diff --git a/changelog.d/3248.misc.rst b/changelog.d/3248.misc.rst
new file mode 100644
index 000000000..aa57d9636
--- /dev/null
+++ b/changelog.d/3248.misc.rst
@@ -0,0 +1 @@
+fix a buggy first page of paginated help
diff --git a/redbot/core/commands/help.py b/redbot/core/commands/help.py
index 1de10cfb6..8204c7d8f 100644
--- a/redbot/core/commands/help.py
+++ b/redbot/core/commands/help.py
@@ -277,16 +277,18 @@ class RedHelpFormatter:
         ret = []
         current_count = 0
 
-        for f in fields:
+        for i, f in enumerate(fields):
             f_len = len(f.value) + len(f.name)
-            if curr_group and (f_len + current_count > max_chars):
+
+            # Commands start at the 1st index of fields, i < 2 is a hacky workaround for now
+            if not current_count or f_len + current_count > max_chars or i < 2:
+                current_count += f_len
+                curr_group.append(f)
+            elif curr_group:
                 ret.append(curr_group)
-                curr_group = []
                 current_count = 0
-            curr_group.append(f)
-            current_count += f_len
+                curr_group = [f]
         else:
-            # Loop cleanup here
             if curr_group:
                 ret.append(curr_group)