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
@@ -53,7 +53,8 @@
   if (messageIDs) {
     messages = await sqliteAPI.getOutboundP2PMessagesByID(messageIDs);
   } else {
-    messages = await sqliteAPI.getAllOutboundP2PMessage();
+    const allMessages = await sqliteAPI.getAllOutboundP2PMessage();
+    messages = allMessages.filter(message => message.supportsAutoRetry);
   }
 
   const devicesMap: { [deviceID: string]: OutboundP2PMessage[] } = {};
@@ -139,6 +140,8 @@
   }
 }
 
+const AUTOMATIC_RETRY_FREQUENCY = 30 * 1000;
+
 function PeerToPeerProvider(props: Props): React.Node {
   const { children } = props;
 
@@ -178,6 +181,14 @@
     [identityContext, sendMessage],
   );
 
+  React.useEffect(() => {
+    const intervalID = setInterval(
+      () => processOutboundMessages(),
+      AUTOMATIC_RETRY_FREQUENCY,
+    );
+    return () => clearInterval(intervalID);
+  }, [processOutboundMessages]);
+
   const value: PeerToPeerContextType = React.useMemo(
     () => ({
       processOutboundMessages,