diff --git a/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java b/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java
index 5a17a4bec9..bdd4d43d21 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/ApplicationContext.java
@@ -230,6 +230,7 @@ public class ApplicationContext extends Application implements AppForegroundObse
               .addPostRender(() -> ActiveCallManager.clearNotifications(this))
               .addPostRender(RestoreOptimizedMediaJob::enqueueIfNecessary)
               .addPostRender(RetryPendingSendsJob::enqueueForAll)
+              .addPostRender(() -> AppDependencies.getPinnedMessageManager().scheduleIfNecessary())
               .execute();
 
     Log.d(TAG, "onCreate() took " + (System.currentTimeMillis() - startTime) + " ms");
diff --git a/app/src/main/java/org/thoughtcrime/securesms/recipients/Recipient.kt b/app/src/main/java/org/thoughtcrime/securesms/recipients/Recipient.kt
index 38eb61d496..53be1a4888 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/recipients/Recipient.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/recipients/Recipient.kt
@@ -406,7 +406,7 @@ class Recipient(
   private val resolved: Recipient
     get() = if (isResolving) live().resolve() else this
 
-  /** Convenience method to get a non-null [serviceId] hen you know it is there. */
+  /** Convenience method to get a non-null [serviceId] when you know it is there. */
   fun requireServiceId(): ServiceId {
     return resolved.aciValue ?: resolved.pniValue ?: throw MissingServiceIdError(id)
   }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/service/PinnedMessageManager.kt b/app/src/main/java/org/thoughtcrime/securesms/service/PinnedMessageManager.kt
index d11ef2b046..536fb138bd 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/service/PinnedMessageManager.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/service/PinnedMessageManager.kt
@@ -13,6 +13,8 @@ import org.thoughtcrime.securesms.database.SignalDatabase
 import org.thoughtcrime.securesms.database.model.MmsMessageRecord
 import org.thoughtcrime.securesms.dependencies.AppDependencies
 import org.thoughtcrime.securesms.recipients.RecipientId
+import org.thoughtcrime.securesms.util.GroupUtil
+import org.whispersystems.signalservice.api.messages.SignalServiceDataMessage
 
 /**
  * Manages waking up and unpinning pinned messages at the correct time
@@ -51,7 +53,20 @@ class PinnedMessageManager(
     val pinnedMessagesToUnpin = messagesTable.getPinnedMessagesBefore(System.currentTimeMillis())
     for (record in pinnedMessagesToUnpin) {
       messagesTable.unpinMessage(messageId = record.id, threadId = record.threadId)
-      // TODO(michelle): Send sync message to linked device to unpin message (done to ensure consistency)
+      val dataMessageBuilder = SignalServiceDataMessage.newBuilder()
+        .withTimestamp(System.currentTimeMillis())
+        .withUnpinnedMessage(
+          SignalServiceDataMessage.UnpinnedMessage(
+            targetAuthor = record.fromRecipient.requireServiceId(),
+            targetSentTimestamp = record.dateSent
+          )
+        )
+
+      val conversationRecipient = SignalDatabase.threads.getRecipientForThreadId(record.threadId) ?: continue
+      if (conversationRecipient.isGroup) {
+        GroupUtil.setDataMessageGroupContext(application, dataMessageBuilder, conversationRecipient.requireGroupId().requirePush())
+      }
+      AppDependencies.signalServiceMessageSender.sendSyncMessage(dataMessageBuilder.build())
     }
   }