Hi Dan,

Thank you for reporting this.

There is an  open issue <https://www.jfrog.com/jira/browse/RTFACT-8248>  
regarding this.
Currently, you can only use the  REST API
<https://www.jfrog.com/confluence/display/RTF/Artifactory+REST+API#ArtifactoryRESTAPI-SetItemProperties>
  
to upload multi value properties. You have to use a comma separator in order
for this to work correctly.
i.e:
curl -X PUT -uadmin:password
"http://localhost:8081/artifactory/api/storage/libs-release-local/org/itamarb/test/test.txt?properties=test=1,2,3";

HTH,
Itamar




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