diff --git a/commands/upload/upload.go b/commands/upload/upload.go
index 5fe21089848..bc7aafe2067 100644
--- a/commands/upload/upload.go
+++ b/commands/upload/upload.go
@@ -575,6 +575,9 @@ func detectUploadPort(
 					waitForUploadPort = true
 					timeout = time.After(5 * time.Second)
 					log.Debug("User-specified port has been disconnected, now waiting for upload port, timeout extended by 5 seconds")
+				} else {
+					timeout = time.After(time.Second)
+					log.Debug("Candidate port has been disconnected, timeout extended by 1 second")
 				}
 				continue
 			}