diff --git a/parser/helpers.go b/parser/helpers.go
index 15a74f8..d994aca 100644
--- a/parser/helpers.go
+++ b/parser/helpers.go
@@ -111,9 +111,35 @@ func (f *ConfigurationFile) IterateOverJson(data []byte) (*gabs.Container, error
 // Sets the value at a specific pathway, but checks if we were looking for a specific
 // value or not before doing it.
 func (cfr *ConfigurationFileReplacement) SetAtPathway(c *gabs.Container, path string, value []byte) error {
-	if cfr.IfValue != nil {
-		if !c.Exists(path) || (c.Exists(path) && !bytes.Equal(c.Bytes(), []byte(*cfr.IfValue))) {
+	if cfr.IfValue != "" {
+		// If this is a regex based matching, we need to get a little more creative since
+		// we're only going to replacing part of the string, and not the whole thing.
+		if c.Exists(path) && strings.HasPrefix(cfr.IfValue, "regex:") {
+			// We're doing some regex here.
+			r, err := regexp.Compile(strings.TrimPrefix(cfr.IfValue, "regex:"))
+			if err != nil {
+				zap.S().Warnw(
+					"configuration if_value using invalid regexp, cannot do replacement",
+					zap.String("if_value", strings.TrimPrefix(cfr.IfValue, "regex:")),
+					zap.Error(err),
+				)
+				return nil
+			}
+
+			// If the path exists and there is a regex match, go ahead and attempt the replacement
+			// using the value we got from the key. This will only replace the one match.
+			v := strings.Trim(string(c.Path(path).Bytes()), "\"")
+			if r.Match([]byte(v)) {
+				_, err := c.SetP(r.ReplaceAllString(v, string(value)), path)
+
+				return err
+			}
+
 			return nil
+		} else {
+			if !c.Exists(path) || (c.Exists(path) && !bytes.Equal(c.Bytes(), []byte(cfr.IfValue))) {
+				return nil
+			}
 		}
 	}
 
@@ -154,7 +180,7 @@ func (f *ConfigurationFile) LookupConfigurationValue(cfr ConfigurationFileReplac
 			return match, errors.WithStack(err)
 		}
 
-		zap.S().Warnw(
+		zap.S().Debugw(
 			"attempted to load a configuration value that does not exist",
 			zap.Strings("path", path),
 			zap.String("filename", f.FileName),
@@ -162,7 +188,7 @@ func (f *ConfigurationFile) LookupConfigurationValue(cfr ConfigurationFileReplac
 
 		// If there is no key, keep the original value intact, that way it is obvious there
 		// is a replace issue at play.
-		return cfr.ReplaceWith.Value(), nil
+		return match, nil
 	} else {
 		replaced := []byte(configMatchRegex.ReplaceAllString(cfr.ReplaceWith.String(), string(match)))
 
diff --git a/parser/parser.go b/parser/parser.go
index d03c343..61d63cf 100644
--- a/parser/parser.go
+++ b/parser/parser.go
@@ -43,26 +43,34 @@ type ConfigurationFile struct {
 // Defines a single find/replace instance for a given server configuration file.
 type ConfigurationFileReplacement struct {
 	Match       string       `json:"match"`
-	IfValue     *string      `json:"if_value"`
+	IfValue     string       `json:"if_value"`
 	ReplaceWith ReplaceValue `json:"replace_with"`
 }
 
 // Handles unmarshaling the JSON representation into a struct that provides more useful
 // data to this functionality.
 func (cfr *ConfigurationFileReplacement) UnmarshalJSON(data []byte) error {
-	if m, err := jsonparser.GetString(data, "match"); err != nil {
-		return err
-	} else {
-		cfr.Match = m
+	m, err := jsonparser.GetString(data, "match")
+	if err != nil {
+		return errors.WithStack(err)
 	}
+	cfr.Match = m
 
-	if v, dt, _, err := jsonparser.Get(data, "replace_with"); err != nil {
-		return err
-	} else {
-		cfr.ReplaceWith = ReplaceValue{
-			value:     v,
-			valueType: dt,
-		}
+	iv, err := jsonparser.GetString(data, "if_value")
+	// We only check keypath here since match & replace_with should be present on all of
+	// them, however if_value is optional.
+	if err != nil && err != jsonparser.KeyPathNotFoundError {
+		return errors.WithStack(err)
+	}
+	cfr.IfValue = iv
+
+	rw, dt, _, err := jsonparser.Get(data, "replace_with")
+	if err != nil {
+		return errors.WithStack(err)
+	}
+	cfr.ReplaceWith = ReplaceValue{
+		value:     rw,
+		valueType: dt,
 	}
 
 	return nil
@@ -370,7 +378,7 @@ func (f *ConfigurationFile) parsePropertiesFile(path string) error {
 		// Don't attempt to replace the value if we're looking for a specific value and
 		// it does not match. If there was no match at all in the file for this key but
 		// we're doing an IfValue match, do nothing.
-		if replace.IfValue != nil && (!ok || (ok && v != *replace.IfValue)) {
+		if replace.IfValue != "" && (!ok || (ok && v != replace.IfValue)) {
 			continue
 		}