f5326150b242 ,
displayed result of
{{issue.fixVersions.name.equals("Version 1.0")}}
is iteration over all names in the collection, that's why for one element collection the displayed text looks like single result.
To properly observe difference please check following smart value:
This is original one:
* issue.fixVersions.name.equals("v1.0.0"): {{issue.fixVersions.name.equals("v1.0.0")}}
* or(issue.fixVersions.name.equals("v1.0.0"), false): {{or(issue.fixVersions.name.equals("v1.0.0"), false)}}
* or(issue.fixVersions.first.name.equals("v1.0.0"), false): {{or(issue.fixVersions.first.name.equals("v1.0.0"), false)}}
Iterating through fixVersions
{{#issue.fixVersions}}
* current version name: *{{name}}*
** name.equals("v1.0.0"): {{name.equals("v1.0.0")}}
** or(name.equals("v1.0.0"), false):{{or(name.equals("v1.0.0"), false)}}
{{/}}
For the Issue where just single fix version is set the result is:

In case of the issue where multiple fix versions are set, the result is

Regards
Daniel Ramotowski
I see now. I was thinking for some reason that this single fix version will be casted to string and will be compared as a string.