diff --git a/plugin/src/main/java/com/denizenscript/denizen/utilities/FormattedTextHelper.java b/plugin/src/main/java/com/denizenscript/denizen/utilities/FormattedTextHelper.java
index 67392b5fa9..ddc0e08258 100644
--- a/plugin/src/main/java/com/denizenscript/denizen/utilities/FormattedTextHelper.java
+++ b/plugin/src/main/java/com/denizenscript/denizen/utilities/FormattedTextHelper.java
@@ -3,10 +3,7 @@
 import com.denizenscript.denizen.nms.NMSHandler;
 import com.denizenscript.denizen.nms.NMSVersion;
 import com.denizenscript.denizen.objects.properties.bukkit.BukkitElementExtensions;
-import com.denizenscript.denizencore.objects.core.ColorTag;
-import com.denizenscript.denizencore.objects.core.ElementTag;
-import com.denizenscript.denizencore.objects.core.ListTag;
-import com.denizenscript.denizencore.objects.core.MapTag;
+import com.denizenscript.denizencore.objects.core.*;
 import com.denizenscript.denizencore.utilities.AsciiMatcher;
 import com.denizenscript.denizencore.utilities.CoreConfiguration;
 import com.denizenscript.denizencore.utilities.CoreUtilities;
@@ -19,6 +16,8 @@
 import net.md_5.bungee.chat.ComponentSerializer;
 import net.md_5.bungee.chat.VersionedComponentSerializer;
 
+import java.net.URI;
+import java.net.URISyntaxException;
 import java.util.List;
 
 public class FormattedTextHelper {
@@ -800,11 +799,17 @@ else if (code == 'o' || code == 'O') {
             else if (i + "https://a.".length() < chars.length && chars[i] == 'h' && chars[i + 1] == 't' && chars[i + 2] == 't' && chars[i  + 3] == 'p') {
                 String subStr = str.substring(i, i + "https://a.".length());
                 if (subStr.startsWith("https://") || subStr.startsWith("http://")) {
-                    int nextSpace = CoreUtilities.indexOfAny(str, i, ' ', '\t', '\n', ChatColor.COLOR_CHAR);
-                    if (nextSpace == -1) {
-                        nextSpace = str.length();
+                    int urlEnd = findUrlEndIndex(chars, i);
+                    if (urlEnd - i < "https://a.".length()) {
+                        continue;
+                    }
+                    String url = str.substring(i, urlEnd);
+                    try {
+                        new URI(url);
+                    }
+                    catch (URISyntaxException ignored) {
+                        continue;
                     }
-                    String url = str.substring(i, nextSpace);
                     nextText.setText(nextText.getText() + str.substring(started, i));
                     base.addExtra(nextText);
                     lastText = nextText;
@@ -813,8 +818,8 @@ else if (i + "https://a.".length() < chars.length && chars[i] == 'h' && chars[i
                     TextComponent clickableText = new TextComponent(url);
                     clickableText.setClickEvent(new ClickEvent(ClickEvent.Action.OPEN_URL, url));
                     lastText.addExtra(clickableText);
-                    i = nextSpace - 1;
-                    started = nextSpace;
+                    i = urlEnd - 1;
+                    started = urlEnd;
                     continue;
                 }
             }
@@ -826,6 +831,24 @@ else if (i + "https://a.".length() < chars.length && chars[i] == 'h' && chars[i
         return new BaseComponent[] { cleanBase && !optimize ? root : base };
     }
 
+    public static final AsciiMatcher URL_VALID = new AsciiMatcher(AsciiMatcher.LETTERS_LOWER + AsciiMatcher.LETTERS_UPPER + AsciiMatcher.DIGITS + "-._~:/?#@!$&'()*+,;=");
+
+    public static int findUrlEndIndex(char[] chars, int start) {
+        for (int i = start; i < chars.length; i++) {
+            char current = chars[i];
+            if (current == '%') {
+                if (i + 2 >= chars.length || !BinaryTag.VALID_HEX.isMatch(chars[i + 1]) || !BinaryTag.VALID_HEX.isMatch(chars[i + 2])) {
+                    return i;
+                }
+                i += 2;
+            }
+            else if (!URL_VALID.isMatch(current)) {
+                return i;
+            }
+        }
+        return chars.length;
+    }
+
     public static int indexOfLastColorBlockStart(String text) {
         int result = text.lastIndexOf(ChatColor.COLOR_CHAR + "[");
         if (result == -1 || text.indexOf(']', result + 2) != -1) {