diff --git a/cmd/root.go b/cmd/root.go
index ef846170a..4e0d0f137 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -38,14 +38,15 @@ func NewRootCmd(out io.Writer) (*cobra.Command, *environment.AirshipCTLSettings,
 		SilenceUsage:  true,
 		PersistentPreRun: func(cmd *cobra.Command, args []string) {
 			log.Init(settings.Debug, cmd.OutOrStderr())
+
+			// Load or Initialize airship Config
+			settings.InitConfig()
 		},
 	}
 	rootCmd.SetOutput(out)
 	rootCmd.AddCommand(NewVersionCommand())
 
 	settings.InitFlags(rootCmd)
-	// Load or Initialize airship Config
-	settings.InitConfig()
 
 	return rootCmd, settings, nil
 }
diff --git a/cmd/root_test.go b/cmd/root_test.go
index a87d11583..6f56cdf95 100644
--- a/cmd/root_test.go
+++ b/cmd/root_test.go
@@ -1,9 +1,11 @@
 package cmd_test
 
 import (
+	"bytes"
 	"testing"
 
 	"github.com/spf13/cobra"
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
 	"opendev.org/airship/airshipctl/cmd"
@@ -36,6 +38,41 @@ func TestRoot(t *testing.T) {
 	}
 }
 
+func TestFlagLoading(t *testing.T) {
+	tests := []struct {
+		name     string
+		args     []string
+		expected string
+	}{
+		{
+			name:     "default, no flags",
+			args:     []string{},
+			expected: "$HOME/.airship/config",
+		},
+		{
+			name:     "alternate airshipconfig",
+			args:     []string{"--airshipconf", "/custom/path/to/airshipconfig"},
+			expected: "/custom/path/to/airshipconfig",
+		},
+	}
+
+	for _, tt := range tests {
+		tt := tt
+		t.Run(tt.name, func(subTest *testing.T) {
+			// We don't care about the output of this test, so toss
+			// it into a thowaway &bytes.buffer{}
+			rootCmd, settings, err := cmd.NewRootCmd(&bytes.Buffer{})
+			require.NoError(t, err)
+			rootCmd.SetArgs(tt.args)
+
+			err = rootCmd.Execute()
+			require.NoError(t, err)
+
+			assert.Equal(t, settings.AirshipConfigPath(), tt.expected)
+		})
+	}
+}
+
 func getVanillaRootCmd(t *testing.T) *cobra.Command {
 	t.Helper()
 	rootCmd, _, err := cmd.NewRootCmd(nil)