Techniques for deploying a server stack having a cross-server dependency are disclosed. A deployment engine initiates a deployment process for a server stack. The deployment engine provisions servers of one server type (“requisite servers”). The deployment engine attempts to provision servers of another server type (“dependent servers”). The deployment engine executes a test that requires the dependent servers to invoke a service executed by the requisite servers. Based on the test results, the deployment engine determines that an operational requirement of the dependent servers is not satisfied. The deployment engine modifies a configuration for the requisite servers to satisfy the operational requirement of the dependent servers. The deployment engine re-provisions the requisite servers using the modified configuration. The deployment engine completes the deployment process for the server stack.