diff --git a/Makefile b/Makefile
index 3966535b168..9533b15d6ae 100644
--- a/Makefile
+++ b/Makefile
@@ -290,4 +290,6 @@ SMOKETEST_VERSIONS ?= latest
 
 .PHONY: smoketest
 smoketest:
-	@ for version in $(shell echo $(SMOKETEST_VERSIONS) | tr ',' ' '); do cd ./testing/smoke/basic_upgrade && ./test.sh $$version; cd - ; done
+	@ echo "-> Running smoke tests for versions: $(SMOKETEST_VERSIONS)..."
+	@ for version in $(shell echo $(SMOKETEST_VERSIONS) | tr ',' ' '); do cd ./testing/smoke/basic_upgrade && ./basic-upgrade.sh $$version; if [ $$version == 7.17 ]; then ./legacy-managed.sh && ./standalone-major-managed.sh; fi; cd -; done
+	@ echo "-> Smoke tests passed!"
diff --git a/testing/smoke/basic_upgrade/test.sh b/testing/smoke/basic_upgrade/basic-upgrade.sh
similarity index 79%
rename from testing/smoke/basic_upgrade/test.sh
rename to testing/smoke/basic_upgrade/basic-upgrade.sh
index 2a7279f3a9e..3bab3a67615 100755
--- a/testing/smoke/basic_upgrade/test.sh
+++ b/testing/smoke/basic_upgrade/basic-upgrade.sh
@@ -25,28 +25,19 @@ else
     exit 5
 fi
 
+echo "-> Running basic upgrade smoke test for version ${VERSION}"
+
 . $(git rev-parse --show-toplevel)/testing/smoke/lib.sh
 
 trap "terraform_destroy" EXIT
 
 terraform_apply ${PREV_LATEST_VERSION} ${INTEGRATIONS_SERVER}
-
-ELASTICSEARCH_URL=$(terraform output -raw elasticsearch_url)
-ELASTICSEARCH_USER=$(terraform output -raw elasticsearch_username)
-ELASTICSEARCH_PASS=$(terraform output -raw elasticsearch_password)
-APM_AUTH_HEADER="Authorization: Bearer $(terraform output -raw apm_secret_token)"
-APM_SERVER_URL=$(terraform output -raw apm_server_url)
-
 healthcheck 1
 send_events
 ${ASSERT_EVENTS_FUNC} ${PREV_LATEST_VERSION}
 
 echo "-> Upgrading APM Server to ${LATEST_VERSION}"
-echo stack_version=\"${LATEST_VERSION}\" > terraform.tfvars
 terraform_apply ${LATEST_VERSION} ${INTEGRATIONS_SERVER}
-
 healthcheck 1
 send_events
 ${ASSERT_EVENTS_FUNC} ${LATEST_VERSION}
-
-echo "-> Smoke tests passed!"
diff --git a/testing/smoke/basic_upgrade/legacy-managed.sh b/testing/smoke/basic_upgrade/legacy-managed.sh
new file mode 100755
index 00000000000..4d5dd05d68a
--- /dev/null
+++ b/testing/smoke/basic_upgrade/legacy-managed.sh
@@ -0,0 +1,23 @@
+#!/bin/bash
+
+set -eo pipefail
+
+VERSION=7.17
+LATEST_VERSION=$(curl -s --fail https://artifacts-api.elastic.co/v1/versions/${VERSION} | jq -r '.version.builds[0].version')
+
+echo "-> Running ${LATEST_VERSION} standalone to ${LATEST_VERSION} managed upgrade"
+
+. $(git rev-parse --show-toplevel)/testing/smoke/lib.sh
+
+trap "terraform_destroy" EXIT
+
+terraform_apply ${LATEST_VERSION}
+healthcheck 1
+send_events
+legacy_assert_events ${LATEST_VERSION}
+
+echo "-> Upgrading APM Server to managed mode"
+upgrade_managed ${LATEST_VERSION}
+healthcheck 1
+send_events
+data_stream_assert_events ${LATEST_VERSION}
diff --git a/testing/smoke/basic_upgrade/main.tf b/testing/smoke/basic_upgrade/main.tf
index fc63c1a74ec..8d547157ce5 100644
--- a/testing/smoke/basic_upgrade/main.tf
+++ b/testing/smoke/basic_upgrade/main.tf
@@ -50,9 +50,14 @@ output "apm_server_url" {
   description = "The APM Server URL"
 }
 
+output "kibana_url" {
+  value       = module.ec_deployment.kibana_url
+  description = "The Kibana URL"
+}
+
 output "elasticsearch_url" {
   value       = module.ec_deployment.elasticsearch_url
-  description = "The APM Server URL"
+  description = "The Elasticsearch URL"
 }
 
 output "elasticsearch_username" {
diff --git a/testing/smoke/basic_upgrade/standalone-major-managed.sh b/testing/smoke/basic_upgrade/standalone-major-managed.sh
new file mode 100755
index 00000000000..6dadc210543
--- /dev/null
+++ b/testing/smoke/basic_upgrade/standalone-major-managed.sh
@@ -0,0 +1,30 @@
+#!/bin/bash
+
+set -eo pipefail
+
+VERSION=7.17
+LATEST_VERSION=$(curl -s --fail https://artifacts-api.elastic.co/v1/versions/${VERSION} | jq -r '.version.builds[0].version')
+VERSIONS=$(curl -s --fail https://artifacts-api.elastic.co/v1/versions)
+NEXT_MAJOR_LATEST=$(echo ${VERSIONS} | jq -r '.versions[]' | grep -v 'SNAPSHOT' | grep '^8' | tail -1)
+
+echo "-> Running ${LATEST_VERSION} standalone to ${NEXT_MAJOR_LATEST} to ${NEXT_MAJOR_LATEST} managed"
+
+. $(git rev-parse --show-toplevel)/testing/smoke/lib.sh
+
+trap "terraform_destroy" EXIT
+
+terraform_apply ${LATEST_VERSION}
+healthcheck 1
+send_events
+legacy_assert_events ${LATEST_VERSION}
+
+terraform_apply ${NEXT_MAJOR_LATEST}
+healthcheck 1
+send_events
+data_stream_assert_events ${NEXT_MAJOR_LATEST}
+
+upgrade_managed ${NEXT_MAJOR_LATEST}
+healthcheck 1
+send_events
+Assert there are 2 instances of the same event, since we ingested data twice.
+data_stream_assert_events ${NEXT_MAJOR_LATEST} 2
diff --git a/testing/smoke/lib.sh b/testing/smoke/lib.sh
index 745892c75a5..820337e1bcd 100644
--- a/testing/smoke/lib.sh
+++ b/testing/smoke/lib.sh
@@ -6,14 +6,28 @@ terraform_apply() {
     if [[ ! -z ${2} ]] && [[ ${2} ]]; then echo integrations_server=true >> terraform.tfvars; fi
     terraform init
     terraform apply -auto-approve
+
+    if [[ ${EXPORTED_AUTH} ]]; then
+        return
+    fi
+    ELASTICSEARCH_URL=$(terraform output -raw elasticsearch_url)
+    ELASTICSEARCH_USER=$(terraform output -raw elasticsearch_username)
+    ELASTICSEARCH_PASS=$(terraform output -raw elasticsearch_password)
+    APM_AUTH_HEADER="Authorization: Bearer $(terraform output -raw apm_secret_token)"
+    APM_SERVER_URL=$(terraform output -raw apm_server_url)
+    KIBANA_URL=$(terraform output -raw kibana_url)
+    EXPORTED_AUTH=true
 }
 
 terraform_destroy() {
     exit_code=$?
+    if [[ ${exit_code} -gt 0 ]]; then
+        echo "-> Smoke tests FAILED!!"
+    fi
     echo "-> Destroying the underlying infrastructure..." 
     terraform destroy -auto-approve
     rm -f terraform.tfvars
-    exit $exit_code
+    exit ${exit_code}
 }
 
 assert_document() {
@@ -21,28 +35,31 @@ assert_document() {
     local FIELD=${2}
     local VALUE=${3}
     local VERSION=${4}
+    local ENTRIES=${5}
+    if [[ -z ${ENTRIES} ]]; then ENTRIES=1; fi
     local AUTH=${ELASTICSEARCH_USER}:${ELASTICSEARCH_PASS}
     local URL=${ELASTICSEARCH_URL}/${INDEX}/_search
     # RESULT needs to be a global variable in order to be able to parse
-    # the whole result in assert_single_entry. Passing it as a string
+    # the whole result in assert_entry. Passing it as a string
     # argument doesn't work well.
     RESULT=$(curl -s -u ${AUTH} -XGET "${URL}" -H 'Content-Type: application/json' -d"{\"query\":{\"bool\":{\"must\":[{\"match\":{\"${FIELD}\":\"${VALUE}\"}},{\"match\":{\"observer.version\":\"${VERSION}\"}}]}}}")
 
     echo "-> Asserting ${INDEX} contains expected documents documents..."
-    assert_single_entry ${FIELD} ${VALUE}
+    assert_entry ${FIELD} ${VALUE} ${ENTRIES}
 }
 
-assert_single_entry() {
+assert_entry() {
     local FIELD=${1}
     local VALUE=${2}
+    local ENTRIES=${3}
     local HITS=$(echo ${RESULT} | jq .hits.total.value)
     local MSG="${FIELD}=${VALUE}"
-    if [[ ${HITS} -ne 1 ]]; then
-        echo "Didn't find the indexed document ${MSG}, total hits ${HITS}"
+    if [[ ${HITS} -ne ${ENTRIES} ]]; then
+        echo "Didn't find ${ENTRIES} indexed documents ${MSG}, total hits ${HITS}"
         echo ${RESULT}
         exit 2
     else
-        echo "-> Asserted 1 ${MSG} exists"
+        echo "-> Asserted ${ENTRIES} ${MSG} exists"
     fi
 }
 
@@ -56,16 +73,17 @@ send_events() {
     curl --fail --data-binary @${INTAKE_DATA} -H "${APM_AUTH_HEADER}" -H "${INTAKE_HEADER}" ${APM_SERVER_INTAKE}
 
     # TODO(marclop). It would be best to query Elasticsearch until at least X documents have been ingested.
-    sleep 5
+    sleep 10
 }
 
 legacy_assert_events() {
     local INDEX="apm-${1}"
     local VERSION=${1}
-    assert_document "${INDEX}-error-*" "error.id" "9876543210abcdeffedcba0123456789" ${VERSION}
-    assert_document "${INDEX}-span-*" "span.id" "1234567890aaaade" ${VERSION}
-    assert_document "${INDEX}-transaction-*" "transaction.id" "4340a8e0df1906ecbfa9" ${VERSION}
-    assert_document "${INDEX}-metric-*" "transaction.type" "request" ${VERSION}
+    local ENTRIES=${2}
+    assert_document "${INDEX}-error-*" "error.id" "9876543210abcdeffedcba0123456789" ${VERSION} ${ENTRIES}
+    assert_document "${INDEX}-span-*" "span.id" "1234567890aaaade" ${VERSION} ${ENTRIES}
+    assert_document "${INDEX}-transaction-*" "transaction.id" "4340a8e0df1906ecbfa9" ${VERSION} ${ENTRIES}
+    assert_document "${INDEX}-metric-*" "transaction.type" "request" ${VERSION} ${ENTRIES}
 }
 
 data_stream_assert_events() {
@@ -73,16 +91,17 @@ data_stream_assert_events() {
     local ERRORS_INDEX="logs-apm.error-*"
     local METRICS_INDEX="metrics-apm.internal-*"
     local VERSION=${1}
-    assert_document ${ERRORS_INDEX} "error.id" "9876543210abcdeffedcba0123456789" ${VERSION}
-    assert_document ${TRACES_INDEX} "span.id" "1234567890aaaade" ${VERSION}
-    assert_document ${TRACES_INDEX} "transaction.id" "4340a8e0df1906ecbfa9" ${VERSION}
-    assert_document ${METRICS_INDEX} "transaction.type" "request" ${VERSION}
+    local ENTRIES=${2}
+    assert_document ${ERRORS_INDEX} "error.id" "9876543210abcdeffedcba0123456789" ${VERSION} ${ENTRIES}
+    assert_document ${TRACES_INDEX} "span.id" "1234567890aaaade" ${VERSION} ${ENTRIES}
+    assert_document ${TRACES_INDEX} "transaction.id" "4340a8e0df1906ecbfa9" ${VERSION} ${ENTRIES}
+    assert_document ${METRICS_INDEX} "transaction.type" "request" ${VERSION} ${ENTRIES}
 }
 
 healthcheck() {
     local PUBLISH_READY=$(curl -s --fail -H "${APM_AUTH_HEADER}" ${APM_SERVER_URL} | jq '.publish_ready')
     if [[ ! ${PUBLISH_READY} ]]; then
-        local MAX_RETRIES=5
+        local MAX_RETRIES=10
         if [[ ${1} -gt 0 ]] && [[ ${1} -lt ${MAX_RETRIES} ]]; then
             echo "-> APM Server isn't ready to receive events, retrying (${1}/${MAX_RETRIES})..."
             sleep $((1 * ${1}))
@@ -96,3 +115,23 @@ healthcheck() {
         echo "-> APM Server ready!"
     fi
 }
+
+upgrade_managed() {
+    local CURR_VERSION=${1}
+    local AUTH=${ELASTICSEARCH_USER}:${ELASTICSEARCH_PASS}
+    local URL_MIGRATE=${KIBANA_URL}/internal/apm/fleet/cloud_apm_package_policy
+
+    echo "-> Upgrading APM Server ${CURR_VERSION} to managed mode..."
+    local RESULT=$(curl -s --fail -H 'kbn-xsrf: true' -u "${AUTH}" -XPOST ${URL_MIGRATE})
+    local ENABLED=$(echo ${RESULT} | jq '.cloudApmPackagePolicy.enabled')
+
+    if [[ ! ${ENABLED} ]]; then
+        echo "-> Failed migrating and enabling the APM Integration"
+        exit 6
+    fi  
+
+    # Allow the new server to start serving requets. Waiting for an arbitrary 70 seconds
+    # period is not ideal, but there aren't any other APIs we can query.
+    echo "-> Waiting for 70 seconds for the APM Server to become available..."
+    sleep 70
+}