diff --git a/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/MessagingControllerImpl.kt b/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/MessagingControllerImpl.kt
index b0b6c3586..c3bdb96ee 100644
--- a/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/MessagingControllerImpl.kt
+++ b/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/MessagingControllerImpl.kt
@@ -109,11 +109,11 @@ constructor(
     override fun deleteAllMessages(ctx: Context): Context {
         val contactId = ctx.getContactIdFromPathParam()
         try {
-            conversationManager.deleteAllMessages(contactId)
+            val result = conversationManager.deleteAllMessages(contactId)
+            return ctx.json(result.output())
         } catch (e: NoSuchContactException) {
             throw NotFoundResponse()
         }
-        return ctx
     }
 
     override fun eventOccurred(e: Event) {
diff --git a/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/OutputConversationMessage.kt b/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/OutputConversationMessage.kt
index 3c42a39d0..487bcdbb0 100644
--- a/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/OutputConversationMessage.kt
+++ b/briar-headless/src/main/java/org/briarproject/briar/headless/messaging/OutputConversationMessage.kt
@@ -5,6 +5,7 @@ import org.briarproject.bramble.api.sync.MessageId
 import org.briarproject.bramble.api.sync.event.MessagesAckedEvent
 import org.briarproject.bramble.api.sync.event.MessagesSentEvent
 import org.briarproject.briar.api.conversation.ConversationMessageHeader
+import org.briarproject.briar.api.conversation.DeletionResult
 import org.briarproject.briar.api.messaging.PrivateMessage
 import org.briarproject.briar.api.messaging.PrivateMessageHeader
 import org.briarproject.briar.headless.json.JsonDict
@@ -47,6 +48,15 @@ internal fun PrivateMessage.output(contactId: ContactId, text: String) = JsonDic
     "text" to text
 )
 
+internal fun DeletionResult.output() = JsonDict(
+    "allDeleted" to allDeleted(),
+    "hasIntroductionSessionInProgress" to hasIntroductionSessionInProgress(),
+    "hasInvitationSessionInProgress" to hasInvitationSessionInProgress(),
+    "hasNotAllIntroductionSelected" to hasNotAllIntroductionSelected(),
+    "hasNotAllInvitationSelected" to hasNotAllInvitationSelected(),
+    "hasNotFullyDownloaded" to hasNotFullyDownloaded()
+)
+
 internal fun MessagesAckedEvent.output() = JsonDict(
     "contactId" to contactId.int,
     "messageIds" to messageIds.toJson()
diff --git a/briar-headless/src/test/java/org/briarproject/briar/headless/messaging/MessagingControllerImplTest.kt b/briar-headless/src/test/java/org/briarproject/briar/headless/messaging/MessagingControllerImplTest.kt
index 2cecd7b1c..84c7c5ec2 100644
--- a/briar-headless/src/test/java/org/briarproject/briar/headless/messaging/MessagingControllerImplTest.kt
+++ b/briar-headless/src/test/java/org/briarproject/briar/headless/messaging/MessagingControllerImplTest.kt
@@ -33,6 +33,7 @@ import org.junit.jupiter.api.Assertions.assertEquals
 import org.junit.jupiter.api.Assertions.assertThrows
 import org.junit.jupiter.api.Test
 import org.spongycastle.util.encoders.Base64
+import kotlin.random.Random
 
 internal class MessagingControllerImplTest : ControllerTest() {
 
@@ -346,8 +347,10 @@ internal class MessagingControllerImplTest : ControllerTest() {
 
     @Test
     fun testDeleteAllMessages() {
+        val result = DeletionResult()
         every { ctx.pathParam("contactId") } returns "1"
-        every { conversationManager.deleteAllMessages(ContactId(1)) } returns DeletionResult()
+        every { conversationManager.deleteAllMessages(ContactId(1)) } returns result
+        every { ctx.json(result.output()) } returns ctx
         controller.deleteAllMessages(ctx)
     }
 
@@ -368,6 +371,27 @@ internal class MessagingControllerImplTest : ControllerTest() {
         }
     }
 
+    @Test
+    fun testOutputDeletionResult() {
+        val result = DeletionResult()
+        if (Random.nextBoolean()) result.addInvitationNotAllSelected()
+        if (Random.nextBoolean()) result.addInvitationSessionInProgress()
+        if (Random.nextBoolean()) result.addIntroductionNotAllSelected()
+        if (Random.nextBoolean()) result.addIntroductionSessionInProgress()
+        if (Random.nextBoolean()) result.addNotFullyDownloaded()
+        val json = """
+            {
+                "allDeleted": ${result.allDeleted()},
+                "hasIntroductionSessionInProgress": ${result.hasIntroductionSessionInProgress()},
+                "hasInvitationSessionInProgress": ${result.hasInvitationSessionInProgress()},
+                "hasNotAllIntroductionSelected": ${result.hasNotAllIntroductionSelected()},
+                "hasNotAllInvitationSelected": ${result.hasNotAllInvitationSelected()},
+                "hasNotFullyDownloaded": ${result.hasNotFullyDownloaded()}
+            }
+        """
+        assertJsonEquals(json, result.output())
+    }
+
     private fun expectGetContact() {
         every { ctx.pathParam("contactId") } returns contact.id.int.toString()
         every { contactManager.getContact(contact.id) } returns contact