diff --git a/backend/src/plugins/RoleButtons/RoleButtonsPlugin.ts b/backend/src/plugins/RoleButtons/RoleButtonsPlugin.ts
index 60f5a221..aa76140a 100644
--- a/backend/src/plugins/RoleButtons/RoleButtonsPlugin.ts
+++ b/backend/src/plugins/RoleButtons/RoleButtonsPlugin.ts
@@ -8,6 +8,8 @@ import { RoleManagerPlugin } from "../RoleManager/RoleManagerPlugin";
 import { StrictValidationError } from "../../validatorUtils";
 import { onButtonInteraction } from "./events/buttonInteraction";
 import { pluginInfo } from "./info";
+import { createButtonComponents } from "./functions/createButtonComponents";
+import { TooManyComponentsError } from "./functions/TooManyComponentsError";
 
 export const RoleButtonsPlugin = zeppelinGuildPlugin<RoleButtonsPluginType>()({
   name: "role_buttons",
@@ -26,10 +28,6 @@ export const RoleButtonsPlugin = zeppelinGuildPlugin<RoleButtonsPluginType>()({
 
       if (buttonsConfig) {
         buttonsConfig.name = name;
-        // 5 action rows * 5 buttons
-        if (buttonsConfig.options?.length > 25) {
-          throw new StrictValidationError(["A single message can have at most 25 role buttons"]);
-        }
 
         if (buttonsConfig.message) {
           if ("message_id" in buttonsConfig.message) {
@@ -39,6 +37,17 @@ export const RoleButtonsPlugin = zeppelinGuildPlugin<RoleButtonsPluginType>()({
             seenMessages.add(buttonsConfig.message.message_id);
           }
         }
+
+        if (buttonsConfig.options) {
+          try {
+            createButtonComponents(buttonsConfig);
+          } catch (err) {
+            if (err instanceof TooManyComponentsError) {
+              throw new StrictValidationError(["Too many options; can only have max 5 buttons per row on max 5 rows."]);
+            }
+            throw new StrictValidationError(["Error validating options"]);
+          }
+        }
       }
     }
 
diff --git a/backend/src/plugins/RoleButtons/functions/TooManyComponentsError.ts b/backend/src/plugins/RoleButtons/functions/TooManyComponentsError.ts
new file mode 100644
index 00000000..b79be8bb
--- /dev/null
+++ b/backend/src/plugins/RoleButtons/functions/TooManyComponentsError.ts
@@ -0,0 +1 @@
+export class TooManyComponentsError extends Error {}
diff --git a/backend/src/plugins/RoleButtons/functions/applyRoleButtons.ts b/backend/src/plugins/RoleButtons/functions/applyRoleButtons.ts
index 18c8beb5..b171bc2b 100644
--- a/backend/src/plugins/RoleButtons/functions/applyRoleButtons.ts
+++ b/backend/src/plugins/RoleButtons/functions/applyRoleButtons.ts
@@ -4,8 +4,8 @@ import { isSnowflake, snowflakeRegex } from "../../../utils";
 import { LogsPlugin } from "../../Logs/LogsPlugin";
 import { Message, MessageButton, MessageEditOptions, MessageOptions, Snowflake } from "discord.js";
 import { RoleButtonsItem } from "../../../data/entities/RoleButtonsItem";
-import { splitButtonsIntoRows } from "./splitButtonsIntoRows";
 import { buildCustomId } from "../../../utils/buildCustomId";
+import { createButtonComponents } from "./createButtonComponents";
 
 const channelMessageRegex = new RegExp(`^(${snowflakeRegex.source})-(${snowflakeRegex.source})$`);
 
@@ -104,24 +104,8 @@ export async function applyRoleButtons(
   }
 
   // Apply role buttons
-  const buttons = configItem.options.map((opt, index) => {
-    const button = new MessageButton()
-      .setLabel(opt.label ?? "")
-      .setStyle(opt.style ?? "PRIMARY")
-      .setCustomId(buildCustomId("roleButtons", { name: configItem.name, index }));
-
-    if (opt.emoji) {
-      const emo = pluginData.client.emojis.resolve(opt.emoji as Snowflake) ?? opt.emoji;
-      button.setEmoji(emo);
-    }
-
-    return button;
-  });
-  const rows = splitButtonsIntoRows(buttons);
-
-  await message.edit({
-    components: rows,
-  });
+  const components = createButtonComponents(configItem);
+  await message.edit({ components });
 
   return {
     channel_id: message.channelId,
diff --git a/backend/src/plugins/RoleButtons/functions/createButtonComponents.ts b/backend/src/plugins/RoleButtons/functions/createButtonComponents.ts
new file mode 100644
index 00000000..05736484
--- /dev/null
+++ b/backend/src/plugins/RoleButtons/functions/createButtonComponents.ts
@@ -0,0 +1,39 @@
+import { MessageActionRow, MessageButton, Snowflake } from "discord.js";
+import { chunkArray } from "../../../utils";
+import { RoleButtonsPluginType, TRoleButtonOption, TRoleButtonsConfigItem } from "../types";
+import { buildCustomId } from "../../../utils/buildCustomId";
+import { GuildPluginData } from "knub";
+import { TooManyComponentsError } from "./TooManyComponentsError";
+
+export function createButtonComponents(configItem: TRoleButtonsConfigItem): MessageActionRow[] {
+  const rows: MessageActionRow[] = [];
+
+  let currentRow = new MessageActionRow();
+  for (const [index, option] of configItem.options.entries()) {
+    if (currentRow.components.length === 5 || (currentRow.components.length > 0 && option.start_new_row)) {
+      rows.push(currentRow);
+      currentRow = new MessageActionRow();
+    }
+
+    const button = new MessageButton()
+      .setLabel(option.label ?? "")
+      .setStyle(option.style ?? "PRIMARY")
+      .setCustomId(buildCustomId("roleButtons", { name: configItem.name, index }));
+
+    if (option.emoji) {
+      button.setEmoji(option.emoji);
+    }
+
+    currentRow.components.push(button);
+  }
+
+  if (currentRow.components.length > 0) {
+    rows.push(currentRow);
+  }
+
+  if (rows.length > 5) {
+    throw new TooManyComponentsError();
+  }
+
+  return rows;
+}
diff --git a/backend/src/plugins/RoleButtons/functions/splitButtonsIntoRows.ts b/backend/src/plugins/RoleButtons/functions/splitButtonsIntoRows.ts
deleted file mode 100644
index 118f20ce..00000000
--- a/backend/src/plugins/RoleButtons/functions/splitButtonsIntoRows.ts
+++ /dev/null
@@ -1,12 +0,0 @@
-import { MessageActionRow, MessageButton } from "discord.js";
-import { chunkArray } from "../../../utils";
-
-export function splitButtonsIntoRows(buttons: MessageButton[]): MessageActionRow[] {
-  // Max 5 buttons per row
-  const buttonChunks = chunkArray(buttons, 5);
-  return buttonChunks.map((chunk) => {
-    const row = new MessageActionRow();
-    row.setComponents(chunk);
-    return row;
-  });
-}
diff --git a/backend/src/plugins/RoleButtons/types.ts b/backend/src/plugins/RoleButtons/types.ts
index 0dbbcd07..2b23b692 100644
--- a/backend/src/plugins/RoleButtons/types.ts
+++ b/backend/src/plugins/RoleButtons/types.ts
@@ -16,6 +16,7 @@ const RoleButtonOption = t.type({
   label: tNullable(t.string),
   emoji: tNullable(t.string),
   style: tNullable(t.keyof(ButtonStyles)), // https://discord.js.org/#/docs/discord.js/v13/typedef/MessageButtonStyle
+  start_new_row: tNullable(t.boolean),
 });
 export type TRoleButtonOption = t.TypeOf<typeof RoleButtonOption>;