diff --git a/api/process_configuration.go b/api/process_configuration.go
new file mode 100644
index 0000000..a36eaa8
--- /dev/null
+++ b/api/process_configuration.go
@@ -0,0 +1,66 @@
+package api
+
+import (
+	"encoding/json"
+	"github.com/apex/log"
+	"github.com/pterodactyl/wings/parser"
+	"regexp"
+	"strings"
+)
+
+type OutputLineMatcher struct {
+	// The raw string to match against. This may or may not be prefixed with
+	// regex: which indicates we want to match against the regex expression.
+	raw string
+	reg *regexp.Regexp
+}
+
+// Determine if a given string "s" matches the given line.
+func (olm *OutputLineMatcher) Matches(s string) bool {
+	if olm.reg == nil {
+		return strings.Contains(s, olm.raw)
+	}
+
+	return olm.reg.MatchString(s)
+}
+
+// Return the matcher's raw comparison string.
+func (olm *OutputLineMatcher) String() string {
+	return olm.raw
+}
+
+// Unmarshal the startup lines into individual structs for easier matching abilities.
+func (olm *OutputLineMatcher) UnmarshalJSON(data []byte) error {
+	if err := json.Unmarshal(data, &olm.raw); err != nil {
+		return err
+	}
+
+	if strings.HasPrefix(olm.raw, "regex:") && len(olm.raw) > 6 {
+		r, err := regexp.Compile(strings.TrimPrefix(olm.raw, "regex:"))
+		if err != nil {
+			log.WithField("error", err).WithField("raw", olm.raw).Warn("failed to compile output line marked as being regex")
+		}
+
+		olm.reg = r
+	}
+
+	return nil
+}
+
+// Defines the process configuration for a given server instance. This sets what the
+// daemon is looking for to mark a server as done starting, what to do when stopping,
+// and what changes to make to the configuration file for a server.
+type ProcessConfiguration struct {
+	Startup struct {
+		Done            []*OutputLineMatcher `json:"done"`
+		UserInteraction []string            `json:"user_interaction"`
+		StripAnsi       bool                `json:"strip_ansi"`
+	} `json:"startup"`
+
+	Stop struct {
+		Type  string `json:"type"`
+		Value string `json:"value"`
+	} `json:"stop"`
+
+	ConfigurationFiles []parser.ConfigurationFile `json:"configs"`
+}
diff --git a/api/server_endpoints.go b/api/server_endpoints.go
index c0bceda..e974f5c 100644
--- a/api/server_endpoints.go
+++ b/api/server_endpoints.go
@@ -4,7 +4,6 @@ import (
 	"encoding/json"
 	"fmt"
 	"github.com/pkg/errors"
-	"github.com/pterodactyl/wings/parser"
 )
 
 const (
@@ -26,24 +25,6 @@ type ServerConfigurationResponse struct {
 	ProcessConfiguration *ProcessConfiguration `json:"process_configuration"`
 }
 
-// Defines the process configuration for a given server instance. This sets what the
-// daemon is looking for to mark a server as done starting, what to do when stopping,
-// and what changes to make to the configuration file for a server.
-type ProcessConfiguration struct {
-	Startup struct {
-		Done            []string `json:"done"`
-		UserInteraction []string `json:"user_interaction"`
-		StripAnsi       bool     `json:"strip_ansi"`
-	} `json:"startup"`
-
-	Stop struct {
-		Type  string `json:"type"`
-		Value string `json:"value"`
-	} `json:"stop"`
-
-	ConfigurationFiles []parser.ConfigurationFile `json:"configs"`
-}
-
 // Defines installation script information for a server process. This is used when
 // a server is installed for the first time, and when a server is marked for re-installation.
 type InstallationScript struct {
diff --git a/server/listeners.go b/server/listeners.go
index 30c977a..4263f77 100644
--- a/server/listeners.go
+++ b/server/listeners.go
@@ -4,8 +4,6 @@ import (
 	"github.com/apex/log"
 	"github.com/pterodactyl/wings/api"
 	"regexp"
-	"strings"
-	"sync"
 )
 
 // Adds all of the internal event listeners we want to use for a server.
@@ -23,12 +21,7 @@ func (s *Server) AddEventListeners() {
 	}()
 }
 
-var (
-	stripAnsiRegex = regexp.MustCompile("[\u001B\u009B][[\\]()#;?]*(?:(?:(?:[a-zA-Z\\d]*(?:;[a-zA-Z\\d]*)*)?\u0007)|(?:(?:\\d{1,4}(?:;\\d{0,4})*)?[\\dA-PRZcf-ntqry=><~]))")
-
-	regexpCacheMx sync.RWMutex
-	regexpCache   map[string]*regexp.Regexp
-)
+var stripAnsiRegex = regexp.MustCompile("[\u001B\u009B][[\\]()#;?]*(?:(?:(?:[a-zA-Z\\d]*(?:;[a-zA-Z\\d]*)*)?\u0007)|(?:(?:\\d{1,4}(?:;\\d{0,4})*)?[\\dA-PRZcf-ntqry=><~]))")
 
 // Custom listener for console output events that will check if the given line
 // of output matches one that should mark the server as started or not.
@@ -38,10 +31,6 @@ func (s *Server) onConsoleOutput(data string) {
 
 	// Check if the server is currently starting.
 	if s.GetState() == ProcessStartingState {
-		// If the specific line of output is one that would mark the server as started,
-		// set the server to that state. Only do this if the server is not currently stopped
-		// or stopping.
-
 		// Check if we should strip ansi color codes.
 		if processConfiguration.Startup.StripAnsi {
 			// Strip ansi color codes from the data string.
@@ -49,40 +38,19 @@ func (s *Server) onConsoleOutput(data string) {
 		}
 
 		// Iterate over all the done lines.
-		for _, match := range processConfiguration.Startup.Done {
-			if strings.HasPrefix(match, "regex:") && len(match) > 6 {
-				match = match[6:]
-
-				regexpCacheMx.RLock()
-				rxp, ok := regexpCache[match]
-				regexpCacheMx.RUnlock()
-
-				if !ok {
-					var err error
-
-					rxp, err = regexp.Compile(match)
-					if err != nil {
-						log.WithError(err).Warn("failed to compile regexp")
-						break
-					}
-
-					regexpCacheMx.Lock()
-					regexpCache[match] = rxp
-					regexpCacheMx.Unlock()
-				}
-
-				if !rxp.MatchString(data) {
-					continue
-				}
-			} else if !strings.Contains(data, match) {
+		for _, l := range processConfiguration.Startup.Done {
+			if !l.Matches(data) {
 				continue
 			}
 
 			s.Log().WithFields(log.Fields{
-				"match":   match,
+				"match":   l.String(),
 				"against": data,
 			}).Debug("detected server in running state based on console line output")
 
+			// If the specific line of output is one that would mark the server as started,
+			// set the server to that state. Only do this if the server is not currently stopped
+			// or stopping.
 			_ = s.SetState(ProcessRunningState)
 			break
 		}