diff --git a/lib/tunnelbroker/peer-to-peer-context.js b/lib/tunnelbroker/peer-to-peer-context.js
--- a/lib/tunnelbroker/peer-to-peer-context.js
+++ b/lib/tunnelbroker/peer-to-peer-context.js
@@ -78,9 +78,22 @@
 
   const { olmAPI, sqliteAPI } = getConfig();
   await olmAPI.initializeCryptoAccount();
+
+  const sentMessagesMap: { [messageID: string]: boolean } = {};
+
   let messages;
   if (messageIDs) {
     messages = await sqliteAPI.getOutboundP2PMessagesByID(messageIDs);
+    if (messageIDs.length !== messages.length) {
+      const dbMessageIDsSet = new Set<string>(
+        messages.map(message => message.messageID),
+      );
+      for (const messageID of messageIDs) {
+        if (!dbMessageIDsSet.has(messageID)) {
+          sentMessagesMap[messageID] = true;
+        }
+      }
+    }
   } else {
     const allMessages = await sqliteAPI.getAllOutboundP2PMessages();
     messages = allMessages.filter(message => message.supportsAutoRetry);
@@ -95,8 +108,6 @@
     }
   }
 
-  const sentMessagesMap: { [messageID: string]: boolean } = {};
-
   const sendMessageToPeer = async (
     message: OutboundP2PMessage,
   ): Promise<void> => {