diff --git a/go.mod b/go.mod
index f7a8bac..591753a 100644
--- a/go.mod
+++ b/go.mod
@@ -36,6 +36,7 @@ require (
 	github.com/gorilla/websocket v1.4.0
 	github.com/gotestyourself/gotestyourself v2.2.0+incompatible // indirect
 	github.com/iancoleman/strcase v0.0.0-20191112232945-16388991a334
+	github.com/icza/dyno v0.0.0-20200205103839-49cb13720835
 	github.com/imdario/mergo v0.3.8
 	github.com/klauspost/pgzip v1.2.3
 	github.com/magiconair/properties v1.8.1
diff --git a/go.sum b/go.sum
index 6d9502e..89d3e3e 100644
--- a/go.sum
+++ b/go.sum
@@ -123,6 +123,8 @@ github.com/hinshun/vt10x v0.0.0-20180616224451-1954e6464174 h1:WlZsjVhE8Af9IcZDG
 github.com/hinshun/vt10x v0.0.0-20180616224451-1954e6464174/go.mod h1:DqJ97dSdRW1W22yXSB90986pcOyQ7r45iio1KN2ez1A=
 github.com/iancoleman/strcase v0.0.0-20191112232945-16388991a334 h1:VHgatEHNcBFEB7inlalqfNqw65aNkM1lGX2yt3NmbS8=
 github.com/iancoleman/strcase v0.0.0-20191112232945-16388991a334/go.mod h1:SK73tn/9oHe+/Y0h39VT4UCxmurVJkR5NA7kMEAOgSE=
+github.com/icza/dyno v0.0.0-20200205103839-49cb13720835 h1:f1irK5f03uGGj+FjgQfZ5VhdKNVQVJ4skHsedzVohQ4=
+github.com/icza/dyno v0.0.0-20200205103839-49cb13720835/go.mod h1:c1tRKs5Tx7E2+uHGSyyncziFjvGpgv4H2HrqXeUQ/Uk=
 github.com/imdario/mergo v0.3.8 h1:CGgOkSJeqMRmt0D9XLWExdT4m4F1vd3FV3VPt+0VxkQ=
 github.com/imdario/mergo v0.3.8/go.mod h1:2EnlNZ0deacrJVfApfmtdGgDfMuh/nq6Ok1EcJh5FfA=
 github.com/inconshreveable/mousetrap v1.0.0 h1:Z8tu5sraLXCXIcARxBp/8cbvlwVa7Z1NHg9XEKhtSvM=
diff --git a/parser/helpers.go b/parser/helpers.go
index afee5ad..a7c4fc8 100644
--- a/parser/helpers.go
+++ b/parser/helpers.go
@@ -9,7 +9,6 @@ import (
 	"go.uber.org/zap"
 	"io/ioutil"
 	"os"
-	"reflect"
 	"regexp"
 	"strconv"
 	"strings"
@@ -48,13 +47,14 @@ func readFileBytes(path string) ([]byte, error) {
 }
 
 // Gets the value of a key based on the value type defined.
-func getKeyValue(value []byte) interface{} {
-	if reflect.ValueOf(value).Kind() == reflect.Bool {
+func (cfr *ConfigurationFileReplacement) getKeyValue(value []byte) interface{} {
+	if cfr.ReplaceWith.Type() == jsonparser.Boolean {
 		v, _ := strconv.ParseBool(string(value))
 		return v
 	}
 
-	// Try to parse into an int, if this fails just ignore the error and
+	// Try to parse into an int, if this fails just ignore the error and continue
+	// through, returning the string.
 	if v, err := strconv.Atoi(string(value)); err == nil {
 		return v
 	}
@@ -70,7 +70,9 @@ func getKeyValue(value []byte) interface{} {
 // configurations per-world (such as Spigot and Bungeecord) where we'll need to make
 // adjustments to the bind address for the user.
 //
-// This does not currently support nested matches. container.*.foo.*.bar will not work.
+// This does not currently support nested wildcard matches. For example, foo.*.bar
+// will work, however foo.*.bar.*.baz will not, since we'll only be splitting at the
+// first wildcard, and not subsequent ones.
 func (f *ConfigurationFile) IterateOverJson(data []byte) (*gabs.Container, error) {
 	parsed, err := gabs.ParseJSON(data)
 	if err != nil {
@@ -143,7 +145,7 @@ func (cfr *ConfigurationFileReplacement) SetAtPathway(c *gabs.Container, path st
 		}
 	}
 
-	_, err := c.SetP(getKeyValue(value), path)
+	_, err := c.SetP(cfr.getKeyValue(value), path)
 
 	return err
 }
diff --git a/parser/parser.go b/parser/parser.go
index 75b4aa2..71177b7 100644
--- a/parser/parser.go
+++ b/parser/parser.go
@@ -5,14 +5,16 @@ import (
 	"encoding/json"
 	"github.com/beevik/etree"
 	"github.com/buger/jsonparser"
-	"github.com/ghodss/yaml"
+	"github.com/icza/dyno"
 	"github.com/magiconair/properties"
 	"github.com/pkg/errors"
 	"github.com/pterodactyl/wings/config"
 	"go.uber.org/zap"
 	"gopkg.in/ini.v1"
+	"gopkg.in/yaml.v2"
 	"io/ioutil"
 	"os"
+	"regexp"
 	"strings"
 )
 
@@ -73,6 +75,11 @@ func (f *ConfigurationFile) UnmarshalJSON(data []byte) error {
 	return nil
 }
 
+// Regex to match paths such as foo[1].bar[2] and convert them into a format that
+// gabs can work with, such as foo.1.bar.2 in this case. This is applied when creating
+// the struct for the configuration file replacements.
+var cfrMatchReplacement = regexp.MustCompile(`\[(\d+)]`)
+
 // Defines a single find/replace instance for a given server configuration file.
 type ConfigurationFileReplacement struct {
 	Match       string       `json:"match"`
@@ -87,7 +94,9 @@ func (cfr *ConfigurationFileReplacement) UnmarshalJSON(data []byte) error {
 	if err != nil {
 		return err
 	}
-	cfr.Match = m
+
+	// See comment on the replacement regex to understand what exactly this is doing.
+	cfr.Match = cfrMatchReplacement.ReplaceAllString(m, ".$1")
 
 	iv, err := jsonparser.GetString(data, "if_value")
 	// We only check keypath here since match & replace_with should be present on all of
@@ -130,7 +139,6 @@ func (f *ConfigurationFile) Parse(path string, internal bool) error {
 		f.configuration = mb
 	}
 
-
 	var err error
 
 	switch f.Parser {
@@ -351,10 +359,15 @@ func (f *ConfigurationFile) parseYamlFile(path string) error {
 		return err
 	}
 
+	i := make(map[string]interface{})
+	if err := yaml.Unmarshal(b, &i); err != nil {
+		return err
+	}
+
 	// Unmarshal the yaml data into a JSON interface such that we can work with
 	// any arbitrary data structure. If we don't do this, I can't use gabs which
 	// makes working with unknown JSON signficiantly easier.
-	jsonBytes, err := yaml.YAMLToJSON(b)
+	jsonBytes, err := json.Marshal(dyno.ConvertMapI2MapS(i))
 	if err != nil {
 		return err
 	}
@@ -367,7 +380,7 @@ func (f *ConfigurationFile) parseYamlFile(path string) error {
 	}
 
 	// Remarshal the JSON into YAML format before saving it back to the disk.
-	marshaled, err := yaml.JSONToYAML(data.Bytes())
+	marshaled, err := yaml.Marshal(data.Data())
 	if err != nil {
 		return err
 	}