diff --git a/CHANGELOG.next.asciidoc b/CHANGELOG.next.asciidoc
index 20948ff8ac5..e46b86b33ed 100644
--- a/CHANGELOG.next.asciidoc
+++ b/CHANGELOG.next.asciidoc
@@ -62,6 +62,7 @@ https://github.com/elastic/beats/compare/v8.2.0\...main[Check the HEAD diff]
 - Fix Google workspace pagination and document ID generation. {pull}33666[33666]
 
 *Heartbeat*
+- Fix broken zip URL monitors. NOTE: Zip URL Monitors will be removed in version 8.7 and replaced with project monitors. {pull}33723[33723]
 - Fix bug affecting let's encrypt and other users of cross-signed certs, where cert expiration was incorrectly calculated. {issue}33215[33215]
 - Fix broken disable feature for kibana configured monitors. {pull}33293[33293]
 - Fix states client support for output options. {pull}33405[33405]
diff --git a/x-pack/heartbeat/monitors/browser/synthexec/enrich.go b/x-pack/heartbeat/monitors/browser/synthexec/enrich.go
index 6e98e26fba8..6cfab119426 100644
--- a/x-pack/heartbeat/monitors/browser/synthexec/enrich.go
+++ b/x-pack/heartbeat/monitors/browser/synthexec/enrich.go
@@ -25,9 +25,10 @@ import (
 type enricher func(event *beat.Event, se *SynthEvent) error
 
 type streamEnricher struct {
-	je         *journeyEnricher
-	sFields    stdfields.StdMonitorFields
-	checkGroup string
+	je           *journeyEnricher
+	journeyCount int
+	sFields      stdfields.StdMonitorFields
+	checkGroup   string
 }
 
 func newStreamEnricher(sFields stdfields.StdMonitorFields) *streamEnricher {
@@ -39,8 +40,15 @@ func (senr *streamEnricher) enrich(event *beat.Event, se *SynthEvent) error {
 		senr.je = newJourneyEnricher(senr)
 	}
 
-	eventext.MergeEventFields(event, map[string]interface{}{"monitor": map[string]interface{}{"check_group": senr.checkGroup}})
+	// TODO: Remove this when zip monitors are removed and we have 1:1 monitor / journey
+	if se != nil && se.Type == JourneyStart {
+		senr.journeyCount++
+		if senr.journeyCount > 1 {
+			senr.checkGroup = makeUuid()
+		}
+	}
 
+	eventext.MergeEventFields(event, map[string]interface{}{"monitor": map[string]interface{}{"check_group": senr.checkGroup}})
 	return senr.je.enrich(event, se)
 }
 
@@ -153,7 +161,7 @@ func (je *journeyEnricher) enrichSynthEvent(event *beat.Event, se *SynthEvent) e
 
 	eventext.MergeEventFields(event, se.ToMap())
 
-	if je.urlFields == nil {
+	if len(je.urlFields) == 0 {
 		if urlFields, err := event.GetValue("url"); err == nil {
 			if ufMap, ok := urlFields.(mapstr.M); ok {
 				je.urlFields = ufMap
@@ -206,10 +214,6 @@ func (je *journeyEnricher) createSummary(event *beat.Event) error {
 	if je.journeyComplete {
 		return je.error
 	}
-
-	// create a new check group for the next journey
-	je.streamEnricher.checkGroup = makeUuid()
-
 	return fmt.Errorf("journey did not finish executing, %d steps ran: %w", je.stepCount, je.error)
 }