diff --git a/include/ChatPage.h b/include/ChatPage.h
index 3cc6e6c8..dcd925e7 100644
--- a/include/ChatPage.h
+++ b/include/ChatPage.h
@@ -127,6 +127,8 @@ private:
         template<class Collection>
         void updateUserMetadata(const std::vector<Collection> &collection);
 
+        void retryInitialSync();
+
         QHBoxLayout *topLayout_;
         Splitter *splitter;
 
@@ -156,6 +158,7 @@ private:
         QTimer *showContentTimer_;
         QTimer *consensusTimer_;
         QTimer *syncTimeoutTimer_;
+        QTimer *initialSyncTimer_;
 
         QString current_room_;
         QString current_community_;
@@ -191,7 +194,7 @@ private:
 
         // If the number of failures exceeds a certain threshold we
         // return to the login page.
-        int initialSyncFailures = 0;
+        int initialSyncFailures_ = 0;
 };
 
 template<class Collection>
diff --git a/include/MatrixClient.h b/include/MatrixClient.h
index 7ae3fdf6..3efd2d0a 100644
--- a/include/MatrixClient.h
+++ b/include/MatrixClient.h
@@ -129,7 +129,7 @@ signals:
         void getOwnProfileResponse(const QUrl &avatar_url, const QString &display_name);
         void getOwnCommunitiesResponse(const QList<QString> &own_communities);
         void initialSyncCompleted(const mtx::responses::Sync &response);
-        void initialSyncFailed(const QString &msg);
+        void initialSyncFailed();
         void syncCompleted(const mtx::responses::Sync &response);
         void syncFailed(const QString &msg);
         void joinFailed(const QString &msg);
diff --git a/src/ChatPage.cc b/src/ChatPage.cc
index d1a76f83..78435713 100644
--- a/src/ChatPage.cc
+++ b/src/ChatPage.cc
@@ -42,8 +42,9 @@
 #include "dialogs/ReadReceipts.h"
 #include "timeline/TimelineViewManager.h"
 
-constexpr int MAX_INITIAL_SYNC_FAILURES = 5;
-constexpr int SYNC_RETRY_TIMEOUT        = 40000;
+constexpr int MAX_INITIAL_SYNC_FAILURES  = 7;
+constexpr int SYNC_RETRY_TIMEOUT         = 40 * 1000;
+constexpr int INITIAL_SYNC_RETRY_TIMEOUT = 240 * 1000;
 
 ChatPage *ChatPage::instance_ = nullptr;
 
@@ -295,29 +296,8 @@ ChatPage::ChatPage(QSharedPointer<MatrixClient> client,
                 &MatrixClient::initialSyncCompleted,
                 this,
                 &ChatPage::initialSyncCompleted);
-        connect(client_.data(), &MatrixClient::initialSyncFailed, this, [=](const QString &msg) {
-                if (client_->getHomeServer().isEmpty()) {
-                        deleteConfigs();
-                        return;
-                }
-
-                initialSyncFailures += 1;
-
-                if (initialSyncFailures >= MAX_INITIAL_SYNC_FAILURES) {
-                        initialSyncFailures = 0;
-
-                        deleteConfigs();
-
-                        emit showLoginPage(msg);
-                        emit contentLoaded();
-                        return;
-                }
-
-                qWarning() << msg;
-                qWarning() << "Retrying initial sync";
-
-                client_->initialSync();
-        });
+        connect(
+          client_.data(), &MatrixClient::initialSyncFailed, this, &ChatPage::retryInitialSync);
         connect(client_.data(), &MatrixClient::syncCompleted, this, &ChatPage::syncCompleted);
         connect(client_.data(),
                 &MatrixClient::getOwnProfileResponse,
@@ -378,6 +358,9 @@ ChatPage::ChatPage(QSharedPointer<MatrixClient> client,
                 }
         });
 
+        initialSyncTimer_ = new QTimer(this);
+        connect(initialSyncTimer_, &QTimer::timeout, this, &ChatPage::retryInitialSync);
+
         syncTimeoutTimer_ = new QTimer(this);
         connect(syncTimeoutTimer_, &QTimer::timeout, this, [=]() {
                 if (client_->getHomeServer().isEmpty()) {
@@ -489,6 +472,8 @@ ChatPage::bootstrap(QString userid, QString homeserver, QString token)
         }
 
         client_->initialSync();
+
+        initialSyncTimer_->start(INITIAL_SYNC_RETRY_TIMEOUT);
 }
 
 void
@@ -519,6 +504,8 @@ ChatPage::syncCompleted(const mtx::responses::Sync &response)
 void
 ChatPage::initialSyncCompleted(const mtx::responses::Sync &response)
 {
+        initialSyncTimer_->stop();
+
         auto joined = response.rooms.join;
 
         for (auto it = joined.cbegin(); it != joined.cend(); ++it) {
@@ -975,4 +962,33 @@ ChatPage::setGroupViewState(bool isEnabled)
         communitiesSideBar_->show();
 }
 
+void
+ChatPage::retryInitialSync()
+{
+        initialSyncTimer_->stop();
+
+        if (client_->getHomeServer().isEmpty()) {
+                deleteConfigs();
+                return;
+        }
+
+        initialSyncFailures_ += 1;
+
+        if (initialSyncFailures_ >= MAX_INITIAL_SYNC_FAILURES) {
+                initialSyncFailures_ = 0;
+
+                deleteConfigs();
+
+                emit showLoginPage(
+                  tr("The client couldn't sync with the server. Please try again."));
+                emit contentLoaded();
+                return;
+        }
+
+        qWarning() << "Retrying initial sync";
+
+        client_->initialSync();
+        initialSyncTimer_->start(INITIAL_SYNC_RETRY_TIMEOUT);
+}
+
 ChatPage::~ChatPage() {}
diff --git a/src/MatrixClient.cc b/src/MatrixClient.cc
index 69888719..b51c14c8 100644
--- a/src/MatrixClient.cc
+++ b/src/MatrixClient.cc
@@ -270,7 +270,7 @@ MatrixClient::sync() noexcept
                         mtx::responses::Sync response = nlohmann::json::parse(data);
                         emit syncCompleted(response);
                 } catch (std::exception &e) {
-                        qWarning() << "Sync malformed response: " << e.what();
+                        qWarning() << "Sync error: " << e.what();
                 }
         });
 }
@@ -384,7 +384,8 @@ MatrixClient::initialSync() noexcept
                 int status = reply->attribute(QNetworkRequest::HttpStatusCodeAttribute).toInt();
 
                 if (status == 0 || status >= 400) {
-                        emit initialSyncFailed(reply->errorString());
+                        qDebug() << "Error code received" << status;
+                        emit initialSyncFailed();
                         return;
                 }
 
@@ -394,7 +395,8 @@ MatrixClient::initialSync() noexcept
                         mtx::responses::Sync response = nlohmann::json::parse(data);
                         emit initialSyncCompleted(response);
                 } catch (std::exception &e) {
-                        qWarning() << "Sync malformed response" << e.what();
+                        qWarning() << "Initial sync error:" << e.what();
+                        emit initialSyncFailed();
                         return;
                 }