diff --git a/xplat/Sonar/SonarState.cpp b/xplat/Sonar/SonarState.cpp
index 75a1195c8..9df342634 100644
--- a/xplat/Sonar/SonarState.cpp
+++ b/xplat/Sonar/SonarState.cpp
@@ -41,7 +41,7 @@ void SonarState::success(std::string step) {
 }
 
 void SonarState::failed(std::string step, std::string errorMessage) {
-  log = log + "[Failed] " + step + "\n";
+  log = log + "[Failed] " + step + ": " + errorMessage + "\n";
   stateMap[step] = State::failed;
   if (mListener) {
     mListener->onUpdate();
diff --git a/xplat/Sonar/SonarStep.cpp b/xplat/Sonar/SonarStep.cpp
index 74475394f..46c1fe7e3 100644
--- a/xplat/Sonar/SonarStep.cpp
+++ b/xplat/Sonar/SonarStep.cpp
@@ -9,17 +9,22 @@
 #include "SonarState.h"
 
 void SonarStep::complete() {
-  isCompleted = true;
+  isLogged = true;
   state->success(name);
 }
 
+void SonarStep::fail(std::string message) {
+  isLogged = true;
+  state->failed(name, message);
+}
+
 SonarStep::SonarStep(std::string step, SonarState* s) {
   state = s;
   name = step;
 }
 
 SonarStep::~SonarStep() {
-  if (!isCompleted) {
+  if (!isLogged) {
     state->failed(name, "");
   }
 }
diff --git a/xplat/Sonar/SonarStep.h b/xplat/Sonar/SonarStep.h
index 37bfef11a..afb18923a 100644
--- a/xplat/Sonar/SonarStep.h
+++ b/xplat/Sonar/SonarStep.h
@@ -15,11 +15,12 @@ class SonarState;
 class SonarStep {
  public:
   void complete();
+  void fail(std::string message);
   SonarStep(std::string name, SonarState* state);
   ~SonarStep();
 
  private:
   std::string name;
-  bool isCompleted = false;
+  bool isLogged = false;
   SonarState* state;
 };
diff --git a/xplat/Sonar/SonarWebSocketImpl.cpp b/xplat/Sonar/SonarWebSocketImpl.cpp
index 8ee31fb5a..8b31085d6 100644
--- a/xplat/Sonar/SonarWebSocketImpl.cpp
+++ b/xplat/Sonar/SonarWebSocketImpl.cpp
@@ -123,19 +123,23 @@ void SonarWebSocketImpl::startSync() {
       doCertificateExchange();
       return;
     }
-    connectSecurely();
 
+    connectSecurely();
     connect->complete();
   } catch (const folly::AsyncSocketException& e) {
     if (e.getType() == folly::AsyncSocketException::NOT_OPEN) {
       // The expected code path when flipper desktop is not running.
+      // Don't count as a failed attempt.
+      connect->fail("Port not open");
     } else {
       SONAR_LOG(e.what());
       failedConnectionAttempts_++;
+      connect->fail(e.what());
     }
     reconnect();
   } catch (const std::exception& e) {
     SONAR_LOG(e.what());
+    connect->fail(e.what());
     failedConnectionAttempts_++;
     reconnect();
   }