diff --git a/ts/models/conversation.ts b/ts/models/conversation.ts
index 42d6e3111..bb2bbe274 100644
--- a/ts/models/conversation.ts
+++ b/ts/models/conversation.ts
@@ -635,11 +635,9 @@ export class ConversationModel extends Backbone.Model<ConversationAttributes> {
 
       if (this.isPrivate()) {
         if (this.isMe()) {
-          if (this.isDisappearingMode) {
-            // TODO legacy messages support will be removed in a future release
-            if (!this.isDisappearingMode('legacy') || !this.isDisappearingMode('deleteAfterSend')) {
-              return;
-            }
+          // TODO legacy messages support will be removed in a future release
+          if (!this.isDisappearingMode('legacy') && !this.isDisappearingMode('deleteAfterSend')) {
+            return;
           }
           chatMessageParams.syncTarget = this.id;
           const chatMessageMe = new VisibleMessage(chatMessageParams);
@@ -670,9 +668,11 @@ export class ConversationModel extends Backbone.Model<ConversationAttributes> {
       }
 
       if (this.isMediumGroup()) {
-        if (!this.isDisappearingMode('deleteAfterSend')) {
+        // TODO legacy messages support will be removed in a future release
+        if (!this.isDisappearingMode('legacy') && !this.isDisappearingMode('disappearAfterSend')) {
           return;
         }
+
         const chatMessageMediumGroup = new VisibleMessage(chatMessageParams);
         const closedGroupVisibleMessage = new ClosedGroupVisibleMessage({
           chatMessage: chatMessageMediumGroup,
@@ -2237,6 +2237,7 @@ export class ConversationModel extends Backbone.Model<ConversationAttributes> {
     return [];
   }
 
+  // TODO I think this is flawed
   private isDisappearingMode(mode: DisappearingMessageType) {
     // TODO legacy messages support will be removed in a future release
     const success =
@@ -2247,7 +2248,12 @@ export class ConversationModel extends Backbone.Model<ConversationAttributes> {
         : this.get('expirationType') === 'deleteAfterSend';
 
     if (!success) {
-      window.log.info(`WIP: This message should be disappear after ${mode}`, this);
+      window.log.info(
+        `WIP: This message should be ${
+          mode === 'legacy' ? ' a legacy disappearing message' : ` disappear after ${mode}`
+        }`,
+        this
+      );
     }
 
     return success;
diff --git a/ts/receiver/contentMessage.ts b/ts/receiver/contentMessage.ts
index 1aa54d6bc..7a1f1942c 100644
--- a/ts/receiver/contentMessage.ts
+++ b/ts/receiver/contentMessage.ts
@@ -382,7 +382,7 @@ export async function innerHandleSwarmContentMessage(
      * For a closed group message, this holds the conversation with that specific user outside of the closed group.
      * For a private conversation message, this is just the conversation with that user
      */
-    const senderConversationModel = await getConversationController().getOrCreateAndWait(
+    let conversationModel = await getConversationController().getOrCreateAndWait(
       isPrivateConversationMessage ? envelope.source : envelope.senderIdentity,
       ConversationTypeEnum.PRIVATE
     );
@@ -393,7 +393,7 @@ export async function innerHandleSwarmContentMessage(
      */
     if (!isPrivateConversationMessage) {
       // this is a closed group message, we have a second conversation to make sure exists
-      await getConversationController().getOrCreateAndWait(
+      conversationModel = await getConversationController().getOrCreateAndWait(
         envelope.source,
         ConversationTypeEnum.GROUP
       );
@@ -416,14 +416,22 @@ export async function innerHandleSwarmContentMessage(
 
       // TODO account for outdated groups separately probably
       if (isLegacyMessage) {
-        window.log.info('WIP: Received a legacy disappearing message', content);
+        window.log.info(
+          'WIP: Received a legacy disappearing message',
+          content,
+          `${
+            !isPrivateConversationMessage
+              ? ` in closed group ${conversationModel.get('displayNameInProfile')}`
+              : ''
+          }`
+        );
         // trigger notice banner
-        if (!senderConversationModel.get('hasOutdatedClient')) {
-          senderConversationModel.set({ hasOutdatedClient: true });
+        if (!conversationModel.get('hasOutdatedClient')) {
+          conversationModel.set({ hasOutdatedClient: true });
         }
       } else {
-        if (senderConversationModel.get('hasOutdatedClient')) {
-          senderConversationModel.set({ hasOutdatedClient: false });
+        if (conversationModel.get('hasOutdatedClient')) {
+          conversationModel.set({ hasOutdatedClient: false });
         }
       }
 
@@ -449,7 +457,7 @@ export async function innerHandleSwarmContentMessage(
         sentAtTimestamp,
         dataMessage as SignalService.DataMessage,
         messageHash,
-        senderConversationModel,
+        conversationModel,
         expireUpdate
       );
       perfEnd(`handleSwarmDataMessage-${envelope.id}`, 'handleSwarmDataMessage');
diff --git a/ts/session/messages/outgoing/visibleMessage/ClosedGroupVisibleMessage.ts b/ts/session/messages/outgoing/visibleMessage/ClosedGroupVisibleMessage.ts
index d40853112..98a2282b8 100644
--- a/ts/session/messages/outgoing/visibleMessage/ClosedGroupVisibleMessage.ts
+++ b/ts/session/messages/outgoing/visibleMessage/ClosedGroupVisibleMessage.ts
@@ -45,6 +45,11 @@ export class ClosedGroupVisibleMessage extends ClosedGroupMessage {
 
     dataProto.group = groupMessage;
 
+    // TODO legacy messages support will be removed in a future release
+    if (this.expirationType === 'legacy' && this.expireTimer) {
+      dataProto.expireTimer = this.expireTimer;
+    }
+
     return dataProto;
   }
 }
diff --git a/ts/session/sending/MessageSentHandler.ts b/ts/session/sending/MessageSentHandler.ts
index f55d85a65..f667c3069 100644
--- a/ts/session/sending/MessageSentHandler.ts
+++ b/ts/session/sending/MessageSentHandler.ts
@@ -125,8 +125,9 @@ async function handleMessageSentSuccess(
   const expirationType = fetchedMessage.get('expirationType');
   // TODO legacy messages support will be removed in a future release
   const convo = fetchedMessage.getConversation();
-  const isLegacyMode = convo && convo.isPrivate() && expirationType === 'legacy';
-  const markAsUnread = isLegacyMode || expirationType === 'deleteAfterRead';
+  const isLegacyReadMode = convo && convo.isPrivate() && expirationType === 'legacy';
+  const isLegacySentMode = convo && convo.isMediumGroup() && expirationType === 'legacy';
+  const markAsUnread = isLegacyReadMode || expirationType === 'deleteAfterRead';
 
   fetchedMessage.set({
     sent_to: sentTo,
@@ -136,16 +137,16 @@ async function handleMessageSentSuccess(
     unread: markAsUnread ? 1 : 0,
   });
 
+  // TODO legacy messages support will be removed in a future release
   if (
-    fetchedMessage.get('expirationType') === 'deleteAfterSend' &&
+    (isLegacySentMode || expirationType === 'deleteAfterSend') &&
     Boolean(fetchedMessage.get('expirationStartTimestamp')) === false
   ) {
-    const expirationType = fetchedMessage.get('expirationType');
-    if (expirationType === 'deleteAfterSend') {
+    if (expirationType === 'legacy' || expirationType === 'deleteAfterSend') {
       // TODO message timer start is a few seconds less than the amount due to it's position in the pipeline, not sure on a fix yet
       fetchedMessage.set({
         expirationStartTimestamp: setExpirationStartTimestamp(
-          expirationType,
+          'deleteAfterSend',
           fetchedMessage.get('sent_at')
         ),
       });