We have a growing number of Jenkins plugins in our company's repository. 
They are all for specific purposes, reason why there is no plan to release 
them in public repository any time soon *(plus legal issues :-( shame)*.
Anyway, we had plugin docs scattered all over our departments worldwide 
until we decided to provide a central confluence and a template plugin in 
which the URL is set to a generated page. We still don't have 100% of 
adoption, but the culture is growing...

Another issue as to keep sync between the documentation and the plugin 
version. Confluence has this nasty thing of assigning a fix id to the *latest 
*version of the page. So, if you want to get a permanent id for the current 
page, you actually have to bump the page version once, get the fixed id 
from the history etc... Plus, there is no mapping between plugin version 
and the corresponding documentation for that release.

For the reasons above, I was thinking about introducing the documentation 
in markdown format directly from the Jenkins plugin itself. That is, an 
extra doc folder in the plugin's source that will be part of the snapshot 
(tag, revision, release.. you name it). This way, there is a direct 
correlation between the source and the doc, devs feel motivated (or 
compelled) to update docs accordingly, and I can generate the pages 
automatically saving people the trouble of managing confluence pages.

I'm suggesting it here because not long ago you established that plugins 
without documentation in your confluence are to be considered deprecated. 
So, maybe providing the template doc with the plugin (in your maven 
template skeleton, for example) might be the next step.

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