diff --git a/src/main/java/net/skullian/updater/UpdateListener.java b/src/main/java/net/skullian/updater/UpdateListener.java
index 1ab06c6..29ece0a 100644
--- a/src/main/java/net/skullian/updater/UpdateListener.java
+++ b/src/main/java/net/skullian/updater/UpdateListener.java
@@ -25,6 +25,8 @@ public void onJoin(PlayerJoinEvent event) {
 
     @EventHandler
     public void onStart(ServerLoadEvent event) {
-        checkUpdate(Bukkit.getConsoleSender());
+        Scheduler.runTaskAsynchronously(
+                InteractiveChatPacketEvents.instance,
+                () -> checkUpdate(Bukkit.getConsoleSender()));
     }
 }
diff --git a/src/main/java/net/skullian/updater/Updater.java b/src/main/java/net/skullian/updater/Updater.java
index e628d77..52b5f04 100644
--- a/src/main/java/net/skullian/updater/Updater.java
+++ b/src/main/java/net/skullian/updater/Updater.java
@@ -7,46 +7,93 @@
 import net.skullian.util.GithubBuildInfo;
 import net.skullian.util.GithubUtils;
 import org.bukkit.command.CommandSender;
-import org.bukkit.event.Listener;
 
 import java.io.IOException;
 import java.util.Locale;
 
-public class Updater implements Listener {
+public final class Updater {
+
+    private Updater() {
+    }
 
     public static UpdateStatus checkUpdate(CommandSender... senders) {
         GithubBuildInfo currentBuild = GithubBuildInfo.CURRENT;
-        GithubBuildInfo latestBuild;
-        GithubUtils.GitHubStatusLookup lookupStatus;
-
         UpdateStatus updateStatus = new UpdateStatus(false, false);
 
         try {
             if (currentBuild.stable()) {
-                latestBuild = GithubUtils.lookupLatestRelease();
-                lookupStatus = GithubUtils.compare(latestBuild.id(), currentBuild.id());
-            } else {
-                latestBuild = null;
-                lookupStatus = GithubUtils.compare(GithubUtils.MAIN_BRANCH, currentBuild.id());
+                return checkStableUpdate(currentBuild, senders, updateStatus);
             }
+
+            return checkDevelopmentUpdate(currentBuild, senders, updateStatus);
         } catch (IOException error) {
-            ChatUtils.sendMessage("<red>Failed to fetch latest version: " + error, senders);
+            ChatUtils.sendMessage(
+                    "<red>Failed to check for updates. Please try again later.",
+                    senders);
+
             updateStatus.setFailed(true);
             return updateStatus;
         }
+    }
+
+    private static UpdateStatus checkStableUpdate(
+            GithubBuildInfo currentBuild,
+            CommandSender[] senders,
+            UpdateStatus updateStatus) throws IOException {
+        GithubBuildInfo latestBuild = GithubUtils.lookupLatestRelease();
+
+        // Stable builds must compare release versions, not a release tag
+        // against the installed build's commit SHA.
+        if (currentBuild.name().equals(latestBuild.name())) {
+            updateStatus.setUpToDate(true);
+            return updateStatus;
+        }
+
+        String url = "https://github.com/TerraByteDev/InteractiveChat-PacketEvents/releases/tag/"
+                + latestBuild.id();
+
+        ChatUtils.sendMessage(
+                "<green>A new version of InteractiveChat-PacketEvents is available: "
+                        + latestBuild.name() + "!",
+                senders);
+        ChatUtils.sendMessage(
+                "<grey>Download at: <click:open_url:'" + url + "'>"
+                        + url + "</click>",
+                senders);
+
+        return updateStatus;
+    }
+
+    private static UpdateStatus checkDevelopmentUpdate(
+            GithubBuildInfo currentBuild,
+            CommandSender[] senders,
+            UpdateStatus updateStatus) throws IOException {
+        GithubUtils.GitHubStatusLookup lookupStatus = GithubUtils.compare(
+                GithubUtils.MAIN_BRANCH,
+                currentBuild.id());
 
         if (lookupStatus.isBehind()) {
-            if (currentBuild.stable()) {
-                String url = "https://github.com/TerraByteDev/InteractiveChat-PacketEvents/releases/tag/" + latestBuild.id();
+            ChatUtils.sendMessage(
+                    "<yellow>You are running a development build of InteractiveChat-PacketEvents!\n"
+                            + "The latest available development build is "
+                            + String.format(Locale.ROOT, "%,d", lookupStatus.getDistance())
+                            + " commits ahead.",
+                    senders);
 
-                ChatUtils.sendMessage("<green>A new version of InteractiveChat-PacketEvents is available: " + latestBuild.id() + "!", senders);
-                ChatUtils.sendMessage("<grey>Download at: <click:open_url:'" + url + "'>" + url + "</click>", senders);
-            } else {
-                ChatUtils.sendMessage("<yellow>You are running a development build of InteractiveChat-PacketEvents!\nThe latest available development build is " + String.format(Locale.ROOT, "%,d", lookupStatus.getDistance()) + " commits ahead.", senders);
-            }
+            return updateStatus;
+        }
+
+        if (lookupStatus.getStatus() == GithubUtils.GitHubStatus.FAILURE
+                || lookupStatus.getStatus() == GithubUtils.GitHubStatus.UNKNOWN
+                || lookupStatus.getStatus() == GithubUtils.GitHubStatus.DIVERGED) {
+            ChatUtils.sendMessage(
+                    "<red>Failed to determine whether a newer development build is available.",
+                    senders);
+            updateStatus.setFailed(true);
+            return updateStatus;
         }
 
-        updateStatus.setUpToDate(!lookupStatus.isBehind());
+        updateStatus.setUpToDate(true);
         return updateStatus;
     }
 
@@ -57,5 +104,4 @@ public static final class UpdateStatus {
         private boolean isUpToDate;
         private boolean failed;
     }
-
 }
diff --git a/src/main/java/net/skullian/util/GithubUtils.java b/src/main/java/net/skullian/util/GithubUtils.java
index cea0ffd..90dd673 100644
--- a/src/main/java/net/skullian/util/GithubUtils.java
+++ b/src/main/java/net/skullian/util/GithubUtils.java
@@ -22,21 +22,25 @@ public class GithubUtils {
     private static final String API_BASE = "https://api.github.com/repos/";
 
     // https://docs.github.com/en/rest/releases/releases#get-the-latest-release
-    private static final String API_LATEST_RELEASE = API_BASE + "TerraByteDev/InteractiveChat-PacketEvents/releases/latest";
+    private static final String API_LATEST_RELEASE = API_BASE
+            + "TerraByteDev/InteractiveChat-PacketEvents/releases/latest";
 
     // https://docs.github.com/en/rest/commits/commits#compare-two-commits
     private static final String API_COMPARE = API_BASE + "TerraByteDev/InteractiveChat-PacketEvents/compare/%s...%s";
 
-    private GithubUtils() {}
+    private GithubUtils() {
+    }
 
     public static GithubBuildInfo lookupLatestRelease() throws IOException {
         URL url = new URL(API_LATEST_RELEASE);
         HttpsURLConnection https = (HttpsURLConnection) url.openConnection();
+        https.setConnectTimeout(5000);
+        https.setReadTimeout(5000);
         final int responseCode = https.getResponseCode();
 
         if (isSuccessfulResponse(responseCode)) {
             try (InputStream in = https.getInputStream();
-                 BufferedReader reader = new BufferedReader(new InputStreamReader(in, StandardCharsets.UTF_8))) {
+                    BufferedReader reader = new BufferedReader(new InputStreamReader(in, StandardCharsets.UTF_8))) {
                 return parseBuildInfo(reader);
             }
         } else {
@@ -53,11 +57,13 @@ private static GithubBuildInfo parseBuildInfo(BufferedReader reader) {
     public static GitHubStatusLookup compare(@NotNull String base, @NotNull String head) throws IOException {
         URL url = new URL(String.format(API_COMPARE, base, head));
         HttpsURLConnection https = (HttpsURLConnection) url.openConnection();
+        https.setConnectTimeout(5000);
+        https.setReadTimeout(5000);
         final int responseCode = https.getResponseCode();
 
         if (isSuccessfulResponse(responseCode)) {
             try (InputStream in = https.getInputStream();
-                 BufferedReader reader = new BufferedReader(new InputStreamReader(in, StandardCharsets.UTF_8))) {
+                    BufferedReader reader = new BufferedReader(new InputStreamReader(in, StandardCharsets.UTF_8))) {
                 return parseComparison(reader);
             }
         } else if (responseCode == HttpsURLConnection.HTTP_NOT_FOUND) {
@@ -119,7 +125,8 @@ public enum GitHubStatus {
         // Internal types
 
         /**
-         * Represents the case when a BASEHEAD is unknown to GitHub, private builds, for example.
+         * Represents the case when a BASEHEAD is unknown to GitHub, private builds, for
+         * example.
          */
         UNKNOWN,