diff --git a/reaper.go b/reaper.go
index 4f288ed48d1..cd1c8ba0c97 100644
--- a/reaper.go
+++ b/reaper.go
@@ -170,6 +170,27 @@ func reuseOrCreateReaper(ctx context.Context, sessionID string, provider ReaperP
 		if err != nil {
 			return nil, err
 		}
+
+		Logger.Printf("⏳  Waiting for Reaper port to be ready")
+
+		var containerJson *types.ContainerJSON
+
+		if containerJson, err = reaperContainer.Inspect(ctx); err != nil {
+			return nil, fmt.Errorf("failed to inspect reaper container %s: %w", reaperContainer.ID[:8], err)
+		}
+
+		if containerJson != nil && containerJson.NetworkSettings != nil {
+			for port := range containerJson.NetworkSettings.Ports {
+				err := wait.ForListeningPort(port).
+					WithPollInterval(100*time.Millisecond).
+					WaitUntilReady(ctx, reaperContainer)
+				if err != nil {
+					return nil, fmt.Errorf("failed waiting for reaper container %s port %s/%s to be ready: %w",
+						reaperContainer.ID[:8], port.Proto(), port.Port(), err)
+				}
+			}
+		}
+
 		return reaperInstance, nil
 	}