diff --git a/cmd/fleet/calendar_cron_test.go b/cmd/fleet/calendar_cron_test.go
index 84f5ece527..c6db483c55 100644
--- a/cmd/fleet/calendar_cron_test.go
+++ b/cmd/fleet/calendar_cron_test.go
@@ -1,6 +1,11 @@
 package main
 
 import (
+	"context"
+	"github.com/fleetdm/fleet/v4/server/fleet"
+	"github.com/fleetdm/fleet/v4/server/mock"
+	kitlog "github.com/go-kit/log"
+	"os"
 	"testing"
 	"time"
 
@@ -8,6 +13,7 @@ import (
 )
 
 func TestGetPreferredCalendarEventDate(t *testing.T) {
+	t.Parallel()
 	date := func(year int, month time.Month, day int) time.Time {
 		return time.Date(year, month, day, 0, 0, 0, 0, time.UTC)
 	}
@@ -103,3 +109,84 @@ func TestGetPreferredCalendarEventDate(t *testing.T) {
 		})
 	}
 }
+
+// TestEventForDifferentHost tests case when event exists, but for a different host. Nothing should happen.
+// The old event will eventually be cleaned up by the cleanup job, and afterward a new event will be created.
+func TestEventForDifferentHost(t *testing.T) {
+	t.Parallel()
+	ds := new(mock.Store)
+	ctx := context.Background()
+	logger := kitlog.With(kitlog.NewLogfmtLogger(os.Stdout))
+	ds.AppConfigFunc = func(ctx context.Context) (*fleet.AppConfig, error) {
+		return &fleet.AppConfig{
+			Integrations: fleet.Integrations{
+				GoogleCalendar: []*fleet.GoogleCalendarIntegration{
+					{},
+				},
+			},
+		}, nil
+	}
+	teamID1 := uint(1)
+	ds.ListTeamsFunc = func(ctx context.Context, filter fleet.TeamFilter, opt fleet.ListOptions) ([]*fleet.Team, error) {
+		return []*fleet.Team{
+			{
+				ID: teamID1,
+				Config: fleet.TeamConfig{
+					Integrations: fleet.TeamIntegrations{
+						GoogleCalendar: &fleet.TeamGoogleCalendarIntegration{
+							Enable: true,
+						},
+					},
+				},
+			},
+		}, nil
+	}
+	policyID1 := uint(10)
+	ds.GetCalendarPoliciesFunc = func(ctx context.Context, teamID uint) ([]fleet.PolicyCalendarData, error) {
+		require.Equal(t, teamID1, teamID)
+		return []fleet.PolicyCalendarData{
+			{
+				ID:   policyID1,
+				Name: "Policy 1",
+			},
+		}, nil
+	}
+	hostID1 := uint(100)
+	hostID2 := uint(101)
+	userEmail1 := "user@example.com"
+	ds.GetTeamHostsPolicyMembershipsFunc = func(
+		ctx context.Context, domain string, teamID uint, policyIDs []uint,
+	) ([]fleet.HostPolicyMembershipData, error) {
+		require.Equal(t, teamID1, teamID)
+		require.Equal(t, []uint{policyID1}, policyIDs)
+		return []fleet.HostPolicyMembershipData{
+			{
+				HostID:  hostID1,
+				Email:   userEmail1,
+				Passing: false,
+			},
+		}, nil
+	}
+	// Return an existing event, but for a different host
+	eventTime := time.Now().Add(time.Hour)
+	ds.GetHostCalendarEventByEmailFunc = func(ctx context.Context, email string) (*fleet.HostCalendarEvent, *fleet.CalendarEvent, error) {
+		require.Equal(t, userEmail1, email)
+		calEvent := &fleet.CalendarEvent{
+			ID:        1,
+			Email:     email,
+			StartTime: eventTime,
+			EndTime:   eventTime,
+		}
+		hcEvent := &fleet.HostCalendarEvent{
+			ID:              1,
+			HostID:          hostID2,
+			CalendarEventID: 1,
+			WebhookStatus:   fleet.CalendarWebhookStatusNone,
+		}
+		return hcEvent, calEvent, nil
+	}
+
+	err := cronCalendarEvents(ctx, ds, logger)
+	require.NoError(t, err)
+
+}