diff --git a/paper-api/src/main/java/org/bukkit/Bukkit.java b/paper-api/src/main/java/org/bukkit/Bukkit.java
index 1ada54827a..13fa39ed3d 100644
--- a/paper-api/src/main/java/org/bukkit/Bukkit.java
+++ b/paper-api/src/main/java/org/bukkit/Bukkit.java
@@ -2396,6 +2396,13 @@ public final class Bukkit {
     public static org.bukkit.command.CommandMap getCommandMap() {
         return server.getCommandMap();
     }
+
+    /**
+     * Reload the Permissions in permissions.yml
+     */
+    public static void reloadPermissions() {
+        server.reloadPermissions();
+    }
     // Paper end
 
     @NotNull
diff --git a/paper-api/src/main/java/org/bukkit/Server.java b/paper-api/src/main/java/org/bukkit/Server.java
index 93d924c586..6567d1746f 100644
--- a/paper-api/src/main/java/org/bukkit/Server.java
+++ b/paper-api/src/main/java/org/bukkit/Server.java
@@ -2096,4 +2096,6 @@ public interface Server extends PluginMessageRecipient, net.kyori.adventure.audi
     @NotNull
     Spigot spigot();
     // Spigot end
+
+    void reloadPermissions(); // Paper
 }
diff --git a/paper-api/src/main/java/org/bukkit/command/defaults/ReloadCommand.java b/paper-api/src/main/java/org/bukkit/command/defaults/ReloadCommand.java
index 50cc311be7..5fa9d648bc 100644
--- a/paper-api/src/main/java/org/bukkit/command/defaults/ReloadCommand.java
+++ b/paper-api/src/main/java/org/bukkit/command/defaults/ReloadCommand.java
@@ -13,15 +13,35 @@ public class ReloadCommand extends BukkitCommand {
     public ReloadCommand(@NotNull String name) {
         super(name);
         this.description = "Reloads the server configuration and plugins";
-        this.usageMessage = "/reload";
+        this.usageMessage = "/reload [permissions]"; // Paper
         this.setPermission("bukkit.command.reload");
         this.setAliases(Arrays.asList("rl"));
     }
 
     @Override
-    public boolean execute(@NotNull CommandSender sender, @NotNull String currentAlias, @NotNull String[] args) {
+    public boolean execute(@NotNull CommandSender sender, @NotNull String currentAlias, @NotNull String[] args) { // Paper
         if (!testPermission(sender)) return true;
 
+        // Paper start - Reload permissions.yml & require confirm
+        boolean confirmed = System.getProperty("LetMeReload") != null;
+        if (args.length == 1) {
+            if (args[0].equalsIgnoreCase("permissions")) {
+                Bukkit.getServer().reloadPermissions();
+                Command.broadcastCommandMessage(sender, net.kyori.adventure.text.Component.text("Permissions successfully reloaded.", net.kyori.adventure.text.format.NamedTextColor.GREEN));
+                return true;
+            } else if ("confirm".equalsIgnoreCase(args[0])) {
+                confirmed = true;
+            } else {
+                Command.broadcastCommandMessage(sender, net.kyori.adventure.text.Component.text("Usage: " + usageMessage, net.kyori.adventure.text.format.NamedTextColor.RED));
+                return true;
+            }
+        }
+        if (!confirmed) {
+            Command.broadcastCommandMessage(sender, net.kyori.adventure.text.Component.text("Are you sure you wish to reload your server? Doing so may cause bugs and memory leaks. It is recommended to restart instead of using /reload. To confirm, please type ", net.kyori.adventure.text.format.NamedTextColor.RED).append(net.kyori.adventure.text.Component.text("/reload confirm", net.kyori.adventure.text.format.NamedTextColor.YELLOW)));
+            return true;
+        }
+        // Paper end
+
         Command.broadcastCommandMessage(sender, ChatColor.RED + "Please note that this command is not supported and may cause issues when using some plugins.");
         Command.broadcastCommandMessage(sender, ChatColor.RED + "If you encounter any issues please use the /stop command to restart your server.");
         Bukkit.reload();
@@ -33,6 +53,6 @@ public class ReloadCommand extends BukkitCommand {
     @NotNull
     @Override
     public List<String> tabComplete(@NotNull CommandSender sender, @NotNull String alias, @NotNull String[] args) throws IllegalArgumentException {
-        return Collections.emptyList();
+        return java.util.Collections.singletonList("permissions"); // Paper
     }
 }