diff --git a/web/src/components/MemoContent/ConditionalComponent.tsx b/web/src/components/MemoContent/ConditionalComponent.tsx
deleted file mode 100644
index 6bb1142e6..000000000
--- a/web/src/components/MemoContent/ConditionalComponent.tsx
+++ /dev/null
@@ -1,36 +0,0 @@
-import type { Element } from "hast";
-import React from "react";
-import { isMentionElement, isTagElement, isTaskListItemElement } from "@/types/markdown";
-
-/**
- * Creates a conditional component that renders different components
- * based on AST node type detection
- *
- * @param CustomComponent - Custom component to render when condition matches
- * @param DefaultComponent - Default component/element to render otherwise
- * @param condition - Function to test AST node
- * @returns Conditional wrapper component
- */
-export const createConditionalComponent = <P extends Record<string, unknown>>(
-  CustomComponent: React.ComponentType<P>,
-  DefaultComponent: React.ComponentType<P> | keyof JSX.IntrinsicElements,
-  condition: (node: Element) => boolean,
-) => {
-  return (props: P & { node?: Element }) => {
-    const { node, ...restProps } = props;
-
-    // Check AST node to determine which component to use
-    if (node && condition(node)) {
-      return <CustomComponent {...(restProps as P)} node={node} />;
-    }
-
-    // Render default component/element
-    if (typeof DefaultComponent === "string") {
-      return React.createElement(DefaultComponent, restProps);
-    }
-    return <DefaultComponent {...(restProps as P)} />;
-  };
-};
-
-// Re-export type guards for convenience
-export { isMentionElement as isMentionNode, isTagElement as isTagNode, isTaskListItemElement as isTaskListItemNode };
diff --git a/web/src/components/MemoContent/MemoMarkdownRenderer.tsx b/web/src/components/MemoContent/MemoMarkdownRenderer.tsx
new file mode 100644
index 000000000..159c6f4dd
--- /dev/null
+++ b/web/src/components/MemoContent/MemoMarkdownRenderer.tsx
@@ -0,0 +1,139 @@
+import type { Element } from "hast";
+import type { Components } from "react-markdown";
+import ReactMarkdown from "react-markdown";
+import rehypeKatex from "rehype-katex";
+import rehypeRaw from "rehype-raw";
+import rehypeSanitize from "rehype-sanitize";
+import remarkBreaks from "remark-breaks";
+import remarkGfm from "remark-gfm";
+import remarkMath from "remark-math";
+import { isMentionElement, isTagElement, isTaskListItemElement } from "@/types/markdown";
+import { rehypeHeadingId } from "@/utils/rehype-plugins/rehype-heading-id";
+import { remarkDisableSetext } from "@/utils/remark-plugins/remark-disable-setext";
+import { remarkMention } from "@/utils/remark-plugins/remark-mention";
+import { remarkPreserveType } from "@/utils/remark-plugins/remark-preserve-type";
+import { remarkSplitMixedTaskLists } from "@/utils/remark-plugins/remark-split-mixed-task-lists";
+import { remarkTag } from "@/utils/remark-plugins/remark-tag";
+import { CodeBlock } from "./CodeBlock";
+import { SANITIZE_SCHEMA } from "./constants";
+import { Mention } from "./Mention";
+import { Blockquote, Heading, HorizontalRule, Image, InlineCode, Link, List, ListItem, Paragraph } from "./markdown";
+import { Table, TableBody, TableCell, TableHead, TableHeaderCell, TableRow } from "./Table";
+import { Tag } from "./Tag";
+import { TaskListItem } from "./TaskListItem";
+import { TrustedIframe } from "./TrustedIframe";
+
+interface MemoMarkdownRendererProps {
+  content: string;
+  resolvedMentionUsernames: Set<string>;
+}
+
+function getMentionUsername(node: Element, children?: React.ReactNode): string {
+  const dataMention = node.properties?.["data-mention"];
+  if (typeof dataMention === "string" && dataMention !== "") {
+    return dataMention;
+  }
+
+  const camelDataMention = (node.properties as Record<string, unknown> | undefined)?.dataMention;
+  if (typeof camelDataMention === "string" && camelDataMention !== "") {
+    return camelDataMention;
+  }
+
+  const text = Array.isArray(children) ? children.join("") : children;
+  if (typeof text === "string" && text.startsWith("@")) {
+    return text.slice(1).toLowerCase();
+  }
+
+  return "";
+}
+
+export const MemoMarkdownRenderer = ({ content, resolvedMentionUsernames }: MemoMarkdownRendererProps) => {
+  const markdownComponents: Components = {
+    input: ({ node, ...inputProps }) => {
+      if (node && isTaskListItemElement(node)) {
+        return <TaskListItem {...inputProps} node={node} />;
+      }
+      return <input {...inputProps} />;
+    },
+    span: ({ node, ...spanProps }) => {
+      if (node && isMentionElement(node)) {
+        const username = getMentionUsername(node, spanProps.children);
+        return <Mention {...spanProps} node={node} data-mention={username} resolved={resolvedMentionUsernames.has(username)} />;
+      }
+      if (node && isTagElement(node)) {
+        return <Tag {...spanProps} node={node} />;
+      }
+      return <span {...spanProps} />;
+    },
+    h1: ({ children, ...props }) => (
+      <Heading level={1} {...props}>
+        {children}
+      </Heading>
+    ),
+    h2: ({ children, ...props }) => (
+      <Heading level={2} {...props}>
+        {children}
+      </Heading>
+    ),
+    h3: ({ children, ...props }) => (
+      <Heading level={3} {...props}>
+        {children}
+      </Heading>
+    ),
+    h4: ({ children, ...props }) => (
+      <Heading level={4} {...props}>
+        {children}
+      </Heading>
+    ),
+    h5: ({ children, ...props }) => (
+      <Heading level={5} {...props}>
+        {children}
+      </Heading>
+    ),
+    h6: ({ children, ...props }) => (
+      <Heading level={6} {...props}>
+        {children}
+      </Heading>
+    ),
+    p: ({ children, ...props }) => <Paragraph {...props}>{children}</Paragraph>,
+    blockquote: ({ children, ...props }) => <Blockquote {...props}>{children}</Blockquote>,
+    hr: (props) => <HorizontalRule {...props} />,
+    ul: ({ children, ...props }) => <List {...props}>{children}</List>,
+    ol: ({ children, ...props }) => (
+      <List ordered {...props}>
+        {children}
+      </List>
+    ),
+    li: ({ children, ...props }) => <ListItem {...props}>{children}</ListItem>,
+    a: ({ children, ...props }) => <Link {...props}>{children}</Link>,
+    code: ({ children, ...props }) => <InlineCode {...props}>{children}</InlineCode>,
+    iframe: TrustedIframe,
+    img: (props) => <Image {...props} />,
+    pre: CodeBlock,
+    table: ({ children, ...props }) => <Table {...props}>{children}</Table>,
+    thead: ({ children, ...props }) => <TableHead {...props}>{children}</TableHead>,
+    tbody: ({ children, ...props }) => <TableBody {...props}>{children}</TableBody>,
+    tr: ({ children, ...props }) => <TableRow {...props}>{children}</TableRow>,
+    th: ({ children, ...props }) => <TableHeaderCell {...props}>{children}</TableHeaderCell>,
+    td: ({ children, ...props }) => <TableCell {...props}>{children}</TableCell>,
+  };
+
+  return (
+    <ReactMarkdown
+      remarkPlugins={[
+        remarkDisableSetext,
+        remarkMath,
+        remarkGfm,
+        remarkSplitMixedTaskLists,
+        remarkBreaks,
+        remarkMention,
+        remarkTag,
+        remarkPreserveType,
+      ]}
+      rehypePlugins={[rehypeRaw, [rehypeSanitize, SANITIZE_SCHEMA], rehypeHeadingId, [rehypeKatex, { throwOnError: false, strict: false }]]}
+      components={markdownComponents}
+    >
+      {content}
+    </ReactMarkdown>
+  );
+};
diff --git a/web/src/components/MemoContent/index.tsx b/web/src/components/MemoContent/index.tsx
index 232d434bd..67fa19953 100644
--- a/web/src/components/MemoContent/index.tsx
+++ b/web/src/components/MemoContent/index.tsx
@@ -1,53 +1,14 @@
-import type { Element } from "hast";
 import { ChevronDown, ChevronUp } from "lucide-react";
 import { memo, useMemo } from "react";
-import ReactMarkdown from "react-markdown";
-import rehypeKatex from "rehype-katex";
-import rehypeRaw from "rehype-raw";
-import rehypeSanitize from "rehype-sanitize";
-import remarkBreaks from "remark-breaks";
-import remarkGfm from "remark-gfm";
-import remarkMath from "remark-math";
 import { cn } from "@/lib/utils";
 import { useTranslate } from "@/utils/i18n";
-import { rehypeHeadingId } from "@/utils/rehype-plugins/rehype-heading-id";
-import { remarkDisableSetext } from "@/utils/remark-plugins/remark-disable-setext";
-import { extractMentionUsernames, remarkMention } from "@/utils/remark-plugins/remark-mention";
-import { remarkPreserveType } from "@/utils/remark-plugins/remark-preserve-type";
-import { remarkSplitMixedTaskLists } from "@/utils/remark-plugins/remark-split-mixed-task-lists";
-import { remarkTag } from "@/utils/remark-plugins/remark-tag";
-import { CodeBlock } from "./CodeBlock";
-import { isMentionNode, isTagNode, isTaskListItemNode } from "./ConditionalComponent";
-import { COMPACT_MODE_CONFIG, SANITIZE_SCHEMA } from "./constants";
+import { extractMentionUsernames } from "@/utils/remark-plugins/remark-mention";
+import { COMPACT_MODE_CONFIG } from "./constants";
 import { useCompactLabel, useCompactMode } from "./hooks";
-import { Mention } from "./Mention";
+import { MemoMarkdownRenderer } from "./MemoMarkdownRenderer";
 import { useResolvedMentionUsernames } from "./MentionResolutionContext";
-import { Blockquote, Heading, HorizontalRule, Image, InlineCode, Link, List, ListItem, Paragraph } from "./markdown";
-import { Table, TableBody, TableCell, TableHead, TableHeaderCell, TableRow } from "./Table";
-import { Tag } from "./Tag";
-import { TaskListItem } from "./TaskListItem";
-import { TrustedIframe } from "./TrustedIframe";
 import type { MemoContentProps } from "./types";
 
-function getMentionUsername(node: Element, children?: React.ReactNode): string {
-  const dataMention = node.properties?.["data-mention"];
-  if (typeof dataMention === "string" && dataMention !== "") {
-    return dataMention;
-  }
-
-  const camelDataMention = (node.properties as Record<string, unknown> | undefined)?.dataMention;
-  if (typeof camelDataMention === "string" && camelDataMention !== "") {
-    return camelDataMention;
-  }
-
-  const text = Array.isArray(children) ? children.join("") : children;
-  if (typeof text === "string" && text.startsWith("@")) {
-    return text.slice(1).toLowerCase();
-  }
-
-  return "";
-}
-
 const MemoContent = (props: MemoContentProps) => {
   const { className, contentClassName, content, onClick, onDoubleClick } = props;
   const t = useTranslate();
@@ -79,104 +40,7 @@ const MemoContent = (props: MemoContentProps) => {
         onMouseUp={onClick}
         onDoubleClick={onDoubleClick}
       >
-        <ReactMarkdown
-          remarkPlugins={[
-            remarkDisableSetext,
-            remarkMath,
-            remarkGfm,
-            remarkSplitMixedTaskLists,
-            remarkBreaks,
-            remarkMention,
-            remarkTag,
-            remarkPreserveType,
-          ]}
-          rehypePlugins={[
-            rehypeRaw,
-            [rehypeSanitize, SANITIZE_SCHEMA],
-            rehypeHeadingId,
-            [rehypeKatex, { throwOnError: false, strict: false }],
-          ]}
-          components={{
-            // Child components consume from MemoViewContext directly
-            input: ((inputProps: React.ComponentProps<"input"> & { node?: Element }) => {
-              const { node, ...rest } = inputProps;
-              if (node && isTaskListItemNode(node)) {
-                return <TaskListItem {...inputProps} />;
-              }
-              return <input {...rest} />;
-            }) as React.ComponentType<React.ComponentProps<"input">>,
-            span: ((spanProps: React.ComponentProps<"span"> & { node?: Element }) => {
-              const { node, ...rest } = spanProps;
-              if (node && isMentionNode(node)) {
-                const username = getMentionUsername(node, spanProps.children);
-                return <Mention {...spanProps} data-mention={username} resolved={resolvedMentionUsernames.has(username)} />;
-              }
-              if (node && isTagNode(node)) {
-                return <Tag {...spanProps} />;
-              }
-              return <span {...rest} />;
-            }) as React.ComponentType<React.ComponentProps<"span">>,
-            // Headings
-            h1: ({ children, ...props }) => (
-              <Heading level={1} {...props}>
-                {children}
-              </Heading>
-            ),
-            h2: ({ children, ...props }) => (
-              <Heading level={2} {...props}>
-                {children}
-              </Heading>
-            ),
-            h3: ({ children, ...props }) => (
-              <Heading level={3} {...props}>
-                {children}
-              </Heading>
-            ),
-            h4: ({ children, ...props }) => (
-              <Heading level={4} {...props}>
-                {children}
-              </Heading>
-            ),
-            h5: ({ children, ...props }) => (
-              <Heading level={5} {...props}>
-                {children}
-              </Heading>
-            ),
-            h6: ({ children, ...props }) => (
-              <Heading level={6} {...props}>
-                {children}
-              </Heading>
-            ),
-            // Block elements
-            p: ({ children, ...props }) => <Paragraph {...props}>{children}</Paragraph>,
-            blockquote: ({ children, ...props }) => <Blockquote {...props}>{children}</Blockquote>,
-            hr: (props) => <HorizontalRule {...props} />,
-            // Lists
-            ul: ({ children, ...props }) => <List {...props}>{children}</List>,
-            ol: ({ children, ...props }) => (
-              <List ordered {...props}>
-                {children}
-              </List>
-            ),
-            li: ({ children, ...props }) => <ListItem {...props}>{children}</ListItem>,
-            // Inline elements
-            a: ({ children, ...props }) => <Link {...props}>{children}</Link>,
-            code: ({ children, ...props }) => <InlineCode {...props}>{children}</InlineCode>,
-            iframe: TrustedIframe as React.ComponentType<React.ComponentProps<"iframe">>,
-            img: ({ ...props }) => <Image {...props} />,
-            // Code blocks
-            pre: CodeBlock,
-            // Tables
-            table: ({ children, ...props }) => <Table {...props}>{children}</Table>,
-            thead: ({ children, ...props }) => <TableHead {...props}>{children}</TableHead>,
-            tbody: ({ children, ...props }) => <TableBody {...props}>{children}</TableBody>,
-            tr: ({ children, ...props }) => <TableRow {...props}>{children}</TableRow>,
-            th: ({ children, ...props }) => <TableHeaderCell {...props}>{children}</TableHeaderCell>,
-            td: ({ children, ...props }) => <TableCell {...props}>{children}</TableCell>,
-          }}
-        >
-          {content}
-        </ReactMarkdown>
+        <MemoMarkdownRenderer content={content} resolvedMentionUsernames={resolvedMentionUsernames} />
         {showCompactMode === "ALL" && (
           <div
             className={cn(
diff --git a/web/src/components/MemoContent/markdown/List.tsx b/web/src/components/MemoContent/markdown/List.tsx
index 79942cd51..c34e6a075 100644
--- a/web/src/components/MemoContent/markdown/List.tsx
+++ b/web/src/components/MemoContent/markdown/List.tsx
@@ -20,8 +20,8 @@ export const List = ({ ordered, children, className, node: _node, ...domProps }:
       className={cn(
         "my-0 mb-2 list-outside",
         isTaskList
-          ? // Task list: no bullets, nested lists get left margin for indentation
-            "list-none [&_ul.contains-task-list]:ml-6"
+          ? // Task list indentation is handled by task item grid columns.
+            "list-none"
           : // Regular list: standard padding and list style
             cn("pl-6", ordered ? "list-decimal" : "list-disc"),
         className,
@@ -40,7 +40,6 @@ interface ListItemProps extends React.LiHTMLAttributes<HTMLLIElement>, ReactMark
 /**
  * List item component for both regular and task list items
  * Detects task items via the "task-list-item" class added by remark-gfm
- * Applies specialized styling for task checkboxes
  */
 export const ListItem = ({ children, className, node: _node, ...domProps }: ListItemProps) => {
   const isTaskListItem = className?.includes(TASK_LIST_ITEM_CLASS);
@@ -49,11 +48,9 @@ export const ListItem = ({ children, className, node: _node, ...domProps }: List
     return (
       <li
         className={cn(
-          "mt-0.5 leading-6 list-none",
-          // Checkbox styling: margin and alignment
-          "[&>button]:mr-2 [&>button]:align-middle",
-          // Inline paragraph for task text
-          "[&>p]:inline [&>p]:m-0",
+          "mt-0.5 leading-6 list-none grid grid-cols-[auto_1fr] items-center gap-x-2",
+          "[&>ul]:col-start-2 [&>ul]:col-span-1 [&>ol]:col-start-2 [&>ol]:col-span-1",
+          "[&>p:first-child]:contents [&>p:not(:first-child)]:col-start-2 [&>p:not(:first-child)]:col-span-1",
           className,
         )}
         {...domProps}
diff --git a/web/src/components/MemoContent/markdown/README.md b/web/src/components/MemoContent/markdown/README.md
index a6ba08cc7..ece9757af 100644
--- a/web/src/components/MemoContent/markdown/README.md
+++ b/web/src/components/MemoContent/markdown/README.md
@@ -1,97 +1,18 @@
 # Markdown Components
 
-Modern, type-safe React components for rendering markdown content via react-markdown.
+Small React components used by `MemoMarkdownRenderer` to style HTML emitted by `react-markdown`.
 
-## Architecture
+## Responsibilities
 
-### Component-Based Rendering
-Following patterns from popular AI chat apps (ChatGPT, Claude, Perplexity), we use React components instead of CSS selectors for markdown rendering. This provides:
+- Keep element styling local to each semantic HTML element.
+- Strip the `node` prop from DOM output through `ReactMarkdownProps`.
+- Preserve existing markdown behavior while avoiding structural fixes in CSS.
 
-- **Type Safety**: Full TypeScript support with proper prop types
-- **Maintainability**: Components are easier to test, modify, and understand
-- **Performance**: No CSS specificity conflicts, cleaner DOM
-- **Modularity**: Each element is independently styled and documented
+## Task Lists
 
-### Type System
+GFM task lists are normalized before rendering by `remarkSplitMixedTaskLists`.
 
-All components extend `ReactMarkdownProps` which includes the AST `node` prop passed by react-markdown. This is explicitly destructured as `node: _node` to:
-1. Filter it from DOM props (avoids `node="[object Object]"` in HTML)
-2. Keep it available for advanced use cases (e.g., detecting task lists)
-3. Maintain type safety without `as any` casts
-
-### GFM Task Lists
-
-Task lists (from remark-gfm) are handled by:
-- **Detection**: `contains-task-list` and `task-list-item` classes from remark-gfm
-- **Styling**: Tailwind utilities with arbitrary variants for nested elements
-- **Checkboxes**: Custom `TaskListItem` component with Radix UI checkbox
-- **Interactivity**: Updates memo content via `toggleTaskAtIndex` utility
-
-### Component Patterns
-
-Each component follows this structure:
-```tsx
-import { cn } from "@/lib/utils";
-import type { ReactMarkdownProps } from "./types";
-
-interface ComponentProps extends React.HTMLAttributes<HTMLElement>, ReactMarkdownProps {
-  children?: React.ReactNode;
-  // component-specific props
-}
-
-/**
- * JSDoc description
- */
-export const Component = ({ children, className, node: _node, ...props }: ComponentProps) => {
-  return (
-    <element className={cn("base-classes", className)} {...props}>
-      {children}
-    </element>
-  );
-};
-```
-
-## Components
-
-| Component | Element | Purpose |
-|-----------|---------|---------|
-| `Heading` | h1-h6 | Semantic headings with level-based styling |
-| `Paragraph` | p | Compact paragraphs with consistent spacing |
-| `Link` | a | External links with security attributes |
-| `List` | ul/ol | Regular and GFM task lists |
-| `ListItem` | li | List items with task checkbox support |
-| `Blockquote` | blockquote | Quotes with left border accent |
-| `InlineCode` | code | Inline code with background |
-| `Image` | img | Responsive images with rounded corners |
-| `HorizontalRule` | hr | Section separators |
-
-## Styling Approach
-
-- **Tailwind CSS**: All styling uses Tailwind utilities
-- **Design Tokens**: Colors use CSS variables (e.g., `--primary`, `--muted-foreground`)
-- **Responsive**: Max-width constraints, responsive images
-- **Accessibility**: Semantic HTML, proper ARIA attributes via Radix UI
-
-## Integration
-
-Components are mapped to HTML elements in `MemoContent/index.tsx`:
-
-```tsx
-<ReactMarkdown
-  components={{
-    h1: ({ children }) => <Heading level={1}>{children}</Heading>,
-    p: ({ children, ...props }) => <Paragraph {...props}>{children}</Paragraph>,
-    // ... more mappings
-  }}
->
-  {content}
-</ReactMarkdown>
-```
-
-## Future Enhancements
-
-- [ ] Syntax highlighting themes for code blocks
-- [ ] Table sorting/filtering interactions
-- [ ] Image lightbox/zoom functionality
-- [ ] Collapsible sections for long content
-- [ ] Copy button for code blocks
+- Mixed task/bullet lists are split into separate lists so regular bullets keep bullets.
+- Single-block split items are rendered as tight list items, preventing accidental `<p>` wrappers.
+- `ListItem` uses a two-column grid: checkbox/control in the first column, task text and nested content in the second.
+- Loose task items keep paragraph structure; the first paragraph contributes its checkbox/text to the grid, while later paragraphs align with the text column.
diff --git a/web/src/utils/remark-plugins/remark-split-mixed-task-lists.ts b/web/src/utils/remark-plugins/remark-split-mixed-task-lists.ts
index 5957ebc83..4a1d9a99e 100644
--- a/web/src/utils/remark-plugins/remark-split-mixed-task-lists.ts
+++ b/web/src/utils/remark-plugins/remark-split-mixed-task-lists.ts
@@ -1,11 +1,18 @@
 import type { List, ListItem, Root } from "mdast";
 import type { Parent } from "unist";
 
-const isTaskListItem = (item: ListItem): boolean => typeof item.checked === "boolean";
+const isTaskItem = (item: ListItem): boolean => typeof item.checked === "boolean";
+
+const isSingleBlockItem = (item: ListItem): boolean => item.children.length <= 1;
+
+const hasLooseBlockItem = (item: ListItem): boolean => !isSingleBlockItem(item) && Boolean(item.spread);
+
+const normalizeSplitListItems = (items: ListItem[]): ListItem[] =>
+  items.map((item) => (isSingleBlockItem(item) ? { ...item, spread: false } : item));
 
 const splitMixedList = (list: List): List[] => {
-  const hasTaskItem = list.children.some(isTaskListItem);
-  const hasRegularItem = list.children.some((item) => !isTaskListItem(item));
+  const hasTaskItem = list.children.some(isTaskItem);
+  const hasRegularItem = list.children.some((item) => !isTaskItem(item));
 
   if (!hasTaskItem || !hasRegularItem) {
     return [list];
@@ -13,7 +20,7 @@ const splitMixedList = (list: List): List[] => {
 
   const groups: Array<{ isTaskGroup: boolean; items: ListItem[] }> = [];
   for (const item of list.children) {
-    const isTaskGroup = isTaskListItem(item);
+    const isTaskGroup = isTaskItem(item);
     const previousGroup = groups.at(-1);
 
     if (previousGroup && previousGroup.isTaskGroup === isTaskGroup) {
@@ -23,11 +30,14 @@ const splitMixedList = (list: List): List[] => {
     }
   }
 
-  return groups.map(({ isTaskGroup, items }) => ({
-    ...list,
-    children: isTaskGroup ? items : items.map((item) => ({ ...item, spread: false })),
-    spread: isTaskGroup ? list.spread : false,
-  }));
+  return groups.map(({ items }) => {
+    const children = normalizeSplitListItems(items);
+    return {
+      ...list,
+      children,
+      spread: children.some(hasLooseBlockItem),
+    };
+  });
 };
 
 const splitMixedTaskListsInParent = (parent: Parent): void => {
diff --git a/web/tests/memo-content-list.test.tsx b/web/tests/memo-content-list.test.tsx
index cfc6ecb4a..9b5abfd01 100644
--- a/web/tests/memo-content-list.test.tsx
+++ b/web/tests/memo-content-list.test.tsx
@@ -34,6 +34,8 @@ describe("memo content lists", () => {
     expect(html).toContain('<li class="mt-0.5 leading-6">milk</li>');
     expect(html).not.toContain('<li class="mt-0.5 leading-6">\n<p>milk</p>');
     expect(html).toContain(TASK_LIST_ITEM_CLASS);
+    expect(html).toContain("grid grid-cols-[auto_1fr] items-center gap-x-2");
+    expect(html).not.toMatch(/<li class="[^"]*task-list-item[^"]*"><p\b/);
   });
 
   it("keeps compact styling for pure task lists", () => {
@@ -41,5 +43,25 @@ describe("memo content lists", () => {
 
     expect(html).toMatch(/<ul class="[^"]*\blist-none\b[^"]*"/);
     expect(html).not.toMatch(/<ul class="[^"]*\blist-disc\b[^"]*"/);
+    expect(html).not.toMatch(/<li class="[^"]*task-list-item[^"]*"><p\b/);
+  });
+
+  it("keeps nested task lists on their own row", () => {
+    const html = renderListContent("- [ ] asdas\n  - [ ] zzzz");
+
+    expect(html).toContain("grid grid-cols-[auto_1fr] items-center gap-x-2");
+    expect(html).toContain("[&amp;&gt;ul]:col-start-2");
+    expect(html).not.toContain("[&amp;_ul.contains-task-list]:ml-6");
+    expect(html).toContain("zzzz");
+  });
+
+  it("keeps loose task list paragraphs while aligning the first line", () => {
+    const html = renderListContent("- [ ] plan\n\n  keep details\n\n- [ ] zzzz");
+
+    expect(html).toMatch(/<li class="[^"]*task-list-item[^"]*">\s*<p>/);
+    expect(html).toContain("[&amp;&gt;p:first-child]:contents");
+    expect(html).toContain("[&amp;&gt;p:not(:first-child)]:col-start-2");
+    expect(html).toContain("<p>keep details</p>");
+    expect(html).toContain("zzzz");
   });
 });