diff --git a/src/buttons/dev-watch.ts b/src/buttons/dev-watch.ts
index 3d85b7b..cfddb0c 100644
--- a/src/buttons/dev-watch.ts
+++ b/src/buttons/dev-watch.ts
@@ -4,20 +4,27 @@ import { Database } from '../shared/Database';
 export default {
   name: 'dev-watch',
   handler: async function (client: Client, interaction: ButtonInteraction) {
-    const member = await interaction.guild!.members.fetch(interaction.user.id);
+    try {
+      if (!interaction.guild) throw new Error('This action must be run in a guild.');
 
-    if (!member) return await interaction.reply({ flags: [MessageFlags.Ephemeral], content: 'There was an error. Please try again later.' });
+      const settings = await Database.getGuildSettings(interaction.guild.id);
+      if (!settings || !settings.devwatch_role_id) throw new Error('`devwatch_role_id` was not configured. Please configure a role then try again.');
+      const member = await interaction.guild.members.fetch(interaction.user.id);
+      if (!member) throw new Error('Unable to retreive the member executing this command.');
 
-    const settings = await Database.getGuildSettings(interaction.guild!.id);
+      const bot = await interaction.guild.members.fetchMe();
+      const role = await interaction.guild?.roles.fetch(settings.devwatch_role_id);
+      if (role?.position! > bot.roles.highest.position) throw new Error('The configured `devwatch_role_id` is higher than my highest role.');
 
-    if (!settings || !settings.devwatch_role_id) return await interaction.reply({ flags: [MessageFlags.Ephemeral], content: 'There was an error. Please try again later.' });
-
-    if (member.roles.cache.has(settings.devwatch_role_id)) {
-      await member.roles.remove(settings.devwatch_role_id);
-      await interaction.reply({ flags: [MessageFlags.Ephemeral], content: 'Removed role.' });
-    } else {
-      await member.roles.add(settings.devwatch_role_id);
-      await interaction.reply({ flags: [MessageFlags.Ephemeral], content: 'Added role.' });
+      if (member.roles.cache.has(settings.devwatch_role_id)) {
+        await member.roles.remove(settings.devwatch_role_id);
+        await interaction.reply({ flags: [MessageFlags.Ephemeral], content: 'Removed role.' });
+      } else {
+        await member.roles.add(settings.devwatch_role_id);
+        await interaction.reply({ flags: [MessageFlags.Ephemeral], content: 'Added role.' });
+      }
+    } catch (error: Error | any) {
+      await interaction.reply({ flags: [MessageFlags.Ephemeral], content: error.message });
     }
   }
 };
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