I can reproduce the above issue also on dev2.
@valentina.marioli@isti.cnr.it you can see following:
2017-01-23 11:31:45,732 DEBUG o.g.c.h.j.w.JCRWorkspaceItem [http-bio-9090-exec-63,setACL:1141][PORTAL] 161379030 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.JCRWorkspaceItem - Has ACL been modified correctly for users [francesco.mangiacrapa, valentina.marioli, massimiliano.assante, roberto.cirillo]in path /Share/3cc8c31b-08ee-49f2-a0d4-8566bc0a9e6d? true
2017-01-23 11:31:45,732 DEBUG o.g.c.h.j.w.JCRWorkspaceItem [http-bio-9090-exec-63,setAdministrators:1149][PORTAL] 161379030 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.JCRWorkspaceItem - set ADMINISTRATORS: [francesco.mangiacrapa, valentina.marioli]
2017-01-23 11:31:45,734 DEBUG o.g.c.h.j.w.JCRWorkspaceItem [http-bio-9090-exec-63,setAdministrators:1160][PORTAL] 161379032 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.JCRWorkspaceItem - Set francesco.mangiacrapa ad administrator
[PORTAL] 161379032 [http-bio-9090-exec-63] TRACE org.gcube.common.homelibrary.jcr.workspace.JCRWorkspaceItem - Getting absolute path of: test_change_administrator
2017-01-23 11:31:45,749 DEBUG o.g.c.h.j.w.a.JCRAccessManager [http-bio-9090-exec-63,setAdminACL:317][PORTAL] 161379047 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.accessmanager.JCRAccessManager - Set ADMIN ACL on resource /Share/3cc8c31b-08ee-49f2-a0d4-8566bc0a9e6d for users: [francesco.mangiacrapa]
2017-01-23 11:31:45,749 DEBUG o.g.c.h.j.w.a.JCRAccessManager [http-bio-9090-exec-63,modifyAce:116][PORTAL] 161379047 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.accessmanager.JCRAccessManager - Modify ACL on resource /Share/3cc8c31b-08ee-49f2-a0d4-8566bc0a9e6d for users: [francesco.mangiacrapa]
2017-01-23 11:31:45,749 DEBUG o.g.c.h.j.w.a.JCRAccessManager [http-bio-9090-exec-63,getACL:79][PORTAL] 161379047 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.accessmanager.JCRAccessManager - Get ACL for resource /Share/3cc8c31b-08ee-49f2-a0d4-8566bc0a9e6d
2017-01-23 11:31:45,758 DEBUG o.g.c.h.j.w.a.JCRAccessManager [http-bio-9090-exec-63,getACL:91][PORTAL] 161379056 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.accessmanager.JCRAccessManager - Response <map>
<entry>
<string>valentina.marioli</string>
<list>
<string>jcr:write</string>
</list>
</entry>
<entry>
<string>massimiliano.assante</string>
<list>
<string>jcr:write</string>
</list>
</entry>
<entry>
<string>francesco.mangiacrapa</string>
<list>
<string>jcr:write</string>
</list>
</entry>
<entry>
<string>roberto.cirillo</string>
<list>
<string>jcr:write</string>
</list>
</entry>
</map>
2017-01-23 11:31:45,760 DEBUG o.g.c.h.j.w.a.JCRAccessManager [http-bio-9090-exec-63,deleteAces:335][PORTAL] 161379058 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.accessmanager.JCRAccessManager - Delete ACES on resource /Share/3cc8c31b-08ee-49f2-a0d4-8566bc0a9e6d for users: [francesco.mangiacrapa]
2017-01-23 11:31:45,778 DEBUG o.g.c.h.j.w.a.JCRAccessManager [http-bio-9090-exec-63,deleteAces:349][PORTAL] 161379076 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.accessmanager.JCRAccessManager - Response DeleteAcesServlet: <boolean>true</boolean>
2017-01-23 11:31:45,805 DEBUG o.g.c.h.j.w.a.JCRAccessManager [http-bio-9090-exec-63,modifyAce:146][PORTAL] 161379103 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.accessmanager.JCRAccessManager - Response <boolean>true</boolean>
[PORTAL] 161379105 [http-bio-9090-exec-63] TRACE org.gcube.common.homelibrary.jcr.workspace.JCRWorkspaceItem - Getting absolute path of: test_change_administrator
2017-01-23 11:31:45,826 DEBUG o.g.c.h.j.w.JCRWorkspaceItem [http-bio-9090-exec-63,setAdministrators:1162][PORTAL] 161379124 [http-bio-9090-exec-63] DEBUG org.gcube.common.homelibrary.jcr.workspace.JCRWorkspaceItem - Has ACL been modified correctly for users [francesco.mangiacrapa]in path /Share/3cc8c31b-08ee-49f2-a0d4-8566bc0a9e6d? true
2017-01-23 11:31:45,828 INFO server.GWTWorkspaceServiceImpl [http-bio-9090-exec-63,setACLs:2468] %[PORTAL] 13184259 [http-bio-9090-exec-63] INFO org.gcube.portlets.user.workspace.server.GWTWorkspaceServiceImpl - Setting ACL for test_change_administrator completed, returning
It seems that the ACL for administrators is not updated correctly..
Let me know if there is a problem related to parameters passed to HL through the WS portlet.