diff --git a/projects/manage-supervision-and-delius/src/integrationTest/kotlin/uk/gov/justice/digital/hmpps/CreateAppointmentIntegrationTests.kt b/projects/manage-supervision-and-delius/src/integrationTest/kotlin/uk/gov/justice/digital/hmpps/CreateAppointmentIntegrationTests.kt
index 1dd1b44def..90c3700d0b 100644
--- a/projects/manage-supervision-and-delius/src/integrationTest/kotlin/uk/gov/justice/digital/hmpps/CreateAppointmentIntegrationTests.kt
+++ b/projects/manage-supervision-and-delius/src/integrationTest/kotlin/uk/gov/justice/digital/hmpps/CreateAppointmentIntegrationTests.kt
@@ -23,12 +23,15 @@ import uk.gov.justice.digital.hmpps.data.generator.OffenderManagerGenerator.STAF
 import uk.gov.justice.digital.hmpps.data.generator.OffenderManagerGenerator.STAFF_USER_1
 import uk.gov.justice.digital.hmpps.data.generator.OffenderManagerGenerator.TEAM
 import uk.gov.justice.digital.hmpps.data.generator.PersonGenerator
+import uk.gov.justice.digital.hmpps.datetime.DeliusDateFormatter
+import uk.gov.justice.digital.hmpps.datetime.EuropeLondon
 import uk.gov.justice.digital.hmpps.integrations.delius.sentence.entity.AppointmentRepository
 import uk.gov.justice.digital.hmpps.test.CustomMatchers.isCloseTo
 import uk.gov.justice.digital.hmpps.test.MockMvcExtensions.contentAsJson
 import uk.gov.justice.digital.hmpps.test.MockMvcExtensions.withJson
 import uk.gov.justice.digital.hmpps.test.MockMvcExtensions.withToken
 import java.time.LocalDate
+import java.time.LocalTime
 import java.time.ZonedDateTime
 import java.util.*
 
@@ -161,8 +164,8 @@ class CreateAppointmentIntegrationTests {
         val appointment = CreateAppointment(
             Companion.user,
             CreateAppointment.Type.HomeVisitToCaseNS,
-            ZonedDateTime.now().plusHours(1),
-            ZonedDateTime.now().plusHours(2),
+            ZonedDateTime.of(LocalDate.now().plusDays(1), LocalTime.NOON, EuropeLondon),
+            ZonedDateTime.of(LocalDate.now().plusDays(1), LocalTime.NOON.plusHours(1), EuropeLondon),
             numberOfAppointments = 3,
             eventId = PersonGenerator.EVENT_1.id,
             uuid = UUID.randomUUID()
@@ -179,12 +182,19 @@ class CreateAppointmentIntegrationTests {
             .andReturn().response.contentAsJson<AppointmentDetail>()
 
 
-        val conflict = mockMvc.perform(
+        val dateNowPlusOneDay = LocalDate.now().plusDays(1).format(DeliusDateFormatter)
+        val dateNowPlusTwoDays = LocalDate.now().plusDays(2).format(DeliusDateFormatter)
+        val dateNowPlusThreeDays = LocalDate.now().plusDays(3).format(DeliusDateFormatter)
+
+        val errorMsg = """
+            Appointment(s) conflicts with an existing future appointment [{"start":"$dateNowPlusOneDay 12:00","end":"$dateNowPlusOneDay 13:00"},{"start":"$dateNowPlusTwoDays 12:00","end":"$dateNowPlusTwoDays 13:00"},{"start":"$dateNowPlusThreeDays 12:00","end":"$dateNowPlusThreeDays 13:00"}]
+        """.trimIndent()
+        mockMvc.perform(
             post("/appointment/${person.crn}")
                 .withToken()
                 .withJson(appointment))
             .andExpect(MockMvcResultMatchers.status().isConflict)
-//            .andExpect(jsonPath("$.message", equalTo("Appointment conflicts with an existing future appointment")))
+            .andExpect(jsonPath("$.message", equalTo(errorMsg)))
 
         val appointments = appointmentRepository.findAllById(response.appointments.map { it.id })
         appointmentRepository.deleteAll(appointments)
diff --git a/projects/manage-supervision-and-delius/src/main/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentService.kt b/projects/manage-supervision-and-delius/src/main/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentService.kt
index f0ddeb553d..8b07bd9b59 100644
--- a/projects/manage-supervision-and-delius/src/main/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentService.kt
+++ b/projects/manage-supervision-and-delius/src/main/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentService.kt
@@ -1,9 +1,11 @@
 package uk.gov.justice.digital.hmpps.service
 
+import com.fasterxml.jackson.databind.ObjectMapper
 import org.springframework.stereotype.Service
 import uk.gov.justice.digital.hmpps.api.model.appointment.AppointmentDetail
 import uk.gov.justice.digital.hmpps.api.model.appointment.CreateAppointment
 import uk.gov.justice.digital.hmpps.api.model.appointment.CreatedAppointment
+import uk.gov.justice.digital.hmpps.api.model.appointment.OverlappingAppointment
 import uk.gov.justice.digital.hmpps.audit.service.AuditableService
 import uk.gov.justice.digital.hmpps.audit.service.AuditedInteractionService
 import uk.gov.justice.digital.hmpps.datetime.DeliusDateTimeFormatter
@@ -28,7 +30,8 @@ class SentenceAppointmentService(
     private val eventSentenceRepository: EventSentenceRepository,
     private val requirementRepository: RequirementRepository,
     private val licenceConditionRepository: LicenceConditionRepository,
-    private val staffUserRepository: StaffUserRepository
+    private val staffUserRepository: StaffUserRepository,
+    private val objectMapper: ObjectMapper
 ) : AuditableService(auditedInteractionService) {
     fun createAppointment(
         crn: String,
@@ -74,7 +77,7 @@ class SentenceAppointmentService(
                 }
             }
 
-           createAppointments.forEach {
+            val overlappingAppointments = createAppointments.mapNotNull {
                 if (it.start.isAfter(ZonedDateTime.now()) && appointmentRepository.appointmentClashes(
                         om.person.id,
                         it.start.toLocalDate(),
@@ -82,10 +85,15 @@ class SentenceAppointmentService(
                         it.end
                     )
                 ) {
-                    throw ConflictException("Appointment conflicts with an existing future appointment ${createAppointment.start.toLocalDateTime().format(
-                        DeliusDateTimeFormatter).dropLast(3)} and ${createAppointment.end.toLocalDateTime().format(
-                        DeliusDateTimeFormatter).dropLast(3)}")
-                }
+                    OverlappingAppointment(
+                        it.start.toLocalDateTime().format(DeliusDateTimeFormatter).dropLast(3),
+                        it.end.toLocalDateTime().format(DeliusDateTimeFormatter).dropLast(3)
+                    )
+                } else null
+            }
+
+            if (overlappingAppointments.isNotEmpty()) {
+                throw ConflictException("Appointment(s) conflicts with an existing future appointment ${objectMapper.writeValueAsString(overlappingAppointments)}")
             }
 
             val appointments = createAppointments.map { it.withManager(om, userAndLocation) }
diff --git a/projects/manage-supervision-and-delius/src/test/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentServiceTest.kt b/projects/manage-supervision-and-delius/src/test/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentServiceTest.kt
index 7a1fd50db3..0665a5fef5 100644
--- a/projects/manage-supervision-and-delius/src/test/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentServiceTest.kt
+++ b/projects/manage-supervision-and-delius/src/test/kotlin/uk/gov/justice/digital/hmpps/service/SentenceAppointmentServiceTest.kt
@@ -1,5 +1,6 @@
 package uk.gov.justice.digital.hmpps.service
 
+import com.fasterxml.jackson.databind.ObjectMapper
 import org.hamcrest.MatcherAssert.assertThat
 import org.hamcrest.Matchers.equalTo
 import org.junit.jupiter.api.Test
@@ -50,6 +51,9 @@ class SentenceAppointmentServiceTest {
     @Mock
     lateinit var staffUserRepository: StaffUserRepository
 
+    @Mock
+    lateinit var objectMapper: ObjectMapper
+
     @InjectMocks
     lateinit var service: SentenceAppointmentService