We've recently configured our JIRA Server instance to use SSL. We added it due to an issue with the Slack Add-on not being able to complete setup (when adding the JIRA URL on the api.slack side it would always say it couldn't communicate).
Unfortunately after enabling and configuring SSL slack still can't contact the server (though we have no issues contacting it externally). So that's still an issue. Maybe related, on the JIRA side for Slack the entire project/channel list doesn't populate.
Additionally after setting up SSL, some widgets we started getting gadget.common.error.500, and what look like variable names for a lot of titles of widgets (even in the list of widgets).
We're run various tests on the SSL configuration and everything seems to check out, and we're able to otherwise access the site.