When the Jenkins Artifactory Plugin deploys build-info, it opens a connection to Artifactory, which triggers it to execute several processes relevant to the deployment. Accordingly, if you’re experiencing deployment timeouts, it might be because Artifactory is deleting many old builds that were configured in the build retention of your Jenkins job. And this might take longer to complete than the connection-timeout configured in Jenkins.
To resolve this issue, prior to running your build with build retention enabled, you can manually delete the old builds using the Delete Builds REST query available HERE. Alternatively, you can increase the length of your connection timeout by navigating to Jenkins UI > Manage Jenkins > Configure System > Artifactory > Advanced > Connection Timeout.