diff --git a/pkg/config/profile.go b/pkg/config/profile.go
index 71b4786e3..8b86375ea 100644
--- a/pkg/config/profile.go
+++ b/pkg/config/profile.go
@@ -7,6 +7,7 @@ import (
 	"strings"
 	"time"
 
+	log "github.com/sirupsen/logrus"
 	"github.com/spf13/viper"
 
 	"github.com/stripe/stripe-cli/pkg/validators"
@@ -135,7 +136,7 @@ func (p *Profile) GetAPIKey(livemode bool) (string, error) {
 			p.RegisterAlias(TestModeAPIKeyName, "api_key")
 		}
 
-		if err := viper.ReadInConfig(); err == nil {
+		if err = viper.ReadInConfig(); err == nil {
 			key = viper.GetString(p.GetConfigField(TestModeAPIKeyName))
 		}
 	} else {
@@ -153,6 +154,13 @@ func (p *Profile) GetAPIKey(livemode bool) (string, error) {
 		return key, nil
 	}
 
+	// If the log level is debug, return the raw error message. otherwise
+	// return a generic configuration message
+	level := log.GetLevel()
+	if level == log.DebugLevel {
+		return "", err
+	}
+
 	return "", validators.ErrAPIKeyNotConfigured
 }
 
diff --git a/pkg/config/profile_test.go b/pkg/config/profile_test.go
index be40bf9bb..e7eb5ad64 100644
--- a/pkg/config/profile_test.go
+++ b/pkg/config/profile_test.go
@@ -5,9 +5,12 @@ import (
 	"io/ioutil"
 	"os"
 	"path/filepath"
+	"runtime"
 	"testing"
 
+	"github.com/sirupsen/logrus"
 	"github.com/spf13/viper"
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
 
@@ -101,6 +104,43 @@ test_mode_key_expires_at = '` + expiresAt + `'
 	cleanUp(c.ProfilesFile)
 }
 
+func TestAPIKeyLogLevel(t *testing.T) {
+	// Set the level to debug
+	logrus.SetLevel(logrus.DebugLevel)
+
+	c := &Config{
+		Color:    "auto",
+		LogLevel: "debug",
+		Profile: Profile{
+			ProfileName:    "tests",
+			TestModeAPIKey: "asdas",
+		},
+		ProfilesFile: "",
+	}
+
+	// For debug mode, the error should complain about a config file missing
+	// since we did not init the config
+	key, err := c.Profile.GetAPIKey(false)
+
+	// Little weird but windows returns a different error message than others
+	os := runtime.GOOS
+	switch os {
+	case "windows":
+		assert.ErrorContains(t, err, `config.toml: The system cannot find the file specified.`)
+	default:
+		assert.ErrorContains(t, err, `config.toml: no such file or directory`)
+	}
+
+	assert.Equal(t, "", key)
+
+	// In info mode, it should give a cleaner error about the key not being
+	// configured
+	logrus.SetLevel(logrus.InfoLevel)
+	key, err = c.Profile.GetAPIKey(false)
+	assert.EqualError(t, err, "you have not configured API keys yet")
+	assert.Equal(t, "", key)
+}
+
 func helperLoadBytes(t *testing.T, name string) []byte {
 	bytes, err := ioutil.ReadFile(name)
 	if err != nil {