diff --git a/lib/tunnelbroker/use-peer-to-peer-message-handler.js b/lib/tunnelbroker/use-peer-to-peer-message-handler.js
--- a/lib/tunnelbroker/use-peer-to-peer-message-handler.js
+++ b/lib/tunnelbroker/use-peer-to-peer-message-handler.js
@@ -260,31 +260,56 @@
               resultDescription =
                 'Race condition while creating session with ' +
                 `${senderDeviceID}, session version: ${sessionVersion}, ` +
-                `this device has a higher deviceID and the session will be kept`;
+                'this device has a higher deviceID and the session will be ' +
+                'kept';
             } else {
               resultDescription =
                 'Race condition while creating session with ' +
                 `${senderDeviceID}, session version: ${sessionVersion}, ` +
-                `this device has a lower deviceID and the session will overwritten`;
-
-              const result = await olmAPI.contentInboundSessionCreator(
-                deviceKeys.identityKeysBlob.primaryIdentityPublicKeys,
-                encryptedData,
-                sessionVersion,
-                true,
-              );
+                'this device has a lower deviceID and the session will be ' +
+                'overwritten';
+
+              let result;
+              try {
+                result = await olmAPI.contentInboundSessionCreator(
+                  deviceKeys.identityKeysBlob.primaryIdentityPublicKeys,
+                  encryptedData,
+                  sessionVersion,
+                  true,
+                );
+              } catch (e2) {
+                const error2Message = getMessageForException(e2) ?? '';
+                resultDescription =
+                  'Race condition while creating session with ' +
+                  `${senderDeviceID}, session version: ${sessionVersion}, ` +
+                  'this device has a lower deviceID but overriding the' +
+                  ` session failed ${error2Message}`;
+                throw e2;
+              }
 
               resultDescription =
                 'Overwrite session with device ' +
                 `${senderDeviceID}: ${result}, ` +
-                `session version: ${sessionVersion}, starting resending messages`;
-
-              await resendPeerToPeerMessages(senderDeviceID);
+                `session version: ${sessionVersion}, starting resending ` +
+                'messages';
+
+              try {
+                await resendPeerToPeerMessages(senderDeviceID);
+              } catch (e2) {
+                const error2Message = getMessageForException(e2) ?? '';
+                resultDescription =
+                  'Race condition while creating session with ' +
+                  `${senderDeviceID}, session version: ${sessionVersion}, ` +
+                  'this device has a lower deviceID but resending the' +
+                  ` messages failed ${error2Message}`;
+                throw e2;
+              }
 
               resultDescription =
                 'Overwrite session with device ' +
                 `${senderDeviceID}: ${result}, ` +
-                `session version: ${sessionVersion}, finished resending messages`;
+                `session version: ${sessionVersion}, finished resending ` +
+                'messages';
             }
           } else {
             resultDescription =
diff --git a/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp b/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp
--- a/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp
+++ b/native/cpp/CommonCpp/CryptoTools/CryptoModule.cpp
@@ -311,9 +311,9 @@
   if (this->hasSessionFor(targetDeviceId)) {
     std::shared_ptr<Session> existingSession =
         getSessionByDeviceId(targetDeviceId);
-    if (existingSession->getVersion() > sessionVersion) {
+    if (!overwrite && existingSession->getVersion() > sessionVersion) {
       throw std::runtime_error{"OLM_SESSION_ALREADY_CREATED"};
-    } else if (existingSession->getVersion() == sessionVersion) {
+    } else if (!overwrite && existingSession->getVersion() == sessionVersion) {
       throw std::runtime_error{"OLM_SESSION_CREATION_RACE_CONDITION"};
     }