diff --git a/script/tools/ck-docker b/script/tools/ck-docker
index 6c118561b7..19e539909f 100755
--- a/script/tools/ck-docker
+++ b/script/tools/ck-docker
@@ -112,6 +112,19 @@ cmd_exec() {
     local docker_flags=()
     [ -t 0 ] && [ -t 1 ] && docker_flags+=("-it")
 
+    # Auto-detect Python commands and enable unbuffered output for live streaming
+    local is_python=false
+    for arg in "$@"; do
+        if [[ "$arg" == "python" || "$arg" == "python3" || "$arg" == *.py ]]; then
+            is_python=true
+            break
+        fi
+    done
+
+    if [ "$is_python" = true ]; then
+        docker_flags+=("-e" "PYTHONUNBUFFERED=1")
+    fi
+
     docker exec "${docker_flags[@]}" "${CONTAINER_NAME}" "$@"
 }
 
diff --git a/script/tools/ck-exec b/script/tools/ck-exec
index dfc7655774..5d5dd2bded 100755
--- a/script/tools/ck-exec
+++ b/script/tools/ck-exec
@@ -103,9 +103,18 @@ for arg in "${command_args[@]}"; do
     cmd_string="${cmd_string} $(printf '%q' "$arg")"
 done
 
+# Auto-detect Python commands and enable unbuffered output for live streaming
+env_flags=""
+for arg in "${command_args[@]}"; do
+    if [[ "$arg" == "python" || "$arg" == "python3" || "$arg" == *.py ]]; then
+        env_flags="-e PYTHONUNBUFFERED=1"
+        break
+    fi
+done
+
 # Execute command
 if [ "$interactive" = true ]; then
-    docker exec -it -w "${workdir}" "${CONTAINER_NAME}" bash -c "${cmd_string}"
+    docker exec -it ${env_flags} -w "${workdir}" "${CONTAINER_NAME}" bash -c "${cmd_string}"
 else
-    docker exec -w "${workdir}" "${CONTAINER_NAME}" bash -c "${cmd_string}"
+    docker exec ${env_flags} -w "${workdir}" "${CONTAINER_NAME}" bash -c "${cmd_string}"
 fi