diff --git a/cli/config/config.go b/cli/config/config.go
index 5a637805091c..ad5ca1cecf9d 100644
--- a/cli/config/config.go
+++ b/cli/config/config.go
@@ -136,6 +136,24 @@ func load(configDir string) (*configfile.ConfigFile, error) {
 
 	file, err := os.Open(filename)
 	if err != nil {
+		// The config-directory must be a directory. If it is a regular file
+		// (for example, when DOCKER_CONFIG or --config points at the config
+		// file itself instead of the directory holding it), opening the file
+		// fails with a platform-specific error; ENOTDIR on unix, and a
+		// "not exist" error on Windows. Detect that situation here, so that
+		// we consistently report the actual problem instead of either
+		// silently ignoring it, or producing an error for a path that
+		// does not exist.
+		//
+		// The check must come before the [os.IsNotExist] branch below, as
+		// the Windows error satisfies it. The underlying error is not
+		// wrapped for the same reason: it would still satisfy
+		// [errors.Is](err, [fs.ErrNotExist]) on Windows, making this
+		// misconfiguration indistinguishable from "no config file present"
+		// for callers that check for it.
+		if fi, statErr := os.Stat(configDir); statErr == nil && !fi.IsDir() {
+			return configFile, fmt.Errorf("loading config file: config directory (%s) is not a directory", configDir)
+		}
 		if os.IsNotExist(err) {
 			// It is OK for no configuration file to be present, in which
 			// case we return a default struct.
diff --git a/cli/config/config_test.go b/cli/config/config_test.go
index 922641a726ad..dc1db291255c 100644
--- a/cli/config/config_test.go
+++ b/cli/config/config_test.go
@@ -50,6 +50,34 @@ func TestMissingFile(t *testing.T) {
 	saveConfigAndValidateNewFormat(t, config, tmpHome)
 }
 
+// TestLoadConfigDirIsFile verifies that we produce an error if the
+// config-directory is not a directory, which happens when DOCKER_CONFIG
+// or --config is set to the config file itself instead of the directory
+// containing it.
+func TestLoadConfigDirIsFile(t *testing.T) {
+	cfgDir := filepath.Join(t.TempDir(), ConfigFileName)
+	err := os.WriteFile(cfgDir, []byte(`{}`), 0o644)
+	assert.NilError(t, err)
+
+	expected := fmt.Sprintf("loading config file: config directory (%s) is not a directory", cfgDir)
+
+	t.Run("Load", func(t *testing.T) {
+		_, err := Load(cfgDir)
+		assert.Check(t, is.Error(err, expected))
+	})
+
+	t.Run("LoadDefaultConfigFile", func(t *testing.T) {
+		oldDir := Dir()
+		SetDir(cfgDir)
+		t.Cleanup(func() { SetDir(oldDir) })
+
+		buffer := new(bytes.Buffer)
+		configFile := LoadDefaultConfigFile(buffer)
+		assert.Check(t, configFile != nil)
+		assert.Check(t, is.Contains(buffer.String(), "WARNING: Error "+expected))
+	})
+}
+
 // TestLoadDanglingSymlink verifies that we gracefully handle dangling symlinks.
 //
 // TODO(thaJeztah): consider whether we want dangling symlinks to be an error condition instead.