First, simplify a little bit. Forget Jira Service Management - you should look at Jira Software, get that upgraded, and then Jira will select and upgrade the JSM application to the best version for your Software version!
I would make three recommendations here:
- Go for the latest version of each - more functions, fewer bugs, and usually better than the previous versions
- Caveat 1: I would not go for a .0.0 release. Jira 9.0.0 for example, that's gone out to a load of people and although Atlassian have tested, there will be things they have missed that real life systems will pick up and report back on. Atlassian fix these and release again. I would happily test with 9.0.0, but I wouldn't upgrade production to it, I'd wait for at least 9.0.1
- Caveat 2: "Latest" are rolling releases, and you'll need to be considering regular large upgrades like 9.0 -> 9.1 -> 9.2 etc. If you want a bit more stability, look to the "long term support" releases instead. The latest of these will get point releases and security patches up until the end of server support in February, and that applies to their Data Center versions as well (so if you stick with Jira Server 8.13 LTS, moving to Jira DC 8.13 LTS will be a trivial migration)
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