diff --git a/Jenkinsfile b/Jenkinsfile
index 856b1494..b2868f1d 100644
--- a/Jenkinsfile
+++ b/Jenkinsfile
@@ -30,21 +30,17 @@ pipeline {
             }
         }
 
-        stage('Bump version') {
+        stage('Build recog-content') {
             steps {
                 script {
-                    String currentVersion = sh(script: 'git describe --abbrev=0 | cut -c 2-', returnStdout: true).trim()
-                    echo "${currentVersion}"
+                    OLD_VERSION = sh(script: 'git describe --abbrev=0 | cut -c 2-', returnStdout: true).trim()
+                    echo "Current version: ${OLD_VERSION}"
 
-                    VERSION = sh(script: "./semver bump ${params.VERSION_BUMP} ${currentVersion}", returnStdout: true).trim()
-                    echo "${VERSION}"
-                }
-            }
-        }
+                    VERSION = sh(script: "./semver bump ${params.VERSION_BUMP} ${OLD_VERSION}", returnStdout: true).trim()
+                    echo "New version: ${VERSION}"
 
-        stage('Zip recog-content') {
-            steps {
-                sh "zip -r recog-content-${VERSION}.zip xml"
+                    sh "zip -r recog-content-${VERSION}.zip xml"
+                }
             }
         }
 
@@ -56,7 +52,7 @@ pipeline {
             }
 
             stages {
-                stage('tag') {
+                stage('Create Github tag') {
                     steps {
                         withCredentials([usernamePassword(credentialsId: 'github-app-key', usernameVariable: 'GH_APP', passwordVariable: 'GH_TOKEN')]) {
                             setGitConfig()
@@ -65,16 +61,63 @@ pipeline {
                     }
                 }
 
-                stage('Release') {
+                stage('Initialise Release') {
+                    steps {
+                        withCredentials([usernamePassword(credentialsId: 'github-app-key', usernameVariable: 'GH_APP', passwordVariable: 'GH_TOKEN')]) { 
+                            sh """
+                                curl --silent --show-error \
+                                    -H "Content-Type: application/json" \
+                                    -H "Accept: application/vnd.github.v3+json" \
+                                    -H "Authorization: token \${GH_TOKEN}" \
+                                    -d '{"tag_name":"'"v${VERSION}"'", "generate_release_notes": true, "name": "'"v${VERSION} - \$(date +"%Y.%m.%d")"'"}' \
+                                    https://api.github.com/repos/rapid7/recog/releases > recog-content-releases-response.json
+                            """
+                        }
+                    }
+                }
+
+                stage('Process release response') {
+                    steps {
+                        script {
+                            // Note: Inspect the response for error message since curl exits with code 0
+                            // for the "Validation failed" response with status code 422 Unprocessable Entity
+                            RELEASE_ERROR_MSG=sh( script: '\$(cat recog-content-releases-response.json | jq -r .message)', returnStdout: true).trim()
+                            echo "[DEBUG] RELEASE_ERROR_MSG = ${RELEASE_ERROR_MSG}"
+                            if (RELEASE_ERROR_MSG) {
+                                echo 'Failed to create release.'
+                                sh 'cat recog-content-releases-response.json'
+                                currentBuild.result = 'FAILURE'
+                                return
+                            }
+
+                            echo "[DEBUG] Create release response:"
+                            sh 'cat recog-content-releases-response.json'
+                            echo "[DEBUG] upload_url:"
+                            sh 'cat recog-content-releases-response.json | jq .upload_url'
+                            echo "[DEBUG] processed upload_url:"
+                            sh 'cat recog-content-releases-response.json | jq -r .upload_url | cut -f 1 -d "{"'
+
+                            RELEASE_HTML_URL=sh(script: '\$(cat recog-content-releases-response.json | jq -r .html_url)', returnStdout: true).trim()
+                            echo "[*] Release v${VERSION} available at: ${RELEASE_HTML_URL}"
+
+                            // Note: This returns an `upload_url` key corresponding to the endpoint for uploading release assets.
+                            // This key is a [hypermedia resource](https://docs.github.com/rest/overview/resources-in-the-rest-api#hypermedia).
+                            // All URLs are expected to be proper RFC 6570 URI templates.
+                            UPLOAD_URL=sh(script: '\$(cat recog-content-releases-response.json | jq -r .upload_url | cut -f 1 -d "{")', returnStdout: true).trim()
+                        }
+                    }
+                }
+
+                stage('Upload release asset') {
                     steps {
                         withCredentials([usernamePassword(credentialsId: 'github-app-key', usernameVariable: 'GH_APP', passwordVariable: 'GH_TOKEN')]) { 
                             sh """
                                 curl --silent --show-error \
-     -H "Content-Type: application/json" \
-     -H "Accept: application/vnd.github.v3+json" \
-     -H "Authorization: token ${GH_TOKEN}" \
-     -d '{"tag_name":"'"v${VERSION}"'", "generate_release_notes": true, "name": "'"v${VERSION} - \$(date +"%Y.%m.%d")"'"}' \
-     https://api.github.com/repos/rapid7/recog/releases > recog-content-releases-response.json
+                                    -H "Content-Type: application/zip" \
+                                    -H "Accept: application/vnd.github.v3+json" \
+                                    -H "Authorization: token \${GH_TOKEN}" \
+                                    --data-binary @recog-content-${VERSION}.zip \
+                                    "${UPLOAD_URL}?name=recog-content-${VERSION}.zip"
                             """
                         }
                     }