diff --git a/Quotient/connection.cpp b/Quotient/connection.cpp
index 2071dfe73..433e3f6c5 100644
--- a/Quotient/connection.cpp
+++ b/Quotient/connection.cpp
@@ -378,7 +378,6 @@ QFuture<void> Connection::Private::setupPicklingKey()
             default:
                 qWarning(E2EE) << "Error loading pickling key - please fix your keychain:"
                                << readJob->errorString();
-                //TODO: We probably want to fail entirely here.
             }
             return {};
         })
@@ -583,6 +582,7 @@ void Connection::sync(int timeout)
         auto result = (*d->cryptoMachine)->has_pending_backup_key();
         if (!result->has_error()) {
             if (result->value()) {
+                //TODO only if backup is not already initialized
                 d->initializeExistingBackup();
             }
 
@@ -592,8 +592,7 @@ void Connection::sync(int timeout)
                     auto request = requestResult->value();
                     if (request->has_request()) {
                         //TODO make sure that this is only run once simultaneously
-                        auto transaction_id = request->transaction_id();
-                        callApi<PutRoomKeysJob>(stringFromRust(request->version()), fromJson<QHash<RoomId, RoomKeyBackup>>(jsonFromRust(request->rooms()))).onResult([this, transaction_id](const auto& job){
+                        callApi<PutRoomKeysJob>(stringFromRust(request->version()), fromJson<QHash<RoomId, RoomKeyBackup>>(jsonFromRust(request->rooms()))).onResult([this, transaction_id = request->transaction_id()](const auto& job){
                             (*d->cryptoMachine)->mark_keys_backup_as_sent(bytesToRust(job->rawData()), transaction_id);
                         });
                     }
@@ -714,11 +713,13 @@ void Connection::Private::processOutgoingRequests()
                 (*cryptoMachine)->mark_keys_upload_as_sent(bytesToRust(job->rawData()), stringToRust(id));
             }).QFuture<UploadKeysJob*>::then([](auto){}));
         } else if (type == 1) { // Keys query
-            futures.append(q->callApi<QueryKeysJob>(fromJson<QHash<UserId, QStringList>>(jsonFromRust(request.keys_query_device_keys())), request.keys_query_timeout() /*TODO check correctness*/).then([id, this](const auto &job){
+            auto timeout = request.keys_query_timeout();
+            futures.append(q->callApi<QueryKeysJob>(fromJson<QHash<UserId, QStringList>>(jsonFromRust(request.keys_query_device_keys())), timeout > 0 ? timeout : std::optional<int>()).then([id, this](const auto &job){
                 (*cryptoMachine)->mark_keys_query_as_sent(bytesToRust(job->rawData()), stringToRust(id));
             }).QFuture<QueryKeysJob*>::then([](auto){}));
         } else if (type == 2) { // keys claim
-            futures.append(q->callApi<ClaimKeysJob>(fromJson<QHash<UserId, QHash<QString, QString>>>(jsonFromRust(request.keys_claim_one_time_keys())), std::nullopt /*TODO: timeout */).then([id, this](const auto& job){
+            auto timeout = request.keys_claim_timeout();
+            futures.append(q->callApi<ClaimKeysJob>(fromJson<QHash<UserId, QHash<QString, QString>>>(jsonFromRust(request.keys_claim_one_time_keys())), timeout > 0 ? timeout : std::optional<int>()).then([id, this](const auto& job){
                 (*cryptoMachine)->mark_keys_claim_as_sent(bytesToRust(job->rawData()), stringToRust(id));
             }).QFuture<ClaimKeysJob*>::then([](auto){}));
         } else if (type == 3) { // to device
@@ -735,7 +736,7 @@ void Connection::Private::processOutgoingRequests()
             auto transactionId = stringFromRust(request.room_msg_txn_id());
             //TODO: this is wrong (content <-> full), but i also think we don't need it json[u"unsigned"_s] = QJsonObject { {u"transaction_id"_s, transactionId} };
             //TODO: make Room::postJson return a future, then also append to the outer future
-            auto actualTransactionId = room->postJson(stringFromRust(request.room_msg_matrix_type()), json);
+            auto actualTransactionId = room->postJson(stringFromRust(request.room_msg_matrix_type()), json)->transactionId();
             connectUntil(room, &Room::messageSent, q, [this, actualTransactionId, id](const auto& txnId, const auto &event) {
                 if (txnId != actualTransactionId) {
                     return false;
@@ -2211,7 +2212,7 @@ void Connection::Private::requestUserVerification(KeyVerificationSession* sessio
         qWarning() << stringFromRust(request->error_string());
         return;
     }
-    auto transactionId = session->room()->postJson(u"m.room.message"_s, jsonFromRust(request->value()));
+    auto transactionId = session->room()->postJson(u"m.room.message"_s, jsonFromRust(request->value()))->transactionId();
     connectUntil(session->room(), &Room::pendingEventAboutToMerge, q, [this, transactionId, session](const auto &event) {
         if (event->transactionId() != transactionId) {
             return false;
diff --git a/Quotient/crypto-sdk/src/lib.rs b/Quotient/crypto-sdk/src/lib.rs
index 7bb800c88..ba9acd010 100644
--- a/Quotient/crypto-sdk/src/lib.rs
+++ b/Quotient/crypto-sdk/src/lib.rs
@@ -225,6 +225,7 @@ mod ffi {
         fn keys_upload_fallback_keys(self: &OutgoingRequest) -> String;
         fn keys_query_device_keys(self: &OutgoingRequest) -> String;
         fn keys_query_timeout(self: &OutgoingRequest) -> usize;
+        fn keys_claim_timeout(self: &OutgoingRequest) -> usize;
         fn keys_claim_one_time_keys(self: &OutgoingRequest) -> String;
         fn to_device_event_type(self: &OutgoingRequest) -> String;
         fn to_device_messages(self: &OutgoingRequest) -> String;
diff --git a/Quotient/crypto-sdk/src/request.rs b/Quotient/crypto-sdk/src/request.rs
index 3b6943706..fbeda3810 100644
--- a/Quotient/crypto-sdk/src/request.rs
+++ b/Quotient/crypto-sdk/src/request.rs
@@ -192,6 +192,17 @@ impl OutgoingRequest {
         }
     }
 
+    pub(crate) fn keys_claim_timeout(&self) -> usize {
+        if let OutgoingRequests::KeysClaim(request) = self.0.request() {
+            request
+                .timeout
+                .unwrap_or(Duration::from_millis(0))
+                .as_millis() as usize
+        } else {
+            panic!()
+        }
+    }
+
     pub(crate) fn keys_claim_one_time_keys(&self) -> String {
         if let OutgoingRequests::KeysClaim(request) = self.0.request() {
             serde_json::to_string(&request.one_time_keys).unwrap()
diff --git a/Quotient/room.cpp b/Quotient/room.cpp
index 40ef952c5..6f1a97f5d 100644
--- a/Quotient/room.cpp
+++ b/Quotient/room.cpp
@@ -2110,9 +2110,9 @@ const PendingEventItem& Room::post(RoomEventPtr event)
     return d->sendEvent(std::move(event));
 }
 
-QString Room::postJson(const QString& matrixType, const QJsonObject& eventContent)
+const PendingEventItem& Room::postJson(const QString& matrixType, const QJsonObject& eventContent)
 {
-    return d->sendEvent(loadEvent<RoomEvent>(matrixType, eventContent))->transactionId();
+    return d->sendEvent(loadEvent<RoomEvent>(matrixType, eventContent));
 }
 
 SetRoomStateWithKeyJob* Room::setState(const StateEvent& evt)
diff --git a/Quotient/room.h b/Quotient/room.h
index 0248821f0..7fa2f1f1c 100644
--- a/Quotient/room.h
+++ b/Quotient/room.h
@@ -767,7 +767,7 @@ public Q_SLOTS:
      */
     [[deprecated("Use post() instead")]]
     QString postEvent(RoomEvent* event);
-    QString postJson(const QString& matrixType, const QJsonObject& eventContent);
+    const PendingEventItem& postJson(const QString& matrixType, const QJsonObject& eventContent);
     QString retryMessage(const QString& txnId);
     void discardMessage(const QString& txnId);