diff --git a/src/paude/backends/openshift/session_connection.py b/src/paude/backends/openshift/session_connection.py
index 9e5b6d1..3e4afd5 100644
--- a/src/paude/backends/openshift/session_connection.py
+++ b/src/paude/backends/openshift/session_connection.py
@@ -339,8 +339,10 @@ def _build_exec_cmd(
         else:
             cmd = ["oc", "exec", "-it", "-n", ns, pname, "--"]
 
+        env_args = ["env", "PAUDE_HEADLESS=0"]
         if port_urls:
-            cmd.extend(["env", f"PAUDE_PORT_URLS={';'.join(port_urls)}"])
+            env_args.append(f"PAUDE_PORT_URLS={';'.join(port_urls)}")
+        cmd.extend(env_args)
 
         cmd.append("/usr/local/bin/entrypoint-session.sh")
         return cmd
diff --git a/tests/test_openshift_backend.py b/tests/test_openshift_backend.py
index 0431d3d..bc6d45c 100644
--- a/tests/test_openshift_backend.py
+++ b/tests/test_openshift_backend.py
@@ -1076,7 +1076,7 @@ def _make_connector(self, context: str | None = None) -> Any:
         )
 
     def test_exec_cmd_without_port_urls(self) -> None:
-        """Exec command has no env prefix when no port URLs."""
+        """Exec command overrides PAUDE_HEADLESS even without port URLs."""
         connector = self._make_connector()
         cmd = connector._build_exec_cmd("pod-0", "test-ns")
         assert cmd == [
@@ -1087,6 +1087,8 @@ def test_exec_cmd_without_port_urls(self) -> None:
             "test-ns",
             "pod-0",
             "--",
+            "env",
+            "PAUDE_HEADLESS=0",
             "/usr/local/bin/entrypoint-session.sh",
         ]
 
@@ -1099,6 +1101,7 @@ def test_exec_cmd_with_port_urls(self) -> None:
             port_urls=["http://localhost:18789"],
         )
         assert "env" in cmd
+        assert "PAUDE_HEADLESS=0" in cmd
         assert "PAUDE_PORT_URLS=http://localhost:18789" in cmd
         # env and PAUDE_PORT_URLS must come before entrypoint
         env_idx = cmd.index("env")
@@ -1113,6 +1116,7 @@ def test_exec_cmd_with_multiple_port_urls(self) -> None:
             "test-ns",
             port_urls=["http://localhost:8080", "http://localhost:8443"],
         )
+        assert "PAUDE_HEADLESS=0" in cmd
         env_val = [c for c in cmd if c.startswith("PAUDE_PORT_URLS=")][0]
         assert env_val == (
             "PAUDE_PORT_URLS=http://localhost:8080;http://localhost:8443"
@@ -1128,6 +1132,7 @@ def test_exec_cmd_with_context_and_port_urls(self) -> None:
         )
         assert cmd[:4] == ["oc", "--context", "my-ctx", "exec"]
         assert "env" in cmd
+        assert "PAUDE_HEADLESS=0" in cmd
         assert "PAUDE_PORT_URLS=http://localhost:18789" in cmd