-xr-x@ 4   vs   -rwxr-xr-x  4
>>> 
>>> could the '@' have anything to do with it?
>>> 
>>> Otherwise, I seem to be stuck.
>>> 
>>> Thanks,
>>> 
>>> Lawson
>>> 
>>> On 10/4/10 10:59 AM, Andreas Raab wrote:
>>>> Hi -
>>>> 
>>>> Most likely this means that plugin isn't installed correctly. Make sure the bundle is in the right place (i.e., Contents/Resources) and that the actual executable (SqueakSSL.bundle/Contents/MacOS/SqueakSSL) has executable permissions.
>>>> 
>>>> Cheers,
>>>>  - Andreas
>>>> 
>>>> On 10/3/2010 8:08 PM, Lawson English wrote:
>>>>> I'm probably doing this completely wrong, but this fails:
>>>>> 
>>>>> (WebClient httpGet: 'https://login.agni.lindenlab.com/cgi-bin/login.cgi')
>>>>> 
>>>>> Error: primitiveSSLCreateFailed/
>>>>> 
>>>>> 
>>>>> I've got the latest SqueakSSL package and plugin installed, and the
>>>>> latest webclient on Squeak 4.1 VM.
>>>>> 
>>>>> The URL doesn't return a valid certificate anyway, its just an xml-rpc
>>>>> portal for getting a login URL via an encrypted connection.
>>>>> 
>>>>> 
>>>>> Lawson
>>>>> 
>>>>> 
>> 
>> 
>> 
> 
> 

--
Tom Rushworth