diff --git a/Lib/test/test_cmd_line.py b/Lib/test/test_cmd_line.py
index 209d37095a6c0b..797615c915c3d5 100644
--- a/Lib/test/test_cmd_line.py
+++ b/Lib/test/test_cmd_line.py
@@ -1018,6 +1018,17 @@ def res2int(self, res):
         out = res.out.strip().decode("utf-8")
         return tuple(int(i) for i in out.split())
 
+    def test_dump_path_config(self):
+        # gh-151253: At the first import (import encodings) during Python
+        # startup, if the import fails, dump the Python path configuration.
+        nonexistent = '/nonexistent-python-path'
+        # Use -X frozen_modules=off to disable frozen encodings module
+        # on release build.
+        cmd = ["-X", "frozen_modules=off", "-c", "pass"]
+        proc = assert_python_failure(*cmd, PYTHONHOME=nonexistent)
+        self.assertIn(b'Python path configuration:', proc.err)
+        self.assertIn(f"PYTHONHOME = '{nonexistent}'".encode(), proc.err)
+
 
 @unittest.skipIf(interpreter_requires_environment(),
                  'Cannot run -I tests when PYTHON env vars are required.')
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2026-06-10-15-42-46.gh-issue-151253.7MMQ8P.rst b/Misc/NEWS.d/next/Core_and_Builtins/2026-06-10-15-42-46.gh-issue-151253.7MMQ8P.rst
new file mode 100644
index 00000000000000..56d2f3b2633bb0
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2026-06-10-15-42-46.gh-issue-151253.7MMQ8P.rst
@@ -0,0 +1,3 @@
+If ``import encodings`` (first import) fails at Python startup, dump the
+Python path configuration to help users debugging their configuration. Patch
+by Victor Stinner.
diff --git a/Python/codecs.c b/Python/codecs.c
index d2e3f25157144a..6fa68cdbda71a5 100644
--- a/Python/codecs.c
+++ b/Python/codecs.c
@@ -10,6 +10,7 @@ Copyright (c) Corporation for National Research Initiatives.
 
 #include "Python.h"
 #include "pycore_call.h"          // _PyObject_CallNoArgs()
+#include "pycore_initconfig.h"    // _Py_DumpPathConfig()
 #include "pycore_interp.h"        // PyInterpreterState.codec_search_path
 #include "pycore_lock.h"          // PyMutex
 #include "pycore_pyerrors.h"      // _PyErr_FormatNote()
@@ -1504,6 +1505,8 @@ _PyCodec_InitRegistry(PyInterpreterState *interp)
     // search functions, so this is done after everything else is initialized.
     PyObject *mod = PyImport_ImportModule("encodings");
     if (mod == NULL) {
+        PyThreadState *tstate = _PyThreadState_GET();
+        _Py_DumpPathConfig(tstate);
         return PyStatus_Error("Failed to import encodings module");
     }
     Py_DECREF(mod);