diff --git a/internal/cli/run.go b/internal/cli/run.go
index 3686b56fd7..b8331a53d2 100644
--- a/internal/cli/run.go
+++ b/internal/cli/run.go
@@ -651,6 +651,18 @@ func bootstrapEnv(sshConfigPath, sandboxName, repoDir string, h *harness.Harness
 				return fmt.Errorf("copying host file %s to %s: %w", hf.Src, hf.Dest, err)
 			}
 		}
+
+		// TODO(#345): remove this once admin install preserves the executable
+		// bit when writing files to .fullsend/. The GitHub Contents API commits
+		// everything as 100644, so scripts lose +x. Force it back for anything
+		// landing in a bin/ directory.
+		// https://github.com/fullsend-ai/fullsend/issues/345#issuecomment-4300740512
+		if strings.Contains(hf.Dest, "/bin/") {
+			chmodCmd := fmt.Sprintf("chmod +x %s", hf.Dest)
+			if _, _, _, sshErr := sandbox.SSH(sshConfigPath, sandboxName, chmodCmd, 10*time.Second); sshErr != nil {
+				return fmt.Errorf("chmod host file %s in sandbox: %w", hf.Dest, sshErr)
+			}
+		}
 	}
 
 	return nil