diff --git a/source/common/http/conn_pool_grid.cc b/source/common/http/conn_pool_grid.cc
index 18cf101e0a3e9..e41007825e01b 100644
--- a/source/common/http/conn_pool_grid.cc
+++ b/source/common/http/conn_pool_grid.cc
@@ -36,13 +36,14 @@ ConnectivityGrid::WrapperCallbacks::ConnectionAttemptCallbacks::ConnectionAttemp
     WrapperCallbacks& parent, PoolIterator it)
     : parent_(parent), pool_it_(it), cancellable_(nullptr) {}
 
-bool ConnectivityGrid::WrapperCallbacks::ConnectionAttemptCallbacks::newStream() {
+ConnectivityGrid::StreamCreationResult
+ConnectivityGrid::WrapperCallbacks::ConnectionAttemptCallbacks::newStream() {
   auto* cancellable = pool().newStream(parent_.decoder_, *this);
   if (cancellable == nullptr) {
-    return true;
+    return StreamCreationResult::ImmediateResult;
   }
   cancellable_ = cancellable;
-  return false;
+  return StreamCreationResult::StreamCreationPending;
 }
 
 void ConnectivityGrid::WrapperCallbacks::ConnectionAttemptCallbacks::onPoolFailure(
@@ -82,7 +83,7 @@ void ConnectivityGrid::WrapperCallbacks::deleteThis() {
   removeFromList(grid_.wrapped_callbacks_);
 }
 
-bool ConnectivityGrid::WrapperCallbacks::newStream() {
+ConnectivityGrid::StreamCreationResult ConnectivityGrid::WrapperCallbacks::newStream() {
   ENVOY_LOG(trace, "{} pool attempting to create a new stream to host '{}'.",
             describePool(**current_), grid_.host_->hostname());
   auto attempt = std::make_unique<ConnectionAttemptCallbacks>(*this, current_);
@@ -137,7 +138,10 @@ bool ConnectivityGrid::WrapperCallbacks::tryAnotherConnection() {
     // If there are no other pools to try, return false.
     return false;
   }
-  // Create a new connection attempt for the next pool.
+  // Create a new connection attempt for the next pool. If we reach this point
+  // return true regardless of if newStream resulted in an immediate result or
+  // an async call, as either way the attempt will result in success/failure
+  // callbacks.
   current_ = next_pool.value();
   newStream();
   return true;
@@ -209,7 +213,7 @@ ConnectionPool::Cancellable* ConnectivityGrid::newStream(Http::ResponseDecoder&
   ConnectionPool::Cancellable* ret = wrapped_callback.get();
   LinkedList::moveIntoList(std::move(wrapped_callback), wrapped_callbacks_);
   // Note that in the case of immediate attempt/failure, newStream will delete this.
-  if (wrapped_callbacks_.front()->newStream()) {
+  if (wrapped_callbacks_.front()->newStream() == StreamCreationResult::ImmediateResult) {
     // If newStream succeeds, return nullptr as the caller has received their
     // callback and does not need a cancellable handle.
     return nullptr;
diff --git a/source/common/http/conn_pool_grid.h b/source/common/http/conn_pool_grid.h
index db1dea5f28994..bd1989f81e6e6 100644
--- a/source/common/http/conn_pool_grid.h
+++ b/source/common/http/conn_pool_grid.h
@@ -19,6 +19,11 @@ class ConnectivityGrid : public ConnectionPool::Instance,
     std::vector<Http::Protocol> protocols_;
   };
 
+  enum class StreamCreationResult {
+    ImmediateResult,
+    StreamCreationPending,
+  };
+
   using PoolIterator = std::list<ConnectionPool::InstancePtr>::iterator;
 
   // This is a class which wraps a caller's connection pool callbacks to
@@ -38,8 +43,7 @@ class ConnectivityGrid : public ConnectionPool::Instance,
     public:
       ConnectionAttemptCallbacks(WrapperCallbacks& parent, PoolIterator it);
 
-      // Returns true if a stream is immediately created, false if it is pending.
-      bool newStream();
+      StreamCreationResult newStream();
 
       // ConnectionPool::Callbacks
       void onPoolFailure(ConnectionPool::PoolFailureReason reason,
@@ -67,9 +71,8 @@ class ConnectivityGrid : public ConnectionPool::Instance,
     // ConnectionPool::Cancellable
     void cancel(Envoy::ConnectionPool::CancelPolicy cancel_policy) override;
 
-    // Attempt to create a new stream for pool(). Returns true if the stream has
-    // been created.
-    bool newStream();
+    // Attempt to create a new stream for pool().
+    StreamCreationResult newStream();
 
     // Removes this from the owning list, deleting it.
     void deleteThis();