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So I'll be setting up a production environment for WSO2 soon. I'll be using the API Manager and Identity Server. I'll be clustering the Manager with two workers and the Identity Server will have two instances. My question is, when first starting up the servers does the order matter much? Also, should I run the servers once before doing any configurations? So it can build anything it needs to, or does that not matter, once I start configuring the different databases and such?

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You can refer to WSO2 Production Guideline Doc for more details about a prod deployment https://docs.wso2.com/display/CLUSTER44x/Production+Deployment+Guidelines

My question is, when first starting up the servers does the order matter much

If you are clustering products, then you need to start the manager nodes first and then start the worker nodes.

Also, should I run the servers once before doing any configurations?

No. You can first do the configurations and then start the servers