diff --git a/src/EditorFeatures/Core/EditAndContinue/ManagedHotReloadLanguageServiceImpl.cs b/src/EditorFeatures/Core/EditAndContinue/ManagedHotReloadLanguageServiceImpl.cs
index 392acd89fed8e..9eb1cd932ac03 100644
--- a/src/EditorFeatures/Core/EditAndContinue/ManagedHotReloadLanguageServiceImpl.cs
+++ b/src/EditorFeatures/Core/EditAndContinue/ManagedHotReloadLanguageServiceImpl.cs
@@ -71,10 +71,11 @@ public async ValueTask StartSessionAsync(CancellationToken cancellationToken)
     {
         sessionState.IsSessionActive = true;
 
-        if (_disabled)
-        {
-            return;
-        }
+        // Reset the disabled flag so that a previous session's failure does not permanently
+        // disable Hot Reload for subsequent sessions. Any exception that caused _disabled to be
+        // set is a product bug, but resetting here gives the user a chance to try again after
+        // restarting the debug session, instead of having to restart the Roslyn process.
+        _disabled = false;
 
         try
         {