diff --git a/config/config.go b/config/config.go
index eefffda2..8aaaea0e 100644
--- a/config/config.go
+++ b/config/config.go
@@ -91,7 +91,15 @@ func ParseBoilerplateConfig(configContents []byte) (*BoilerplateConfig, error) {
 		return nil, errors.WithStackTrace(err)
 	}
 
-	boilerplateConfig = variables.Convert(boilerplateConfig).(*BoilerplateConfig)
+	converted, err := variables.ConvertYAMLToStringMap(boilerplateConfig)
+	if err != nil {
+		return boilerplateConfig, err
+	}
+
+	boilerplateConfig, ok := converted.(*BoilerplateConfig)
+	if !ok {
+		return nil, variables.YAMLConversionErr{Key: converted}
+	}
 
 	return boilerplateConfig, nil
 }
diff --git a/variables/variables.go b/variables/variables.go
index 4d0935c0..fd7ed00c 100644
--- a/variables/variables.go
+++ b/variables/variables.go
@@ -234,7 +234,11 @@ func ConvertType(value interface{}, variable Variable) (interface{}, error) {
 		}
 	case Map:
 		if reflect.TypeOf(value).Kind() == reflect.Map {
-			return Convert(value), nil
+			value, err := ConvertYAMLToStringMap(value)
+			if err != nil {
+				return nil, err
+			}
+			return value, nil
 		}
 		if isString {
 			return parseStringAsMap(asString)
diff --git a/variables/yaml_helpers.go b/variables/yaml_helpers.go
index b7d58bea..98c44358 100644
--- a/variables/yaml_helpers.go
+++ b/variables/yaml_helpers.go
@@ -282,7 +282,12 @@ func ParseYamlString(str string) (interface{}, error) {
 		return nil, errors.WithStackTrace(err)
 	}
 
-	return Convert(parsedValue), nil
+	parsedValue, err = ConvertYAMLToStringMap(parsedValue)
+	if err != nil {
+		return nil, errors.WithStackTrace(err)
+	}
+
+	return parsedValue, nil
 }
 
 // Parse a list of YAML files that define variables into a map from variable name to variable value. Along the way,
@@ -320,7 +325,17 @@ func parseVariablesFromVarFileContents(varFileContents []byte) (map[string]inter
 		return vars, err
 	}
 
-	return Convert(vars).(map[string]interface{}), nil
+	converted, err := ConvertYAMLToStringMap(vars)
+	if err != nil {
+		return nil, errors.WithStackTrace(err)
+	}
+
+	vars, ok := converted.(map[string]interface{})
+	if !ok {
+		return nil, YAMLConversionErr{converted}
+	}
+
+	return vars, nil
 }
 
 // Parse variables passed in via command line options, either as a list of NAME=VALUE variable pairs in varsList, or a
@@ -342,27 +357,47 @@ func ParseVars(varsList []string, varFileList []string) (map[string]interface{},
 	return util.MergeMaps(varsFromVarsList, varsFromVarFiles), nil
 }
 
-// Convert updates i of type map[interface{}]interface{} to a map[string]interface{} so that it may be properly
-// marshalled in to JSON.
+// convertYAMLToStringMap modifies an input with type map[interface{}]interface{} to map[string]interface{} so that it may be
+// properly marshalled in to JSON.
 // See: https://github.com/go-yaml/yaml/issues/139
-func Convert(i interface{}) interface{} {
-	switch x := i.(type) {
+func ConvertYAMLToStringMap(yamlMapOrList interface{}) (interface{}, error) {
+	switch mapOrList := yamlMapOrList.(type) {
 	case map[interface{}]interface{}:
-		m2 := map[string]interface{}{}
-		for k, v := range x {
-			m2[k.(string)] = Convert(v)
+		outputMap := map[string]interface{}{}
+		for k, v := range mapOrList {
+			strK, ok := k.(string)
+			if !ok {
+				return nil, YAMLConversionErr{k}
+			}
+			res, err := ConvertYAMLToStringMap(v)
+			if err != nil {
+				return nil, err
+			}
+			outputMap[strK] = res
 		}
-		return m2
+		return outputMap, nil
 	case []interface{}:
-		for i, v := range x {
-			x[i] = Convert(v)
+		for index, value := range mapOrList {
+			res, err := ConvertYAMLToStringMap(value)
+			if err != nil {
+				return nil, err
+			}
+			mapOrList[index] = res
 		}
 	}
-	return i
+	return yamlMapOrList, nil
 }
 
 // Custom error types
 
+type YAMLConversionErr struct {
+	Key interface{}
+}
+
+func (err YAMLConversionErr) Error() string {
+	return fmt.Sprintf("YAML value has type %s and cannot be cast to to the correct type.", reflect.TypeOf(err.Key))
+}
+
 type OptionsMissing string
 
 func (err OptionsMissing) Error() string {
diff --git a/variables/yaml_helpers_test.go b/variables/yaml_helpers_test.go
index 651edf69..f2116f16 100644
--- a/variables/yaml_helpers_test.go
+++ b/variables/yaml_helpers_test.go
@@ -110,10 +110,20 @@ func TestConvert(t *testing.T) {
 			},
 			expectedType: []interface{}{},
 		},
+		{
+			input: map[string]interface{}{
+				"key3": 42,
+				"key1": map[string]interface{}{
+					"key2": "value2",
+				},
+			},
+			expectedType: map[string]interface{}{},
+		},
 	}
 
 	for _, testCase := range testCases {
-		actual := Convert(testCase.input)
+		actual, err := ConvertYAMLToStringMap(testCase.input)
+		assert.NoError(t, err)
 		assert.IsType(t, testCase.expectedType, actual)
 	}
 }