diff --git a/apps/client/src/features/editor/styles/index.css b/apps/client/src/features/editor/styles/index.css
index 44793724..e426e0ba 100644
--- a/apps/client/src/features/editor/styles/index.css
+++ b/apps/client/src/features/editor/styles/index.css
@@ -11,3 +11,4 @@
 @import "./print.css";
 @import "./find.css";
 @import "./mention.css";
+@import "./ordered-list.css";
diff --git a/apps/client/src/features/editor/styles/ordered-list.css b/apps/client/src/features/editor/styles/ordered-list.css
new file mode 100644
index 00000000..d3aadb39
--- /dev/null
+++ b/apps/client/src/features/editor/styles/ordered-list.css
@@ -0,0 +1,34 @@
+/* Ordered list type cycling based on nesting depth */
+ol,
+ol ol ol ol,
+ol ol ol ol ol ol ol,
+ol ol ol ol ol ol ol ol ol ol {
+  list-style-type: decimal;
+}
+
+ol ol,
+ol ol ol ol ol,
+ol ol ol ol ol ol ol ol,
+ol ol ol ol ol ol ol ol ol ol ol {
+  list-style-type: lower-alpha;
+}
+
+ol ol ol,
+ol ol ol ol ol ol,
+ol ol ol ol ol ol ol ol ol,
+ol ol ol ol ol ol ol ol ol ol ol ol {
+  list-style-type: lower-roman;
+}
+
+ol {
+  list-style-position: outside;
+  margin-left: 0.25rem;
+}
+
+/* Nested list spacing */
+ol ol,
+ol ul,
+ul ol {
+  margin-top: 0.1rem;
+  margin-bottom: 0.1rem;
+}
diff --git a/apps/server/src/collaboration/collaboration.util.ts b/apps/server/src/collaboration/collaboration.util.ts
index db2771b2..8a41d79d 100644
--- a/apps/server/src/collaboration/collaboration.util.ts
+++ b/apps/server/src/collaboration/collaboration.util.ts
@@ -48,7 +48,9 @@ export const tiptapExtensions = [
   Comment,
   TextAlign.configure({ types: ["heading", "paragraph"] }),
   TaskList,
-  TaskItem,
+  TaskItem.configure({
+    nested: true,
+  }),
   Underline,
   LinkExtension,
   Superscript,