diff --git a/pkg/config/profile.go b/pkg/config/profile.go
index cb9dd2b0..61156cd5 100644
--- a/pkg/config/profile.go
+++ b/pkg/config/profile.go
@@ -60,7 +60,7 @@ var KeyRing keyring.Keyring
 
 // CreateProfile creates a profile when logging in
 func (p *Profile) CreateProfile() error {
-	// Remove existing profile first
+	// Remove all keys under existing profile first
 	v := p.deleteProfile(viper.GetViper())
 
 	writeErr := p.writeProfile(v)
@@ -72,7 +72,16 @@ func (p *Profile) CreateProfile() error {
 }
 
 func (p *Profile) deleteProfile(v *viper.Viper) *viper.Viper {
-	return p.safeRemove(v, p.ProfileName)
+	for _, key := range v.AllKeys() {
+		if strings.HasPrefix(key, p.ProfileName+".") {
+			newViper, err := removeKey(v, key)
+			if err == nil {
+				// failure to remove a key should not break the login flow
+				v = newViper
+			}
+		}
+	}
+	return v
 }
 
 // GetColor gets the color setting for the user based on the flag or the
@@ -342,9 +351,6 @@ func (p *Profile) writeProfile(runtimeViper *viper.Viper) error {
 		runtimeViper = p.safeRemove(runtimeViper, "publishable_key")
 	}
 
-	// Remove experimental fields during login
-	runtimeViper = p.removeExperimentalFields(runtimeViper)
-
 	runtimeViper.SetConfigFile(profilesFile)
 
 	// Ensure we preserve the config file type
@@ -510,11 +516,6 @@ func (p *Profile) GetExperimentalFields() ExperimentalFields {
 	}
 }
 
-func (p *Profile) removeExperimentalFields(v *viper.Viper) *viper.Viper {
-	v = p.safeRemove(v, experimentalPrefix)
-	return v
-}
-
 // SessionCredentials are the credentials needed for this session
 type SessionCredentials struct {
 	UAT        string `json:"uat"`
diff --git a/pkg/config/profile_test.go b/pkg/config/profile_test.go
index 42e0ae1d..da890f9b 100644
--- a/pkg/config/profile_test.go
+++ b/pkg/config/profile_test.go
@@ -143,6 +143,65 @@ func TestExperimentalFields(t *testing.T) {
 	cleanUp(c.ProfilesFile)
 }
 
+func TestOldProfileDeleted(t *testing.T) {
+	profilesFile := filepath.Join(os.TempDir(), "stripe", "config.toml")
+	p := Profile{
+		ProfileName:    "test",
+		DeviceName:     "device-before-test",
+		TestModeAPIKey: "sk_test_123",
+		DisplayName:    "display-name-before-test",
+	}
+	c := &Config{
+		Color:        "auto",
+		LogLevel:     "info",
+		Profile:      p,
+		ProfilesFile: profilesFile,
+	}
+	c.InitConfig()
+
+	p.WriteConfigField("experimental.stripe_headers", "test-headers")
+
+	v := viper.New()
+
+	v.SetConfigFile(profilesFile)
+	err := p.writeProfile(v)
+	require.NoError(t, err)
+
+	untouchedProfile := Profile{
+		ProfileName:    "foo",
+		DeviceName:     "foo-device-name",
+		TestModeAPIKey: "foo_test_123",
+	}
+	err = untouchedProfile.writeProfile(v)
+	require.NoError(t, err)
+
+	p = Profile{
+		ProfileName:    "test",
+		DeviceName:     "device-after-test",
+		TestModeAPIKey: "sk_test_456",
+		DisplayName:    "",
+	}
+
+	v = p.deleteProfile(v)
+	err = p.writeProfile(v)
+	require.NoError(t, err)
+
+	require.FileExists(t, c.ProfilesFile)
+
+	// Overwrites keys
+	require.Equal(t, "device-after-test", v.GetString(p.GetConfigField(DeviceNameName)))
+	require.Equal(t, "sk_test_456", v.GetString(p.GetConfigField(TestModeAPIKeyName)))
+	require.Equal(t, "", v.GetString(p.GetConfigField(DisplayNameName)))
+	// Deletes nested keys
+	require.False(t, v.IsSet(v.GetString(p.GetConfigField("experimental.stripe_headers"))))
+	require.False(t, v.IsSet(v.GetString(p.GetConfigField("experimental"))))
+	// Leaves the other profile untouched
+	require.Equal(t, "foo-device-name", v.GetString(untouchedProfile.GetConfigField(DeviceNameName)))
+	require.Equal(t, "foo_test_123", v.GetString(untouchedProfile.GetConfigField(TestModeAPIKeyName)))
+
+	cleanUp(c.ProfilesFile)
+}
+
 func helperLoadBytes(t *testing.T, name string) []byte {
 	bytes, err := os.ReadFile(name)
 	if err != nil {