diff --git a/ts/background.preload.ts b/ts/background.preload.ts
index cde3da358a..cbe3289b53 100644
--- a/ts/background.preload.ts
+++ b/ts/background.preload.ts
@@ -2495,6 +2495,8 @@ export async function startApp(): Promise<void> {
         pinnedByAci: data.sourceAci,
         sentAtTimestamp: data.timestamp,
         receivedAtTimestamp: data.receivedAtDate,
+        expireTimer: data.message.expireTimer,
+        expirationStartTimestamp: null,
       });
       confirm();
       return;
@@ -3003,6 +3005,8 @@ export async function startApp(): Promise<void> {
         pinnedByAci: sourceServiceId,
         sentAtTimestamp: data.timestamp,
         receivedAtTimestamp: data.receivedAtDate,
+        expireTimer: data.message.expireTimer,
+        expirationStartTimestamp: data.expirationStartTimestamp ?? null,
       });
       confirm();
       return;
diff --git a/ts/jobs/conversationJobQueue.preload.ts b/ts/jobs/conversationJobQueue.preload.ts
index 12460605b0..dee724de04 100644
--- a/ts/jobs/conversationJobQueue.preload.ts
+++ b/ts/jobs/conversationJobQueue.preload.ts
@@ -209,6 +209,7 @@ const pinMessageJobDataSchema = z.object({
   targetAuthorAci: aciSchema,
   targetSentTimestamp: z.number(),
   pinDurationSeconds: z.number().nullable(),
+  pinnedAt: z.number(),
 });
 export type PinMessageJobData = z.infer<typeof pinMessageJobDataSchema>;
 
@@ -290,6 +291,7 @@ const unpinMessageJobDataSchema = z.object({
   targetMessageId: z.string(),
   targetAuthorAci: aciSchema,
   targetSentTimestamp: z.number(),
+  unpinnedAt: z.number(),
 });
 export type UnpinMessageJobData = z.infer<typeof unpinMessageJobDataSchema>;
 
diff --git a/ts/jobs/helpers/createSendMessageJob.preload.ts b/ts/jobs/helpers/createSendMessageJob.preload.ts
index 8ec99b1bd3..2f8e190f57 100644
--- a/ts/jobs/helpers/createSendMessageJob.preload.ts
+++ b/ts/jobs/helpers/createSendMessageJob.preload.ts
@@ -27,9 +27,9 @@ export type SendMessageJobOptions<Data> = Readonly<{
   sendType: SendTypesType;
   getMessageId: (data: Data) => string | null;
   getMessageOptions: (
-    data: Data,
-    jobTimestamp: number
+    data: Data
   ) => Omit<SharedMessageOptionsType, 'recipients'>;
+  getExpirationStartTimestamp: (data: Data) => number | null;
 }>;
 
 export function createSendMessageJob<Data>(
@@ -40,7 +40,13 @@ export function createSendMessageJob<Data>(
     job: ConversationQueueJobBundle,
     data: Data
   ): Promise<void> {
-    const { sendName, sendType, getMessageId, getMessageOptions } = options;
+    const {
+      sendName,
+      sendType,
+      getMessageId,
+      getMessageOptions,
+      getExpirationStartTimestamp,
+    } = options;
 
     const logId = `${sendName}(${conversation.idForLogging()}/${job.timestamp})`;
     const log = job.log.child(logId);
@@ -71,7 +77,12 @@ export function createSendMessageJob<Data>(
     }
 
     const messageId = getMessageId(data);
-    const messageOptions = getMessageOptions(data, job.timestamp);
+    const messageOptions = {
+      ...getMessageOptions(data),
+      expireTimer: conversation.get('expireTimer'),
+      expireTimerVersion: conversation.getExpireTimerVersion(),
+    };
+    const expirationStartTimestamp = getExpirationStartTimestamp(data);
 
     try {
       if (recipientServiceIdsWithoutMe.length === 0) {
@@ -96,7 +107,7 @@ export function createSendMessageJob<Data>(
                 timestamp: job.timestamp,
                 destinationE164: conversation.get('e164'),
                 destinationServiceId: conversation.getServiceId(),
-                expirationStartTimestamp: null,
+                expirationStartTimestamp,
                 isUpdate: false,
                 options: sendOptions,
                 urgent: false,
@@ -128,7 +139,7 @@ export function createSendMessageJob<Data>(
               send: sender => {
                 return sender.sendMessageToServiceId({
                   serviceId: recipientServiceId,
-                  messageOptions: getMessageOptions(data, job.timestamp),
+                  messageOptions,
                   groupId: undefined,
                   contentHint: ContentHint.Resendable,
                   options: sendOptions,
@@ -138,6 +149,7 @@ export function createSendMessageJob<Data>(
               },
               sendType,
               timestamp: job.timestamp,
+              expirationStartTimestamp,
             });
           }
         );
@@ -162,8 +174,8 @@ export function createSendMessageJob<Data>(
                   abortSignal,
                   contentHint: ContentHint.Resendable,
                   groupSendOptions: {
+                    ...messageOptions,
                     groupV2: groupV2Info,
-                    ...getMessageOptions(data, job.timestamp),
                   },
                   messageId: messageId ?? undefined,
                   sendOptions,
@@ -174,6 +186,7 @@ export function createSendMessageJob<Data>(
               },
               sendType,
               timestamp: job.timestamp,
+              expirationStartTimestamp,
             });
           }
         );
diff --git a/ts/jobs/helpers/sendDeleteForEveryone.preload.ts b/ts/jobs/helpers/sendDeleteForEveryone.preload.ts
index f96c1e9338..e065ab23d4 100644
--- a/ts/jobs/helpers/sendDeleteForEveryone.preload.ts
+++ b/ts/jobs/helpers/sendDeleteForEveryone.preload.ts
@@ -213,6 +213,7 @@ export async function sendDeleteForEveryone(
               }),
             sendType,
             timestamp,
+            expirationStartTimestamp: null,
           });
 
           await updateMessageWithSuccessfulSends(message);
@@ -252,6 +253,7 @@ export async function sendDeleteForEveryone(
               }),
             sendType,
             timestamp,
+            expirationStartTimestamp: null,
           });
 
           await updateMessageWithSuccessfulSends(message);
diff --git a/ts/jobs/helpers/sendDirectExpirationTimerUpdate.preload.ts b/ts/jobs/helpers/sendDirectExpirationTimerUpdate.preload.ts
index 58ef6d7a60..9edfa54553 100644
--- a/ts/jobs/helpers/sendDirectExpirationTimerUpdate.preload.ts
+++ b/ts/jobs/helpers/sendDirectExpirationTimerUpdate.preload.ts
@@ -153,6 +153,7 @@ export async function sendDirectExpirationTimerUpdate(
           }),
         sendType,
         timestamp,
+        expirationStartTimestamp: null,
       });
     }
   } catch (error: unknown) {
diff --git a/ts/jobs/helpers/sendGroupCallUpdate.preload.ts b/ts/jobs/helpers/sendGroupCallUpdate.preload.ts
index d58c51da88..81ef0f607f 100644
--- a/ts/jobs/helpers/sendGroupCallUpdate.preload.ts
+++ b/ts/jobs/helpers/sendGroupCallUpdate.preload.ts
@@ -97,6 +97,7 @@ export async function sendGroupCallUpdate(
         ),
       sendType,
       timestamp,
+      expirationStartTimestamp: null,
     });
   } catch (error: unknown) {
     await handleMultipleSendErrors({
diff --git a/ts/jobs/helpers/sendGroupUpdate.preload.ts b/ts/jobs/helpers/sendGroupUpdate.preload.ts
index de4d49ced1..9be62ab550 100644
--- a/ts/jobs/helpers/sendGroupUpdate.preload.ts
+++ b/ts/jobs/helpers/sendGroupUpdate.preload.ts
@@ -117,6 +117,7 @@ export async function sendGroupUpdate(
             }),
           sendType,
           timestamp,
+          expirationStartTimestamp: null,
         })
     );
   } catch (error: unknown) {
diff --git a/ts/jobs/helpers/sendPinMessage.preload.ts b/ts/jobs/helpers/sendPinMessage.preload.ts
index e2f2e48222..3ad7300cbd 100644
--- a/ts/jobs/helpers/sendPinMessage.preload.ts
+++ b/ts/jobs/helpers/sendPinMessage.preload.ts
@@ -9,9 +9,9 @@ export const sendPinMessage = createSendMessageJob<PinMessageJobData>({
   getMessageId(data) {
     return data.targetMessageId;
   },
-  getMessageOptions(data, jobTimestamp) {
+  getMessageOptions(data) {
     return {
-      timestamp: jobTimestamp,
+      timestamp: data.pinnedAt,
       pinMessage: {
         targetAuthorAci: data.targetAuthorAci,
         targetSentTimestamp: data.targetSentTimestamp,
@@ -19,4 +19,7 @@ export const sendPinMessage = createSendMessageJob<PinMessageJobData>({
       },
     };
   },
+  getExpirationStartTimestamp(data) {
+    return data.pinnedAt;
+  },
 });
diff --git a/ts/jobs/helpers/sendPollTerminate.preload.ts b/ts/jobs/helpers/sendPollTerminate.preload.ts
index 54f13a9beb..9111c18431 100644
--- a/ts/jobs/helpers/sendPollTerminate.preload.ts
+++ b/ts/jobs/helpers/sendPollTerminate.preload.ts
@@ -133,6 +133,7 @@ export async function sendPollTerminate(
             }),
           sendType: 'pollTerminate',
           timestamp,
+          expirationStartTimestamp: null,
         });
 
         await markTerminateSuccess(pollMessage, jobLog);
diff --git a/ts/jobs/helpers/sendUnpinMessage.preload.ts b/ts/jobs/helpers/sendUnpinMessage.preload.ts
index 5def2ff373..d44a9aae82 100644
--- a/ts/jobs/helpers/sendUnpinMessage.preload.ts
+++ b/ts/jobs/helpers/sendUnpinMessage.preload.ts
@@ -10,13 +10,16 @@ export const sendUnpinMessage = createSendMessageJob<UnpinMessageJobData>({
   getMessageId(data) {
     return data.targetMessageId;
   },
-  getMessageOptions(data, jobTimestamp) {
+  getMessageOptions(data) {
     return {
-      timestamp: jobTimestamp,
+      timestamp: data.unpinnedAt,
       unpinMessage: {
         targetAuthorAci: data.targetAuthorAci,
         targetSentTimestamp: data.targetSentTimestamp,
       },
     };
   },
+  getExpirationStartTimestamp(data) {
+    return data.unpinnedAt;
+  },
 });
diff --git a/ts/messageModifiers/PinnedMessages.preload.ts b/ts/messageModifiers/PinnedMessages.preload.ts
index d85902d937..2fec799352 100644
--- a/ts/messageModifiers/PinnedMessages.preload.ts
+++ b/ts/messageModifiers/PinnedMessages.preload.ts
@@ -30,6 +30,8 @@ export type PinnedMessageAddProps = Readonly<{
   pinnedByAci: AciString;
   sentAtTimestamp: number;
   receivedAtTimestamp: number;
+  expireTimer: DurationInSeconds | null;
+  expirationStartTimestamp: number | null;
 }>;
 
 export type PinnedMessageRemoveProps = Readonly<{
@@ -125,6 +127,8 @@ export async function onPinnedMessageAdd(
       senderAci: props.pinnedByAci,
       sentAtTimestamp: props.sentAtTimestamp,
       receivedAtTimestamp: props.receivedAtTimestamp,
+      expireTimer: props.expireTimer,
+      expirationStartTimestamp: props.expirationStartTimestamp,
     });
   }
 
diff --git a/ts/models/conversations.preload.ts b/ts/models/conversations.preload.ts
index 3876a624fc..62fadb8d32 100644
--- a/ts/models/conversations.preload.ts
+++ b/ts/models/conversations.preload.ts
@@ -3567,6 +3567,8 @@ export class ConversationModel {
     senderAci: AciString;
     sentAtTimestamp: number;
     receivedAtTimestamp: number;
+    expireTimer: DurationInSeconds | null;
+    expirationStartTimestamp: number | null;
   }): Promise<void> {
     const ourAci = itemStorage.user.getCheckedAci();
     const senderIsMe = params.senderAci === ourAci;
@@ -3581,8 +3583,8 @@ export class ConversationModel {
       readStatus: senderIsMe ? ReadStatus.Read : ReadStatus.Unread,
       seenStatus: senderIsMe ? SeenStatus.Seen : SeenStatus.Unseen,
       sourceServiceId: params.senderAci,
-      expireTimer: this.get('expireTimer'),
-      expirationStartTimestamp: senderIsMe ? params.sentAtTimestamp : null,
+      expireTimer: params.expireTimer ?? undefined,
+      expirationStartTimestamp: params.expirationStartTimestamp,
       pinMessage: params.pinMessage,
     });
 
diff --git a/ts/state/ducks/conversations.preload.ts b/ts/state/ducks/conversations.preload.ts
index ac9c006f20..d17dbe3b32 100644
--- a/ts/state/ducks/conversations.preload.ts
+++ b/ts/state/ducks/conversations.preload.ts
@@ -5199,15 +5199,17 @@ function onPinnedMessageAdd(
     );
     strictAssert(targetConversation != null, 'Missing target conversation');
 
+    const pinnedAt = Date.now();
+
     await conversationJobQueue.add({
       type: conversationQueueJobEnum.enum.PinMessage,
       ...target,
       pinDurationSeconds,
+      pinnedAt,
     });
 
     const pinnedMessagesLimit = getPinnedMessagesLimit();
 
-    const pinnedAt = Date.now();
     const expiresAt = getPinnedMessageExpiresAt(pinnedAt, pinDurationSeconds);
 
     await DataWriter.appendPinnedMessage(pinnedMessagesLimit, {
@@ -5226,6 +5228,8 @@ function onPinnedMessageAdd(
       senderAci: itemStorage.user.getCheckedAci(),
       sentAtTimestamp: pinnedAt,
       receivedAtTimestamp: pinnedAt,
+      expireTimer: targetConversation.get('expireTimer') ?? null,
+      expirationStartTimestamp: pinnedAt,
     });
 
     dispatch(onPinnedMessagesChanged(target.conversationId));
@@ -5238,6 +5242,7 @@ function onPinnedMessageRemove(targetMessageId: string): StateThunk {
     await conversationJobQueue.add({
       type: conversationQueueJobEnum.enum.UnpinMessage,
       ...target,
+      unpinnedAt: Date.now(),
     });
     await DataWriter.deletePinnedMessageByMessageId(targetMessageId);
     drop(pinnedMessagesCleanupService.trigger('onPinnedMessageRemove'));
diff --git a/ts/util/wrapWithSyncMessageSend.preload.ts b/ts/util/wrapWithSyncMessageSend.preload.ts
index 8672829ebd..d19ac6cdb0 100644
--- a/ts/util/wrapWithSyncMessageSend.preload.ts
+++ b/ts/util/wrapWithSyncMessageSend.preload.ts
@@ -25,6 +25,7 @@ export async function wrapWithSyncMessageSend({
   send,
   sendType,
   timestamp,
+  expirationStartTimestamp,
 }: {
   conversation: ConversationModel;
   logId: string;
@@ -32,6 +33,7 @@ export async function wrapWithSyncMessageSend({
   send: (sender: MessageSender) => Promise<CallbackResultType>;
   sendType: SendTypesType;
   timestamp: number;
+  expirationStartTimestamp: number | null;
 }): Promise<void> {
   const logId = `wrapWithSyncMessageSend(${parentLogId}, ${timestamp})`;
 
@@ -84,7 +86,7 @@ export async function wrapWithSyncMessageSend({
           destinationE164: conversation.get('e164'),
           destinationServiceId: conversation.getServiceId(),
           encodedDataMessage: dataMessage,
-          expirationStartTimestamp: null,
+          expirationStartTimestamp,
           options,
           timestamp,
           urgent: false,