diff --git a/native/cpp/CommonCpp/DatabaseManagers/DatabaseQueryExecutor.h b/native/cpp/CommonCpp/DatabaseManagers/DatabaseQueryExecutor.h
--- a/native/cpp/CommonCpp/DatabaseManagers/DatabaseQueryExecutor.h
+++ b/native/cpp/CommonCpp/DatabaseManagers/DatabaseQueryExecutor.h
@@ -140,7 +140,8 @@
   virtual std::vector<OutboundP2PMessage>
   getAllOutboundP2PMessages(const std::string &deviceID) const = 0;
   virtual void removeOutboundP2PMessagesOlderThan(
-      const OutboundP2PMessage &lastConfirmedMessage) const = 0;
+      std::string lastConfirmedMessageID,
+      std::string deviceID) const = 0;
   virtual void
   removeAllOutboundP2PMessages(const std::string &deviceID) const = 0;
   virtual void setCiphertextForOutboundP2PMessage(
diff --git a/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.h b/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.h
--- a/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.h
+++ b/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.h
@@ -150,7 +150,8 @@
   std::vector<OutboundP2PMessage>
   getAllOutboundP2PMessages(const std::string &deviceID) const override;
   void removeOutboundP2PMessagesOlderThan(
-      const OutboundP2PMessage &lastConfirmedMessage) const override;
+      std::string lastConfirmedMessageID,
+      std::string deviceID) const override;
   void removeAllOutboundP2PMessages(const std::string &deviceID) const override;
   void setCiphertextForOutboundP2PMessage(
       std::string messageID,
diff --git a/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.cpp b/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.cpp
--- a/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.cpp
+++ b/native/cpp/CommonCpp/DatabaseManagers/SQLiteQueryExecutor.cpp
@@ -2141,33 +2141,26 @@
 }
 
 void SQLiteQueryExecutor::removeOutboundP2PMessagesOlderThan(
-    const OutboundP2PMessage &lastConfirmedMessageClient) const {
-  static std::string query =
+    std::string lastConfirmedMessageID,
+    std::string deviceID) const {
+  std::string query =
       "DELETE FROM outbound_p2p_messages "
-      "WHERE timestamp <= ? AND device_id IN (?);";
-
-  SQLiteOutboundP2PMessage lastConfirmedMessage =
-      lastConfirmedMessageClient.toSQLiteOutboundP2PMessage();
+      "WHERE timestamp <= ("
+      "   SELECT timestamp "
+      "   FROM outbound_p2p_messages"
+      "   WHERE message_id = ?"
+      ") "
+      "AND device_id IN (?);";
 
   comm::SQLiteStatementWrapper preparedSQL(
       SQLiteQueryExecutor::getConnection(),
       query,
       "Failed to remove messages to device");
 
-  sqlite3_bind_int64(preparedSQL, 1, lastConfirmedMessage.timestamp);
-  sqlite3_bind_text(
-      preparedSQL,
-      2,
-      lastConfirmedMessage.device_id.c_str(),
-      -1,
-      SQLITE_TRANSIENT);
+  bindStringToSQL(lastConfirmedMessageID.c_str(), preparedSQL, 1);
+  bindStringToSQL(deviceID.c_str(), preparedSQL, 2);
 
-  int result = sqlite3_step(preparedSQL);
-  if (result != SQLITE_DONE) {
-    throw std::runtime_error(
-        "Failed to execute removeOutboundP2PMessagesOlderThan statement: " +
-        std::string(sqlite3_errmsg(SQLiteQueryExecutor::getConnection())));
-  }
+  sqlite3_step(preparedSQL);
 }
 
 void SQLiteQueryExecutor::removeAllOutboundP2PMessages(
diff --git a/web/shared-worker/_generated/comm_query_executor.wasm b/web/shared-worker/_generated/comm_query_executor.wasm
index 0000000000000000000000000000000000000000..0000000000000000000000000000000000000000
GIT binary patch
literal 0
Hc$@<O00001

literal 0
Hc$@<O00001

diff --git a/web/shared-worker/queries/outbound-p2p-message-queries.test.js b/web/shared-worker/queries/outbound-p2p-message-queries.test.js
--- a/web/shared-worker/queries/outbound-p2p-message-queries.test.js
+++ b/web/shared-worker/queries/outbound-p2p-message-queries.test.js
@@ -100,12 +100,19 @@
   });
 
   it('should remove when there is only one message', () => {
-    queryExecutor?.removeOutboundP2PMessagesOlderThan(TEST_MSG_2);
+    queryExecutor?.removeOutboundP2PMessagesOlderThan(
+      TEST_MSG_2.messageID,
+      TEST_MSG_2.deviceID,
+    );
+
     expect(queryExecutor?.getAllOutboundP2PMessages(device2).length).toBe(0);
   });
 
   it('should remove older messages', () => {
-    queryExecutor?.removeOutboundP2PMessagesOlderThan(TEST_MSG_1);
+    queryExecutor?.removeOutboundP2PMessagesOlderThan(
+      TEST_MSG_1.messageID,
+      TEST_MSG_1.deviceID,
+    );
     expect(queryExecutor?.getAllOutboundP2PMessages(device1)).toStrictEqual([
       TEST_MSG_4,
     ]);
diff --git a/web/shared-worker/types/sqlite-query-executor.js b/web/shared-worker/types/sqlite-query-executor.js
--- a/web/shared-worker/types/sqlite-query-executor.js
+++ b/web/shared-worker/types/sqlite-query-executor.js
@@ -159,7 +159,8 @@
 
   addOutboundP2PMessages(messages: $ReadOnlyArray<OutboundP2PMessage>): void;
   removeOutboundP2PMessagesOlderThan(
-    lastConfirmedMessage: OutboundP2PMessage,
+    lastConfirmedMessageID: string,
+    deviceID: string,
   ): void;
   removeAllOutboundP2PMessages(deviceID: string): void;
   getAllOutboundP2PMessages(