diff --git a/src/Insight/Insight.cpp b/src/Insight/Insight.cpp
index fad78993..6fa9d421 100644
--- a/src/Insight/Insight.cpp
+++ b/src/Insight/Insight.cpp
@@ -9,6 +9,9 @@
 #include "src/Exceptions/InvalidConfig.hpp"
 #include "src/Targets/TargetState.hpp"
 
+#include "src/Application.hpp"
+#include "InsightWorker/Tasks/QueryLatestVersionNumber.hpp"
+
 using namespace Bloom;
 using namespace Bloom::Exceptions;
 
@@ -132,6 +135,10 @@ void Insight::startup() {
     this->connect(this->workerThread, &QThread::finished, this->insightWorker, &QObject::deleteLater);
     this->connect(this->workerThread, &QThread::finished, this->workerThread, &QThread::deleteLater);
 
+    this->connect(this->insightWorker, &InsightWorker::ready, this, [this] {
+        this->checkBloomVersion();
+    });
+
     this->mainWindow->show();
 }
 
@@ -152,6 +159,30 @@ void Insight::shutdown() {
     this->setThreadState(ThreadState::STOPPED);
 }
 
+void Insight::checkBloomVersion() {
+    auto currentVersionNumber = QString::fromStdString(Application::VERSION_STR);
+
+    auto versionQueryTask = new QueryLatestVersionNumber(
+        QString::fromStdString(Application::VERSION_STR)
+    );
+
+    this->connect(
+        versionQueryTask,
+        &QueryLatestVersionNumber::latestVersionNumberRetrieved,
+        this,
+        [this, currentVersionNumber] (const QString& latestVersionNumber) {
+            if (latestVersionNumber != currentVersionNumber) {
+                Logger::warning(
+                    "Bloom v" + latestVersionNumber.toStdString()
+                        + " is available to download - upgrade via https://bloom.oscillate.io"
+                );
+            }
+        }
+    );
+
+    this->insightWorker->queueTask(versionQueryTask);
+}
+
 void Insight::onShutdownApplicationEvent(const Events::ShutdownApplication&) {
     /*
      * Once Insight shuts down, control of the main thread will be returned to Application::run(), which
diff --git a/src/Insight/Insight.hpp b/src/Insight/Insight.hpp
index 6b128858..4c316bcf 100644
--- a/src/Insight/Insight.hpp
+++ b/src/Insight/Insight.hpp
@@ -100,6 +100,13 @@ namespace Bloom
          */
         void shutdown();
 
+        /**
+         * Queries the Bloom server for the latest version number. If the current version number doesn't match the
+         * latest version number returned by the server, we'll display a warning in the logs to instruct the user to
+         * upgrade.
+         */
+        void checkBloomVersion();
+
         /**
          * Because Insight occupies the main thread, it must handle any application shutdown requests.
          *