I know I can add JIRA Service Desk to my JIRA Software Server, but if I have JIRA ServiceDesk installed as a standalone, can I update that to add JIRA Software to the same server?
It seems that you can only "start" with JIRA Software and then add servcedesk but I'm concerned that this will wipe out all the servicedesk setup and data
You can start with JIRA Core and add Service Desk and/or Software in either order. You can start with Service Desk and add Software, or start with Software and add Service Desk.
The last option is generally the recommended one for a new starter because Service Desk is less complex than Software (in terms of how much it entangles itself with Core - JSD is more a layer over the top, whereas Software adds fields and changes behaviour of certain issue types).
But yes, you can simply install Software on your system. It won't do anything to your data that can't be undone. The only thing I'd check is if you've used Epics in any Service Desk projects, as their behaviour changes when Software is installed and it might not be quite what you wanted (I'd be strongly tempted to change the Epics to a different type before installing Software)
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