diff --git a/cli/cmd/lib_cli_config.go b/cli/cmd/lib_cli_config.go
index ead82f1758..57147565b3 100644
--- a/cli/cmd/lib_cli_config.go
+++ b/cli/cmd/lib_cli_config.go
@@ -414,7 +414,9 @@ func promptLocalEnv(env *cliconfig.Environment, defaults cliconfig.Environment)
 }
 
 func promptAWSEnv(env *cliconfig.Environment, defaults cliconfig.Environment) error {
-	fmt.Print("you can get your cortex operator endpoint using `cortex cluster info` if you already have a cortex cluster running, otherwise run `cortex cluster up` to create a cortex cluster\n\n")
+	if env.OperatorEndpoint == nil {
+		fmt.Print("you can get your cortex operator endpoint using `cortex cluster info` if you already have a cortex cluster running, otherwise run `cortex cluster up` to create a cortex cluster\n\n")
+	}
 	for true {
 		err := cr.ReadPrompt(env, &cr.PromptValidation{
 			SkipNonEmptyFields: true,
diff --git a/pkg/lib/configreader/int32_ptr.go b/pkg/lib/configreader/int32_ptr.go
index b8411cdfba..0f8a8656db 100644
--- a/pkg/lib/configreader/int32_ptr.go
+++ b/pkg/lib/configreader/int32_ptr.go
@@ -50,13 +50,13 @@ func makeInt32ValValidation(v *Int32PtrValidation) *Int32Validation {
 
 func Int32Ptr(inter interface{}, v *Int32PtrValidation) (*int32, error) {
 	if inter == nil {
-		return ValidateInt32PtrProvdied(nil, v)
+		return ValidateInt32PtrProvided(nil, v)
 	}
 	casted, castOk := cast.InterfaceToInt32(inter)
 	if !castOk {
 		return nil, ErrorInvalidPrimitiveType(inter, PrimTypeInt)
 	}
-	return ValidateInt32PtrProvdied(&casted, v)
+	return ValidateInt32PtrProvided(&casted, v)
 }
 
 func Int32PtrFromInterfaceMap(key string, iMap map[string]interface{}, v *Int32PtrValidation) (*int32, error) {
@@ -99,7 +99,7 @@ func Int32PtrFromStr(valStr string, v *Int32PtrValidation) (*int32, error) {
 	if !castOk {
 		return nil, ErrorInvalidPrimitiveType(valStr, PrimTypeInt)
 	}
-	return ValidateInt32PtrProvdied(&casted, v)
+	return ValidateInt32PtrProvided(&casted, v)
 }
 
 func Int32PtrFromEnv(envVarName string, v *Int32PtrValidation) (*int32, error) {
@@ -172,7 +172,7 @@ func ValidateInt32PtrMissing(v *Int32PtrValidation) (*int32, error) {
 	return validateInt32Ptr(v.Default, v)
 }
 
-func ValidateInt32PtrProvdied(val *int32, v *Int32PtrValidation) (*int32, error) {
+func ValidateInt32PtrProvided(val *int32, v *Int32PtrValidation) (*int32, error) {
 	if !v.AllowExplicitNull && val == nil {
 		return nil, ErrorCannotBeNull(v.Required)
 	}
diff --git a/pkg/lib/configreader/reader.go b/pkg/lib/configreader/reader.go
index 7f05e4ecbe..53f3421e6d 100644
--- a/pkg/lib/configreader/reader.go
+++ b/pkg/lib/configreader/reader.go
@@ -585,6 +585,72 @@ func ReadPrompt(dest interface{}, promptValidation *PromptValidation) error {
 	var err error
 	shouldPrintTrailingNewLine := false
 
+	// Validate any skipped fields first, so that any errors are returned before prompting
+	if promptValidation.SkipNonEmptyFields {
+		for _, promptItemValidation := range promptValidation.PromptItemValidations {
+			v := reflect.ValueOf(dest).Elem().FieldByName(promptItemValidation.StructField)
+			if !v.IsZero() {
+				if promptItemValidation.StringValidation != nil && promptItemValidation.Parser == nil {
+					if _, err := ValidateString(v.Interface().(string), promptItemValidation.StringValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.StringPtrValidation != nil && promptItemValidation.Parser == nil {
+					if _, err := ValidateStringPtrProvided(v.Interface().(*string), promptItemValidation.StringPtrValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.BoolValidation != nil {
+					if _, err := ValidateBool(v.Interface().(bool), promptItemValidation.BoolValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.BoolPtrValidation != nil {
+					if _, err := ValidateBoolPtrProvided(v.Interface().(*bool), promptItemValidation.BoolPtrValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.IntValidation != nil {
+					if _, err := ValidateInt(v.Interface().(int), promptItemValidation.IntValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.IntPtrValidation != nil {
+					if _, err := ValidateIntPtrProvided(v.Interface().(*int), promptItemValidation.IntPtrValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Int32Validation != nil {
+					if _, err := ValidateInt32(v.Interface().(int32), promptItemValidation.Int32Validation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Int32PtrValidation != nil {
+					if _, err := ValidateInt32PtrProvided(v.Interface().(*int32), promptItemValidation.Int32PtrValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Int64Validation != nil {
+					if _, err := ValidateInt64(v.Interface().(int64), promptItemValidation.Int64Validation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Int64PtrValidation != nil {
+					if _, err := ValidateInt64PtrProvided(v.Interface().(*int64), promptItemValidation.Int64PtrValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Float32Validation != nil {
+					if _, err := ValidateFloat32(v.Interface().(float32), promptItemValidation.Float32Validation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Float32PtrValidation != nil {
+					if _, err := ValidateFloat32PtrProvided(v.Interface().(*float32), promptItemValidation.Float32PtrValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Float64Validation != nil {
+					if _, err := ValidateFloat64(v.Interface().(float64), promptItemValidation.Float64Validation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				} else if promptItemValidation.Float64PtrValidation != nil {
+					if _, err := ValidateFloat64PtrProvided(v.Interface().(*float64), promptItemValidation.Float64PtrValidation); err != nil {
+						return errors.Wrap(err, inferPromptFieldName(reflect.TypeOf(dest), promptItemValidation.StructField))
+					}
+				}
+			}
+		}
+	}
+
 	for _, promptItemValidation := range promptValidation.PromptItemValidations {
 		if promptValidation.SkipNonEmptyFields {
 			v := reflect.ValueOf(dest).Elem().FieldByName(promptItemValidation.StructField)
@@ -1090,6 +1156,15 @@ func inferKey(structType reflect.Type, typeStructField string, typeKey string) s
 	return typeStructField
 }
 
+func inferPromptFieldName(structType reflect.Type, typeStructField string) string {
+	field, _ := structType.Elem().FieldByName(typeStructField)
+	tag, ok := getTagFieldName(field)
+	if ok {
+		return tag
+	}
+	return typeStructField
+}
+
 func getTagFieldName(field reflect.StructField) (string, bool) {
 	tag, ok := field.Tag.Lookup("json")
 	if ok {