Currently, I use jira server with a lot of modifications
I am unsure to migrate to cloud or to datacenter
pro
contra
What are your experiences with cloud migration?
The other obvious pro of cloud is that cloud will be supported by Atlassian as the continually focus on the product.
I'm curious @Alexander Pappert, What's your situation regarding the apps you have on the Server? Did you check all of them have the same functionalities in Cloud?
I'm with @Alex regarding the cost; Cloud is a long-term investment, which seems a lot at first, but after a couple of years, the ROI would be evident.
Regarding your second pain point against Cloud, I would look at it differently: by relying your data on Atlassian (which is not an easy choice to make, I get it -Check their Trust Center), you will be earning more productivity from your IT team, which also affects indirectly and positively in the impact of the initial cost.
And regarding the speed, in this "remote-first" situation, it would be appropriate to consider Cloud.
Either way, we always will have Data Center, at least for the short term. In the long-term, I'm all-in with the comment @Jack Brickey made.
Whatever your choice will be, it would be great if you shared it here as well. It is always cool to learn from other experiences as well as people have done on this thread.
Wow, this answer was longer than I expected 😅
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