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You can synchronize JIRA Server with JIRA Cloud using IssueSYNC.

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Server	Cloud
	Image Removed	Add new Connection to your Server (use Passive instance if your Server is not visible in public network). It will generate authentication key (blurred on screen below):Image Removed
Image Removed	Add new Connection providing Remote Auth Key. Use myJIRA.atlassian.net URL.Image Removed It will generate local authentication key as well.	Update Remote Auth Key.Image Removed
Setup Synchronization Scheme.	Setup Contract as described in How to configure synchronization Cloud Documentation.
Synchronization scheme - Contract binding is shown on screen below: Server contract name is shown as it is Cloud contract name is a concatenation of Contract name and named context (project + issue type).
Image Removed	Setup Fields Types & Mapping Server.	Setup How to synchronize issues' fields Cloud.
Set your triggers and enable Contract.

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